PRIVATE SAILING, SUP & KAYAK EXPERIENCES

Chatham Sailboat Rentals is your go-to beachfront watersports destination for the perfect day in the sun. Let our experts show you the ropes with sailing lessons, available for all ages and experience levels.

 

Looking for a more relaxing day on Cape Cod's waters?

Let us do all the work. Private tours are available for sailing,

kayaking and stand-up paddleboarding.

TOURS & LESSONS

Sailing, Kayak, and SUP Tours and Lessons in Chatham, MA
Family sailing tours & lessons, Chatham, MA, Cape Cod

 

EXPLORE CAPE COD

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Experience the beauty of Cape Cod's waterways with private sailing tours of Chatham on the Nantucket Sound. Cruise over to Monomoy Island, catch a glimpse of the local seals, and have your camera handy for the most picturesque views of Chatham during a spectacular sightseeing tour on our Hobie Getaway sailboat.

A memorable experience for the whole family.

SAILING TOURS

$225

Approximately 1.5 hours

Up to five (5) people

Tours are given on our Hobie Getaway catamaran

*Contact us to make a reservation.
We recommend booking at least one week prior during peak summer months.

 

 

LEARN & DISCOVER

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Whether you’re a beginner looking to learn the fundamentals, a rusty former expert looking to brush up on your knowledge, or a thrill seeker looking to haul with an experienced teacher, our team will provide friendly, personalized sailing lessons for each future sailor.

SAILING LESSONS

$225 

Approximately 1.5 hours

Lessons are given on our Hobie Getaway catamaran

*Contact us to make a reservation or to learn about scheduling multiple lessons.

We recommend booking at least one week prior during peak summer months.

 

GREAT FOR GROUPS, FAMILIES & FRIENDS

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For a calm, breezy day on the water, take a guided stand-up paddleboard or kayak tour of Bucks Creek, Nantucket Sound and Taylor's Pond. Get acquainted with local wildlife and enjoy an active outdoor experience that’s great for kids, families and teams of all ages.

 

Launch right from the beach or creek.

We'll handle all of the heavy lifting, setup and lifejackets.

You bring the fun!

$75 for tour guide

+hourly rate for each kayak/paddleboard

Approximately 1 hour

Contact us for reservations

*We recommend booking at least one week prior during peak summer months

PADDLE & KAYAK TOURS

 

For questions about large private groups or multi-day lessons, please contact us by phone or email

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