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Chatham Sailboat Rentals, located in South Chatham, MA, right on Ridgevale Beach, is Cape Cod's best destination for waterfront sailing, kayaking and stand-up paddleboarding (SUP), as well as expert-led boat tours and lessons. 

In conjunction with the Ridgevale Beach Snack Bar, a family owned and operated business for more than 60 years, our location gives you convenient access to the kid-friendly beach and expansive creek, plus a range of top-notch Hobie Catamaran, Sunfish, Kayak, and Stand-up Paddleboard rental and tour options.


Sailing guests enjoy complimentary parking for the duration of their rental, and all rental rates include life jackets, rigging, launching and de-rigging services to ensure a fun and hassle-free day by the sea.


Whether you’re a novice kayaker ready to explore the intricate estuaries of Bucks Creek, or a more experienced sailor wanting to cruise the coast of Monomoy Island, you'll enjoy the most breathtaking views Cape Cod has to offer when renting our paddleboards & boats, with a fleet of Hobie Getaways, Hobie Waves, Sunfish, Hobie Kayaks, and a range of stand-up paddleboards for all ages. 



We launch our sailboats right off of Ridgevale Beach and onto Nantucket Sound where protected warm waters let you cruise the Chatham shoreline at your leisure and within your comfort zone. 

Stay close and spot Cape Cod's iconic landmarks, or take a short sail out to Monomoy Island for prime seal watching.

Kayakers and paddleboarders can explore the calm creeks and wildlife within the estuaries along the family-friendly beach.



Expert-led private sailing tours and lessons offer an authentic look at Cape Cod by sea, with chances for Seal spotting and ideal sightseeing opportunities. Ridgevale Beach is only a quick sail to two of Chatham's famous Lighthouses and an easy cruise to Monomoy Island for day trips & discovery.


The perfect outdoor activity for families, couples, kids and marine life enthusiasts.




Enjoy a laid-back beach-style lunch of made-to-order Lobster Rolls, cheeseburgers, fries, and other Cape Cod favorites at the Ridgevale Beach Snack Bar.

Our historic, family-run store also offers items like beach chairs and umbrellas for rent or purchase, floats, toys, sunscreen, nets, sunglasses, drinks, and ice cream.


Everything you need for a day at the beach.

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SUP Rentals Ridgevale Beach
Sailboat Rentals
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SUP Paddleboarding Chatham
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Cape Cod Sailing Exit 11
Hobie Kayak Rentals Chatham, MA
Sailboat Rentals Cape Cod
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