Top Boston Cruises &amp; Sailing - page 4

Flynn Cruise Port Boston to Boston hotels - Arrival Private Transfer

35 minutesFree Cancellation

Price varies by group size

from $121

Boston to Portland ME Private Car service

2 to 3 hoursFree Cancellation

from $439

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

Price varies by group size

(2)

from $81

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

15 minutes to 1 hourFree Cancellation

4.4

(30)

from $129

Travel privately between Boston and the Woods Hole/Falmouth area in a clean, professionally chauffeured vehicle reserved exclusively for your group. Choose from a black sedan, SUV, or passenger van based on your group size and luggage needs. For Logan Airport arrivals, we track your flight and provide clear instructions for meeting your chauffeur at the designated Limo Pickup Area. Tolls, airport fees, bottled water, and luggage assistance are included, helping make the trip straightforward from pickup to drop-off. This service is especially convenient for travelers connecting with Martha’s Vineyard ferry service, while also serving hotels, residences, and other approved addresses within the designated pickup and drop-off zones. Communication may be available in English, Portuguese, or Spanish, subject to chauffeur availability. Each reservation is private and covers one-way transportation only, allowing your group to travel without shared-ride stops or unnecessary detours.

Boston Logan to Woods Hole and Falmouth Private Car Service

Boston Logan to Woods Hole and Falmouth Private Car Service

1 hour 30 minutes to 3 hoursFree Cancellation

from $411

Round trip Airport Transfer: Boston Logan to Downton Boston

30 minutesFree Cancellation

3.0

(4)

from $325

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

Price varies by group size

from $94

Local Bostonian and Historical Driving Tours

1 to 3 hoursFree Cancellation

from $600

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

2 hoursFree Cancellation

4.8

(9)

from $106

City Cruises Boston Premier Lunch Cruise

2 hoursFree Cancellation

4.3

(7)

from $92

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Top Attractions in Boston

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Attractions

What are people saying about Boston

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.

Boston Harbor Sunset Sail Tour

Teri_P, Jul 2026

Simply Wonderful

Make sure to get there 15-30 minutes early for check-in and make sure to dress accordingly and enjoy the experience of the wind in your face the smell of the ocean and the BEAUTIFUL skyline and the most helpful & knowledgeable staff. Happy Sailing ⛵️ 😀

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.

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 Harbor Brunch Cruise

Michelle_W, Apr 2026

Fabulous Staff and Brunch

The breakfast brunch was amazing! And the staff was also superb. The 2 girls working the event were super kind and did everything they could to ensure a fabulous experience. Definitely a 10/10 experience! The only downside was it was a bit hard to hear the narration. But I know the guide was going to try to address it for future voyages.

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 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!