Top Boston Cruises &amp; Sailing - page 3

Private City Tour of Boston and Cambridge

7 hoursFree 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

Special Offer

Explore America’s historic roots on a private day trip from Boston to Plymouth. This immersive experience includes a visit to the Mayflower II, where you’ll walk the decks of a full-scale reproduction of the Pilgrims' ship. See Plymouth Rock, the iconic landing site of the Pilgrims. Explore the 17th-Century English Village and Patuxet Homesite, meet interpreters, enter traditional homes, and discover how people cooked, farmed, fished, raised animals, and made tools 400 years ago. With a full day dedicated to exploration, this tour offers a range of interactive, family-friendly activities and insights into Native American culture and colonial life. Enjoy flexible pick-up from your Boston hotel in a private vehicle, making it a great adventure for any group. - Full-day private tour with a local guide - Visit historic sites including Plymouth Rock and Mayflower II - Interact with living history at Plimoth Patuxet Museums - Comfortable transport with hotel pick-up and drop-off included

Private Plymouth Tour from Boston with Mayflower II

8 hoursFree Cancellation

Highlights of Boston Private Tour

5 hours 30 minutesFree Cancellation

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

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.

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

Boston Harbor Private Sunset & Foliage Cruise, on Yacht Trinacria

Private Tour of Boston for Families & Kids

4 hoursFree Cancellation

Private Day Tour of Salem and Boston

7 hours 30 minutesFree Cancellation

Private Day Trip to Lexington and Concord from Boston

6 hours 30 minutesFree Cancellation

Book your Private Arrival Transfer from Flynn Cruiseport Boston to Boston . 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 • Door-to-door Service • No Hidden Charges • Clean cars & Professional drivers

Flynn Cruise Port Boston to Boston hotels - Arrival Private Transfer

Flynn Cruise Port Boston to Boston hotels - Arrival Private Transfer

35 minutesFree Cancellation

Private 4-Hour Driving & Walking City Tour

Start the day in Little Italy, with traditional cannoli and espresso at the oldest Italian café in Boston. Proceed through the historic "Little Italy" neighborhood to learn about Boston's history! Listen to stories about the neighborhood's ties to the American Revolution such as the ride of Paul Revere. Try traditional sandwiches from an Italian Salumeria. Drive through Boston's historical downtown while learning about the city's colorful past. Walk through Beacon Hill, Boston's most prestigious neighborhood. Visit Boston Common, the oldest public park in America. Stop at a local seafood chain for lobster rolls and New England clam chowder. Take a drive through Back Bay, Boston's man-made neighborhood lined with 19th century Victorian houses. Take a quick drive through Cambridge for stunning views of Boston and MIT. End the tour with seeing the stunning Copley Library! Be sure to come hungry! The tour includes pick-up and drop-off anywhere in the Boston area (up to 6 people).

Boston Food and History Private Tour

5 hours 30 minutesFree Cancellation

Experience the pinnacle of luxury travel with premium Black SUV transportation services. Ideal for airport transfers, corporate travel, or special events, each ride promises unparalleled comfort and style. Enjoy a seamless journey as you glide through the city in a pristine, spacious vehicle, expertly driven by professional chauffeurs dedicated to your safety and satisfaction. Whether it’s a long-distance trip or an hourly service, every detail is crafted to exceed expectations, ensuring you arrive on time and in style. - Premium Black SUV fleet for maximum comfort and spaciousness - Professional, reliable chauffeurs focused on your safety - Ideal for corporate travel, airport transfers, and special events - On-time arrivals guaranteed for all services

Boston Private Black SUV Transfers

10 hoursFree Cancellation

This private car tour is comprehensive enough for any history buff, but as interesting in other ways for non history nerds. It's a unique combination of the Revolutionary War sites in Boston and Cambridge that you won't have seen. Then onto Lexington and Concord to see the towns where the "shot heard round the world" was fired. We'll take the same route as Paul Revere, stopping at the most significant, and lesser known sites along the way giving a detailed account of events in April 1775. For those less interested in the details of the battles, there's the option to visit the home of Louisa May Alcott or just take some time to enjoy the pretty main street of Concord. The itinerary gives the list of sites we'll visit, but timings are flexible to let us spend time at the places you're most interested in. We'll also stop for lunch (not included in price of tour) and there's plenty of photo opportunities.

Boston, Lexington and Concord Revolutionary War Car Tour

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!

Private Tour of Lexington, Concord, and Boston

7 hoursFree Cancellation

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

3 hoursFree Cancellation

Navigating the dynamic landscapes of Boston, Los Angeles, and Washington D.C. becomes effortless with this luxury chauffeur service. Enjoy seamless airport transfers and city-to-city rides in meticulously maintained vehicles, whether traveling for business or leisure. Professional chauffeurs provide a warm welcome, ensuring a comfortable ride while catering to your every need. With 24/7 availability and a fleet that includes business class sedans and luxury SUVs, your travel experience is customized to reflect your expectations and style. - Comprehensive 24/7 service for airport transfers and city rides - Professional, vetted chauffeurs ensure safety and comfort - Diverse fleet including luxury sedans, SUVs, and stretch limousines - Travel limits and amenities designed for a stress-free journey

Luxury Chauffeur Service Boston Great Area

15 minutes to 5 hoursFree Cancellation

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

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

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

Boston to Portland ME Private Car service

2 to 3 hoursFree Cancellation

This is an action packed private day tour of the sites, history and events of the Revolutionary War era in Boston, Cambridge Lexington & Concord. We drive the Freedom Trail with stories of the city's 400 year history, the events, people and sites which led up to the war. In the oldest neighborhoods of the city, we'll give context to historic events like the Boston Tea Party, Boston Massacre and Battle of Bunker Hill. We'll take a quick walking tour of Harvard, explain the role it played in the start of the war and where George Washington himself spent time. A 10 mile drive gets us to Lexington Green where we take in the significance of the site and the story of what happened that night in April 1775. Next the picturesque town of Concord, to the Old North Bridge and how the second battle of the war took the British by surprise. Pick up and drop off in Downtown Boston, a stop for lunch along the way (not included in price of tour) and as light or heavy on history as you'd like.

Boston, Cambridge, Lexington and Concord Private Car Tour

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

Enjoy a private, customizable day trip from Boston to Newport in a comfortable vehicle reserved for your group. This is private transportation with flexible sightseeing stops; the chauffeur does not provide guided commentary. Visit one, two, or up to three Newport mansions based on your tickets, entry times, attraction hours, and preferred pace. Most guests visit two mansions, stop for lunch, then choose a third mansion or another Newport attraction. When time allows, options may include downtown Newport, Ocean Drive, or a brief Cliff Walk stop. Your chauffeur handles transportation between stops, so your group can relax without navigating traffic or parking. All customization must fit within the included 8.5-hour service period and is subject to traffic, weather, attraction hours, and ticket times. To stay on schedule, the return to Boston should begin around 4:00 PM. Mansion tickets and lunch are not included.

Private Newport Mansions Day Trip from Boston

8 hours 30 minutesFree Cancellation

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Top Attractions in Boston

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Attractions

What are people saying about Boston

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!

Lexington and Concord 3 hour private car tour from Boston

Timothy_P, Aug 2026

We thoroughly enjoyed our...

We thoroughly enjoyed our tour to Lexington and Concord. Martin was a fantastic guide who did a great job engaging our kids. We had a brief tour of Beacon Hill on our way out of town. The amount of time in Lexington and Concord was perfect with a lot of great information shared. We highly recommend this tour.

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!

Boston Private 3-Hour Tour by Car

Katherine_F, Apr 2026

Don't hesitate to book!

Joan was the best! We had a great time cruising around Boston, and learned a ton. It was a wonderful combination of historical facts and fun. Doing a private tour let us ask all kinds of questions and have the tour fully customized. Joan was flexible with where she dropped us off at the end too. My 12 year old son said it was his favorite part of our trip to Boston! Highly recommend!

Boston Private City Tour

Preety_K, Feb 2026

Sam is hands-down the...

Sam is hands-down the best guide we’ve ever had. He went completely out of his way to make sure we had a great time, even adjusting the itinerary on the fly to suit our interests. He knows all the 'hidden gems' away from the tourist crowds and felt more like a local friend than a tour guide. Our trip wouldn't have been the same without him!

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.

Boston Sightseeing Tour - a fully-narrated driving tour

Dyan_K, Oct 2025

Fantastic tour w/Peter

Peter was punctual & full of historic information + he was funny. We had a wonderful time with him. He filled us in on all the points of interest, giving us from the time the British and other countries came here all the way through about the 1950s. If we needed to make a stop, he was willing to do that. And all the anecdotal information that you can’t find in a book was such fun to hear.

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!

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!