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Old Saybrook, Connecticut Boat Rentals

24 listings
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
$350hour
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
31’ Bertram Classic with captain. Greenport NY
Events in Greenport · 6 guests

31’ Bertram Classic with captain. Greenport NY

New
$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
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
SeaRay Sundancer 41' Power Sport Yacht Crusie in Sag Harbor
Events in Sag Harbor · 6 guests

SeaRay Sundancer 41' Power Sport Yacht Crusie in Sag Harbor

5.0
$700hour
Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

5.0
$300hour
29' 2022 Sea Ray Sdx Deck Boat in Sag Harbor, New York
Powerboats in Sag Harbor · 10 guests

29' 2022 Sea Ray Sdx Deck Boat in Sag Harbor, New York

New
$723hour
29' 2021 Sea Ray Sdx Deck Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 10 guests

29' 2021 Sea Ray Sdx Deck Boat Rental in Sag Harbor, New York

New
$723hour
62' Pershing Power Mega Yacht With 2 Seabobs Rental in Shelter Island, New York
Events in Sag Harbor · 12 guests

62' Pershing Power Mega Yacht With 2 Seabobs Rental in Shelter Island, New York

New
$2,748hour
Charter the 57' Okean 2023 Power Mega Yacht in Sag Harbor, New York
Events in Sag Harbor · 12 guests

Charter the 57' Okean 2023 Power Mega Yacht in Sag Harbor, New York

New
$1,998hour
44' Solaris 2023 Motor Yacht + Seabob Rental in Sag Harbor, New York
Events in Sag Harbor · 12 guests

44' Solaris 2023 Motor Yacht + Seabob Rental in Sag Harbor, New York

New
$1,498hour
42' Catalina Sailing Yacht in the Hamptons - 4 Hours
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 4 Hours

5.0
$325hour
42' Catalina Sailing Yacht in the Hamptons - 3 Hours
Events in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - 3 Hours

New
$350hour
22' Bayliner 2021 Deck Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 8 guests

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

New
$487hour
43' Pardo 2021 Motor Yacht + Seabob in Shelter Island, New York
Events in Sag Harbor · 12 guests

43' Pardo 2021 Motor Yacht + Seabob in Shelter Island, New York

New
$1,248hour
29' Yacht Hampton Escape 2021 Deck Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 10 guests

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

New
$723hour

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. Maria
    Maria
    Classic Beauty: Nautor Swan 46 Bluewater Cruiser, Sag Harbor, New York

    Everything was top notch, Alan was very considerable and did everything to make this trip as pleasant for us as possible. The vessel is amazing and the experience was outstanding. I traveled with my two children (3&5) and it worked out really well. Highly recommend!