Top Boston Cruises &amp; Sailing - page 2

Pastries & Prosecco Aboard a Tall Ship in Boston Harbor

(17)

from $73

New England Fall Lunch Cruise in Boston Harbor

(44)

from $82

Boston Harbor Moonlight Cruise

4.2

(6)

from $31

Boston Holiday Cocoa Cruise

4.6

(85)

from $82

Boston Harbor Night Cruise

1 hourFree Cancellation

(14)

from $46

Dog Day of Summer Harbor Cruise in Boston

Boston Ghosts and Gravestones Trolley Tour

4.7

(10)

from $28

Boston Sightseeing Tour - a fully-narrated driving tour

(2,522)

from $47

3 hoursFree Cancellation

4.9

(59)

from $495

If you've always wanted to see Plymouth Rock, this 4 hour tour lets you check it off the bucket list. It can fit snuggly into a Boston city break without using up too much of your time in the city. We pick up in downtown Boston and travel 50 minutes directly to Plymouth. There we'll do a walking tour around the town, explaining why the Pilgrims landed here and how they settled in to the area. Go aboard the Mayflower II (seasonal) to see for yourself how awful their journey must have been and stop by the memorial for the legend of the rock. Quick stop at an impressive monument, built to honor the Pilgrims and then it's back to Boston. Boston is 50 minutes drive from Plymouth, so you will be in the car a chunk of time on this tour. You will have approximately 2 hours in Plymouth.

Plymouth Half Day Private Tour from Boston

4 hoursFree Cancellation

(7)

from $695

This half day private car tour is a perfect way to visit the Revolutionary War towns of Lexington and Concord and see the site where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant sites along the way to give a detailed account of what and how things unfolded in April 1775. The travel time from Boston to these towns is 45 minutes each way and you'll be in one of our comfortable private vehicles with an experienced, knowledgeable and licensed tour guide.

Lexington and Concord 3 hour private car tour from Boston

3 hoursFree Cancellation

(37)

from $550

Set sail on the magnificent tall ship Denis Sullivan, a Great Lakes schooner offering a unique opportunity to connect with the sea. Whether you choose to help the crew raise the sails or simply soak in the stunning views, this public sail is a perfect outing for family and friends. All ticket proceeds contribute to the World Ocean School's educational programs, ensuring a meaningful experience on the water. Enjoy an enriching day while supporting maritime and experiential education.

Harbor Sail Aboard the Tall Ship Denis Sullivan

Harbor Sail Aboard the Tall Ship Denis Sullivan

from $55

Boston Private 3-Hour Tour by Car

Boston's cobblestone streets & red bricks

3 hoursFree Cancellation

(134)

from $550

City Cruises Boston Premier Lunch Cruise

Private Luxury Transportation to/from Boston Logan Airport (BOS)

4.3

(7)

from $92

15 minutes to 1 hourFree Cancellation

4.3

(28)

from $129

Enjoy a private pickup and ride to historic Salem with your guide. Walk the streets where hysteria once ruled, and learn about the Puritan past that shaped daily life in early New England. Uncover the tragic history of the witch trials during a visit to the moving Witch Trials Memorial. Discover Salem's prosperity during the "Old China Trade," when ships sailed to Asia and returned with exotic goods like silk and porcelain, making it one of the wealthiest towns in the early United States and home to the country's first millionaire. See how this era shaped the city beyond the witch trials with a visit to the Salem Maritime National Historic Site. You'll have 1.5 hours of free time to grab lunch and browse for souvenirs, from classic mementos to mystical finds like tarot decks and potion ingredients. Afterward, we'll continue exploring Salem's landmarks before your private ride returns you to Boston.

Salem Full Day Private Tour from Boston

8 hoursFree Cancellation

(5)

from $419

If you've always wanted to visit this infamous town, then let's do it during your visit to Boston. This half day Boston to Salem tour consists of: - Downtown Boston pick up, ~45 minute drive to Salem - Stories of what happened before, during & after the Salem Witch trials - Walking tour of movie scenes, sites and fun facts of Salem - Go into one of the main Salem attractions (entry fee not included, and availability not guaranteed) - 45 minute drive back to Boston If you'd rather skip going into any of the sites, we use that time to take you to Marblehead for some amazing ocean views. The return journey and tour is 4 hours, we're happy to customize it to accomplish the things you're most interested in.

Salem half day private tour from Boston

4 hoursFree Cancellation

(15)

from $695

Celebrate a special occasion or just enjoy the company of your family and friends on this leaf-peeping Boston Harbor brunch cruise. On board a 1920s-style yacht, the Northern Lights, you’ll sail through Boston Harbor, cruise past the Harbor Islands, and spot landmarks and beautiful fall scenery along the way. Indulge in a fresh, gourmet brunch prepared by the onboard chef as you take in the waterfront views.

Boston Harbor Fall Brunch Cruise

Witness the breathtaking Boston Harbor skyline and many landmarks from the unique perspective of the harbor. We are one of the only Private Sunset Cruises in Boston. The Boat will only have you, your guests and our crew. We will provide complimentary Water and Soft Drinks. You are welcome bring you favorite food and Beverages on-board to enjoy during your cruise. As a reminder Gratuities are not included in your fare. This Tour runs over a 10 to 12 mile loop of the harbor which takes 2 Hours and 30 Minutes. You will have plenty of time to take photos and make lasting memories. we travel at a slow rate of speed and the cruise is very enjoyable. AS THE DAYS GET SHORTER Start and end times will be modified in order to coincide with sunset times. TRIP MAY BECOME LESS THAN 2.5 HOURS Trip ends 30 minutes after sunset in Aug/Sept.

(23)

from $106

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

from $1,200

Experience the best of Newport, Rhode Island on a private, guided day trip tour in a comfortable luxury vehicle. If you value privacy, comfort, and the flexibility to explore at your own pace, our tour is the perfect choice for you. We will take you to all of Newport's most important sights, and our tour is completely customizable to suit your preferences. Whether you want to explore the opulent Gilded Age mansions, take a scenic drive along Ocean Drive, or stroll through the charming downtown area, we will create an itinerary that meets your needs. With our private tour, you can relax and enjoy the sights of Newport without having to worry about keeping a schedule or sharing your experience with strangers.

Boston to Newport Mansions Private Day Trip

9 hours 30 minutesFree Cancellation

(3)

from $1,012

Highlights of Boston Private Tour

5 hours 30 minutesFree Cancellation

4.9

(32)

from $387

Private Day Trip to Lexington and Concord from Boston

6 hours 30 minutesFree Cancellation

(29)

from $423

This full day private tour combines some of the best coastal views in the region with Pilgrim history. First stop focuses on the Presidential history of John Adams and then for something completely different we swing by the first Dunkin' Donuts (how's that for random). Then it's sit back and enjoy the views, through south of Boston towns Hingham, Cohasset, Scituate and Duxbury. There's some great photo opps along the shoreline that you won't be able to resist. Next onto Plymouth and it's Pilgrim history as well as it's own lovely ocean views. This is a break from your city break. We pick up and drop back to downtown Boston, will stop for lunch along the way (not included in price of tour) and will make sure you have a calm and relaxed day.

Plymouth & South Shore Private Tour from Boston

6 hoursFree Cancellation

(5)

from $995

Take a private day trip from Boston to the North Shore, combining coastal scenery with two of Massachusetts’ most distinctive historic sights. Enjoy door-to-door hotel pickup and flexible pacing that lets you explore without group constraints. Travel comfortably while your guide provides context on regional history, architecture, and folklore, with meaningful time for exploration and photos.

Private Day Trip to Salem and Hammond Castle from Boston

7 hoursFree Cancellation

4.8

(17)

from $445

See all of Boston and Cambridge from the comfort of a heated and air-conditioned modern minivan. This is a half-day driving tour that takes you through every highlight of Boston and Cambridge. The drive will include sights such as the Old North Church, Paul Revere's house, Faneuil Hall, Boston Common, Beacon Hill, Bunker Hill Monument, USS Constitution, Harvard, MIT, Copley Square, Boston Public Library and so much more! The tour is mainly driving, however we will (optionally) stop a few times to briefly (5-10 minutes) get out of the car for photo opportunities and a closer look at some sights! Listen to stories about Boston's past, learning about the American Revolution and the city's duality of religious morals and corruption.

Private Half-Day Driving Tour of Boston and Cambridge

4 hoursFree Cancellation

(4)

from $311

Boston Harbor Sunset Sail Tour

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Top Attractions in Boston

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What are people saying about Boston

gail_V, May 2026

Just book it ! You will not be disappointed.

Just book it ! The captain Eric and crew were wonderful. The energy on the boat was fantastic. The temp was unseasonably low . They offered blanket's with their logo for $7 each . Great price and such a classy thing to do . The view as the sunset, going from light to dark stunning . The city lights were gorgeous

Private Luxury Transportation to/from Boston Logan Airport (BOS)

Cassie_W, Apr 2026

Great communication and quality transportation!

Our flight had several delays throughout the day, but I was able to stay in communication with them and they watched the flight updates for changes. Our driver, Eric, was helpful and friendly, even though our flight arrived at midnight. We were so grateful to have him ready for our arrival!

Boston Holiday Cocoa Cruise

Liliana_S, Dec 2025

Family-Friendly Holiday Cruise

We had a wonderful time on the Boston Holiday Cocoa Cruise! The whole vibe was so festive and relaxed, with amazing holiday music that really set the mood. The yacht itself was decorated beautifully, cozy, cheerful, and perfect for families. We mostly just had snacks, so I can’t speak much to the food, but the drinks were fantastic. The staff was super friendly and welcoming. The highlight for us was definitely the view. The Boston skyline at night from the water is just breathtaking. I’d definitely recommend this cruise, It’s festive cheer, gorgeous scenery, and a relaxed atmosphere.

Private City Tour of Boston, Lexington, and Concord

Amanda_M, Oct 2025

Fun, educational and custom tailored for us

I’ve been on numerous group tours, but this was our first private tour as a couple. We loved that it was tailored to our interests and not your typical group tour that tries to cater to everyone’s interests. Our guide, Curtis, is very knowledgeable on history of the area and we learned a lot while getting not only historical information but asking the questions we wanted to know. It was a great tour and a wonderful addition to our trip!

Boston Sightseeing Tour - a fully-narrated driving tour

Patricia_C, Oct 2025

The Best Way to See Boston

I booked the 3-hour private driving tour in Boston, and from start to finish it was unforgettable — all thanks to our guide, Peter. From the moment we were picked up at the cruise port, it was clear we were in good hands. The van was spotless, comfortable, and climate-controlled. Peter’s punctuality and friendliness instantly put us at ease. As we rolled through Boston’s neighborhoods — Back Bay, Beacon Hill, the South End — Peter seamlessly wove together stories, historical context, and fun anecdotes. He navigated tight streets like a pro, making sure we caught striking views (and photo stops) without compromising the itinerary. His knowledge is seemingly bottomless: he referenced dates, personalities, lesser-known tales, and surprised us with this fun facts. We passed by so many iconic sites: the Paul Revere House, Old North Church, the USS Constitution, Bunker Hill, Faneuil Hall, Copley Square, Fenway Park, Harvard, MIT, and more. None of that felt like mere “drive-by” narration — Peter made each landmark come alive through storytelling. He has a warm, inviting personality — we felt like we were touring with a knowledgeable friend rather than a guide “on duty.” His passion for Boston is infectious! By the end we walked away feeling like insiders, not just tourists. In short: Peter exceeded every expectation. If you visit Boston (even for just a few hours), book this tour. You’ll see the city, yes—but more importantly, you’ll feel the city, through stories, context, and heart. We will remember this tour for years to come — thank you, Peter!

New England Fall Lunch Cruise in Boston Harbor

Dottie_J, Oct 2025

Wonderful Cruise

What wonderful lunch cruise. The captain gave us information about local history while we gently cruised around Boston Harbor! The food on the buffet was excellent with roasted pork loin, turkey, butternut squash ravioli, salad, saffron rice, garlic rolls, and brownies. Everything was delicious! My husband and I enjoyed this very much. The crew were also very nice and professional. When we finished eating, there were still all the sights to see. This a must do on a Boston visit!

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.

Boston Private City Tour

Ingrid_D, Aug 2025

Touring Boston with our Siblings

My husband and I traveled to Boston via train with our sisters the weekend of August 22. One of our activities was a four hour private tour of Boston. We had a fantastic time with our guide/driver, Sam! Sam was very professional and knowledgeable and arrived at our hotel at the designated time. He also allowed us to get out of the vehicle to take photos numerous times. I definitely recommend this particular tour of beautiful Boston, MA! It’s an experience we’ll never forget. Thanks again, Sam!

Lexington and Concord 3 hour private car tour from Boston

David_C, Aug 2025

Really Enjoyable Experience

Our guide, Christian, was very informative and really pleasant. We really enjoyed how he related the experience to us. Picked us up at our hotel and dropped us off at the place of our choice. I would definitely recommend this tour to anyone interested in learning more about Lexington and Concord.

Boston to Kennebunkport with Optional Lobster Tour

Caren_C, Jun 2025

This is a must do Excursion. Lovely Matt, history galore!

Matt was outstanding. Very personal and knows his history. Absolutely would do this Excursion again. He was so great we took 2 other Excursions with him. He is fantastic and what an addition to the beauty of the New England states. This is a must do!!!!