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Old Saybrook, Connecticut Boat Rentals

Overspray in Old Saybrook
Powerboats in Old Saybrook · 6 guests

Overspray in Old Saybrook

New
$300hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
44ft Sea Ray Motor Yacht with Licensed USCG Captain in Lyme, Connecticut
Events in Connecticut · 12 guests

44ft Sea Ray Motor Yacht with Licensed USCG Captain in Lyme, Connecticut

5.0
Snoozed - Active 02 Jan 2025
Captained 24ft Key West - fishing or cruising out of Clinton, CT
Fishing in Clinton · 4 guests

Captained 24ft Key West - fishing or cruising out of Clinton, CT

5.0
$130hour
Wellcraft Martinique Motor Yacht Charter in Chester, Connecticut
Powerboats in Chester · 6 guests

Wellcraft Martinique Motor Yacht Charter in Chester, Connecticut

5.0
$250hour
40 Foot Tiara Motor Yacht Rental in Greenport, New York
Powerboats in Greenport · 6 guests

40 Foot Tiara Motor Yacht Rental in Greenport, New York

New
$600hour
31’ Bertram Classic with captain. Greenport NY
Events in Greenport · 6 guests

31’ Bertram Classic with captain. Greenport NY

New
$250hour
Italian Luxury Sanlorenzo 76SX in Greenport
Events in Greenport · 12 guests

Italian Luxury Sanlorenzo 76SX in Greenport

New
$2,063-$3,125hour
Enjoy the Hamptons by water on our Monterey 328 SS!
Powerboats in Greenport · 12 guests

Enjoy the Hamptons by water on our Monterey 328 SS!

5.0
$500hour
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
$150person
Hobie One 12 ft Sailboat for rent in Sag Harbor
Sailing in Sag Harbor · 3 guests

Hobie One 12 ft Sailboat for rent in Sag Harbor

New
$99hour
Explore Sag Harbor on 32ft Defiant Monterey 328 SS Motor Yacht!
Events in Sag Harbor · 12 guests

Explore Sag Harbor on 32ft Defiant Monterey 328 SS Motor Yacht!

5.0
$500hour
Vintage Yachting Lifestyle in the Hamptons NY
Events in Sag Harbor · 12 guests

Vintage Yachting Lifestyle in the Hamptons NY

5.0
$1,000-$1,900hour
57' 2023 Okean + 2 Seabobs Yacht Charter in Sag Harbor, New York
Events in Sag Harbor · 12 guests

57' 2023 Okean + 2 Seabobs Yacht Charter in Sag Harbor, New York

New
$1,830hour
22' 2021 Bayliner Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 8 guests

22' 2021 Bayliner Boat Rental in Sag Harbor, New York

New
$514hour
29' 2021 Yacht Hampton Escape Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 10 guests

29' 2021 Yacht Hampton Escape Boat Rental in Sag Harbor, New York

New
$743hour
26' 2023 Mastercraft-Watersports Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 12 guests

26' 2023 Mastercraft-Watersports Boat Rental in Sag Harbor, New York

New
$743hour
 22’ 2025 Yacht Hampton Electric Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 10 guests

22’ 2025 Yacht Hampton Electric Boat Rental in Sag Harbor, New York

New
$545hour
 32' 2020 Sundancer + Seabob Yacht Rental in Sag Harbor, New York
Events in Sag Harbor · 12 guests

32' 2020 Sundancer + Seabob Yacht Rental in Sag Harbor, New York

New
$1,063hour
29' 2022 Sea Ray SDX Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 12 guests

29' 2022 Sea Ray SDX Boat Rental in Sag Harbor, New York

New
$743hour
 18' 2025 Volt Electric Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 12 guests

18' 2025 Volt Electric Boat Rental in Sag Harbor, New York

New
$545hour
16' 2024 Fiat 500 Water Taxi/Tubing Car Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 3 guests

16' 2024 Fiat 500 Water Taxi/Tubing Car Boat Rental in Sag Harbor, New York

New
$604hour
44' 2023 Solaris + 2 Seabobs Yacht Charter in Sag Harbor, New York
Events in Sag Harbor · 12 guests

44' 2023 Solaris + 2 Seabobs Yacht Charter in Sag Harbor, New York

New
$1,463hour
43' 2021 Pardo + Seabob Yacht Charter in Sag Harbor, New York
Events in Sag Harbor · 12 guests

43' 2021 Pardo + Seabob Yacht Charter in Sag Harbor, New York

New
$1,482hour

Old Saybrook Reviews

  1. TT

    Tara

    44ft Sea Ray Motor Yacht with Licensed USCG Captain in Lyme, Connecticut

    I would highly recommend!! Captain Jared and Tucker made our anniversary memorable. Communication was excellent, Jared reached out and made helpful suggestions on how we could make the most out of our ride. He was very accommodating, our guests continue to comment on how much they enjoyed our trip. We will book again soon. Thanks Jared!!

  2. Robert

    Robert

    Wellcraft Martinique Motor Yacht Charter in Chester, Connecticut

    I highly recommend David’s services. David holds Captain License issued by US Coast Guards is extremely patient and very good teacher. If you want to learn boating/ navigation rules or just want to experience CT River and Long Island Sound boating, David is your best choice. I purchased larger boat and insurance company would not insure my boat unless I was trained by licensed Captain. I was able to book training with David right away, he adjusted his schedule and set up required course within a week. I’m very happy that I met David. I also plan to keep in touch with David in the future and organize couple trips together. Thank you David!!!

  3. JR

    Jai

    Sail to Fishers Island on a fast and classy 35' Sailboat

    We had a wonderful experience and found Captain Eric to be an excellent sailor and gracious host. He is extremely friendly, relaxed and a great conversationalist who has many stories to tell about the Thimble Islands and other topics. We had a large party with a two year old child and Captain Eric made us all comfortable and provided us with a perfect trip.

  4. Lauri

    Lauri

    Sail to Fishers Island on a fast and classy 35' Sailboat

    CaptIn Eric provided an amazing experience for my family. Not only did he display his professional sailing skills but he accommodated time for dining and swimming and the thrill of being under sail on a beautiful sunny and windy day. We've already shared our great experience with friends and family and hope to join them for another trip on Erics Nomade.

  5. SS

    Sarah

    Explore Sag Harbor on 32ft Defiant Monterey 328 SS Motor Yacht!

    10/10 would recommend this experience. Mike was super communicative and flexible in terms of timing and pickup/drop off. He answered all of my messages with lightening speed. The boat was perfect for a group of 7 of us, and we had a great day! Would definitely charter with Mike again!

  6. NC

    Nathalie

    Sail to Fishers Island on a fast and classy 35' Sailboat

    Eric was a gracious host. His boat was divine and equipped with everything we needed. He sailed us around the Thimble Islands where we swam and took in the glorious surroundings. A perfect way to spend your 50th birthday. Merci beaucoup, Eric!