Top Boston Cruises &amp; Sailing - page 3

Private Tour of Boston for Families & Kids

(2)

from $338

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

4.8

(17)

7 hoursFree Cancellation

from $445

Highlights of Boston Private Tour

4.9

(32)

5 hours 30 minutesFree Cancellation

from $387

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

(15)

from $695

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

(3)

from $311

90min BYOB Boston Harbor Cruise. Pedal as much as you want or just relax and enjoy the amazing harbor views. Bring Your Own Beverages, Food and Music. We provide coolers with ice in our high center bar and Bluetooth connectable speakers. Great for unique fun Birthday and Bachelor/Bachelorette Parties, Outings with Colleagues, School Field Trips or just an amazing time with friends and family. We cruise close to shore at slow speed to get close up views of the harbor attractions and provide a QR code connectable Interactive tour route app with a wealth of information on 36 points of interest that you will pass. Charter groups can chose from 7 boarding locations upon request. Charters can be booked from 10AM to 8:30PM, 7 days per week, mid-April through October.

Cycleboat Boston 90 min BYOB Amazing Harbor Private Charters

1 hour 30 minutesFree Cancellation

from $949

Boston Luxury Chauffeur , is a limousine service provider in the City of Boston. We provide affordable, reliable and quality chauffeur services. You can depend on us to transport you around Boston and take you to your destination efficiently and safely. We are not only knowledgeable with the streets of Boston, but we can also take you to that desired football game or amusement park outside the city limits. Boston Luxury Chauffeur, is fully licensed and insured to provide transportation services in Massachusetts and at Logan Airport We urge you to book with us, let us earn your business and you will not be disappointed.

Luxury Private Limousine Transfer in Boston – 24/7 Service

15 minutes to 1 hourFree Cancellation

from $150

Book your Private Departure Transfer from Flynn Cruiseport Boston to Boston Logan Intl Airport (BOS) . Don't go through all the hassle of waiting in a long taxi or shared shuttles queues and use our private, door to door airport transfer. Your driver will be waiting for you at a scheduled time and you will travel comfortably to your destination. • Meeting with a Nameplate • We track your Flight • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers

Flynn Cruise Port to Boston Logan Intl Airport (BOS)- Departure Private Transfer

(1)

20 minutesFree Cancellation

from $94

Visit the real locations where the American Revolution began. Stand on Lexington Battle Green and listen to stories about the very first days of the war and the "shot heard around the world". Walk the Battle Road Trail, stage of multiple skirmishes between the Minutemen and the Redcoats and other "treasonous" events. Visit Concord's Old North Bridge, where the Minutemen routed the Redcoats on their march back to Boston! Return to Boston to visit important sights along the Freedom Trail, including the Paul Revere House, Old North Church, USS Constitution (aka Old Ironside), the Bunker Hill Monument - home to the phrase "don't fire until you see the white's of their eyes", and more!

Old North Bridge - location of the "shot heard around the world"

Private Tour of Lexington, Concord, and Boston

4.9

(7)

7 hoursFree Cancellation

from $445

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.

Boats and various shops located at the harbor in Newport Rhode Island in the setting sun

Boston to Newport Mansions Private Day Trip

(3)

9 hours 30 minutesFree Cancellation

from $1,190

See all Boston's most important sights in a six hours, private, guided city tour, in a comfortable vehicle. If you value, time, privacy, comfort and would like to have a good overview of the city of Boston, Lexington and Concord at your own convenience and pace, we are the right choice for you. We will drive by or stop and wait at the sights you are most interested in. Our tour is totally customizable and our priority is to please you, not keep a schedule.

Private City Tour of Boston, Lexington, and Concord

4.6

(14)

6 hoursFree Cancellation

from $900

Visit historic sites in Lexington and Concord. Focus on sites related to the start of the War of Independence, early years of the towns, and authors of 19th Century Concord. Experience scenic countryside, town centers and Walden Pond Reservation. We can customize this tour to specific interests and to other locations in Lexington and Concord. Your guide is licensed by the town of Concord.

Boston to Lexington and Concord Historical Sites Shore Excursion

4 to 8 hoursFree Cancellation

from $990

Boston Harbor Night Cruise

Likely to Sell Out

4.4

(14)

1 hourFree Cancellation

from $46

"Embark on a private day trip from Boston to Plymouth, MA, and delve into the profound history of one of New England's most important locales. Begin your journey at Pilgrim Memorial State Park, where the storied Plymouth Rock marks the Pilgrims' landing. Aboard the Mayflower II, a detailed replica, learn about the 1620 voyage. The Plimoth Patuxet Museums offer a lively reenactment of 17th-century life; engage with costumed interpreters and savor a traditional meal at the café. Discover the Pilgrim Hall Museum, the nation's oldest public museum, featuring an array of real Pilgrim artifacts. Stroll along Plymouth Harbor for beautiful views. The tour concludes at the towering National Monument to the Forefathers, before allowing some free time to explore downtown Plymouth's charming shops, galleries, and cafes. This tour not only traces the historical tapestry of Plymouth but also offers a deeply personal connection to America’s foundational stories."

Private Boston Day Trip to Plymouth MA

9 hoursFree Cancellation

from $1,090

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.

Likely to Sell Out

Boston Harbor Fall Brunch Cruise

4.4

(23)

2 hoursFree Cancellation

from $106

Comfortable Roundtrip Tour from your hotel in Boston to Merrimack Premium Outlets - plays host to luxury boutiques and stores selling everything from clothes and accessories to cosmetics and home essentials. Its world-class boutiques showcasing collections from prestigious local and international designers make for a truly memorable shopping experience. Add to all these a unbeatable prices, and a handful of trendy cafés and restaurants, and what you’ll get is one of the best shopping destinations in and around the Boston. After you finish your shopping you will be picked up and will be delivered directly to your hotel in Boston. All our vehicles are fully licensed and insured. We are happy to provide child seats in our cars for all ages upon request. Vehicles are clean inside and outside; our drivers are well-dressed and unfailingly attentive to our guests. They speak English. They will greet you with a name sign and will help with luggage.

Private Shopping Tour from Boston to Merrimack Premium Outlets

6 hoursFree Cancellation

from $431

This private day tour is the perfect way to get to know Boston & Cambridge at a leisurely pace. It's a combination of walking and driving (although can be driving only if you prefer). We start with a walking tour of parts of the Freedom Trail, stopping at some of the city's most significant sites. We'll then drive in and out of the other city neighborhoods, Beacon Hill, Back Bay and Seaport and finish out the Freedom Trail with a stop at Bunker Hill. Then it's across the Charles River to Cambridge, where we drive around the MIT campus, and onto Harvard for a walking tour of the oldest college in the country. We'll share lots of history and legends but also keep it topical with current day fun facts and light hearted stories. After the walk you'll need some lunch and we know some great spots (not included in price of tour). All guides are fully licensed and approved Boston tour guides, driving luxury and livery insured vehicles.

Boston and Cambridge walking and driving private tour

(9)

6 hoursFree Cancellation

from $995

Boston Sightseeing Tour - a fully-narrated driving tour

4.9

(57)

3 hoursFree Cancellation

from $495

Step into the storybook of American history on this 7-hour private tour through the iconic streets of Boston and Cambridge. From the cobblestones of Beacon Hill to the hallowed halls of Harvard, this experience blends revolutionary history, architectural beauty, and vibrant culture into one unforgettable day. Led by a knowledgeable guide and traveling in a comfortable, air-conditioned minivan, you’ll explore historic landmarks, charming neighborhoods, and world-renowned universities. With coffee and a cannoli to start your morning, and plenty of stops for photos, exploration, and a relaxed lunch, this tour is the perfect way to get to know the soul of New England.

Boston & Cambridge Icons: Private 7-Hour Discovery Tour

7 hours

from $648

What makes our black car service unique is the combination of luxury, reliability, and personalized service while traveling to top destinations such as airports, hotels, business districts, events, and popular city attractions. Guests enjoy a smooth, stress free ride in a premium black vehicle with a professional chauffeur who offers local insight, punctual service, and attention to detail. This service is ideal for business travelers, couples, families, and special-occasion guests who value comfort, privacy, and a refined travel experience.

1 to 7 daysFree Cancellation

black car service

from $130

Join Captain Riccardo aboard the Trinacria for a Private tour of Boston Harbor & The Harbor Islands. Choices include Sightseeing, Foliage Tours in Autumn 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. Plan on being on-board for up to 4 Hours for Lighthouse tours if you choose to see the offshore Lighthouses. 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 the price.

Cruise - Sightsee - Foliage in Boston, on Private Yacht Trinacria

(1)

3 to 5 hours

from $2,000

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

(7)

from $695

We'll see the sights on Boston's Freedom Trail and get a closer look by leaving the car and walking inside some locations (depends on day and hours of operation for some sites). We'll have time to go aboard the USS Constitution (closed Mondays). A close-up experience in the oldest neighborhoods of the North End, Beacon Hill, School Street, and Charlestown. Look at places of events and the people from different periods of the settlement of Boston, and the American Revolution. If weather isn't favorable, we can revise the walking portions according to your wishes. A favorite stop is Faneuil Hall, the Great Hall Meeting Room and the Ancient and Honorable Artillery Company Museum (hours vary).

Boston Freedom Trail Private Car Tour

from $656

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

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Top Attractions in Boston

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Attractions

What are people saying about Boston

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!

Lexington and Concord 3 hour private car tour from Boston

Clinton_E, Mar 2026

A highly recommended, brilliant tour!

We absolutely loved our tour of Lexington and Concord with Martin, the best tour guide in New England! He picked us up from our hotel right on time in a clean, new minivan. He gave us a brief photo review of the land-filling that created the Back Bay (as our hotel was there). He then gave us a drive-through bonus tour of a bit of MIT and Harvard on the way to Lexington. We were able to briefly walk the long corridor of MIT and see the unbelievable freshman dining hall at Harvard. Both on the road and when out of the van in Lexington and Corcord, Martin demonstrated a captivating style of history telling that really intrigued the listener. He is clearly passionate about the details of the events of April 19, 1775. I was easily able to visualize the incredible drama that unfolded in these towns on that day. Because of this, standing on Lexington green was very moving for me. Near the end of our tour, he gave us a bonus drive-by of Bunker Hill and provided us with some additional history. He then walked us in to the Warren Tavern, so to insure that we found a great seat. This was my fifth or sixth trip to Boston, and can say without hesitation that this or any of Martin’s company’s tours will stand above the rest (we also took the full-day private tour of Salem and the coast with Martin)!

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.

Beacon Hill Boston Walking Tour: History + Fun Photo Tips

Amy_K, Oct 2025

Lovely time in Beacon Hill

Saba is a delightful host for the Beacon Hill neighborhood. She has been giving tours for 20 years or so, and knows the back stories of the area. She gave us some great tips on how to photograph the area and our pictures are gorgeous! If you are interested in learning things about Beacon Hill that are not in the guidebooks, and you want to come away with some beautiful photographs, this tour is for you.

Boston Architecture + History Walking Tour + Fun Photo Tips

Irina_Y, Oct 2025

A gem

It was an absolutely delightful experience, like walking with a friend who shares their favorite gems in the city with you. Saba is a fantastic guide, very knowledgeable and wonderful to learn from. She gave many tips how to improve photos and I have a great collection of photos now. Thank you, Saba, for a wonderful experience!

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!

Boston Harbor Sunset Sail Tour

Sara_J, Aug 2025

What an amazing way to...

What an amazing way to experience the Boston Harbor! The deckhands and captain were attentive and friendly, always ready to answer questions or get your drink order. The views were unbeatable and we topped off the night with our sister-in-law getting engaged at the bow of the boat right after we docked. Highly recommend for out of town visitors or locals alike!

Boston Private City Tour and Chauffeur Service

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!

Boston Summer Nights Trolley Tour plus River Cruise

Michelle_P, Aug 2025

It was worth it.

This was pretty cool. You got an idea of where things are and places to go back and check out and places to eat SEAFOOD! The sky at dusk on the river boat cruise was gorgeous, but it had just rained before we got on the boat and the sun starting to set was hitting the clouds. What a beautiful view of the city skyline from the river boat. “Red “was our driver. He had some funny one liners. he was good. The two ladies on the river boat Cruz did a great job too. I don’t recall their names. Unfortunately I know the captain was from Providence Rhode Island. She was very nice.

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!!!!