gloucester ma sunset cruise

SUNSET CRUISE

Come aboard the lady sea for a great night of fun, friends, and dancing.

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THE BEST PRIVATE CHARTER IN GLOUCESTER!  

4-hour sunset cruises 

Harbor cruises

Water skiing and tubing excursions

Beach Transport

THE SETTING

Owned and operated by Captain Ty Wood of Gloucester, TRIBE is a new and unsinkable Boston Whaler 210 Montauk (21') powered by a Mercury 200HP Verado. Known as the "unsinkable legend", TRIBE provides comfortable seating and sunbathing space for up to four adult guests plus crew. TRIBE'S shallow draft allows her to be "beached" for easy boarding at the many secluded beaches around Gloucester. TRIBE also has plenty of power for an action-packed day of water skiing and tubing.

Gloucester, Massachusetts is widely known for its natural beauty and lively waterfront. Aboard TRIBE, guests can choose between an unforgettable day of waterfront restaurant hopping, a romantic sunset cruise through the Annisquam River, an exciting day of water sports or simply spend a relaxing afternoon anchored in the crystal-clear water off of Wingaersheek Beach.

Afternoon trip (noon to 4PM)  

Guests will board TRIBE at the city dock in St. Peter's Sq. (easy walk from The Beauport Hotel) 

$450.00 (plus tips for crew)

Sunset Cruise (5PM to roughly 9PM)

Guests board at the city dock in St. Peter's Sq. near the Beauport Hotel. TRIBE will cruise through the Annisquam River and out to Ipswich Bay, stopping at Lanes Cove for a south westerly view of the setting sun across the water. $450.00 (plus tips for crew)

PHOTOS FROM PAST GLOUCESTER BOAT CHARTERS ABOARD TRIBE

We expect this summer will be very busy so call or email to reserve your charter aboard TRIBE today!

Captain Ty Wood (978) 491-0209

Gloucester, MA

(978) 491-0209 [email protected]

Inquire about your charter here!

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THE Friki Tiki of Gloucester harbor

Island style vibes on enchanting gloucester harbor..

Book a Private Charter

Celebrate your special occasion with a private charter on The Friki Tiki in Gloucester, MA! Ideal for birthdays, bachelor/bachelorette parties, retirements, and more!. Bring your snacks, beverages, and playlist for our Bluetooth speaker.  Enjoy a 90-minute Harbor or Annisquam River Cruise, with options to extend. 

Available Fri/ Sat/ Sun

Book a sunset tiki cruise.

Experience picture-perfect sunsets on our 90-minute Gloucester Harbor cruise. Enjoy views of the Gloucester fishing fleet, Ten Pound Island, Rocky Neck Art Colony, and Norman's Woe. Bring your friends, snacks, and beverages of your choice! Sunset cruise departures vary by season.

Bookable up to 21 days in advance.

Meet the Team!

CRUISE WITH THE LOCALS! 

The Friki Tiki of Gloucester is locally owned and operated by Ginger Attaya, a local resident of Gloucester.. Our crew knows the local waters and the best spots to cruise aboard our custom floating tiki boat.  With an “island vibe”  and the beauty of Gloucester Harbor and Annisquam River, it’s sure to be everything you need for you and your friends to have a great time.   

Our vessel, "The Friki Tiki," is 36 feet long and over 11.4 feet wide. The Friki Tiki is fully licensed and insured. and equipped with all safety gear required by the USCG.  

Captain Mark Sinkinson is a Coast Guard certified boat captain and holds a 25 ton Masters license.  He has years of experience on fresh and salt waters and now resides here in Gloucester.  

 Captain Forrest got his start lobstering at the young age of 11.  He would work weekends when he was in school and continued to do so through the time he graduated.    Using his several years of sea time experience both in Gloucester and Alaska,  Forrest has now proceeded to acquire his 100 ton Masters License.  

Crew subject to change due to scheduling conflicts.

Frequently Asked Questions

Please reach us at  if you cannot find an answer to your question.  Our contact information is listed below. 

Our tours require a minimum of 9 total persons to run. If we are unable to meet that minimum, we will gladly reschedule to a time and day of your choice or refund your purchase.    (For public cruises only)  The Friki Tiki reserves the right to change, cancel, or reschedule a cruise as needed. Notice will be given as soon as possible.

The Captain reserves the right to adjust the trip as he/she sees fit.  This means that a harbor tour might go up the river and vs. versa depending on tides, weather, etc.    Note that on cooler days, the captain may decide to stay on the river vs. in the harbor.

Public Cruises - must cancel 24 hours in advance for a refund.   (Public cruises open up 2 weeks prior to departure)

Private Cruises - 50% paid up front and final payment due the day of your cruise .   If you cancel 30 days or more out, your deposit will be refunded.  If you cancel less than 30 days, no refund on deposit but we will try to reschedule you if possible.

If you are a no show, that will be considered a cancellation and you will not receive a refund. 

New England weather forecasts are not entirely reliable and we do not cancel trips based on the forecast.  The Captain decides whether it is safe to sail close to departure time.  If the Captain decides to cancel because of weather, we will work with you to reschedule your cruise or provide a refund.

Yes!   We have one restroom on board.  We call it "The Head."  

You may bring a beverage of your choice (including alcoholic), snacks/ food, sunblock, sunglasses,  jacket.  If you are booking a private charter, please feel free to bring your playlist so that you can enjoy your music while cruising!

We recommend comfortable clothing and casual shoes.  High Heels are not a good choice when walking around the boat.

There is no smoking (of any kind) permitted on The Friki Tiki.   

Yes!  The crew works hard in order to give you the best cruise possible.   Should you decide to provide a gratuity, they would be most appreciative!

Do you have any questions?  Send us a message and we'll get back to you!

The Friki Tiki of Gloucester Harbor

Cripple Cove Landing, 73 East Main St., Gloucester, MA

978-491-7993

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Enjoy Sunset Cruises and Water Excursions in Gloucester, MA 

The summer season is here in Gloucester, which means enjoying the beaches, shoreline, and, of course, the many water activities associated with Gloucester Harbor and the Atlantic. From sunset harbor cruises to whale watching, deep sea fishing, educational tours, and lighthouse tours, there is much to do and see. 

Whether you want to take a laid-back cruise around the harbor and watch the sun go down while enjoying the company of friends and a good cocktail or you want the excitement of reeling in “the big one” while deep sea fishing or spotting a magnificent whale breaching out of the water, Gloucester has something for everyone in terms of water excursions and tours. 

Here are some on-the-water experiences to inspire your next visit to Gloucester and Cape Ann.

Go On a Whale Watch

Witnessing whales in their natural habitat is an amazing adventure. Two options for this type of water excursion in Gloucester include 7 Seas Whale Watch and Cape Ann Whale Watch.  

Both businesses offer spectacular whale watching adventures leaving Gloucester Harbor daily. Whale watching off the coast of Gloucester includes a ride on state-of-the-art vessels that bring guests out to an area called the Stellwagen Bank National Marine Sanctuary . This sanctuary is a location where many varieties of whales can be found as they migrate and feed on the abundant natural resources off the coast of Massachusetts.  

If you are looking for something on the water that isn’t whale watching, there are Gloucester businesses that provide those options as well. Cape Ann Cruises offers a host of options when it comes to water tours including lighthouse cruises, sunset cruises, corporate outings, seal watching, party cruises, and even a wedding venue! These options also come with a catering menu and bar service that can be customized for your event. 

Gloucester Fleet – Deep Sea Fishing Charters 

If fishing is what you like to do out on the open waters, then Gloucester Fleet Deep Sea Fishing is the place to go. The knowledgeable and experienced crew will help you aboard The Lady Sea, a 72′ x 22′ fiberglass vessel built specifically for comfortable fishing. Her wide beam will ensure less tangle time and more fishing time!

Choose from many different types of fishing trips including a Marathon Trip, which includes a 12-hour excursion for avid anglers; a custom Charter Trip, which could be for celebrating a birthday, retirement, bachelor party, or corporate outing; or a Deep Sea Fishing tour, which covers hot spots such as Tillies Ledge, Stellwagen Bank (a National Marine Sanctuary), Jeffreys Ledge, and Straw Hat as well as a few other favorites of deep sea fishing. These are some of the best bottom fishing grounds around and promise some exciting catches. Excursions can last a half day, ¾ of a day, or a full day depending on how long you’d like to angle. 

Maritime Gloucester 

If you are seeking something a little different and learning more about the maritime world, Maritime Gloucester may be right for you. Maritime Gloucester’s mission is to “inspire students and visitors to value marine science, maritime heritage, and environmental stewardship through hands-on education and experiences.” 

Not only can families and individuals learn more about the marine species that inhabit the waters around Gloucester, but you can also find out more through educational programs and summer experiences. Some of these include seeing the Schooner Adventure , ​​a National Historic Landmark and the flagship vessel of Gloucester, or the Schooner Ardelle , the Flagship of Maritime Gloucester used for educational programming. The Schooner Ardelle is currently sailing daily and offering charters. Visit maritimeheritagecharters.com for more information. 

A quick stroll along the busy working harbor of Gloucester will show you that there are copious options for water activities and excursions! Beyond these highlights, there is so much to see and do! Check out Agawam Boat Charters , Beauport Cruiselines , Cape Ann Harbor Tours ,  Charlie’s Charters , Essex River Cruises , North Shore Adventures , and Tuna Hunter Fishing Charters .

Visit our tours page to see a full list of options for your next water adventure.  

Featured Business: 1606 Restaurant

Discover gloucester spotlight.

Located in the Beauport Hotel Gloucester, the 1606 Restaurant & Oyster Bar offers modern American cuisine prepared with local ingredients. Open year-round, guests and visitors can dine in elegance in the main dining room, sit back and unwind at the bar, or cozy up on the deck around the firepit with a delicious seasonal dish, appetizer, or signature cocktail while taking in the oceanfront views.

What's Happening On Cape Ann

Events Calendar: Things to Do in Gloucester

In The News: Gloucester Named One of America’s 15 Best Small Cities and Towns by CNN

In the News: 11 Adorable New England Towns You'll Want To Visit In 2023

VIEW OUR EVENTS CALENDAR

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Evening Sunset Cruise in Gloucester, MA

Home   ›   Evening Sunset Cruise in Gloucester, MA

3+ HOUR - Evening Sunset Cruise

Enjoy a Beautiful Sunset Cruise in Gloucester, MA

Get back to nature, relax, unwind, and take in the views as we cruise along Gloucester Harbor, and the Annisquam River in Gloucester, MA to watch the sun set. Few things are better than cruising along the calm waters of Gloucester Harbor and enjoying the scenery as it passes by. You’ll see beautiful waterfront homes, trees that go on for miles, boats anchored along the shore, birds headed to roost for the night, and a magnificent sunset to cap of the day.

This experience is a great way to unwind after a long day offshore catching your tuna or striped bass of a lifetime, or if you are visiting our amazing town, and simply want to get out on the water to fully experience what we get to every day here in Gloucester. A sunset cruise on Gloucester Harbor with your friends, family or both, will make memories that last a lifetime and will make you wish you could stay forever. Enjoy a drink, maybe a light snack, while you let worries go, and just enjoy the moment.

A summer evening spent on Tuna Tail Charter’s custom-built boat watching the sunset while cruising Gloucester Harbor and Annisquam River is the perfect way to top off your trip to Gloucester, MA. Let us know if you have any questions about our evening sunset cruise trips in MA, and we’ll be happy to answer them all.

• Price:  $479.00/Group
• # of Guests: Max 6
• Availability:  Seasonal
• Departure: 4:45 PM
• Tuna Tail Charters Deep Sea Fishing
• Pickup Location Cripple Cove Landing 79 East Main St Gloucester, MA, 01930
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2024 Sunset & Moonrise Cruises! Gloucester MA. Cruises include live instrumental music!

Only 7  half-price tickets remaining. grab yours.

 Our season is June  through September  on select  full Moon or near full Moon evenings .    For reservations, please u se the same name as used on the tickets purchased, so we can verify.

We cruise through the calm waters of the bay! From the open decks of the boat the talented musicians perform. The instruments are magical as they combine with the beauty of the sunset and the Moonrise! The astronomer will discuss some interesting facts about the Moon!

The large vessels are coast guard certified and feature outside decks for wide open views, two bathrooms, and a galley where you can purchase food and drinks..

Tickets are not date specific and are valid for any holder, so they are easy to give as a gift. Reservations are required. 

                  ​

The boat has soft drinks, alcohol, and snacks, purchased separately, cash only. Each cruise is about 2.5 hours.

The  cruise times change through the season as the sunset times change. The reservation calendar will include the times and details  for each cruise.

Ample free parking adjacent to the boat.

The cruises depart from 415 Main St., Gloucester, MA. For Tickets and information www.rosaevents.com or [email protected]

Come earlier to walk around at Main Street and check out the nice restaurants you will be enjoy the charming of a little town. We have been doing astronomy events for over 10 years and we work to provide a pleasant experience for you!

Frank- Astronomer- [email protected] Rosangela Costa Gamboa Bilingual interpreter - 860 786 20 89

Sunset Sail

Sunset music cruise, tuesday special, saturday mornings, schooner race day, meteor shower sail, moonlight sail.

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Public Sails

Sit back and relax or help the crew raise the sails as we head out through Gloucester’s working harbor and along her rocky coastline. See lighthouses, castles, scenic beaches, and magnificent waterfront homes. Breathe the clean salt air and feel the wind as it fills the schooner’s sails. Join us on a sail and feel your stress disappear.

Since most people enjoy the quiet of sailing, we do not have a narrator onboard. The crew is happy to answer questions you may have, so feel free to ask about anything you see that interests you.

We do have a liquor license and offer beer, wine, rum punch and soft drinks for sale at reasonable prices. Because of our license, carry-on liquor of any type is not allowed. We have a variety of salty crunchy junk food for sale as well.

Seniors (65+)

Kids (infant to 16)

Sailing Season

We usually begin our sailing season in early May, offering public sails on weekends throughout May and June. Starting in late June, we begin to offer daily public sails, sometimes as many as three or four trips a day, throughout July and August. After Labor Day, we again offer public sails on weekends through mid-October.

We offer private charters and group trips seven days a week throughout our entire season. Got an event coming up? Think you might like to charter the boat? Book now to be sure to get your date.

When Do We Sail?

We schedule our sails and take reservations not more than 2 weeks in advance. You can see the upcoming schedule in our Online Ticketing Section. You can either book online or give us a call at 978 281-6634 to make your reservations.

Specialty Sails & Deals

What better place to watch the sunset than on the water from the deck of a Schooner? We don’t think there is a better way to end the day!

We always have lots of fun on our Music Cruises and they always sell out, so remember to reserve your spots early!

Buy one ticket at the regular price and your second ticket is one-half off. (*You must pay in full for the higher priced ticket). Cannot be combined with any other discount. This Tuesday Special is available in July and August.

We offer a great deal for families: Children ages 16 and under sail for free. Each child must be accompanied by an adult.

Fireworks are scheduled on the third of July, and on the Saturday night of Schooner Race weekend.

Every year we race in the Gloucester Schooner Festival Race, held on Labor Day weekend. Upwards of twenty schooners participate every year.

Want an adventure? Join us to see the Perseid Meteor Shower every August.

We try to schedule a sail under the full moon in the summer whenever it’s possible.

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Enjoy Sunset Cruises, Lobster Cruises And More!

Beauport Cruiselines offers everything and more for your tour group. Sailing year round, we offer lobster bake cruises during high season, sunset dinner cruises, holiday cruises, and more! A highlight of your tour of Cape Ann, you will be immersed in the beautiful scenery, calm seas, classic New England scenery and views of historic Gloucester Harbor, America’s oldest port.

Lobster Cruises

A classic cruise, our Lobster Lunch sailings have a group rate of $94 per person, these cruises are most popular with Groups and Tours. Our Prime Rib Lunch Cruise is available at a group rate of $89 per person. Entertainment is even provided on every cruise! Come enjoy the open seas over a lovely summer lunch with us.

Special Features

Seating from 50 to 220 guests, Two luxurious dining floors, Third floor outdoor deck lounge, Year-round private cruises; public cruises in season, Fully enclosed and heated event decks for winter cruising, Handicap accessible, Two full bars available, Full boat rental available for private events, Free parking for guests and motor coaches, Complimentary meal for drivers and tour guides.

Planning your wedding? Join us at Cruiseport Gloucester for our Annual Wedding Showcase featuring the North Shore’s top vendors! Book your tickets here .

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Whale Watching Trips Daily to Stellwagen Bank National Marine Sanctuary

#2 On Tripadvisor’s List of Top Family-fun in the World – Dec 2023

#1 local attraction based on traveler reviews 2012-2023, guaranteed sightings & gauranteed lowest price, welcome aboard the privateer iv.

Privateer IV in Gloucester Harbor

Since 1983 , we have had the privilege of introducing thousands of passengers to the many species of whales and marine wildlife that visit and inhabit the waters just a few miles from our dock in historic Gloucester, Massachusetts. (approx. 50 min drive North from downtown Boston)

Our whale watching tours to Stellwagen Bank National Marine Sanctuary run daily from mid-April to mid-October and are designed to educate, inspire and provide a deeper understanding and appreciation of the fragile marine environment.

7 Seas Whale Watch is a local family business – Three generations of career captains have worked from this very dock for more than 7 decades . We have a love and respect for the marine environment and a passion for providing the best possible customer experience for you and your family.

Browse our website, reserve tickets online , call our sales office ( +1-978-283-1776 ), or use our contact form to ask a question or send a comment. We look forward to seeing you on the water.

What You Could See On Your Whale Watch

The whales and marine wildlife we observe are wild, untrained animals in their natural habitat. It is impossible to predict the quantity, species and behavior of the whales and wildlife that we observe – Each trip is unique. That having been said, the highly productive waters just off the Massachusetts coast often attract a great number and variety of whales and other marine wildlife which is why we have an over 99% sightings record.

Customer Reviews

“exhausted with excitement”.

– UNITED KINGDOM, VIA TRIP ADVISOR

“Well-Treated and Wowed”

… So well treated, wisely taught, and saw three different species of whales up close.” – HOUSTON TX, VIA TRIP ADVISOR

“5 Star Experience”

We’ve Visited 60 Countries And This Whale Watch Excursion Was The Most Memorable!”  – ALABAMA, VIA TRIP ADVISOR

1st Class Accommodations on New England’s Most Comfortable Whale Watching Boat

The Privateer IV

The PRIVATEER IV is the newest, most spacious, and cleanest whale watching boat in the Gloucester area. It is the only whale watch boat in Gloucester with on onboard GPS display for passengers to view throughout the trip. The PRIVATEER IV is fully US Coast Guard certified, inspected, and equipped with all latest navigation and safety equipment. There simply is no better boat in the Gloucester/Cape Ann area.

Latest Trip Reports

Our on-board naturalists post descriptive trip reports to social media regularly.

Some of the humpback whale behaviors you could see on your whale watch.

Underwater video of a humpback whale filmed from the Privateer IV. Including sound!!

Curious humpback whales checking out our passengers – Who is watching who?

7 Seas Whale Watch Gift Certificates are a great gift for all ages.

Humpback Fluke Gallery

Did you know that every Humpback whale has a unique fluke (tail) pattern? That is how we identify the whales that you see on our trips. Visit our gallery to identify the whales you see on your trip.

Editor’s Choice Best Of New England YANKEE MAGAZINE

All of the photographs and videos you see on our website were taken aboard one of our whale-watching trips. Most were taken by one of our onboard naturalists, but many of the most beautiful photographs on this site were taken by our good friend Oktay Kaya who sails with us quite often. If you would like to see more of the wonderful photographs that Oktay has taken while whale watching with us please visit his website at whalesandwhales.com .