Top Boston Cruises &amp; Sailing - page 2

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

15 minutes to 1 hourFree Cancellation

Boston Harbor Night Cruise

1 hourFree Cancellation

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

Dog Day of Summer Harbor Cruise in Boston

1 hour 30 minutesFree Cancellation

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

Private Day Trip to Lexington and Concord from Boston

6 hours 30 minutesFree Cancellation

Boston Private 3-Hour Tour by Car

3 hoursFree Cancellation

Discover Boston, Lexington, Concord, and Cambridge on a private 6-hour guided historical tour by comfortable vehicle. Your knowledgeable chauffeur-guide provides commentary throughout the journey, sharing the history and significance of the landmarks along the route. Follow Boston’s Freedom Trail by vehicle, explore Beacon Hill, visit Revolutionary War sites in Lexington and Concord, and see historic Cambridge and Harvard. Most locations are drive-by sights with brief photo stops available at your preference, subject to traffic, parking, and the remaining tour time. Dedicated stops include the USS Constitution area and Concord’s historic North Bridge. Because the tour is private, the experience can be adjusted to your interests. Spend more time at the places that matter most to you, understanding that additional stops may reduce time at later locations. Return to Boston along Memorial Drive with scenic views across the Charles River.

Private Boston, Lexington & Concord Historical Tour

6 hoursFree Cancellation

Boston Sightseeing Tour - a fully-narrated driving tour

3 hoursFree Cancellation

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

Explore the best of Boston at your own pace on a hop-on hop-off trolley tour of the city. Choose from a 1- or 2-day pass and see Boston’s top attractions, including the USS Constitution, the original bar from TV show “Cheers,” and the Faneuil Hall Marketplace, to name a few. The pass includes discounted admission to the Boston Tea Party Ships and Museum, to enjoy during or after the tour.

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

Discover the best of Boston, without the rush of a large group, and see the sights that interest you most on this private tour. Board your vehicle along with your group and explore key landmarks in the comfort of an air-conditioned vehicle. See Harvard University, Fenway Park, the Boston Public Library, Beacon Hill, and much more while listening to commentary from your driver about Boston’s history.

Boston Private City Tour

6 hoursFree Cancellation

Book your Private 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/port 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.

Private Transfer from Flynn Cruise Port to Boston Airport (BOS)

15 minutesFree Cancellation

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

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

20 minutesFree Cancellation

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

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

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

4 hoursFree Cancellation

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

City Cruises Boston Premier Lunch Cruise

Boston Full Moon Cruise Tour

Combine an indulgent brunch with a sightseeing boat tour on this two-in-one festive outing. Meet at Rowes Wharf, and hop aboard the *Northern Lights*, 1920s-style yacht. Over the course of several hours, you’ll see landmarks ranging from the Bunker Hill Monument and USS Constitution at Charlestown Navy Yard to Castle Island and beyond. You’ll also enjoy a holiday buffet brunch onboard.

Santa Brunch Cruise in Boston Harbor

Book your Private Transfer from Flynn Cruiseport Boston to Boston city. Don't go through all the hassle of waiting in long taxi or shared shuttle queues; use our private, door-to-door airport or port 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 and Professional drivers

Private Transfer from Flynn Cruise Port to Boston city hotels

20 minutesFree Cancellation

Discover the stunning Boston skyline from the unique perspective of the water with customized private boat charters on the Jess~Sea. Whether you're interested in a scenic harbor tour, historical sites like the USS Constitution, or a relaxing picnic on Spectacle Island, the experienced crew will tailor the adventure to your desires. With room for up to six guests, this intimate experience allows for personalized exploration of Boston’s hidden gems. Bring your own food and beverages for a perfect day on the water, all while enjoying expert guidance and local insights. - Private charters tailored to your interests, accommodating up to 6 guests - Explore historical sites, islands, and scenic views unique to Boston - Option to bring your own food and drinks for added convenience - Experienced crew dedicated to creating memorable experiences and sharing insider knowledge

Customized Private Boat Charters in Boston Harbor

Customized Private Boat Charters in Boston Harbor

1 hourFree Cancellation

It can be tough to take in all of Boston’s historic sights on your one in just one day, so this private combination car and walking tour of Boston and Cambridge is here to help. Follow in the footsteps of famous academics exploring Harvard and MIT, learn about Boston’s storied history and the American Revolution at Beacon Hill and the Bunker Hill Monument, and explore the artisanal food options available at the US’s oldest tavern and restaurant.

Private City Tour of Boston and Cambridge

7 hoursFree Cancellation

Lexington and Concord 3 hour private car tour from Boston

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Top Attractions in Boston

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Attractions

What are people saying about Boston

Lavonna_D, Sep 2026

Informative and interesting.

Great tour! Our guide, Christian, was interesting and informative as he lead us back in time to the day the American Revolutionary War started in Lexington and Concord. As a retired history teacher he really knew what he was talking about. Interesting to listen to and follow. The 4 of us had a great day. The drive is beautiful too as you drive in the countryside of Lexington and Concord. I would highly recommend!

Boston Harbor Sunset Sail Tour

Cameron_D, Aug 2026

Great sail aboard the...

Great sail aboard the Adirondack. The ship is beautiful and smaller than the large party-style cruises we saw cruising around at the same time. There were a good number of people on board, but we did not feel cramped for a Wednesday evening sunset ride. Hannah answered all our questions about the boat, the harbor, and even snapped a great picture of us as we celebrated our anniversary! Thanks!

Private Day Trip to Lexington and Concord from Boston

Alan_S, Jul 2026

Great tour, great guide

The tour hit the key sites as advertised. Jenny was knowledgeable and also attentive to my wife’s health needs and adapted the pace as necessary. She was flexible with the schedule because of the summer heat, and kept the journey interesting and meaningful.

Boston Harbor Brunch Cruise

Stacey_M, May 2026

Good food and a Great Experience!

My boyfriend and I truly enjoyed this Brunch/Harbor Cruise. It was, sadly, a rainy day but there is full capacity indoor seating so not to worry, we stayed warm and dry. They way the tables are set up, you can see great from any one of them but we got a great table at the front of the boat. The ship's captain narrates all points of interest and though I practically live in Boston, I still gleaned some new details that I did not already know about some of them. The crew was friendly, accommodating and knowledgeable. There was MORE than enough food for everyone on board and I found the food to be fairly decent enough for a brunch cruise (I mean, it's not a 5 star resort, it's a BOAT) with plenty of variety of foods and everything was tasty and seemingly fresh. I will add that I bought my tickets through Viator last minute because I didn't want to miss out but there were plenty of tickets available at the dock and they were about half the price.

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!

Private 4-Hour Driving & Walking City Tour

Clinton_E, Mar 2026

Outstanding overview of Boston!

We thoroughly enjoyed our 4-hour Boston overview with an amazing guide, Neal! The tour was a well-balanced mix of walking and riding. We saw so much in 4 hours! Neal clearly has a passion for his city, and this made for a fun, interesting, and educational experience. Even though I have been on a few tours of Boston in the past, he still introduced us to several new sites and many new facts! He recommend several great restaurants that we would have never have explored if not for him. Ask him for some “cash only” recs!

Salem half day private tour from Boston

Joan_A, Mar 2026

Fantastic tour!

If you’re visiting Salem, do yourself a favor and take a tour with Martin. Our experience was absolutely fantastic and easily one of the highlights of our trip. Martin led a guided tour of Salem that was both incredibly informative and genuinely entertaining. He showed us six filming locations from Hocus Pocus, which was a really fun addition, and also brought us to the iconic Bewitched statue. Beyond the pop culture stops, his in-depth knowledge of the Salem Witch Trials was impressive—he explained the history in a way that was engaging, thoughtful, and easy to understand. He also made a stop at the oldest candy shop in the United States, which was such a unique and memorable part of the tour. It’s clear Martin truly knows Salem inside and out. What really set the experience apart, though, was how much he went above and beyond. At the end of the tour, he even helped us secure reservations at a restaurant so we could relax and enjoy the rest of our evening without worrying about finding a place to eat. Martin clearly cares about making sure people have a great experience in Salem (and other areas in and around Boston), and it shows in every part of the tour. If you’re looking for a guide who is knowledgeable, personable, and passionate about the history of the area, Martin is the one to go with. Highly recommend!

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.

3-Hour Private "Cold Weather- Warm Van" Driving Tour of Boston

Giulio_M, Dec 2025

The absolute best way to see Boston—Peter is a legend!

If you are looking for the perfect way to see Boston without battling the freezing temperatures, this is it. Our group of four booked this tour on a whim, and it ended up being the highlight of our trip. The 'warm van' promise was fully kept, but the real star of the show was our guide, Peter. I cannot speak highly enough of him. Often, a three-hour drive can feel long, but Peter kept our attention the entire time. He has an endless supply of fascinating stories and local history that you simply wouldn't get from a guide book. He managed to make the city come alive while we stayed perfectly comfortable. If you want a tour that feels personal, engaging, and incredibly comfortable, ask for Peter. Worth every cent!

Private Boston, Lexington & Concord Historical Tour

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!