annapolis harbor cruises

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Watermark immerses you in the history, culture, and fun of the Chesapeake Bay area more completely than any other tour or charter company.

Cruises and Tours in Annapolis & Baltimore

Unforgettable journeys start with Watermark, and we’ve been doing it for more than 50 years.

Experience the best of Annapolis and Baltimore with cruises, walking tours, private yacht charters, and field trips.

This Week's Cruises & Tours

• Annapolis Harbor & USNA Cruise — Available Daily
• Baltimore Sightseeing Cruise — Available Tues-Sun
• Day on the Bay to St. Michaels — Saturdays
• Colonial Annapolis Walking Tour (+USNA Option) – Thurs-Mon
• Maryland State House Tour — Available Thurs-Mon
• Spirits & Spirits: Ghost Tour & Cruise 6/6
• Weird, Wacky, & Unusual History of Annapolis 6/8
• Annapolis Sunset Cruise with Live Music 6/8
• Baltimore Sunset Cruise 6/8
• Historic Ghost Tour — Fridays & Saturdays

Embark on Your Own Watermark Journey

Public Cruises

• Enjoy being out on the water with a variety of cruises from 40 minutes to a full day.

Private Yacht Charters & Weddings

• Take your next event to the water; the perfect venue for any occasion.

Walking Tours & Guided Experiences

• Discover local history with your period-attired tour guide in Historic Annapolis.

Field Trips & Youth Programs

• Field trips that meet your curriculum, grade level, and programming needs.

Group Experiences

• Explore a variety of affordable cruises and tours for your group event.

Annapolis Water Taxi

• Climb aboard the Annapolis Water Taxi — the best way to get around Annapolis!

Why Watermark?

Watermark creates unforgettable journeys for tens of thousands of guests in Annapolis and Baltimore every year.

• A complete Annapolis and Baltimore experience
• Informative and fun, knowledgeable and helpful
• The most refreshing way to see the sights
• Unique educational field trips on land and water
• The most affordable way to get out on the water
• Meticulously maintained classic and elegant yachts
• Customized private yacht charters
• History comes alive in our museum without walls
• Family fun activities for all ages
• Highly trained, certified guides, captains, and crews
• Over 50 years of sharing the best of the Chesapeake

Follow Watermark on Instagram

@ watermarkjourneys . Jun 6

Bring your adventure buddy along for the ride 🐾 Paw-ssengers are welcome on... 🐶 Baltimore Sightseeing Cruise 🐶 Annapolis Harbor & USNA Cruise 🐶 Thomas Point Lighthouse Cruise 🐶 Chesapeake Bay Bridge Cruise 🐶 Scenic Severn River Cruise Find tix here 👉 watermarkjourney.com/public-cruises-water-taxi/ (Pups cruise free 😉) ...

@ watermarkjourneys . Jun 3

We are so excited to announce that Watermark was voted best Rehearsal Dinner/Welcome Party Venue for the @whatsupmags Best of Weddings 2024 awards 🏆 Thank you for this recognition, and here`s to another year of unforgettable journeys 🛥️💍✨ 📸 Tagged in photos ...

@ watermarkjourneys . May 31

Weekend mood 🤣 Yesterday’s DJ Pizza Party was a hit and the perfect end-of-school-year celebration 🍕🎶 ...

@ watermarkjourneys . May 30

Yesterday, we had the opportunity to be a part of a training exercise with the Bowie Police Bloodhound Tracking Unit aboard Harbor Queen 👮🐾 Such a cool experience! ...

@ watermarkjourneys . May 28

Our first Spirits & Spirits of the season is this Thursday night! 👻 Your Ghost Guide will take you for a walking tour through the Annapolis Historic District and will share spooky stories along the way. 🏴‍☠️ Then you will board Miss Anne to continue your journey through haunted waterways and hear nautical myths and pirate tales. 🍻 Add extra "spirit" to your night with the beverages available for purchase during the cruise portion of the tour. Get your tickets! 🎟️ watermarkjourney.com/events/spirits-spirits/ 🎟️ 📸 @hickokphotography ...

@ watermarkjourneys . May 27

On this #MemorialDay, we`d like to take a moment to remember and thank those that made the ultimate sacrifice 🇺🇸❤️ #ThankYouForYourService ...

@ watermarkjourneys . May 24

Last night, we had the privilege of hosting the @visitbmore Spring Connect Event aboard Raven, and it was a blast 🚢🥂🙌 The perfect weather was the cherry on top of a wonderful evening of connecting with our industry partners 😁 Thank you to everyone that joined us! ...

Pop-up Blues Cruise! Join us aboard Harbor Queen tonight at 4pm for a 40-minute cruise with the @annapolisbluesfc team 🦀💙⚽️ 🎟️ Tickets can be purchased at our ticket stand at the end of City Dock. Look for the red umbrella! 🎟️ Or visit watermarkjourney.com/events/annapolis-harbor-usna-cruise/ ...

Watermark Staff over the last 50 Years

Watermark Team Since 1972

A family-owned business since 1972. Learn more about the growth and progression of Watermark.

Our Watermark Team Today

Interested in joining the Watermark family? Get to know our team here and view our open positions.

Guest Journeys

Creating unforgettable journeys for over 50 years.

Watermark Cruises and Tours

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Watermark Cruises and Tours - All You Need to Know BEFORE You Go (2024)

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A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

Corporate Events

Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

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• Destinations

The Sailing Capital of the U.S. Is a Perfect East Coast Getaway — With Historic Charm, Tasty Seafood, and Scenic Harbor Views

Here’s what you need to know about visiting Annapolis, one of the East Coast’s best waterfront destinations.

Best Things to Do in Annapolis

Annapolis hotels.

• Where to Eat and Drink in Annapolis

Best Time to Visit Annapolis

Getting there.

The famous “crab cakes and football” line from “Wedding Crashers” may have firmly planted itself in the cultural zeitgeist 18 years ago, but there’s a lot more to Maryland than seafood and sports (although those are pretty important, too). Given its East Coast location and proximity to the Chesapeake Bay, many of Maryland’s towns and cities have waterfront access — hence, the association with the fishing and crabbing industries as well as sailing and other maritime activities.

As one of the original 13 colonies, Maryland was also influential in the shaping of the United States; in 1791, the state transferred ownership of a portion of its land to the federal government to form the country’s new capital, Washington, D.C.

Sean Pavone/Getty Images

There’s perhaps no city that combines everything Maryland is known for — food, culture, and historical significance — quite like Annapolis. Home to the U.S. Naval Academy, a walkable downtown, and a robust sailing community, the state’s capital is perfect for a long weekend away or an extended visit to the Chesapeake region. 

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With a nickname like the "Sailing Capital of the U.S.,” it should come as no surprise that Annapolis plays host to various water-adjacent activities. The warmer months are particularly buzzy around Annapolis Harbor and City Dock, the heart of the historic district. 

If you’re visiting for the first time, a guided tour of the city is your best bet to cover as much ground as possible. In true Annapolis fashion, there are plenty of options to see the area by boat. Visitors who come aboard the Harbor Queen will explore Annapolis Harbor and cruise by the banks of the Naval Academy while learning about the city’s history and geography (tours are available from April through October). The Annapolis Maritime Museum & Park also offers Skipjack history tours that provide additional information about the Chesapeake Bay and its ecology. Travelers who don’t quite have their sea legs can opt for a 60-minute trolley tour around the charming streets, marinas, and high points of the city. Access to the U.S. Naval Academy is limited, but it’s certainly a must-see spot when in Annapolis. Both public and private tours can be arranged through the Armel-Leftwich Visitor Center .

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If you prefer to discover a new place on your own, be sure to walk down brick-paved Main Street and pop into its shops, art galleries, restaurants, and bars. One block away, you'll find State Circle and the Maryland State House , the only state house to have served as the nation's capital and the oldest state capital in continuous legislative use. Further out in the Annapolis Design District — about two miles from State Circle — numerous murals decorate the city. From the 7,000-square-foot Breonna Taylor mural (located at 14 Dorsey Avenue) to the Carlester “Walking Man” Smith mural (found at 1100 West Street) that honors a local who spent 40-plus years cleaning up the trash from Annapolis streets, these murals can be appreciated via a self-guided walking tour . 

Like the city itself, the best hotels in Annapolis have touches of nautical whimsy and nod to the city’s history. Graduate Annapolis opened in the arts district in 2019 with decor “inspired by Chesapeake blue crabs, Academy colors, and old-school madras plaid.” Like other Graduate hotels, the property proudly celebrates the culture of local colleges — the U.S. Naval Academy and St. John's College. As its name suggests, Annapolis Waterfront Hotel, Autograph Collection , is conveniently located by the harbor, and it’s just a short walk to the Naval Academy. Historic Inns of Annapolis is made up of three landmark buildings in the downtown area: Maryland Inn, Robert Johnson House, and Governor Calvert House. Each house pairs 18th-century details and quaint ambiance with modern amenities (including free Wi-Fi). 

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Where to Eat and Drink in Annapolis

The culinary scene in Annapolis goes above and beyond seafood — but if you’re visiting Maryland in the summer months, oysters and blue crab should make it into your diet at some point during your trip. For a taste of a traditional Maryland crab house, there’s Cantler’s , Mike’s Crab House , or The Choptank . Chick & Ruth’s has been a city staple since the 1960s, and Iron Rooster has a popular all-day breakfast menu. For a post-dinner sweet treat, head to Annapolis Ice Cream Company , where you can indulge in homemade flavors like Funfetti cheesecake, blueberry strudel, and birthday cake. 

If you want a heaping dose of Annapolis history, add Reynolds Tavern and 1747 Pub to your itinerary. You’ll take a step back in time when you enter the tavern for traditional English afternoon tea or the cellar pub (watch out for the low ceilings) for a refreshing Pub Punch or lager. The beer garden behind the tavern also welcomes guests during the spring, summer, and early fall. For something a bit more modern, there’s Preserve for cocktails, Fox’s Den for craft beer and pizza, or Galway Bay Irish Restaurant and Pub , a lively pub on Maryland Avenue. 

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Like most other parts of Maryland, Annapolis is a true four-season destination. The warmer months, however, are ideal for adventuring out on the water. Spring is typically the best time of the year to go to Annapolis, as summer tends to become busier when sailing season kicks into high gear. 

Annapolis can easily be explored on foot, but you’ll need a car if you want to venture further into the Chesapeake region. Washington, D.C. and Baltimore are both about an hour’s drive away, depending on traffic, so flying into any of the area’s three international airports — Baltimore-Washington International Thurgood Marshall Airport (BWI), Washington Dulles International Airport (IAD), and Ronald Reagan Washington National Airport (DCA) — puts you within driving distance of Maryland’s capital.

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2024 Sailing Season is coming! See you April 13, 2024!

Tickets On Sale Now

Public sailing.

Tickets go on sale 6 days prior to the date you want to sail. See “Group Sailing” or “Private Cruise” for booking further in advance.

Special Events

Our specialty sailing cruises are on sale now for this season. Embark on an unforgettable tour with a carefully crafted menu of food & drink.

Groups up to 16 guests

Groups can reserve space more than six days in advance so you can start planning your event now and know you have that date reserved.

Private Cruise

The captains and crew of the Schooner Woodwind look forward to welcoming your guests aboard for your exclusive private and future event!

General Information to Know Before You Buy…

Once tickets are purchased, there are no refunds or exchanges..

We sail rain or shine unless the captain cancels the cruise due to unsafe conditions. We offer complimentary rain ponchos in case of rain.

Please Remember:

• Only soft soled shoes are allowed aboard.
• All departures are from Pusser’s Caribbean Grille at the Annapolis Waterfront Hotel across from the City Dock (unless otherwise noted) . Rates and schedule are subject to change without notice. Our schedule may vary due to weather, special events and group charters.
• Tickets go on sale six days prior to the date you want to sail. Advanced ticket sales are available if you have a group of up to 16 people as a “Group Sail” .  Please call our business office at 410-263-1981.
• Up-to-date schedule information is available by clicking here or calling (410)263-7837.

Questions???

Please visit our frequently asked questions page.

National Outlet Day Shopping Day Sweepstakes Returns!

For the second year in a row,  Arundel Mills  is teaming up with  Live! Casino & Hotel  and  Visit Annapolis & Anne Arundel County  for the ultimate National Outlet Shopping Day Giveaway! Click the link to enter on our website. Contest closes at 11 pm EST on Friday, June 7, 2024.

Award Winning Collaboration

Black history 365, best new festival, annapolis baygrass festival.

There is a lot to see and do in our beautiful Chesapeake Bay region, the only question is, what are you looking to experience?

Where Adventure

Adventure comes in many forms... From the historic charm of Annapolis along the shores of the Chesapeake Bay to the entertainment district of BWI and Arundel Mills, discover all that Annapolis and Anne Arundel County have to offer. Plan your adventure today!

Paint Annapolis: Art on the Avenue

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Join us to celebrate the vibrant arts community in Anne Arundel County with various events, including arts festivals, exhibitions, performances, workshops, and more.

Annapolis Juneteenth Parade & Festival

Come out and join us for our FREE 2nd annual parade and festival on Saturday, June 17, 2023! There will be TWO main stages this year, featuring headliners Therron Fowler & Company, Lil Syxx, Vivian Greene, Rakim, Beverly Crawford, and a host...

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This handy resource includes a complete listing of accommodations, restaurants, shopping destinations, and more in Annapolis and Anne Arundel County!

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Here are the ships you can expect to see at Harborfest 2024

T he 48th annual Norfolk Harborfest kicks off Friday at Town Point Park along the Downtown Norfolk waterfront, the city's annual celebration of the maritime and Naval community that makes Hampton Roads so special.

Part of the festival is the Parade of Sail, where a fleet of tall ships, character vessels, sleek power cruisers, sailing craft, antique and classic wooden boats, military vessels, tugs, and more will make its way down the Elizabeth River toward Town Point Park.

RELATED: What to know about Harborfest 2024 in Norfolk

You'll be able to catch the parade on-air on 13News Now or via live stream on 13News Now+ on Friday starting at noon.

Also, ships will be open for public tours from around 3 to 6 p.m. Friday, and from noon to 6 p.m. Saturday and Sunday. The tours will be free and open to the public. 

RELATED: Here are the Norfolk roads closing for Harborfest 2024

Here's a look at this year's lineup:

American Rover

Owned and operated by Rover Marine, the American Rover is a 135’ 3-masted topsail schooner.  It sails daily from The Waterside Marina in Downtown Norfolk, and for Harborfest it will be docked on the wave screen behind the Waterside Marina this weekend for its harbor cruises and public tours.

19th-century cargo schooners inspired her design, yet she possesses the modern amenities that assure a comfortable cruise: spacious topside decks with seating, climate-controlled below-deck cocktail lounges, clean restrooms, and a ship’s store offering souvenirs, snacks, sandwiches, and beverages.

Kalmar Nyckel

The tall ship Kalmar Nyckel serves as a floating classroom and an inspirational platform for educational outreach and is run by the Kalmar Nyckel Foundation offering sea- and land-based learning and recreational experiences. 

The Kalmar Nyckel Foundation is a non-profit educational organization with a mission of “preserving and promoting the cultural and maritime heritage of Delaware and the Delaware Valley for the education and enrichment of all.”  The Foundation is a volunteer-based organization that built, owns, and operates the Tall Ship of Delaware, Kalmar Nyckel.

The original Kalmar Nyckel was one of America’s pioneering colonial ships, a Mayflower of the Delaware Valley, yet her remarkable story has never been widely told. 

The namesake of Kalmar Nyckel served as Governor Peter Minuit’s flagship for the 1638 expedition that founded the colony of New Sweden, establishing the first permanent European settlement in the Delaware Valley, Fort Christina, in present-day Wilmington, Delaware.  She would make a total of four roundtrip crossings of the Atlantic, more than any other documented ship of the American colonial era.

The historical ship was a new type of gun-armed merchant vessel called a Dutch Pinnace. The Dutch built her in Amsterdam in about the year 1625 and later purchased it in 1629 by a Swedish consortium to serve as an auxiliary warship for the Swedish navy, which she did until her decommissioning in 1651 — except for the years from 1637 to 1644 when she sailed the Atlantic for the New Sweden Company.  

An exceptional ship with a long and remarkable career, she was sold to a private merchant after being decommissioned from the Navy.  No completely definitive records have been uncovered as of yet, but Kalmar Nyckel was probably resold to the Dutch navy as an escort vessel and sunk in the North Sea while fighting for the Dutch in a war against the English in 1652.

Impossible Dream

The Impossible Dream is a catamaran that is uniquely designed as a universally accessible vessel. The Impossible Dream works outside of just a physical vessel as an organization dedicated to the inclusion of marginalized populations into the maritime community, mainly those who are disabled. They offer virtual explorations, experiences, and education for those who are unable to physically visit the Impossible Dream.

This all-carbon-fiber, fast cruising yacht is the world’s only catamaran built from the ground up to be fully universally accessible.

This vessel can be independently and easily handled by wheelchair users. All sail handling, docking, anchoring and maintenance can be performed by wheelchair users.

Designer Nic Bailey’s vision came to fruition in 2002 with an LOA of 58 feet and a 27-foot beam. It has 4 cabins. All areas can be accessed by wheelchair including below deck by using an internal lift in each hull. 

A.J. Meerwald

The A.J. Meerwald is a restored oyster dredging schooner, originally launched almost 100 years ago! She was one of hundreds of schooners built along South Jersey’s Bayshore before the Great Depression and the decline of the shipbuilding industry. Today A.J. Meerwald functions as a traveling classroom and vehicle to enjoy waterways. 

After a 3-year project in 1995, she was fully restored and added to the National Register of Historic Places, leading to Governor Whitman designating her as New Jersey’s official tall ship in 1998.

The A.J. Meerwald is a wooden construction with a white oak hull and an 85-foot cedar deck. It displays over 3,500 sq feet (about the area of a tennis court) of sails and is supported by a John Deer engine with 230 HP.

Schooner Virginia

The Schooner Virginia is a reproduction of the last all-sail vessel built for the Virginia Pilot Association. The original ship sailed for the pilots from 1917-1926, training apprentice pilots in seamanship and navigation, and even served as a pilot vessel during World War I. 

Today’s wooden craft was commissioned by the Virginia Maritime Heritage Foundation in 2005 and was sold to the Nauticus Foundation in 2016. Virginia is 126 feet long, has a beam of 23 feet, and a draft of 12 feet. She carries over 6,500 square feet of canvas and is a gaff topsail schooner. 

The Schooner Virginia is docked at Nauticus and serves Nauticus programming as a platform for sail training and teaching maritime sciences, history, teamwork, and leadership to the youth of Hampton Roads. Youth programs feature dockside education, day trips, and overnight adventures.  

A dedicated group of volunteer and professional crew members maintain and operate the ship throughout the year. New volunteers are welcome. No experience is necessary as they provide training and instruction in tall ship sailing and vessel maintenance.

The Schooner Virginia will be dockside at Otter Berth starting at 3 p.m. Friday and throughout the festival, available for public visitation.  

USACE Ewell

The US Army Corp – Ewell was commissioned in January of 2018 and is homeported at the Norfolk District of the US Army Corp of Engineers. This survey vessel is a 61-foot foil-assisted catamaran outfitted with an aluminum hull, stainless steel hydrofoil, and the latest multibeam SONAR technology. The Ewell proudly displays a crane capable of lifting 4,500 pounds.

The ship serves both as a survey vessel and removes debris from Norfolk Waterways. With a top-end speed of more than 34 knots, the 1,970 horsepower twin-engine, jet-propelled Ewell is the fastest vessel in the district’s fleet.

Norfolk Rebel

The Tugatine “Norfolk Rebel” is a sail-assisted workboat designed for towing and salvage.

Built by Howoy Bailey and designed by Merritt Walter, her unique design was commissioned to use wind power to help save fuel.  This idea was created during the 1920s during the gas shortage. She sometimes works as an escort vessel for tall ships and participates in Opsail 2000 festivities.

In 1984 she circumnavigated Virginia and was featured at the New Orleans World’s Fair.

Her first Captain, Lane Briggs was one of the Founding Fathers of Harborfest, who sadly passed away in 2005. Capt. Briggs worked tirelessly to promote sail training and promote the “Harbor of Hospitality.” Today his sons Steve and Jesse are carrying on with this tradition.

Rainbow Chaser

Rainbow Chaser is a 40’ Chesapeake Bay Deadrise that has been coming to Harborfest for more than 25 years.  She is powered by a Volvo Penta diesel engine and is the fastest wooden deadrise on the Chesapeake Bay, winning workboat racing events since 2006.  Her captain is Shannon Gay.

Spirit of Norfolk (Mount Vernon)

Since 1978, the Spirit has delivered a vibrant and unique combination of dining, dancing, entertainment, and breathtaking views. With a capacity of 400, the Spirit of Norfolk is perfect for cruising year-round from The Waterside in Downtown Norfolk, City Cruises Norfolk offers Lunch, Brunch, Dinner, Cocktail, Moonlight Cruises, and much more!

Victory Rover

Victory Rover is a 95-foot vessel that once served as a crew and supply boat for offshore oil rigs in the Gulf of Mexico.  In 2001, Victory Rover was converted into a sightseeing passenger boat by Rover Marine Co.  She has 3 Detroit V1271 diesel engines, triple screw, with 1,350 HP, which allows her to cruise at 20mph.  

US Coast Guard Cutter Sailfish

The USCG Cutter Sailfish is an 87-foot-long patrol vessel homeported in Little Creek. It is a Coastal Patrol Boat that is manned by highly skilled sailors, responding to emergencies along the coast.

You may ask why are Coast Guard ships called cutters? Government agencies use the term “Cutter” for vessels employed in patrolling their territorial waters and other enforcement activities. This terminology is derived from the sailing cutters which had this sort of role from the 18th century to the end of the 19th century. 

USS Gonzalez (DDG 66)

Rounding out this impressive example of maritime history is the USS Gonzalez (DDG 66). The U.S. Navy destroyer proudly serves “Beyond the Call” in the ship’s namesake of SGT Alfredo Gonzalez, who served from 1965 and was mortally wounded in 1968 while fighting in the Vietnam War. 

Within his 3 years of service, he was awarded the Medal of Honor, the Purple Heart, the Presidential Unit Citation, the National Defense Service Medal, the Vietnam Service Medal with two Bronze Stars, the Vietnamese Cross of Gallantry with star, the Vietnamese Cross of Gallantry with palm, the Military Merit Medal and the Republic of Vietnam Campaign Medal for his bravery, leadership and heroism. 

Today the USS Gonzalez goes “Beyond the Call” in honor of its namesake. This Arleigh Burke Class Destroy spans over 500 feet in length and 66 feet in breadth. 

It is capable of traveling more than 30 knots and is equipped with state-of-the-art weaponry such as an AEGIS Weapons System, Two MK 41 Vertical Launching Systems, 14 triple torpedo tubes, and Mk 36 MOD 12 Decoy launching system. It also utilizes a high-tech surface USW Combat System Suit, hull-mounted surface search radar, Sonobuoy Sensor Processing System, and Electronic Warfare system.

As of today, Commander Kartina Stegner serves as commanding officer with Commander Ashley Carline as Executive Officer and Master Chief Terry Vines by their side.