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All listings in Maine

Incredible sailboat rentals in Maine, United States.

4.2(Average of 22 reviews in this area)
6 listings
32ft
Sailing in Rockland · 6 guests

32ft

5.0
$150hour
28' Classic Sloop in Rockland, Maine
Sailing in Rockland · 6 guests

28' Classic Sloop in Rockland, Maine

5.0
$150hour
Bareboat Midcoast Maine aboard the Schooner Yacht Meteor
Sailing in Rockland · 4 guests

Bareboat Midcoast Maine aboard the Schooner Yacht Meteor

5.0
$395day
On the Rocks Cocktail Cruises - Slow cruises, tasty drinks & relaxing vibes
Events in Portland · 6 guests

On the Rocks Cocktail Cruises - Slow cruises, tasty drinks & relaxing vibes

5.0
$95person
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 6 guests

Experience Maine on 65ft Classic Schooner Yacht

New
$65person
30' Sloop Charter in Boothbay Harbor, Maine
Sailing in Boothbay Harbor · 6 guests

30' Sloop Charter in Boothbay Harbor, Maine

1.0
$125hour

Sailing Reviews in Maine

  1. JP
    Jose
    32ft

    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!

  2. PM
    Philip
    32ft

    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!

  3. JR
    Joanne
    32ft

    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.

  4. AD
    Andrew
    Bareboat Midcoast Maine aboard the Schooner Yacht Meteor

    We just got back from a wonderful day on the water :) We bareboat chartered the Meteor. Captain Neal was able to be flexible on our timing since our original day was bad weather and he did not have many bookings around the same time. He made perfect suggestions regarding weather, currents, tides and routes to help us learn the area quickly and be able to navigate a beautiful day on Penobscot Bay. 100% we will be back again! Treat his boat well and Capt Neal will treat you well in return! Thanks so much for a wonderful day!

  5. Mary
    Mary
    On the Rocks Cocktail Cruises - Slow cruises, tasty drinks & relaxing vibes

    Jill was a fantastic captain and we had so much fun! We are in animal rescue that transports animals from Georgia to Maine. It turns out that that Jill had adopted one of our dogs. This truly is a small world!! As far as the cruise was concerned, we had a wonderful time and saw some really beautiful sights. We plan to book again as soon as we return. Thank you Jill for a wonderful time!!

  6. jb
    jacquelyn
    32ft

    We had a wonderful day on the water with Linda and her beautiful boat. She is a very experienced captain and the kind of adventurous and interesting person that is just fun to spend a day with. We couldn't have asked for a better day