See Boston Harbor’s sights from the water on this day sail aboard a replica of a pilot schooner. Step aboard the boat and sail off through the harbor, bound for Spectacle Island, Fort Independence, Castle Island, and Long Island. Snap photos of Boston's coast from the water and feel free to ask the captain or crew questions about the passing landmarks.

Choice of Several departure times to fit your schedule departures throughout the day
Water cooler available to fill your reusable bottles
Choose between from two duration lengths
Card-only bar on board the boat serves wine, beer, and soft drinks

What's Included

Duration: Choose between a 1.5 or 2 hour sailing experience

Beverages are not included, but are available for purchase by credit card only.
Gratuities (recommended for the captain and crew)

Meeting and Pickup

Meeting point

Classic Harbor Line Boston
60 Rowes Wharf, Boston, MA 02110, USA
The boat departs from Rowes Wharf, directly behind the Boston Harbor Hotel, located at (for GPS) 400 Atlantic Avenue, Boston (02110). Check-in at Rowes Wharf is located in the Ferry Terminal, a climate controlled public space, located on the wharf only steps away from our dock. If guests are lost or running late, please call us at 617-951-2460.

End point

This activity ends back at the meeting point.

What To Expect

Classic Harbor Line Boston MA Day Tours (Pass By)

Fan Pier (Pass By)

Boston Harbor Islands State Park (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Children must be accompanied by an adult
Minimum drinking age is 21 years. Coolers and outside alcoholic beverages are not permitted
Service animals allowed
Dress for the weather - it's often cooler on the water

Near public transportation
Please let us know in advance if assistance is required for boarding
Only animals that perform a manual task to assist a person are permitted aboard. Emotional support animals and pets are not permitted
Most travelers can participate
Plan to arrive at the ticket booth 15-30 minutes prior to the departure time. The meeting point is located directly behind the Boston Harbor Hotel in the Ferry Terminal just steps away from the dock. Boarding begins 5 minutes prior to the scheduled departure time.
This tour/activity will have a maximum of 41 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

For a full refund, you must cancel at least 24 hours before the experience’s start time.
If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
Any changes made less than 24 hours before the experience’s start time will not be accepted.

Cut-off times are based on the experience’s local time.
This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

Featured review

Carol_H

Excellent service, cool seeing the staff hoist the sails… I enjoyed the drink service and the Captain and crew were very knowledgeable about the sights and the views of the Boston Harbor were amazing!

Reviews

4.5

236 reviews

Total review count and overall rating based on Viator and Tripadvisor reviews

Reviews by Viator travelers.

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Showing 1-10 of 236 reviews

Best idea for our trip!

Elanie_W, Oct 2023

10/10 would recommend! Staff was amazing and views exceptional! Will Be taking this trip again next visit to the city.

Viewing Boston from the water

jmhammond, Oct 2023

Despite some clouds and cool Boston weather, it was a great sail. The crew is fantastic. It’s great to see the harbor from the water and hear interesting historical stories. We met great people on board, and enjoyed having a drink while cutting through the beautiful waters.

i’d rather be sailing

Frances_Q, Oct 2023

fun time with captain and crew! they were knowledgeable, professional and enthusiastic. til next time!

Excellent

Kaelah_M, Oct 2023

The team was friendly. It was a relaxing & enjoyable experience! The weather was great, and the views were peaceful and amazing

Great experience!

Vanessa_V, Oct 2023

To be clear… this is NOT a guided tour; this is an experience. It gives you the opportunity to be out in the harbor on a beautiful boat and see the city from a different perspective. It was a great experience and the crew of the boat were wonderful hosts and clearly very competent at sailing. Highly recommend.

A wonderful adventure

Peter_W, Sep 2023

A very enjoyable and relaxing experience! It was wonderful to enjoy a Fall evening overlooking Boston from the water. The staff was very friendly!

Sunny Peaceful Sail Escape

David_G, Sep 2023

Peaceful, sunny sail. Learned a lot watching the awesome Crew Saul the boat, nice breeze and wonderful views, we loved it!!

Sailing, takes me away!

Lori_M, Sep 2023

It was awesome! The weather was perfect. The crew were so nice, and the water was beautiful! Such a relaxing g way to end our trip to Boston! ❤️

Sailing, take me away to where I want to be.

Julie_R, Sep 2023

Such a gorgeous day and beautiful, peaceful sail in the harbor and outer islands. Highly recommend and will most certainly do it again!

It was alright

Emily_M, Sep 2023

The captain and crew were polite and the boat was beautiful, but for this being a sightseeing tour, there wasn’t any sightseeing. There was no guided tour or audio to listen to. The crew didn’t point out any sights or talk about anything. It was really just, you get on a boat and drink. Was a little disappointed that no sights were talked about.

Great Sail

Lisa_R, Aug 2023

Beautiful day to sail. The crew was knowledgeable and friendly. Sailboat was clean and well taken care of.

MUST DO WHEN IN BOSTON

Eve_P, Aug 2023

Beautiful views a definite must do. Crew were friendly and knowledgable about Boston and sailing. I will do this again next time I'm in Boston.

Anniversary gift

Lina_A, Aug 2023

It was a beautiful experience It was a great Anniversary gift The crowd was very awesome Very clean with the instructions for the guest

Smooth sailing

Melvin_S, Aug 2023

First time ever on a sailboat is a perfect day the winds were up the crew was great and very attentive. I highly recommend this trip for couples for a Family.

A little boring

Stephanie_F, Aug 2023

We were so excited to do this cruise because we had never been on a sail boat. The crew was good and safe, but the cruise itself was a bit boring and on this type of boat you are pretty much in the direct sun the entire time. Although we are glad we had the experience we won’t do this type of cruise again.

Response from Host, Aug 2023

Hello, Thank you for providing this review of our day sail. We are glad that you had a great crew, and we are sorry to hear that you were not thrilled by the experience. Sailing can range widely from peaceful and relaxing to very fast and exciting, and that largely depends on the weather of the day. We do our best to provide a special experience on each sail, but some factors are up to nature. We do hope you will reconsider sailing again as you might have a different view if you get to try it on a day with ideal temperatures or more wind! The difference can be as stark as night and day! Warmly, Classic Harbor Line Boston

Relaxing and beautiful views from the Harbor

Marcus_M, Aug 2023

Staff was amazing. Professional and friendly. It was a great relaxing time. The ocean breeze and views from the harbor were great. I highly recommend

It was a wonderful experience. The crew was absolutely great.

Tammy_F, Aug 2023

The whole experience was absolutely wonderful. The whole crew was great, the boat was exceptional and perfect weather.

amazing sail around boston harbor!

Jenna_M, Aug 2023

from start to finish we had the best time setting sail around boston harbor. the staff was amazing, informative, kind, asked to take our photo and so fun! the weather was perfect. my only complaint is that we wish it was longer because we didn’t want it to end! thank you for having us - we will be back for sure!

Peaceful, Relaxing, Awesome Ride

Craig_M, Aug 2023

The trip was very peaceful and relaxing. The crew was patient and attentive. The skyline views are the best Boston has to offer. This boat tour is a must do.

Absolutely lovely sail on...

Kristen_S, Aug 2023

Absolutely lovely sail on a beautiful boat! The Captain and Deckhands were knowledgeable and friendly. Highly recommend!

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