PRIVATE SAILING, SUP & KAYAK EXPERIENCES
Chatham Sailboat Rentals is your go-to beachfront watersports destination for the perfect day in the sun.
Looking for a relaxing day on Cape Cod's waters?
Private sailing tours, kayaking tours, and paddleboarding tours are available for groups, couples, families, friends, retreats, parties, or individuals.
For a hands-on experience, let our experts show you the ropes with private sailing lessons, available for all ages and experience levels.
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Scroll or click for more details on private sailing tours, private sailing lessons, and private kayak & paddleboarding tours.
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Or, check out our reviews here!​
TOURS & LESSONS
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EXPLORE CAPE COD BY SAILBOAT
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Approx. 1.5 hours | up to five (5) people | $269
great for: seal spotting & sightseeing​​
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Experience the beauty of Cape Cod's waterways with private sailing tours of Chatham on the beautiful and protected Nantucket Sound.
A memorable experience for families, kids, groups or corporate retreats, bachelorette parties, couples, or solo adventurers, take in picturesque views of Chatham during a spectacular sightseeing sailing tour on our Hobie Getaway sailboat.
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Highlights on this unique trip often include: chances for seal spotting, a look at Chatham's famous Lighthouses, a cruise over to Monomoy Island, and exploring the Cape Cod waters from a whole new perspective.
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Our friendly, expert sailing captain handles all boat operations and customizes each experience to your interests to ensure you have the best time on the water.​
When you're ready, contact us to make a reservation.
SAILING TOURS
Private sailing ​tours are given on our Hobie Getaway catamaran sailboat.​​​
​We recommend booking at least one week prior during peak summer months.
All participants must know how to swim.
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LEARN TO SAIL IN CHATHAM
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Approx. 1.5 hours | up to five (5) people | $269
private sailing lessons for kids and adults
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Whether you’re a beginner looking to learn the fundamentals of sailing, 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, private, and personalized sailing lessons for each sailor.
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When you're ready, contact us to make a reservation.​
SAILING LESSONS
​Private sailing lessons are given on our Hobie Getaway catamaran.​
We recommend booking at least one week prior during peak summer months.
All participants must know how to swim.
GREAT FOR GROUPS, FAMILIES, & FRIENDS
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For a calm, breezy day on Cape Cod's waters, take a private, guided stand-up paddleboarding or kayaking 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.
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Launch right from Ridgevale Beach or the creek.
We'll handle all of the heavy lifting, setup and lifejackets.
You bring the fun!
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$150 for tour guide
plus +hourly rate for each kayak/paddleboard
Approximately 1 hour
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When you're ready, contact us to make a reservation.​
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*We recommend booking at least one week prior during peak summer months
