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Sailboats
Set sail with these traditional wind-powered boats
$50-$850
Fishing Charters
Let a captain do the driving while you do the fishing
$40-$850
Yachts
From mid-size to mega yachts, these luxury boats are great for groups and celebrations
$150-$525
Fishing Boats
Boats outfitted for fishing, from small inshore angling boats to deep-sea yachts
$40-$850
Tours
Explore local waters with a boat rental dedicated to sightseeing and exploration
$135-$500
Pontoons
Perfect for casual cruising, sandbar stops, swimming, and parties
$150-$350
Kayaks
Who says you need a motor to have fun on the water?
$30-$850
Jet Skis
Fast, fun, and easy to operate, these are a guaranteed good time on the water
$525
SP
Swapnil
Scenic History & Fishing Charters out of Casco Bay
We had a great trip out with Anthony. The boat was comfortable, clean and itinerary was ideal for the time with the trip around the islands ending with a beautiful sunset. Saw some seals along the way. We also learned interesting historical and ecological tidbits about the surrounding islands. Thanks for everything!
James
Scenic History & Fishing Charters out of Casco Bay
Anthony and Alyssa were great! They told us about the history and stories behind places we saw and we’re really nice without being overbearing. They took us by the lighthouses, islands and even stopped at a bar restaurant for lunch/drinks. Would highly recommend them for any kind of boating or fishing day off Portland-wonderful people!
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!
EG
Edward
Sweetwater Pontoon 20ft
Brett was very accommodating to a last minute request and the boat was in excellent condition. He delivered the boat to our rental property and picked it up at the end of the rental. He made this experience as easy as possible and I would highly recommend him!
JD
Julia
24ft Sebago Lake Cruise with Southbay Pontoon!
Anthony was great! He was responsive and timely in our communications beforehand. He was knowledgeable about the lake and had suggestions on where to go but was open to spending the afternoon doing what we wanted. We had a wonderful afternoon and everyone agreed it was our favorite activity of the trip. Would highly recommend booking with Anthony and would absolutely do it again next time I’m back in the area!
Megan
32ft Classic Swedish Sloop Sailing Charter
We had a wonderful sail with Linda on her beautiful boat! It was a really lovely afternoon on the water. The communication about where to meet and weather conditions was clear and easy. She had excellent knowledge of the area as well as great sailing tips. We would book with Linda again!
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!
August 01, 2023
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December 11, 2019
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November 23, 2022
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October 03, 2022
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April 14, 2022
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December 11, 2020
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