Top Boston Cruises &amp; Sailing

Lexington and Concord 3 hour private car tour from Boston

3 hoursFree 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

Premium Private Chauffeur Service

12 hoursFree Cancellation

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

Spend a day tracing America's Revolutionary story in Boston, Lexington and Concord without the inconveniences of self-driving, buses and crowds on this private minivan tour. Sit back and view the sights as your driver-guide recounts facts and snippets you may not hear otherwise. Highlights include Boston's Paul Revere's House and Tea Party ships, plus Lexington's landmarks and Concord's gems, including the home of 19th-century 'Little Women' author, Louisa May Alcott.

Full-Day Minivan Tour of Revolutionary Boston, Lexington and Concord

Cruise Boston Harbor aboard a luxury yacht, complete with superb city views and a buffet brunch featuring both breakfast and lunch offerings. For 2-hours you'll explore the waters from Rowes Wharf to the Charlestown Naval Yard and back, sailing past sights such as Castle Island and Boston Light. Spend some time enjoying the yacht's three climate-controlled decks or dancing to the sounds of a live DJ mix.

City Cruises Boston Premier Brunch Cruise on Odyssey

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

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

3 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

City Cruises Boston Premier Lunch Cruise

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

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

1 hourFree Cancellation

Private Transfer in Boston (BOS) Airport/Home/Hotel/Work

30 minutes to 1 hourFree 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

Boston Full Moon Cruise Tour

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

20 minutesFree 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)

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

15 minutesFree Cancellation

Private Day Trip From Boston to the Newport Mansions

10 hoursFree Cancellation

Boston Sightseeing Tour - a fully-narrated driving tour

3 hoursFree Cancellation

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

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

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

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

Boston Private 3-Hour Tour by Car

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Must-Dos in Boston

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What are people saying about Boston

Rebecca_S, Sep 2026

Christian, #1 tour guide

If you want to see Boston with a 3-Hour Tour by car, I would recommend using this company. Our tour guide, Christian, was polite, considerate of our requests on the trip, and extremely knowledgable regarding all aspects of Boston history. Joan, handling our tour request, was fast getting back to me regarding tour time options and making arranging that insured our tour easy and enjoyable.

Boston Harbor Brunch Cruise

Deborah_B, Sep 2026

Not crowded brunch

We had the brunch at 12:00 and there wasn't a lot of people thank goodness we really enjoyed ourselves a little bit pricey almost $500 for seniors and a child but we had a lovely time and I would do it again. The staff are very sweet and helpful thank you

Lexington and Concord 3 hour private car tour from 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!

City Cruises Boston 90-Minute Harbor Sunset Sightseeing Cruise

David_S, Sep 2026

Narrator was great

The lady who was narrating was great I thought her name was Nancy the whole time, but her real name was Holly, but I'm gonna call her Nancy forever and tell everyone to go see Nancy at Boston Harbor cruisers, cause she was a delight Her real name is Holly, but is it? It's Nancy.

Private City Tour of Boston and Cambridge

Lindsay_B, Aug 2026

Great Day in Boston with BJ!

This tour definitely exceeded my expectations! We had 3 generations of travelers from ages 7-79 and everyone really enjoyed it. It was all of our our first time in Boston and this was a great activity for our first day. We had BJ as our guide and he communicated with me in advance of the tour and picked us up timely at our hotel. Our first stop was an Italian coffee/pastry shop in the North End. There we talked through a loose plan for the day, but the best thing about this tour was that BJ was totally flexible… There were certain places we wanted to spend more time, and BJ accommodated us, provided interesting commentary and even helping entertain the kids when one was bored and the rest of us were taking a little longer at a site/exhibit. His vehicle was clean, fully functioning and he had parking passes at certain key places allowing us to pack a lot into one day. I would definitely recommend this tour and BJ to anyone visiting Boston! We will talk about this day and the places we visited for years to come. Already want to plan a return trip! :)

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!

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

Jude_B, Dec 2025

Romantic and silly date night

Food was honestly so-so, but the drinks were absolutely delicious. The music was great, decor was beautiful, and staff were all obviously having a great time. The view and ride was amazing as well. Being able to step out onto the deck, even though it was cold, to get a perfect view of the skyline was amazing. Thanks for an unforgettable date!

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!