Boston Harbor Sunset Sail Tour

Recommended by 95% of travelers

Badge of Excellence

Boston, USA

High interest

Booked 2 times today.

2 hours (approx.)
Offered in: English

Why travelers loved this

4.8

· Kelsey_D ·

May 2026

This was such a fun experience! I’ve never been sailing before and you really get the sailing experience! Alex was awesome and made sure to get our picture even while working the sails. Claire Hannah were great and really personable! Dante gave us a great ride! It got our adrenaline going while we also felt safe. Also they had drinks!! Great ride thank you!

· gail_V ·

May 2026

Just book it ! The captain Eric and crew were wonderful. The energy on the boat was fantastic. The temp was unseasonably low . They offered blanket's with their logo for $7 each . Great price and such a classy thing to do . The view as the sunset, going from light to dark stunning . The city lights were gorgeous

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Overview

Spend two hours sailing on the Boston Harbor as the sun goes down, taking in the sights of the city skyline. Your captain will set sail and take you on a smooth cruise along the waterfront in a comfortable schooner, with a friendly and informative crew who’s happy to help you have the best possible experience while you’re on the water.

Set sail for two hours of stunning sunset views
Spot local Boston landmarks from the water
Buy beverages on board
A friendly crew on hand to answer any questions about the local area

What's Included

This is a 2 hour sailing experience in Boston Harbor.
This is not a narrated tour, but the crew is available to answer questions on the sights & landmarks

Beverages are not included, but are available for purchase by credit card
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 400 Atlantic Avenue, Boston. Check-in at Rowes Wharf is located in the Ferry Terminal, a climate-controlled public space, only steps away from our dock. If lost or running late, please call us.

End point

This activity ends back at the meeting point.

Ticket Redemption Point

Classic Harbor Line Boston, 60 Rowes Wharf, Boston, MA 02110, USA

Itinerary

Classic Harbor Line Boston

2 hours • Admission Ticket Included

Fan Pier (Pass By)

Boston Harbor Islands State Park (Pass By)

Castle Island (Pass By)

Additional Info

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

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
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 is not a narrated tour, but the crew is available to answer questions on the sights & landmarks as we sail
This experience will take place on Schooner Adirondack II or III
The official route of this experience will depend on the wind
Large group bookings are not permitted. Multiple bookings are subject to added fees or cancellation by operator
This tour/activity will have a maximum of 80 travelers

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Cancellation Policy

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

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Sara_J

What an amazing way to experience the Boston Harbor! The deckhands and captain were attentive and friendly, always ready to answer questions or get your drink order. The views were unbeatable and we topped off the night with our sister-in-law getting engaged at the bow of the boat right after we docked. Highly recommend for out of town visitors or locals alike!

Reviews

4.8

based on 141 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Sunset Cruise

Maria_T, May 2026

Great sunset cruise. Friendly crew. Crew explained history of Boston Harbor. Plenty of room to sit on boat. Cash bar.

Just book it ! You will not be disappointed.

gail_V, May 2026

Fun fun fun

Vyshnavi_S, May 2026

We loved it! The crew was absolutely fun to be around ♥️ Would definitely recommend family and friends

A wonderful way to...

Lisa_S, May 2026

A wonderful way to experience Boston Harbor! A wonderful experienced crew allows you an up close and personal sailing experience. The crew is happy to share stories of how Boston Harbor has changed and not changed over the years. Highly recommend!

Great Sailing Experience

Kelsey_D, May 2026

Beautiful sunset framed...

Sharon_F, May 2026

Beautiful sunset framed views of the Boston skyline. Nice to see the harbor islands up close and to learn some of the history and legends connected with them

This was an incredible...

Nicole_G, May 2026

This was an incredible experience! It was the highlight of my trip. The views were amazing and the staff were very helpful and friendly.

Highly recommend! Captain...

Jodi_R, May 2026

Highly recommend! Captain & crew were amazing. They took excellent care of us! Sunset was stunning! We loved the experience!

Excellent cruise with great city views!

Amanda_S, May 2026

Our sunset cruise was amazing! Great views of the city skyline and the surrounding area. The crew, Alex, Claire, Charlie and Eric were so friendly and shared so much knowledge about the city. We would highly recommend this cruise and hope to go on another when we return to Boston.

Friday October 17th

Anh_F, Oct 2025

Dante, Charlie, n’ Claire had us on one of their last cruises of 2025. They were so friendly, knowledgeable, and constantly made sure we were doing ok. Had the best time.

Love Bos

Andrea_G, Oct 2025

Great Sail in Boston - BOS love my city! Great sail, drinks, beautiful sunset sail. Great crew members

I would recommend it and do it again! Staff super kind and friendly.

Katia_H, Oct 2025

Amazing time. Friendly, small enough and gorgeous sunset! The staff was friendly. They were also offering drinks if you want.

Sunset sail

David_R, Sep 2025

Beautiful cruise in the harbor. Great backdrop of the city at sunset and planes landing over your head. Great and helpful staff.

Beyond our expectations

Kathryn_h, Sep 2025

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!

This trip is a must!...

Marisol_R, Sep 2025

This trip is a must! Beautiful views with amazing weather. The staff was wonderful and full of knowledge. Can't beat the experience well worth every penny.

The boat that I...

Erin_B, Sep 2025

The boat that I originally booked (Adirondack II) was cancelled I’m assuming due to the weather, so the booking office called to rebook for an hour on a “bigger boat” or cancel. I chose to rebook. Once I arrived at the pick up location, the “bigger boat” was more like a booze cruise ferry, not at all what I thought would be the replacement boat. It was quite disappointing.

Response from Host, Oct 2025

Erin, thank you for booking a cruise with us and taking some time to provide your valuable feedback. We are sorry to hear that the motor boat with an enclosed cabin that was offered due to weather was not a satisfactory alternative to sailing on one of our schooners. A manager has reached out to you to provide some options that should provide a satisfactory resolution. We hope to be able to provide you with the sail you were hoping for on another occasion! - Classic Harbor Line Boston

Relaxing

Bonnie_M, Sep 2025

Enhanced by beautiful weather and city scape. Energetic, polite and knowledgeable young staff Maybe up the drink selection??

Perfect evening in the Boston Harbor

Elizabeth_K, Sep 2025

We had a great experience on the sunset sail. It was easy to find and the captain and crew were great.

Sunset cruise

Wayne_B, Sep 2025

Beautiful night for cruise Had fun with crew and guests Entertaining & educational Highly recommend!

Lovely views!

Anne_K, Sep 2025

Beautiful harbor cruise at sunset on a schooner! Great crew and good drinks! The crew was so nice and the views of the city were great

Gorgeous seeing all of...

Max_S, Sep 2025

Gorgeous seeing all of the islands around Boston. What a beautiful view of Boston’s lights from the water. Crew were great!

Perfect activity I’d do again!!

Genel_R, Sep 2025

The staff was AMAZING! And the experience was perfect! It felt peaceful, relaxing, family oriented and provided a chance to connect with lovely people in a gorgeous setting. Would repeat this and recommend.

Sunset sail boston

joan_T, Sep 2025

Dress warm but blankets available for $7 on board.. WONDERFUL trip!! Also bring your own snacks, beer and wine available on boat

Set Sails On The Boston Harbor

Wendy_M, Sep 2025

It was a wonderful experience! The crew was very interactive with everyone and so accommodating! It was as if you had known them for a long time. I would highly recommend this excursion if you ever visit Boston.

Perfect sailing tour

Acamargo, Sep 2025

Great experience: beautiful sunset, perfect views, friendly and knowledgeable crew, and great atmosphere. This experience wax the highly of my trip in Boston

Perfect!!

Elaina_D, Sep 2025

This sunset sail was PERFECT. The crew was awesome. Honestly, what more is there to say? It was a great experience. Highly recommend for date night or a chill evening out!

Amazing Experience & Crew

Barb_R, Sep 2025

Must take the cruise, the whole crew and the captain were fantastic, wonderful hospitality, quiet and peaceful cruise out of the bay in Boston. You can take a snack with you and enjoy the refreshments the crew serves.