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2-Hour Sail on Boston Harbor

Boston, United States

Experience hosted by Caitlyn & Emilio

2 hours
Up to 4 people
Hosted in English

What you'll do

Once we fit you with a life-jacket, you and your instructor will head down to the dock to your 19' sailboat. From there you will head off for a 2-hour sail on historic Boston Harbor. You can take the helm and learn how to steer the boat, or enjoy the city and let us do the work, our instructors will take their lead from you.

Our 2 hour sails are flexible and make for a great date night, family outing, or fun excursion with friends.

Up to 4 adults or 2 adults and 2 kids can comfortably fit on board. The boats are keelboats and are therefore meant to be a stable platform and easy for participants of all ages to move about on (they are designed NOT to flip over).

Leave your favorite high heels, leather shoes, and dress pants at home. This is experience is designed to be relaxed. Clothing should reflect the weather (and bring an extra layer in case it's chilly on the water). We will try to sail even if its raining so waterproof clothing is encouraged if it's raining (we also have some you can borrow if you need it).
Other things to note
We provide lifejackets. Please dress for the weather, closed-toed shoes preferred.

To book a private outing please book all four spots, otherwise groups smaller than four may be paired with others.
Once we fit you with a life-jacket, you and your instructor will head down to the dock to your 19' sailboat. From there you will head off for a 2-hour sail on historic Boston Harbor. You can take the helm and learn how to steer the boat, or enjoy the city and let us do the work, our instructors will take their lead from you.

Our 2 hour sails are flexible and make for a great date night, family outing, or fun excursion with friends.…

Caitlyn & Emilio's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practising good hygiene and ensuring that all participants wear a mask.
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From $50
/ person
No dates available
This experience usually sells out. Book now.

Meet your host, Caitlyn & Emilio

Host on Airbnb since 2018
  • 387 Reviews
  • Identity verified
Courageous Sailing is one of the country's leading non-profit community sailing programs with 30 years of experience making sailing fun and accessible. In addition to offering 2-hour sails, Courageous Sailing offers a variety of programs to adults and youth throughout Boston. More importantly, it is through funding raised by our adult program (and experiences such as the two-hour sail) that we are able to host close to 1,000 youth in our summer sailing programs.
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About the organisation: Courageous Sailing Center for Youth, Inc



Since 1987, Courageous Sailing, a 501(c) nonprofit, has used the sport of sailing to foster unity and life skills in children of all economic and ethnic backgrounds. We are a nationally recognized, year-round educational center for community sailing and youth development, honored by both US Sailing and Sail Magazine as one of the top 10 community sailing programs in the country.

This is a social impact experience where 100% of what you pay for this experience goes to Courageous Sailing Center for Youth, Inc.

Where you'll be

We will depart from Courageous Sailing on pier 4 in Charlestown and then go where the wind takes us. Landmarks can include: Boston TD Garden, The Zakim Bridge, The Tobin Bridge, East Boston, The North End, and Logan Airport. Don't forget, to see all of these places we won't be sitting in any traffic, we'll be enjoying them from the water, free of stress, traffic, lines, and other hustle and bustle associated with the city.
Haylette
September 2020
Make sure to read the email they send you. The meeting address is there. The meeting address is not the one that appears in the main page of Airbnb.
Jordan
October 2019
Great sail on the harbor with a charitable organization, Courageous Sailing, whose mission includes encouraging and promoting youth. Our boat was led by Captain Max who is knowledge, capable, and friendly.
Mstoll
October 2019
We were a tad bit late and they never made us feel out of place. I expected to be rejected, but they transported us to the sailboat.
Annie
October 2019
It was a chilly day when we sailed but the experience was still a good one. Max was our instructor and he was very knowledgeable and kind. We had a great time.
Nicole
October 2019
Wonderful sailing experience which I was lucky enough to enjoy in rough waters and with just me and the sail instructor. It was absolutely thrilling and fun!
Madison
October 2019
Definitely recommend this experience. The feeling of being on the water, wind in your hair bouncing on the waves, is both thrilling and relaxing at once. We took a cruise from 4-6 and the sun was just starting to set as we came back in. I took my camera and got some stunning photos. It was beautiful.
Definitely recommend this experience. The feeling of being on the water, wind in your hair bouncing on the waves, is both thrilling and relaxing at once. We took a cruise from 4-6…

Activity advisory

Expert industry partners
Every adventure follows industry guidelines. We partnered with the Adventure Travel Trade Association, expert leaders in adventure travel, to define best practices and standards for safety.
Know your comfort level
Please note outdoor activities carry risks, and you may be exposed to dangerous situations as part of this experience. Make sure you can participate safely given your abilities and the conditions (such as location, weather, and equipment).

Things to know

Cancellation policy

Any experience can be cancelled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 4 guests of all ages can attend.

What to bring

Sunscreen

Hat