Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in Maine

Incredible sailboat rentals in Maine, United States.

Page 1 of 16 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
★ 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
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. AD

    Andrew

    ★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!

  3. RH

    Rachel

    ★ 28' Classic Schooner in Rockland, Maine ★

    We really enjoyed our trip with Capt Neal aboard the Olive! The Rockland coast was beautiful and we appreciated Capt Neal’s company and knowledge of sailing. We hope to come back to the Rockland area again and recommend this trip!

  4. 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.

  5. JH

    Jennifer

    ★ 28' Classic Schooner in Rockland, Maine ★

    Lovely afternoon sailing with Captain Parker! Recommend this for anyone wanting to spend time on the water while in the area... know Captain Parker is a man of many talents and has many stories to share!

  6. 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.