Top Boston Tours, Sightseeing &amp; Cruises

Boston Hop-On Hop-Off Trolley Tour with 13 Stops

(5,788)

from $51

Enjoy unparalleled views of the Boston Harbor from the water during this 90-minute sightseeing cruise. Set sail aboard a classic tall-ship schooner. Enjoy plenty of time to ask the captain and crew about local landmarks and Boston’s history. You'll also have plenty of time to relax. Soft drinks and alcoholic beverages are available to purchase, including several beers brewed right in South Boston.

Classic Tall Ship Cruise in Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(710)

from $40

Boston: Freedom Trail History Small Group Walking Tour

2 hours 30 minutesFree Cancellation

4.9

(7,285)

from $39

City Cruises Boston Historic Sightseeing Harbor Cruise

See some of the top attractions in Boston from the waterfront on this narrated sightseeing cruise. Explore the world-famous Boston Harbor and see the city’s historic sites while listening to live commentary on board, from tales of the Revolutionary War to local legends. While you cruise, enjoy views of the city skyline as well as the Boston Harbor Islands, USS Constitution (“Old Ironsides”), and the Bunker Hill Monument.

City Cruises Boston Historic Sightseeing Harbor Cruise

1 hourFree Cancellation

(1,459)

from $46

Boston Harbor Sightseeing Cruise

1 hour 30 minutesFree Cancellation

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

(236)

from $46

1 hour 30 minutesFree Cancellation

Explore the best of Boston on this hop-on hop-off trolley tour. Board at one of the stops, then hop off wherever you like, explore independently, and get back onto the trolley when you’re ready. Alternatively, ride the 2-hour loop in one go, listening to the informative commentary. Tickets are valid for one or two days, and while admission tickets aren’t included, enjoy discounts to some top Boston attractions.

(435)

from $56

1 or 2 Day HOP-ON & HOP-OFF Narrated Trolley Tour of Boston

1 or 2 Day HOP-ON & HOP-OFF Narrated Trolley Tour of Boston

1 hour 20 minutesFree Cancellation

4.4

(2,932)

from $48

Sightseeing Day Sail around Boston Harbor

1 hour 30 minutes to 2 hoursFree Cancellation

(583)

from $67

Sunset Sailing Cruise on a Tall Ship in Boston Harbor

The Full Revolutionary Story Epic Small-Group Boston Walking Tour

4.6

(448)

from $71

3 hoursFree Cancellation

5.0

(2,662)

from $59

Experience the best of New England’s marine wildlife on this guided whale-watching cruise around the Stellwagen Bank National Marine Sanctuary. Hop on a high-speed boat in Boston that gets to and from the whales in the least amount of time possible. Look out for humpback and fin whales, plus Atlantic white-sided dolphins, with the help of a naturalist guide. The on-board galley offers food and beverages for purchase during the trip.

City Cruises Boston Whale Watching Cruise by High-Speed Boat

City Cruises Boston Whale Watching Cruise by High-Speed Boat

3 hours 30 minutesFree Cancellation

Boston Ghosts and Gravestones Trolley Tour

(3,237)

from $86

4.4

(2,541)

from $47

See Boston from a whole new angle aboard a Boston Harbor evening cruise. Watch the sunset from the water, and glide out to the Old North Church and Historic Site, the Charlestown Navy Yard, the USS Cassin Young, and more. As a bonus, listen to the cannon fire of the USS Constitution, which marks the sunset each night, and sip a cocktail (own expense) from the onboard bar as you relax and enjoy the views.

Boston Harbor Sunset Cruise

Experience Boston’s history on a non-stop trolley tour that traces the city’s role in the American Revolution and early United States history. This guided overview provides context on key events, ideas, and figures that shaped the nation, while helping you understand how Boston’s neighborhoods and landmarks fit together. The format offers a time-efficient city introduction without the physical demands of a long walking tour.

4.6

(705)

from $54

80-Minutes NON-STOP Trolley of Historic Boston and Freedom Trail

80-Minutes NON-STOP Trolley of Historic Boston and Freedom Trail

1 hour 20 minutesFree Cancellation

Enjoy one of the simplest ways to discover Martha's Vineyard, and leave all the planning and logistics to someone else, on this hassle-free day trip from Boston. Following pickup directly from your centrally located hotel, take a short ferry ride to Martha's Vineyard. Upon arrival, enjoy free time to explore—or upgrade to add on an island tour that visits its highlights. Complimentary snacks, bottled water, and guidebooks are provided during the drive.

(348)

from $38

Boston to Martha's Vineyard Day Trip with Optional Island Tour

12 hoursFree Cancellation

(3,228)

from $129

Boston Harbor Narrated Sunset Cruise

1 hour 30 minutesFree Cancellation

4.2

(560)

from $29

Boston Seafood Experience: A behind the scenes Seaport Tour

Boston Seafood Tour: Behind the Scenes at the Historic Fish Pier

2 hours 30 minutesFree Cancellation

4.9

(431)

from $81

Price varies by group size

Boston Harbor Sunset Sail Tour

Save yourself valuable time in Boston by prebooking admission to the Boston View observation deck before you travel. With entry guaranteed for your preferred slot and date, you're free to then finalize your plans in the city. When it’s time, ride the elevator to the observatory; soak in the 360-degree panoramas from its open-air deck, indoor terraces, and rooftop bar; and enjoy the 3D model of the city and other attractions.

(158)

from $82

View Boston Observation Deck Admission Tickets

View Boston Observation Deck Admission Tickets

1 to 2 hoursFree Cancellation

Discover the thrilling history of Boston on this immersive walking tour of the Freedom Trail. Hear tales of Redcoats, smugglers, riots, and midnight riders while reliving the American Revolution as you explore all 16 official sites of the trail. Learn about Boston’s leadership in abolition, women’s rights, education, and immigration over its 400-year history. Explore downtown Boston, hearing stories of legendary figures such as Paul Revere, John Hancock, and lesser-known pioneers and patriots.

(350)

from $34

Boston's Freedom Trail: A Revolutionary Walking Tour

Boston's Freedom Trail: A Revolutionary Walking Tour

2 hours 30 minutesFree Cancellation

4.9

(1,593)

from $31

Relive one of the most important events leading up to the American Revolution and learn about a side of the story most tourists miss on this guided tour of the Boston Tea Party Ships and Museum. Explore authentically restored tea ships with the help of a guide as you get their insights into this pivotal event, and throw some of your own tea into Boston Harbor. It's an ideal experience for American history buffs, tourists, and locals alike.

Boston Tea Party Ships and Museum Admission

Boston Tea Party Ships and Museum Admission

1 hourFree Cancellation

4.7

(2,746)

from $36

Boston North End Food Tour with Authentic Local Flavors & Dishes

Sample some of the tastiest bites that Boston’s North End has to offer—and enjoy a first-hand introduction to the area’s Italian heritage. Choose between our 3-hour or dynamic 2-hour express tour, and bring your appetite: Follow your guide to top-rated local businesses, and try everything from clam chowder and lobster rolls to cannoli. At the end, enjoy a secret dish revealed only on the day of the tour.

Boston North End Food Tour with Authentic Local Flavors & Dishes

2 to 3 hoursFree Cancellation

Price varies by group size

(1,534)

from $86

Boston’s Politically Incorrect North End Food Tour

3 hoursFree Cancellation

Boston Harbor Sunset Sail Tour

(632)

from $99

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Top Attractions in Boston

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Attractions

What are people saying about Boston

Teri_P, Jul 2026

Simply Wonderful

Make sure to get there 15-30 minutes early for check-in and make sure to dress accordingly and enjoy the experience of the wind in your face the smell of the ocean and the BEAUTIFUL skyline and the most helpful & knowledgeable staff. Happy Sailing ⛵️ 😀

North End Boston Food Tour: Pizza, Pasta, and Pastries

Melissa_H, Jul 2026

Fantastic tour! My family loved it.

Fantastic tour! Bobby was a wonderful guide. He is a local North End resident and told us a lot of history of the area. We got to have yummy food at many locations during a really busy time. He made it look effortless. I highly recommend this tour with Bobby.

Boston's Freedom Trail: A Revolutionary Walking Tour

Mike_M, Jun 2026

Elliot - Tour guide

We really enjoyed our Freedom Tour. It was a great way to learn about the history and hear the stories behind the places we visited. Our guide, Elliot, was fantastic. She was very knowledgeable, friendly, and did a great job explaining things in a way that was interesting and easy to understand. You could tell she really knew the history and enjoyed sharing it with everyone. The tour was well paced, informative, and enjoyable from beginning to end. We would definitely recommend the Freedom Tour and hope others get the chance to experience it too.

Boston’s Politically Incorrect North End Food Tour

Missy_G, Jun 2026

Best Tour of the North End

This is the 2nd time I've done this tour. It is both informative and hysterically funny. It is not for the faint-hearted as "f-bombs" are frequent. This is a tour from a real Italian, born and raised in the North End, with a wealth of information and a great sense of humor. Nothing too crass but if you're offended by foul language, this isn't for you! Anthony is a riot!!! The food is phenominal! Worth every penny!

Boston Freedom Trail Self-Guided Tour with Audio Narration & Map

Jacque_L, May 2026

Great Listening Tour! MUsT Do!

The first time I went to Boston I did one of the guided tours by a man dressed as a colonial. He was awesome. Funny, and it was a very good tour, but when my husband and I went back the following year I felt like there was a lot we skipped over and I needed a better history lesson. This listening tour was excellent! We were able to sync our AirPods so that we stopped and were looking at the same thing at each stop. So much information. Good guides and easy to listen to and navigate!

Boston's Food and History: North End, Freedom Trail, Beacon Hill

Joy_P, May 2026

Best combination tour in Boston

Nabil was a fantastic guide and it was the perfect combination of food and history. We were pleasantly surprised by the amount of food stops and the knowledge of our guide. He was also incredibly accommodating of my dairy allergy with food options. This tour is a great choice if you are visiting Boston.

Boston Architecture + History Walking Tour + Fun Photo Tips

Clifford_H, May 2026

Informational and Educational

Saba did a great job telling us about the culture, history and architects that influenced the Boston skyline. She is very knowledgeable on photography angles, approaches and editing and strives to make everyone a better photographer. She appreciates aches with humor and you can truly tell she enjoys honing peoples skills.

Self Guided Classic Freedom Trail Location Aware (GPS) Walking Audio Tour

Cynthia_W, Sep 2025

Boston Freedom Trail Experience

The stories and explanations are awesome. The GPS feature knows where you are so says things like ‘I’ll wait for you’ until you get to the next place. The directions are spot on. The only downside is that the recordings were obviously made during Covid and make references to places not being open because of COVID. So, time for an update!

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

Leah_C, Aug 2025

Must do!

This was such a fun, informative and beautiful end of the day activity! The tour guide was knowledgeable, friendly and the perfect person for this job. The city views were breathtaking and the sunset just added to the experience. I can’t recommend this enough. If we return to Boston, which we will, this will be back on our list!

Boston Summer Nights Trolley Tour plus River Cruise

Timothy_B, Aug 2025

Well Designed Tour

Well organized and ran smoothly. Red was our trolley driver and he was fun of energy and did a great job driving and sharing information. The trolley was well maintained and there was lots of fun music to listen to as you waited to depart and throughout the presentation with special cues. The boat was just as lovely and our bartender/guide during this part was very good! A great tour and I’d be interested in doing other tours they offer.