SAILING, SUP & KAYAK
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, kayaking and paddleboarding lessons, available for all ages and levels of experience.
Looking for a more relaxing day on the Cape Cod waters? Let us do the work. Private tours are available for sailing, kayaking and stand-up paddleboarding.
PRIVATE TOURS + LESSONS
EXPLORE CAPE COD
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.
LEARN & DISCOVER
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.
For a calm, breezy day on the water, take a guided SUP paddleboard or kayak tour of Bucks Creek, Nantucket Sound and Taylor's Pond. Get acquainted with local wildlife and enjoy a leisurely outdoor experience that’s great for kids, families and teams of all ages.
Launch right from the beach or creek for your tour. We'll handle all of the heavy lifting, setup and lifejackets. You bring the fun!
*Contact us for pricing & reservations
PADDLE & KAYAK TOURS
FOR QUESTIONS ABOUT LARGE PRIVATE
GROUPS OR MULTI-DAY LESSONS,
PLEASE CONTACT US.