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Amazing daysailer rentals in Maine, United States.

5.0(Average of 29 reviews in this area)
View our Maine daysailer boating guide
7 listings
32ftSailing in Rockland · 6 guests


Sunfish Sailboat on Merrymeeting Lake in New HampshireSailing in Lake Winnipesaukee · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

22ft Catalina Daysailer Boat Rental in Montauk, New YorkSailing in Montauk · 5 guests

22ft Catalina Daysailer Boat Rental in Montauk, New York

LEARN TO SAIL on THE MOOSE!Sailing in Brooklyn · 4 guests


Hunter 26.5 Day Sailor - Club Racer - Cleveland, OHSailing in Cleveland · 6 guests

Hunter 26.5 Day Sailor - Club Racer - Cleveland, OH

Melges 32 - The GetMyBoat Racing ExperienceSailing in Chesapeake Bay · 8 guests

Melges 32 - The GetMyBoat Racing Experience

Charter Cruising Monohull In Nassau & Paradise Island, The BahamasSailing in Nassau · 12 guests

Charter Cruising Monohull In Nassau & Paradise Island, The Bahamas


Daysailer Reviews in Maine

  1. DS
    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    Matt was very accomodating, communicated well, and has great boats. I sailed on his Sunfish... Merrymeeting Lake was a perfect sailing lake. I will sail again!

  2. JP

    This experience has been such an amazing swelling ride for our family. Linda has made this trip even special for accommodating with our needs. She has been a great captain from the start to end. Her gorgeous boat was spectacular! We highly recommend Linda for others to experience a moment to remember. Thank you, Linda for everything. We will be back next year!

  3. PM

    Linda is a top-notch captain and wonderful company on a day of sailing. My family of four had a full day of sailing on beautiful Penobscot Bay and Linda was a great teacher for me and my kids who aspire to have a boat of our own some day. Plus she made a delicious lunch for us. Thanks Linda! We'll do it again!

  4. JR

    Linda provided our family with a wonderful family sailing experience. Our family loved laying on the deck with the wind in their faces and the beautiful landscape. We also appreciated her deep history of the area and allowing us to help sail the boat. There is nothing like experiencing Maine from the water with Linda as your captain.

  5. SR
    Melges 32 - The GetMyBoat Racing Experience

    The boat was in perfect condition, ready for anything we could ask for. Doug sails and races on a weekly basis, often in this particular boat, so his feel for the boat, the wind, and the waters we sailed in are well honed. The boat is forgiving, and Doug was unflappable. An encouraging beginner experience, and very fast under experienced guidance. I did not hope for as good an experience, and cannot offer a higher endorsement. Top marks.

  6. DS
    Charter Cruising Monohull In Nassau & Paradise Island, The Bahamas

    Thank you for a fantastic day!! The crew were super courteous, relaxed, welcoming and highly competent. The sail itself was lovely. They pointed out the best snorkeling spots and changed up the itinerary for us with no notice when we decided ON THE BOAT on swimming with the turtles and adding an extra hour! The entire experience was perfect from the ease of booking, the prompt responses to my multiple email questions, the extra adventure add-ons … to the boat itself which is is impeccably kept. The cabin is the cleanest we have ever been in, and we have sailed a lot! The drinks and food were fresh and delicious. All in all a Father’s Day to remember!!

Boating Guide - Maine Daysailer

Explore the waters of Maine with a daysailer rental.

Maine is a great place to enjoy a day of sailing on daysailer rental. Daysailers are small sailboats that are easy to learn on if you're a beginner sailor. They are easy to manage, with one mast and a small capacity. Daysailers are fun for families looking to get out on the water, or individuals looking to learn a new skill. Book a daysailer rental or charter in Maine to make memories you'll never forget.

Using GetMyBoat to rent your next daysailer.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

GetMyBoat has 7 listings for Daysailer experiences in Maine with 29 reviews.

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