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Portland, Connecticut Boat Rentals - 2023

24 listings
Wellcraft Martinique Motor Yacht Charter in Chester, Connecticut
Powerboats in Chester · 6 guests

Wellcraft Martinique Motor Yacht Charter in Chester, Connecticut

5.0
$250hour
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
Enjoy Fishing or Cruising on a Downeast-Style Boat In Branford, Connecticut
Fishing in Branford · 6 guests

Enjoy Fishing or Cruising on a Downeast-Style Boat In Branford, Connecticut

5.0
$190hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$145person
Rent A 2020 Yahama Ar210 Boat
Travel in Old Saybrook · 10 guests

Rent A 2020 Yahama Ar210 Boat

New
$375hour
Overspray in Old Saybrook
Powerboats in Old Saybrook · 6 guests

Overspray in Old Saybrook

New
$300hour
Swim, cruise, sightsee, & TUBING! Dogs welcome! Bantam Lake, Litchfield, CT w/ Captain
Powerboats in Litchfield · 6 guests

Swim, cruise, sightsee, & TUBING! Dogs welcome! Bantam Lake, Litchfield, CT w/ Captain

New
$195hour
Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar
Powerboats in Connecticut · 9 guests

Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar

5.0
$100hour
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
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
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200-$215hour
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
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 12 guests

Slide Pontoon on Candlewood Lake

5.0
$100hour
Tubing and Water Fun on Candlewood Lake
Powerboats in New Fairfield · 11 guests

Tubing and Water Fun on Candlewood Lake

New
$150hour
32ft 2020 Sundancer Motor Yacht + Seabob Rental in Sag Harbor, New York
Events in Sag Harbor · 12 guests

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

New
$923hour
Hunter 170 Sailboat with Honda motor in Sag Harbor, New York
Sailing in Sag Harbor · 6 guests

Hunter 170 Sailboat with Honda motor in Sag Harbor, New York

New
$129hour
Sea Doo RXPX260 affordable and fun machine in New Fairfield!
Water Sports in New Fairfield · 2 guests

Sea Doo RXPX260 affordable and fun machine in New Fairfield!

5.0
$150hour
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

Portland Reviews

  1. 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!!!

  2. 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!!

  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. KG
    Keila
    Slide Pontoon on Candlewood Lake

    Shannon was a great captain/host. We had a wonderful experience, the boat was extremely clean, and the equipment was like new. She gave great suggestions and was very flexible with what we wanted to do. provided clear instructions to find her, gave us life jackets and floaters, and was very patient. Overall a great experience for my family, would definitely do it again.

  6. BM
    Brooke
    Slide Pontoon on Candlewood Lake

    Came from out of town not knowing anything about the area and feel so blessed to have come across Shannon’s listing. The boat is beautiful and Shannon was amazing. It was relaxing for me and so much fun for kids!! We’ll be repeat guests for sure !