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Top Experiences in Castle Island

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City Cruises

Boston Premier Dinner Cruise on Odyssey

USD 157.19

Cruising year-round from Rowes Wharf, the sleek and modern Odyssey is the perfect setting for celebrating with friends, connecting with colleagues, or a romantic evening for two. Enjoy upscale dining and entertainment on Boston Harbor, and watch as the city lights glisten from our climate-controlled decks.
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Classic Harbor Line - Boston

Boston Harbor Sunset Sail Tour

USD 72.53

Experience a beautiful 2-hour Boston Harbor sunset sail on the water and see some of the city's waterfront landmarks as the sun dips below the horizon. You will be aboard the most elegant sailing yacht in town, Adirondack III, a classically styled, 80-foot pilot schooner. Adirondack III is the fastest and most elegant schooner in Boston Harbor. She offers a smooth and gentle sailing experience to her passengers as well as top-notch customer service by her captain and crew. Enjoy a comfortable and relaxing ride for you and your loved ones. Within minutes of leaving the dock, you'll forget the distractions of life on land, as you experience the ambiance of a sunset sailing cruise aboard a stellar vessel.
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Trinacria Fishing and Cruising - Boston

Fishing or Cruising Boston Harbor on Private Yacht Trinacria

USD 1295

Join Captain Riccardo aboard the Trinacria for a Private tour of Boston Harbor & The Harbor Islands. Choices include Sightseeing, Fishing, Lobstering or just Cruising.

This unique tour is one of the very few available that you & your guests have the boat to yourselves. Most Boston tours are shared. We also allow you to bring your own Food & Beverages on-board, making your trip ultra personalized. We are flexible on pick up locations & are happy to entertain special requests. Book with us & we will do everything we can to exceed your expectations.

Tours can last up to 5 Hours depending on activities chosen. Inner Harbor Tours take 2-3 Hours, Fishing adds time. Plan on being on-board a minimum of 4 Hours for Fishing/Lobstering or Lighthouse tours.

We also can preform an Ash Scattering in a burial at sea ceremony for loved ones remains. We attend to filing all required notifications with the US Government free of charge

As a reminder Gratuities are not included in your fare.
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Massachusetts Bay Lines

Boston Harbor Moonlight Cruise

USD 30.8

SEA the skyline twinkle at night as you cruise around the harbor.
Whether you’re ending your evening onboard or starting your night out, come Sea Boston with Mass Bay Lines.

Sit back, relax and enjoy the city views from the water. The sea breeze and smooth cruise will relax you after a busy day about town.
Just add water!
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City Cruises

Boston Father's Day Lunch Cruise

USD 135.43

This Father’s Day, create family memories that will be treasured forever with a Father's Day Signature Lunch Cruise on the Boston Harbor. Spend your day on the water with a chef-prepared lunch buffet, classic cocktails, and incredible views of Boston. Enjoy dining and music from our climate-controlled interior, or soak in the picturesque backdrop from our open-air, outdoor decks. Our lunch cruise is perfect for all ages, and is the perfect way to celebrate the dad in your life!
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Boston Hidden Gems

Private Tour of Boston for Families & Kids

USD 185

Spend a great day in Boston learning about history and exploring all the top attractions! The tour is designed to be fun for the whole family - we have quizzes, we have scavenger hunts, we have prizes, and we have interactive stops so kids can work off some energy!
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Classic Harbor Line - Boston

Boston Harbor Brunch Cruise

USD 93.87

Enjoy a delicious 2-hour brunch cruise and take in historic sights along the water including Castle and Deer Island, Spectacle Island, Long Island, Lovells Island, Georges Island, Independence Fort, Bunker Hill Monument, USS Cassin Young, USS Constitution, Old North Church, Boston’s Seaport District, and Boston’s incredible skyline.

Brunch features a diverse buffet menu to suit all palettes including bakery, fruit, yogurt, eggs, bacon, seasonal salad and more!

Please contact us in advance to inform us of any food allergies. Please note we cannot accommodate all food allergies, but we will do our best if given advance notice.
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City Cruises

Boston Premier Brunch Cruise on Odyssey

USD 108.23

Our afternoon brunch cruise is ideal for group celebrations, or just capping off an incredible weekend with someone special. Enjoy a delicious menu, stocked with breakfast and lunch favorites, as you take in panoramic views of historic Boston Harbor.
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Classic Harbor Line - Boston

Two-Hour Brunch Cruise Past Fall Foliage, Boston Harbor

USD 74.67

Enjoy a fresh, gourmet brunch on this scenic Fall Foliage cruise around Boston Harbor and the Harbor Islands. Set sail aboard the Northern Lights at Rowes Wharf and settle in for a buffet filled with pastries, fruit, yogurt, bagels, potatoes, breakfast meats, eggs, and more. View popular Boston highlights such as Bunker Hill Monument, the USS Constitution, Old North Church, and Castle Island. This brunch cruise offers a great overview of Boston and a lovely morning on the water.
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Classic Harbor Line - Boston

New England Fall Foliage Lunch Cruise in Boston Harbor

USD 60.8

Join the captain and crew of Yacht Northern Lights for a relaxing Boston Harbor cruise featuring the colorful trees of Fall. New England has been known for the vibrant foliage that people are drawn to every year. A gourmet buffet lunch consisting of a selection of entrees and sides is included with your ticket purchase and can vary but may typically include seasonal meat dishes, pasta, salad, and dessert. Beverages are available for purchase by credit card from the bar. This cruise is excellent for families, friends exploring the town, and folks looking for a relaxing adventure. Take in the sights from a heated main cabin, or enjoy the views from the open top-deck of the boat.