Boston by Boat, Like Never Before

Whether cruising or racing, our private sailing events offer a totally unique way to experience the city. Accommodating groups as small as 6 and as large as 150+ in a variety of formats, sailing with Courageous is fun, approachable, and entirely unique.

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Select your group size to see available experiences.

Island Cruise

Set the sails and take in the skyline as you cruise past the city and out to the Historic Boston Islands on our J80s— cruising boats 27’-35’ feet in length. With high booms, open cockpits, and a large keel for stability, the J80 makes for a fast and social sailing experience.

3 Hours | $250 per person

Accommodates up to 12 participants on 2 boats

Courageous Cup — Performance Racing

The “Courageous Cup” puts you on a race course aboard our J80s for fast and strategic competition. Participants will compete in a series of head-to-head races run in the America's Cup/Match race format.

2 Hours | $175 per person

+$250 Race Committee fee.
Accommodates up to 18 participants on 3 boats (4-6 sailors per boat)

Harbor Cruise

Attendees join us for a scenic cruise around Boston Harbor in the comfort of our Rhodes 19 sailing vessels. We invite participants to take the helm and learn the role of the “skipper,” or sit back, relax, and let us do the work.

2 Hours | $120 per person

Accommodates up to 60 participants on 15 boats (2-6 sailors per boat)

Fun Regatta

With the Boston Skyline as a backdrop, participants on Rhodes 19s engage in a fun competition sailors call a regatta. A small race course is set just off the Courageous dock making it perfect for spectators on Pier 4. It starts with 20 minutes of instruction on sailing basics, and then it’s time to race against friends, family, and colleagues.

2 Hours | $150 per person

+$250 Race Committee fee.
Accommodates up to 60 participants on 15 boats (4 sailors per boat)

Model Boats

Students will build their own model boat out of a variety of recycled and new materials. They will learn about how sailboats work, follow the design process, and then compete in buoyancy, speed, and marketing skills.
Duration: 6 weeks
Standards: 3.ETS.1.1, 4.ETS.1.5, 4.ETS.1.3, 5.ETS.3.2, 6.ETS.1.6, 6.PS.1.7, 6.ETS.2.1, 6.ETS.2.2, 6.ETS.2.3

Land Boats

Students explore the properties of wind in the context of sailboats by creating a sailboat with wheels that can travel across land.
Duration: 4 weeks
Standards: 3.ETS.1.1, 4.ETS.1.5, 4.ETS.1.3, 5.ETS.3.2, 6.ETS.1.6, 6.ETS.2.1, 6.ETS.2.2, 6.ETS.2.3

Kites

Students explore air pressure and the forces of flight before creating their own kite. They move through the design process and take inspiration from around the world to develop and build their creation.
Duration: 5 weeks
Standards: 3.PS.2.1, 3.ETS.1.2, 3.ETS.1.4, 4.ETS.1.3, 4.ETS.1.5, 5.PS.1.1, 5.ETS.3.2, 6.ETS.2.2

Wind Turbines

Students will learn about renewable energy, wind pressure, and aerodynamics in order to construct their own simple wind turbine. We’ll then hook the turbines up to a small motor and measure how much electricity they produce.
Duration: 4 weeks
Standards: 3.PS.2.1, 3.ETS.1.1, 3.ETS.1.2, 4.ESS.3.1, 4.PS.3.1, 4.PS.3.4, 4.ETS.1.3, 4.ETS.1.5, 5.ESS.3.1, 5.ETS.3.2, 6.ETS.1.1, 6.ETS.2.2

Egg Drop Challenge

In this classic project, students will explore the force of gravity and its effects on objects, mainly eggs. Using the design process, they will develop an apparatus to protect their egg when it’s dropped from a certain height.
Duration: 3 weeks
Standards: 3.PS.2.1, 3.ETS.1.1, 3.ETS.1.2, 4.PS.3.1, 4.ETS.1.3, 4.ETS.1.5, 5.PS.2.1, 5.ETS.3.2, 6.PS.2.4, 6.ETS.1.1, 6.ETS.2.1, 6.ETS.2.2

Volcanoes

Research volcanoes from around the world and then use paper mache to build and paint it to reflect its location. Finally, learn a simple chemical reaction and use it to create an eruption!
Duration: 3 weeks
Standards: 4.ESS.2.2, 4.ETS.1.3

Marine Debris Skimmer

Using recycled materials, students will design, construct, and test their own marine debris skimmer. Students will learn about the problem of plastic pollution and some of the design solutions currently being deployed in our world’s oceans.
Duration: 4 weeks
Standards: 3.ETS.1.1, 3.ETS.1.2, 3.ETS.1.4, 4.ETS.1.3, 4.ETS.1.5, 5.ESS.3.1, 5.ETS.3.2, 6.ETS.1.1, 6.ETS.2.2

Build-Your-Own Crab Trap + Field Trip

Students will spend some time learning about the crab and lobster fishery in the Gulf of Mexico and then design and construct their own crab trap. We’ll deploy the trap at our site in Charlestown and they can come pull it up and meet some crabs when they visit on a field trip.
Duration: 5 weeks
Standards: 3.ETS.1.1, 3.ETS.1.2, 3.ETS.1.4, 4.ETS.1.3, 4.ETS.1.5, 6.ETS.1.1, 6.ETS.2.1, 6.ETS.2.2

Water Filter

Within the framework of water scarcity and access, both on a local and global scale, students will explore what makes water clean, where we get our water, and then design and construct their own simple water filter.
Duration: 5 weeks
Standards: 3.ETS.1.1, 3.ETS.1.2, 3.ETS.1.4, 4.ETS.1.3, 4.ETS.1.5, 5.ESS.3.1, 5.ESS.3.2, 6.ETS.1.1, 6.ETS.2.2

Local Field Guide (Seasonal)

Whether urban or rural, earth is full of life. In this project, students will explore their schoolyard ecosystem and create a field guide including local species, seasonal things to look out for, and ecosystem functions. Please note that this project takes place mostly outside so it’s best to run it from September to November or March to June.
Duration: 6 weeks
Standards: 3.ETS.1.1, 3.LS.1.1, 4.LS.1.1, 5.LS.2.1

Back on Dry Land

Before, after, or during your private sailing experience, our amenities on Pier 4 create even more possibilities for your event:

End with a toast with complete food and beverage service
Hit the dance floor with live music in our spacious and elegant tent
Head indoors at the Ropewalk Building for gifts and cake, or apps and a silent auction

Explore Venue Rentals at Pier 4