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All listings in Maine

Incredible sailboat rentals in Maine, United States.

Page 1 of 18 listings

Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
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

New
$290/hour
★ 28' Classic Schooner in Rockland, Maine ★
Sailing in Rockland · 6 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
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
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 30 guests

Experience Maine on 65ft Classic Schooner Yacht

5.0
$500/hour
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
Herreshoff 12 1/2 Sailboat Charter
Sailing in North Haven · 3 guests

Herreshoff 12 1/2 Sailboat Charter

New
$50/hour

Top Destinations Nearby

Sailing Reviews in Maine

  1. 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!

  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. GT

    George

    Sailing Adventure Aboard 44' Hunter Sailboat

    Geoff was awesome! His sailboat was very clean and he was very accommodating. My wife and I went out to watch the sunset in Portsmouth and the itinerary was perfect. Geoff was really pleasant and we’ll definitely book with him again.

  4. 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!

  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. Jill

    Jill

    Sailing Adventure Aboard 44' Hunter Sailboat

    My girlfriends and I had an amazing time on Geoff’s boat. He was patient, kind and helpful. We appreciate everything he did for us and would 100% recommend booking with him!