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Key West, FL

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Cruises to Key West are packed with coastal-town energy and layers of American history just waiting to be discovered. Enjoy a laidback Caribbean vibe with a dash of the high life on Carnival cruises to Key West. The southernmost island of the Florida Keys, Key West is a sunny, fun-loving place with plenty of charm, and more than a little touristy goofiness. (But that’s optional.) Key West cruises deliver you to palm-shaded streets lined with gaily-painted bungalows, vintage saloons and blooming tropical flowers. Whether life’s a beach or you’re life of the party, cruises to Key West definitely over-deliver.

  • Stroll amid 19th-century architecture in Key West’s Old Town.
  • Step inside the breeze-filled homes of Hemingway and Audubon.
  • Make a pilgrimage to the southernmost point in the United States.
  • Join the perpetual party in one of the town’s old-time fisherman’s saloons.

Things to do in Key West

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Key West, Florida, US

One of the first things you’ll notice on your Key West cruise is the colorful gingerbread wooden houses and the amazing sunsets, and the constant crowing of roosters. Hundreds of the noisy birds—along with their quieter-clucking mates—roam the streets at all hours, and are nearly as synonymous with Key West cruises as its six-toed cats, the famous furry residents of Ernest Hemingway’s mansion in the Old Town district. They’re all part of the quirky charm of the United States' southernmost point, whose compact 11 square kilometers (4.2 square miles) pack in everything from gorgeous historic architecture and spectacular fishing and sailing to a raucous party scene along famed Duval Street. All of which is truly enjoyed by vacationers who cruise to Key West, Florida.

Featured Shore Excursions

Cruises To Key West, Florida

Key West, Florida

Key West Visiting Cruises Calendar

cruises from boston to florida keys

Use code BAREFOOT for 10% off Guided Tours!

Barefoot Billy’s Inc.

Catamaran Cruises in Key West, FL

Escape the downtown crowd - cruise with billy.

Key West’s nautical history is all based on its proximity to the world’s 3rd largest living coral reef. From pirates and privateers to ship wreckers and fisherman the draw has always been the sanctuary provided by the Florida Great Barrier Reef.  Key West’s coral rock islands trace a contiguous pathway from the Atlantic Ocean & Gulf of Mexico intersect all the way to mainland Florida. To this day our primary industry, tourism, celebrates our unique natural ecosystem in the shadow of the reef. 

Whether you want to cruise a couple of hours, island-hop all day, or see our beautiful wildlife, Billy has you covered! Bring your reef-safe sunscreen, and we’ll take care of the rest!

Ticketed Tours

  • Kid Friendly!
  • Users All ages
  • Info Up to 36 people
  • Clock 3.5 hours

Dolphin Watch & Snorkel Tour

Search for wild dolphins in their natural habitat and snorkel Key West’s backcountry waters off the Seabreeze!

  • Most Popular Cruise
  • Info Up To 38 People
  • Clock 2 hours

Key West Sushi & Sunset Cruise

Dine on fresh sushi while taking in the famous Key West sunset. You will cruise past the southernmost point of the U.S., tropical beaches and a Civil War era Fort Zachary Taylor Historic Sate Park.

Private Experiences

  • Our Newest Boat
  • Info 1-6 People
  • Clock 2 to 8 hours

Barefoot Private Charters

Create the perfect outing for up to 6 with a custom charter! Cast off from the island and explore the unique nature surrounding the Florida Keys!

  • Info 1 to 40 people
  • Clock 3 Hours

Morning Island Charter

Spend your morning at the sandbar and experience the turquoise waters surrounding Key West at a slower pace on this private charter.

  • Clock Varies

Seabreeze Charters

Snorkel, see Dolphin, or visit a sandbar with an open-air cruise for up to 40 people. Create the perfect escape with a private adventure aboard our 45-foot Corinthian catamaran!

cruises from boston to florida keys

Virgin Voyages' guide to Cruise Key West

A haven for artists and sunset-seekers alike, the only poetic rival to the writers who called Key West home is the geography itself.

It’s all a breeze in the keys

With it’s fiercely independent personality and leave-your-last-name-at-the-dock attitude, Key West is a celebration of cultural collision — with Bahamian Conch, Cuban and African-American heritage permeating the spirit and inclusive philosophy of the island known as “One Human Family”.

More than its pirate past and raucous Duval Street parties (although, to be fair, those are worth the hype), Key West is home to an ever-evolving community of boundary-pushing artists and dedicated preservationists—lined with pastel-colored houses and nights spent toasting sunsets so incredible they inspire some of the world’s most sacred art.

What to see and do on the island

The Shore Things, the tour things and Hemingway’s fur things

Dolphin Watch and Wildlife Snorkel

A dolphin-watching and wildlife snorkeling trip

Key West Rum & Cigar Tasting Tour

A tour of the cigar and rum industry in Key West

The Duval Crawl: Key West's Pub Crawl

Pub crawl down Duval Street at the liveliest bars

Head out on the turquoise waters of the gulf to watch bottlenose dolphins as they swim, play, feed and do whatever else they please. Afterwards, head back to the wildlife refuge, where you can snorkel along the shallow backcountry.

Key West Rum and Cigar Tasting Tour

Technically located closer to Cuba than it is to Miami, the cigar and rum industry in Key West is as historically fascinating as it is… straight-up fun. Try some rum at the Papa Pilar Rum Distillery at the Hemingway Rum Company, which functions as both a distillery and a museum.

The Duval Crawl: Key West's Pub Crawl

The best way to see a famous Key West tradition while also letting loose because, yes, you are on vacation via the “Duval Crawl”—the downtown pub crawl. The vibe of the crawl is a cross between the famous chill Florida Keys atmosphere, a splattering of upbeat live music and Caribbean drinks that taste exactly like a vacation should.

More Shore Things for your wishlist...

We have even more in our curated catalog.

From Cayo Hueso to Key West:

Named by spanish settlers — english speakers heard, “key west” instead..

Shore Things

Parasail the Painted Island Skies

Float through the air as one of the 12-passenger parasailing boats glides you past sights that can only be seen from the air. As you parasail, take a look below to spot dolphins playing in the surf, or colorful tropical birds flying past.

When the sun sets in Key West… you’ll know. And not just because a myriad of artists from Jimmy Buffet to Judy Blume will make art inspired by the island’s evening end. You’ll know because the sky lights up like fire—tangerine and gold stretching far and wide across the Caribbean sea as you pull away from the dock. Setting on a day spent in a place that goes far beyond a bachelor and bachelorette party destination—where the best of New Orleans and Nantucket meet in the Caribbean to create a little island with a very big personality.

Set Sail the Virgin Way

Set sail the Virgin way and find a new approach to cruise vacations. Select this special itinerary and let's sail.

Fire & Sunset Soirées

Painted skies in the Florida Keys

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Switching to holiday mode has never been easier. Norwegian Gem is now sailing from Boston, whisking you away to some of the most beautiful destinations in the world. Dip your toes in pink-sand beaches on a cruise from Boston to Bermuda where you will witness the most unforgettable tangerine sunsets. Southern Caribbean cruises from Boston , giving you ample time to get into that island-life rhythm.--> In autumn, re-discover the treasures along the coast on a Canada and New England cruise . Don’t forget your camera – the landscapes you will see are a spectacle.

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With the world's most golf courses per square mile, consider Bermuda your fairway to heaven. With up to three full days in port to explore, you can do it all - from relaxing on the country's famous pink-sand beaches to discovering world-class dive sites and exploring the charming British town of St. George's. Paradise is closer than you think when you cruise with Norwegian Cruise Line.

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Experience the coastline of Canada & New England in a brand-new way on a cruise from Boston. Travel back to the Gilded Age and explore Bar Harbor. Quebec City's iconic Chateau Frontenac is where you'll find the best views of the Saint Lawrence River. Let Norwegian take you where the deep-blue sea meets rich autumn hues.

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Paradise begins the moment you step aboard Norwegian Gem. Kick off vacation with a poolside daiquiri, indulge in a hot stone massage at the award-winning Mandara Spa or splash around with your kids in the Aqua Park. With dining options ranging from French to authentic Brazilian steakhouse, there is something to satisfy every palate. Plus, there are 15+ unique bars and lounges and amazing entertainment to heat up your nights. And, with a wide range of modern accommodations including the luxurious Haven by Norwegian®, wherever you like to unwind, we have you covered.

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A Cruise Family Holiday THEY'LL NEVER FORGET

Enjoy a cruise holiday from Boston with your family

A Cruise Family Holiday for the Whole Family

New england: holiday has never been closer driving to the boston cruise terminal.

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Flynn Cruiseport Boston Cruise Terminal is easily accessible from both I-90 and I-93 and via public transportation, making it the perfect departure point for your next holiday. There is plenty of parking at the cruise terminal, and even more affordable options in the close vicinity. Many garages offer complimentary shuttles, and great deals when you book parking in advance.

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Boston to Fort Lauderdale

From BOSTON, MASSACHUSETTS - onboard CELEBRITY ECLIPSE

†Taxes, fees and port expenses $239.47 USD *

At Celebrity Cruises®, we believe choice matters. That’s why we’ve pre-packaged our most popular amenities—drinks, and Wi-Fi— Tips charged separately. So you can now choose the most convenient way to get the best value from your cruise.

 Drinks

Choose from an incredible array of beers, spirits, cocktails, liqueurs, frozen drinks, wines by the glass, sodas, juices, specialty coffees and bottled water.

 Wi-Fi

We know staying in touch is important, so we’ve included internet access for all guests. Browse the web, check email, and use messaging apps.

Cruise Itinerary

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Boston, Massachusetts

Fri, Oct 11, 2024

Departs: 6:00PM

At Sea - Cruising

Sat, Oct 12, 2024

Royal Naval Dockyard

Sun, Oct 13, 2024

Docked: 10:00AM to 6:00PM

Mon, Oct 14, 2024

Tue, Oct 15, 2024

Willemstad, Curacao

Wed, Oct 16, 2024

Docked: 1:00PM to 9:00PM

Oranjestad, Aruba

Thu, Oct 17, 2024

Docked: 8:00AM to 11:00PM

Kralendijk, Bonaire

Fri, Oct 18, 2024

Docked: 8:00AM to 5:00PM

Sat, Oct 19, 2024

Sun, Oct 20, 2024

Fort Lauderdale, Florida

Mon, Oct 21, 2024

Arrival: 7:00AM

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About This Ship

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Celebrity Eclipse Ship

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Onboard Features

Moonlight Sonata Restaurant

The airy Main Restaurant offers exquisite menu selections, which change nightly to give you a variety of classic and contemporary choices. And the service? Legendary.

Clean, crisp flavors and inventive cuisine meet an extensive list of sustainable and biodynamic wines. Exclusively for AquaClass guests.

The exclusive restaurant for guests of the Retreat. Select and cutting edge, the globally inspired menus at Luminae are not available in any other restaurant on board.

Martini Bar & Crush

Sit back and relax, listening to up-tempo tunes and enjoying a collection of rare vodkas and a portfolio of fine caviars.

A unique music venue with spectacular ocean views. The perfect daytime spot to gaze over the sea with a cocktail in hand.

Ensemble Lounge

Ensemble Lounge is the ideal setting for an aperitif en route to an extraordinary dining experience, or a digestif afterward.

The Retreat is an unparalleled vacation experience that includes every stunning suite, a private restaurant, and an exclusive lounge that rivals any high-end resort.

Say "Ahh" in spa-inspired staterooms designed just for you. Savor clean eating at Blu and escape to the Relaxation Room.

Tailored services and amenities await you in these exceptionally appointed staterooms. We're here to help you make the most of your time on board and on shore.

Relax, recharge, and play the hottest slots and table games at The Casino. It offers a sophisticated ambiance and a captivating atmosphere that comes alive with plenty of action.

Camp at Sea

For our Camp at Sea program, we’ve designed more than 500 activities that make every sailing a brand new experience and an unforgettable memory for our junior cruisers.

Shops on Eclipse

Aboard Eclipse, Celebrity's European-inspired piazza and elegant galleria hold riches of chic sophistication. Marble walkways lead you to modern boutiques and fine jewelry stores.

Fitness Center

Bring your workout routine along on your modern luxury vacation and enjoy a variety of new fitness classes and seminars along with world class cruise fitness amenities.

Basketball Court

Shoot some hoops before or after your day’s adventure. Located centrally aboard the ship, you can enjoy a great basketball game while a nice ocean breeze keeps you cool.

Hot Glass Class

Now, on board Celebrity Eclipse® you can experience our Hot Glass Class, where you'll create a beautiful flower, starfish, bowl, vase, or other memento to take home.

The Lawn Club

Who said grass can’t be on a ship? Enjoy a friendly pick-up game of leisure sports like Croquet, Bocce, golf putting, Blongo or Baggo.

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Price is per person and applies to selected sailing, lowest available fare stateroom category, based on double-occupancy, reflects any promotional savings, and is subject to change and availability until booked. Additional terms and conditions apply to offers. Full deposit must be paid by deposit payment required due date. Standard full deposit penalty is applied if booking is cancelled within final payment period; see Celebrity’s cancellation policy for details. Non-Refundable Deposit Bookings (“NRDB”): To qualify for the lowest available cruise fare, guest must choose a non-refundable deposit. All deposit payments for NRDB made after 03/02/23 are non-refundable from the time of booking. NRDB are applicable to groups at prevailing rates. Not applicable to incentive, contract, or charter groups. Nonrefundable deposit offers are applicable to sailings within final payment, however full deposit is due at time of booking. 

Celebrity Edge® Series Iconic Suites, Edge Villas, Penthouse Suites, Royal Suites, Celebrity Suites, AquaClass® Sky Suites, and Sky Suites (and Family Suites during Holiday sailings) require double the deposit amounts listed.

All Included  pricing applies to sailings booked and departing on or after October 4, 2023, excluding Galapagos cruises, in an inside, ocean view, veranda, Concierge Class, or AquaClass stateroom (“Eligible Bookings”). All guests within an Eligible Booking who choose “All Included” pricing, will receive a Classic Drinks Package and an unlimited Basic Wi-Fi package. All guests in the same stateroom must choose the same rate.  Please visit www.celebritycruises.com/things-to-do-onboard/onboard-packages/beverage-packages for further information on available beverages and full restrictions and www.celebritycruises.com/things-to-do-onboard/onboard-packages/internet-and-phone-packages for further information on wi-fi.

All Included pricing applies to new individual bookings only. Changes to booking may result in removal of Offer. Prices and Offers are subject to availability and change without notice, may be withdrawn at any time, and not applicable to charters or contracted groups. All Included pricing is non-transferable and not combinable with certain rates including, Travel Agent, Interline, Net, Exciting Deals, or worker cabins.  Single occupancy guests paying 200% cruise fare are eligible for All Included pricing. Refer to celebritycruises.com and the Cruise Ticket Contract for additional terms and conditions. Celebrity Cruises reserves the right to cancel offer at any time, correct any errors, inaccuracies, or omissions, and change or update fares, fees, and surcharges at any time without prior notice.

Imagery and messaging may not accurately reflect onboard and destination experiences, offerings, features, or itineraries. These may not be available during your voyage, may vary by ship and destination, and may be subject to change without notice.

*Port sequence may vary by sailing date.

Map

Departing Oct 11, 2024

$1,448 USD * Avg Per Person

DAY 1 - Friday , Oct 11

DAY 2 - Saturday , Oct 12

DAY 3 - Sunday , Oct 13

DAY 4 - Monday , Oct 14

DAY 5 - Tuesday , Oct 15

DAY 6 - Wednesday , Oct 16

DAY 7 - Thursday , Oct 17

DAY 8 - Friday , Oct 18

DAY 9 - Saturday , Oct 19

DAY 10 - Sunday , Oct 20

DAY 11 - Monday , Oct 21

Reader's Digest

Reader's Digest

Your Guide to a Florida Keys Road Trip: Key Largo to Key West

Posted: March 12, 2024 | Last updated: March 13, 2024

<p>One of the <a href="https://www.rd.com/list/best-states-road-trip/" rel="noopener noreferrer">best state road trips</a> in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.</p> <p>So if you're looking for the perfect <a href="https://www.rd.com/article/atlantic-coast-road-trip/" rel="noopener noreferrer">Atlantic Coast road trip</a> or <a href="https://www.rd.com/list/best-budget-friendly-beach-destinations/" rel="noopener noreferrer">cheap beach vacation</a>, look no further than this <a href="https://www.rd.com/article/the-ultimate-american-road-trip-guide/" rel="noopener noreferrer">road trip guide</a> from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.</p> <p>By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.</p> <p><strong>Get <em>Reader's <b><i>Digest</i></b></em><b>’s</b> </strong><a href="https://www.rd.com/newsletter/?int_source=direct&int_medium=rd.com&int_campaign=nlrda_20221001_topperformingcontentnlsignup&int_placement=incontent" rel="noopener noreferrer"><strong>Read Up newsletter</strong></a><strong> for more travel, humor, cleaning, tech and fun facts all week long.</strong></p>

Your road trip guide to the Florida Keys

One of the best state road trips in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.

So if you're looking for the perfect Atlantic Coast road trip or cheap beach vacation , look no further than this road trip guide from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.

By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.

Get Reader's Digest ’s   Read Up newsletter for more travel, humor, cleaning, tech and fun facts all week long.

<p><strong>Mile marker:</strong> 108–90</p> <p>The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.</p> <p>Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.</p> <p>Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.</p> <p><strong>Best beach:</strong> Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.</p> <p><strong>Where to eat: </strong>Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best <a href="https://www.rd.com/list/traditional-restaurant/">traditional restaurants</a> in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.</p> <p><strong>Where to stay:</strong> If you can't get enough of the underwater world, stay at <a href="https://www.tripadvisor.com/Hotel_Review-g34344-d218568-Reviews-Jules_Undersea_Lodge-Key_Largo_Florida_Keys_Florida.html" rel="noopener noreferrer">Jules' Undersea Lodge</a>, the world's first underwater hotel. If you'd rather keep dry, try the adults-only <a href="https://www.tripadvisor.com/Hotel_Review-g34344-d13980722-Reviews-Bungalows_Key_Largo-Key_Largo_Florida_Keys_Florida.html" rel="noopener">Bungalows Key Largo</a>.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34344-d218568-Reviews-Jules_Undersea_Lodge-Key_Largo_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 108–90

The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.

Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.

Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.

Best beach: Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.

Where to eat: Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best traditional restaurants in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.

Where to stay: If you can't get enough of the underwater world, stay at Jules' Undersea Lodge , the world's first underwater hotel. If you'd rather keep dry, try the adults-only Bungalows Key Largo .

<p><strong>Mile marker:</strong> 90–63</p> <p>Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.</p> <p>There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.</p> <p>Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, <a href="https://www.rd.com/list/best-hiking-trails/" rel="noopener noreferrer">go for a hike</a> or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.</p> <p><strong>Best beach:</strong> Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.</p> <p><strong>Where to eat:</strong> For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.</p> <p><strong>Where to stay:</strong> When it's time to lay your head for the night, check in to one of the new oceanfront suites at <a href="https://www.tripadvisor.com/Hotel_Review-g34346-d84610-Reviews-Cheeca_Lodge_Spa-Islamorada_Florida_Keys_Florida.html" rel="noopener noreferrer">Cheeca Lodge & Spa</a>, or your own cottage at <a href="https://www.tripadvisor.com/Hotel_Review-g34346-d113464-Reviews-The_Moorings_Village-Islamorada_Florida_Keys_Florida.html" rel="noopener">The Moorings Village & Spa</a>.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34346-d84610-Reviews-Cheeca_Lodge_Spa-Islamorada_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 90–63

Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.

There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.

Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, go for a hike or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.

Best beach: Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.

Where to eat: For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.

Where to stay: When it's time to lay your head for the night, check in to one of the new oceanfront suites at Cheeca Lodge & Spa , or your own cottage at The Moorings Village & Spa .

<p><strong>Mile marker:</strong> 63–40</p> <p>Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.</p> <p>For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.</p> <p>While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.</p> <p><strong>Best beach: </strong>Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the <a href="https://www.rd.com/list/best-florida-beaches/">best beaches in Florida</a>. And it's not just popular with humans; sea turtles nest here between April and October.</p> <p><strong>Where to eat: </strong>For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.</p> <p><strong>Where to stay:</strong> The <a href="https://www.tripadvisor.com/Hotel_Review-g34347-d6784786-Reviews-Faro_Blanco_Resort_Yacht_Club-Marathon_Florida_Keys_Florida.html" rel="noopener noreferrer">Faro Blanco Resort & Yacht Club</a> is set on the waterfront and gives you a taste of marina life. <a href="https://www.tripadvisor.com/Hotel_Review-g11962583-d113469-Reviews-Lime_Tree_Bay_Resort-Layton_Long_Key_Florida_Keys_Florida.html" rel="noopener">Lime Tree Bay Resort</a> on Long Key has spacious townhomes for rent.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34347-d6784786-Reviews-Faro_Blanco_Resort_Yacht_Club-Marathon_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 63–40

Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.

For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.

While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.

Best beach: Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the best beaches in Florida . And it's not just popular with humans; sea turtles nest here between April and October.

Where to eat: For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.

Where to stay: The Faro Blanco Resort & Yacht Club is set on the waterfront and gives you a taste of marina life. Lime Tree Bay Resort on Long Key has spacious townhomes for rent.

<p><strong>Mile marker:</strong> 40–4</p> <p>After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an <a href="https://www.rd.com/article/ev-road-trip/">electric vehicle on this road trip</a> so you don't disturb the animals.</p> <p>Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.</p> <p>Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.</p> <p><strong>Best beach: </strong>The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.</p> <p><strong>Where to eat: </strong>In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.</p> <p><strong>Where to stay:</strong> Consider the waterfront <a href="https://www.tripadvisor.com/Hotel_Review-g34659-d603177-Reviews-Sugarloaf_Lodge-Sugarloaf_Key_Florida_Keys_Florida.html" rel="noopener noreferrer">Sugarloaf Lodge</a>, stay in an Airstream at <a href="https://www.tripadvisor.com/Hotel_Review-g34085-d113460-Reviews-Big_Pine_Key_Resort-Big_Pine_Key_Florida_Keys_Florida.html" rel="noopener noreferrer">Big Pine Key Resort</a> or pop a tent on one of the reserved campsites at Bahia Honda State Park.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34659-d603177-Reviews-Sugarloaf_Lodge-Sugarloaf_Key_Florida_Keys_Florida.html">Book Now</a></p>

The Lower Keys

Mile marker: 40–4

After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an electric vehicle on this road trip so you don't disturb the animals.

Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.

Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.

Best beach: The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.

Where to eat: In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.

Where to stay: Consider the waterfront Sugarloaf Lodge , stay in an Airstream at Big Pine Key Resort  or pop a tent on one of the reserved campsites at Bahia Honda State Park.

<p><strong>Mile marker:</strong> 4–0</p> <p>You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.</p> <p>If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.</p> <p>Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some <a href="https://www.rd.com/list/states-hidden-gems/">hidden gems</a>. The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.</p> <p><strong>Best beach: </strong>Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.</p> <p><strong>Where to eat: </strong>No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.</p> <p><strong>Where to stay:</strong> The boutique <a href="https://www.tripadvisor.com/Hotel_Review-g34345-d227346-Reviews-The_Gardens_Hotel-Key_West_Florida_Keys_Florida.html" rel="noopener noreferrer">Gardens Hotel</a>, the adults-only Kimpton Hotels <a href="https://www.tripadvisor.com/Hotel_Review-g34345-d296023-Reviews-Kimpton_Ridley_House-Key_West_Florida_Keys_Florida.html" rel="noopener noreferrer">Ridley House</a> or the new <a href="https://www.tripadvisor.com/Hotel_Review-g34345-d21408966-Reviews-The_Capitana_Key_West-Key_West_Florida_Keys_Florida.html" rel="noopener noreferrer">Capitana Key West</a>, to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.</p> <p class="listicle-page__cta-button-shop"><a class="shop-btn" href="https://www.tripadvisor.com/Hotel_Review-g34345-d227346-Reviews-The_Gardens_Hotel-Key_West_Florida_Keys_Florida.html">Book Now</a></p>

Mile marker: 4–0

You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.

If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.

Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some hidden gems . The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.

Best beach: Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.

Where to eat: No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.

Where to stay: The boutique Gardens Hotel , the adults-only Kimpton Hotels Ridley House  or the new Capitana Key West , to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.

<p>Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for <a href="https://www.rd.com/article/what-is-ecotourism/">eco-travelers,</a> but artists and history buffs too.</p> <p>It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.</p> <p>For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.</p>

Art and history in the Florida Keys

Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for eco-travelers, but artists and history buffs too.

It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.

For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.

<p>Now that you're inspired to hit the road, it's time to start planning. After <a href="https://www.rd.com/article/road-trip-cost/" rel="noopener noreferrer">budgeting for a road trip</a>, your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.</p> <p>If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.</p> <p>If you're already driving one of the <a href="https://www.rd.com/list/best-road-trip-cars/" rel="noopener noreferrer">best road trip cars</a> to get to Florida, you're all set. But if you need a loaner, choose one of the <a href="https://www.rd.com/list/best-cars-to-rent-for-a-road-trip/" rel="noopener noreferrer">best cars to rent for a road trip</a>. Consider packing these <a href="https://www.rd.com/list/road-trip-essentials/" rel="noopener noreferrer">road trip essentials</a> and download some of the <a href="https://www.rd.com/article/best-podcasts-for-road-trips/" rel="noopener noreferrer">best podcasts for road trips</a> to make the miles fly by.</p>

Planning your Florida Keys road trip

Now that you're inspired to hit the road, it's time to start planning. After budgeting for a road trip , your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.

If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.

If you're already driving one of the best road trip cars to get to Florida, you're all set. But if you need a loaner, choose one of the best cars to rent for a road trip . Consider packing these road trip essentials and download some of the best podcasts for road trips to make the miles fly by.

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    Search for cruises from Boston with Royal Caribbean. Start planning your next cruise vacation by finding the best travel destinations & departure ports.

  18. Boston to Fort Lauderdale

    Set sail on the Celebrity Eclipse for 10 Nights and experience the best of Caribbean on the Boston to Fort Lauderdale. Book your Celebrity Cruise today!

  19. Cruises from Boston

    Norwegian Gem is now sailing from Boston, whisking you away to some of the most beautiful destinations in the world. Dip your toes in pink-sand beaches on a cruise from Boston to Bermuda where you will witness the most unforgettable tangerine sunsets. In autumn, re-discover the treasures along the coast on a Canada and New England cruise.

  20. Cruises from Florida to Key West

    Looking for cruises from Florida to Key West? Find and plan your next cruise from Florida to Key West on Cruise Critic. We offer a wide selection of departure dates for cruises from Florida to Key ...

  21. Boston to Fort Lauderdale

    Set sail on the Celebrity Eclipse for 10 Nights and experience the best of Caribbean on the Boston to Fort Lauderdale. Book your Celebrity Cruise today!

  22. Cruises from Florida to Boston

    Looking for cruises from Florida to Boston? Find and plan your next cruise from Florida to Boston on Cruise Critic. We offer a wide selection of departure dates for cruises from Florida to Boston ...

  23. Your Guide to a Florida Keys Road Trip: Key Largo to Key West

    The post Your Guide to a Florida Keys Road Trip: Key Largo to Key West appeared first on Reader's Digest. ... mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance ...