Top Boston Cruises &amp; Sailing - page 4

Boston Freedom Trail Private Car Tour

4 hoursFree Cancellation

from $656

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

Price varies by group size

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

5.0

(1)

35 minutesFree Cancellation

from $122

Price varies by group size

3.0

(4)

Round trip Airport Transfer: Boston Logan to Downton Boston

30 minutesFree Cancellation

from $325

This private car tour is a special edition Rev War 250 tour. We've combined a few lesser known, yet hugely significant Revolutionary War sites in Boston, with the main events in the towns of Lexington and Concord in to a half day tour. Starting in Boston we'll take you to sites where very few tours go and give context to events leading up to the outbreak of the war. 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 sites along the way giving a detailed account of events of April 1775. The itinerary gives the list of sites we'll visit, timings are flexible and the 4 hour tour time includes travel to and from Concord. This tour is perfect for those groups who have limited time available in Boston or groups who have different degrees of interest in the history of that time.

Revolutionary War Boston Lexington and Concord Tour

550

4 hoursFree Cancellation

from $695

Why Choose Boston Pro's Private Historic Tour? Luxury Experience: Our luxury SUV ensures a comfortable and stylish exploration of Boston's best attractions, including a scenic drive along the picturesque Waterfront. Customized Itinerary: Enjoy the flexibility to customize your tour. Whether it's spending more time at Harvard, MIT, or lingering in the charming streets of Beacon Hill, the itinerary is tailored to your preferences. Photo Opportunities: Our tour is designed for avid photographers. From the iconic Acorn Street to the scenic views along the Waterfront, every moment is a photo opportunity that captures the essence of your Boston experience.

2 to 3 hoursFree Cancellation

3.0

(1)

Boston City Private Tour

from $578

Boston Freedom Trail Walking Tour | Small Group

4.5

(99)

1 hour 30 minutesFree Cancellation

from $45

5.0

(1)

Boston to Portland ME Private Car service

2 to 3 hoursFree Cancellation

from $439

1 hour to 1 dayFree Cancellation

from $125

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

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

1 2 3 4

Top Attractions in Boston

1 / 2

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!

Boston Architecture + History Walking Tour + Fun Photo Tips

Kristina_H, Mar 2026

Book now! Saba is wonderful!

We had such a great experience on the Boston Architecture, History + Photo Walking Tour—this was easily one of the highlights of our trip. Our guide, Saba, was incredibly informative, engaging, and thoughtful throughout the entire tour. What really stood out was how attentive she was to our interests. Based on a conversation we had during the walk, she even took us to see an additional statue that wasn’t originally on the route, which made the experience feel very personalized. Her knowledge of Boston’s architecture—especially in the Back Bay and Beacon Hill areas—was impressive. She shared so many fun facts and historical insights that brought the buildings and streets to life in a way we wouldn’t have experienced on our own. It never felt like a scripted tour; it felt like walking through the city with someone who genuinely loves and understands it. If you’re looking for a tour that blends history, architecture, and great storytelling (with plenty of photo-worthy spots), I highly recommend this one—especially if you get Saba as your guide!

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.

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 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

Kathryn_h, Sep 2025

Beyond our expectations

Beyond our expectation - the sunset cruise takes you to the parts of the harbor that have spectacular views. Planes landing at Logan airport was a sight to behold as they flew over head. The crew were engaging and knowledgeable and added some history and insight to points of interest. Highly recommend!

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!!!!