What to do and see in Boston, Massachusetts (MA): The Best Boat Tours & Water Sports

April 25, 2022 Agatha Simes

Walk the Freedom Trail the first time you visit Boston and you'll quickly get a sense of this coastal city's revolutionary spirit and history. But make sure you also explore some of Boston's fine museums (try the Isabella Stewart Gardner, featuring masterpieces displayed in their collector's mansion) and old neighborhoods (like the North End, Boston's Little Italy). You can't claim to have experienced real Boston culture, though, until you've watched a Red Sox game from the bleachers.
Restaurants in Boston

1. Gondola di Venezia

Excellent
91%
Good
6%
Satisfactory
2%
Poor
1%
Terrible
0%
Overall Ratings

5.0 based on 127 reviews

Gondola di Venezia

Gondola Di Venezia also known as Boston Gondolas is a one of a kind WOW!! experience. With our 2 authentic gondolas that were built and shipped from Venice ,Italy , we offer PRIVATE tours on The Charles River at The Esplanade. Located only steps away from the heart of Boston , The Esplanade is the gateway to The Charles River, complete with Venetian style, canals, bridges and Lagoons. Indulge in The History , Mystery and Romance of this very private experience. Sit back and sip your champagne or wine ,take in the sights and sounds of Boston and Cambridge, incredible skyline views, live music with our accordion/violin player, a complimentary basket of cheese ,crackers and chocolates . Your gondolier will pamper you and provide you with glasses, ice ,ice buckets and warm blankets when necessary. There are 4 different tour package available, all are PRIVATE!! Voted "Boston's Best Place to POP The Question" A great way to celebrate any occasion in a very unique and unforgettable way! RESERVATIONS are required, on line or by phone 24 hours a day Open from late May through mid October , Fridays, Saturdays and Sundays from 3 PM to 11 PM. Special arrangements can be made for Monday through Thursday tours at additional cost. Come see what Boston's Best Kept Secret is all about!

2. Night Rider Private Charters of Boston

Excellent
100%
Good
0%
Satisfactory
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Overall Ratings

5.0 based on 124 reviews

Night Rider Private Charters of Boston

We specialize in all types of day and evening events including: weddings, celebrations, meetings, sightseeing tours and much more! Whether you choose to cruise on Night Rider or Timeless, expect to have an amazing event and experience the extravagant views of the Boston Harbor. The best part of all is that it's your private boat for the event; no sharing with other people!

3. Paddle Boston - Charles River Canoe & Kayak

Excellent
85%
Good
14%
Satisfactory
0%
Poor
0%
Terrible
1%
Overall Ratings

5.0 based on 100 reviews

Paddle Boston - Charles River Canoe & Kayak

Enjoy an outing on one of the most scenic sections of urban river in the country. An experience on the Charles River from our Boston location in Allston/Brighton is a wonderful respite from the surrounding city, with parkland on both shores and rowers plying the waters. Head downstream and you'll encounter local colleges (Harvard, M.I.T., and B.U.) and eventually the Esplanade (a great picnic spot!) and the unforgettable Boston skyline.This nine-mile stretch of river has no current, allowing painless round trips. However, renters can also enjoy one-way trips to or from our Cambridge location in Kendall Square — a unique way to see the city!

4. Boston Harbor Mini Speed Boats, Inc.

Excellent
88%
Good
6%
Satisfactory
3%
Poor
1%
Terrible
2%
Overall Ratings

5.0 based on 155 reviews

Boston Harbor Mini Speed Boats, Inc.

Captain your own mini speedboat as you navigate Boston Harbor while following our knowledgeable instructor. During your excursion you’ll pass many historical sites such as; the Tea Party Ship and Museum, USS Constitution, Nantucket Light Ship, JFK Library, Fort Independence and many more harbor sites. The adventure starts out nice and slow, this will give you time to get familiar with the boat and its operation. Once we pass the no wake zone, it’s time to pick up the speed and have some FUN as we navigate our way to JFK library, Fort Independence and pass many small islands. On the return, we’ll once again enter the no wake zone and view the Nantucket Light Ship, USS Constitution, Charlestown Navy Yard and Boston’s iconic Zakim Bridge. It’s the most unique way to see Boston…it’s PURE FUN! Bring your camera and cherish the memories. We have a limited number of boats for each adventure, don’t miss out…reserve your boat soon.

5. C.J. Victoria Fishing Charters

Excellent
100%
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Overall Ratings

5.0 based on 10 reviews

C.J. Victoria Fishing Charters

C.J. Victoria fishing charters is providing deep sea fishing trips departing Boston Massachusetts. Half day, 3/4 day and full day fishing trips with Captain Rob Savino.

6. Classic Sail Boston

Excellent
100%
Good
0%
Satisfactory
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Poor
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Overall Ratings

5.0 based on 40 reviews

Classic Sail Boston

We offer private sail charters and tours of Boston Harbor and Boston Outer Harbor Islands aboard a classic wooden Chesapeake Skipjack sailboat. 2,4, and 8 hour private charter cruises are available. Pick-up/Drop-off locations available throughout Boston Harbor: Charlestown, East Boston, Seaport District/Downtown Boston. BYOB or let us Cater.

7. Schooner Roseway

Excellent
90%
Good
10%
Satisfactory
0%
Poor
0%
Terrible
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Overall Ratings

5.0 based on 10 reviews

Schooner Roseway

worldoceanschool.org Roseway is a National Historic Landmark ship, the only one of its kind in Boston. She is the primary platform for the World Ocean School’s programs that motivate and inspire underserved kids throughout the city. So come aboard a genuine piece of maritime history with your family, friends, clients and colleagues and have fun while supporting our fundraising efforts to change kids’ lives one sail at a time. The cost is a donation. Half is tax-deductible. Roseway is conveniently docked in the Seaport district May through September.

8. Indiscretion Yacht Charters

Excellent
94%
Good
0%
Satisfactory
6%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 17 reviews

Indiscretion Yacht Charters

We offer Charters aboard Indiscretion and also offer a food and beverage package which is quite exceptional! Fishing, Family, Corporate, and Fun Charters! Cruise away from Downtown Boston on your way to Hours of adventure on Historic Boston Harbor. Relax aboard a luxurious Classic 42' Post Sportfish with plenty of room for all, enjoy seeing the many historic sights and rich History of Boston Harbor and the Islands.snorkeling in crystal clear Harbor waters brimming with marine life, and do some sightseeing with so much to see in an always changing seascape! Meet up with your skipper for the day at the New England Aquarium dock and climb aboard a 42' Post Sportfish, setting your sights on discovery in the bountiful sunshine. Watch the crew toss off the mooring lines, settle into a comfy seat for the voyage ahead, and chat with your Skipper or First Mate about what you might see during your History-packed cruise.

9. Classic Harbor Line Boston MA Day Tours

Excellent
85%
Good
9%
Satisfactory
3%
Poor
2%
Terrible
1%
Overall Ratings

5.0 based on 940 reviews

Classic Harbor Line Boston MA Day Tours

Dedicated to providing the most luxurious and hospitable sailing experience in Boston, we here at Classic Harbor Line are looking forward to the privilege of escorting you on a breathtaking excursion aboard the most elegant sailing vessel in Boston Harbor: Schooner Adirondack III and yacht Northern Lights. Boston’s rich maritime history is best viewed from the water, so why not do it in style?

10. Boston Elite

Excellent
100%
Good
0%
Satisfactory
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Poor
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Terrible
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Overall Ratings

5.0 based on 5 reviews

Boston Elite

With sensational skyline views and completely customizable options, the Boston Elite is Boston’s most innovative dining and entertainment experience. Work with our crew to create a totally unique event, and enjoy all the prestige of cruising Boston Harbor on your own private yacht.

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