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All listings in Maine

Incredible sailboat rentals in Maine, United States.

Page 1 of 18 listings

Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch
Sailing in Southwest Harbor · 6 guests

Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch

5.0
$290/hour
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast
Sailing in Friendship · 6 guests

Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

5.0
$125/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 4 guests

★ 28' Classic Schooner in Rockland, Maine ★

5.0
$175/hour
★Midcoast Maine aboard the Schooner Yacht Meteor ★
Sailing in Rockland · 4 guests

★Midcoast Maine aboard the Schooner Yacht Meteor ★

5.0
$175/hour
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 30 guests

Experience Maine on 65ft Classic Schooner Yacht

5.0
$500/hour
Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!
Powerboats in Nobleboro · 8 guests

Enjoy beautiful Maine at Damariscotta Lake with Mariah SX19 Bowrider!

New
$260+/day
Instant Book
Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.
Sailing in Portland · 6 guests

Day and term sailing charters out New Bedford, Massachusetts and Cape Cod.

New
$850/day

Sailing Reviews in Maine

  1. SS

    Susan

    Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch

    Shana, Thank you and Nicholas for a wonderful experience on Saturday. Your communication was so helpful each time you texted especially with regard to weather and moving up the sail. We ladies had a fabulous private time on your boat and would absolutely do it again if the opportunity arises.

  2. Diane

    Diane

    Acadia/Mount Desert Island Sail onboard the classic 46-foot sailing ketch

    I would recommend booking a trip with Shana. The boat was great. All communication was easy and quick. We had a lovely day out on the waters of the Maine coast.

  3. MV

    Michael

    ★ 28' Classic Schooner in Rockland, Maine ★

    Great experience. Captain Neal is a wealth of sailing knowledge and a lot of fun. My girls were thrilled for a chance to take the tiller! Would definitely book again.

  4. rp

    rita

    ★ 28' Classic Schooner in Rockland, Maine ★

    Great experience traveling through Rockland harbor! Captain Neal very nice and accompanying. Bathroom on board too

  5. JA

    Jeremy

    Sail the Maine Archipeligo - Muscongus Bay or the Entire Coast

    Ralph made bareboating a great experience end to end. His Morgan 36-5 Nelson Marek was just right, in working order and easy to sail for just my wife who does not sail and me. The equipment was all good, including a new and simple to use chart plotter mounted right at the helm. Beautiful location, conditions and waters made for great sailing. Convenient getting answers in advance, getting started and finished. All good. Highly recommendation. And there’s a super lobster place right nearby.

  6. MM

    Monica

    Sailing Adventure Aboard 44' Hunter Sailboat

    I cannot rave more about how AMAZING our experience was with Geoff! 1000 stars! It was absolutely beautiful and he made sure we had the best view of the sunset. We booked with him for an engagement photoshoot and he was super professional, fun, and incredibly helpful throughout helping us get the perfect shots. I’d recommend booking with Geoff for any occasion. I will definitely book again! Thanks Geoff!