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Old Lyme, Connecticut Boat Rentals & Yacht Charters

Page 1 of 124 listings

Overspray in Old Saybrook | 37ft Silverton Yacht
Powerboats in Old Saybrook · 6 guests

Overspray in Old Saybrook | 37ft Silverton Yacht

5.0
$400/hour
85 Pacific Mariner-Serving Luxury to Connecticut and Eastern Long Island
Events in Old Saybrook · 12 guests

85 Pacific Mariner-Serving Luxury to Connecticut and Eastern Long Island

New
$2,250+/hour
Luxe 68ft Fairline w/ A Paddleboard, Kayak & More in Northeast, USA
Events in Westbrook · 12 guests

Luxe 68ft Fairline w/ A Paddleboard, Kayak & More in Northeast, USA

New
$1,475+/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
Sea Ray 39ft Yacht Charter in Deep River.  A great day on the water !
Events in Clinton · 6 guests

Sea Ray 39ft Yacht Charter in Deep River. A great day on the water !

5.0
$175+/hour
84ft Azimut – Luxury Yacht + Jet Skis, Seabobs & Jacuzzi
Events in Greenport · 12 guests

84ft Azimut – Luxury Yacht + Jet Skis, Seabobs & Jacuzzi

5.0
Superowner
Best of 2026
$950/hour
40ft Red VanDutch in The Northeast. 4, 6 & 8-hour Day Charters Available
Events in Greenport · 8 guests

40ft Red VanDutch in The Northeast. 4, 6 & 8-hour Day Charters Available

New
$850+/hour
Captained sail on a beautiful and comfortable 50' wooden ketch
Sailing in Greenport · 6 guests

Captained sail on a beautiful and comfortable 50' wooden ketch

New
$475/hour
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
$600/hour
31’ Bertram Classic with captain. Greenport NY
Events in Greenport · 6 guests

31’ Bertram Classic with captain. Greenport NY

5.0
$250/hour
40ft Silverton Convertible Flybridge Yacht in Southold, New York
Events in Noyack · 10 guests

40ft Silverton Convertible Flybridge Yacht in Southold, New York

5.0
$250/hour
A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6
Sailing in Sag Harbor · 6 guests

A large and luxurious French Beneteau Farr 57 Sailing Yacht for up to 6

New
$1,000+/hour
Experience New York Like Never Before — Aboard Our Stunning 76ft Riva Yacht
Events in Sag Harbor · 12 guests

Experience New York Like Never Before — Aboard Our Stunning 76ft Riva Yacht

New
Superowner
Best of 2026
$1,500/hour
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
$700/hour
62' Pershing + 2 Seabobs Yacht Charter in Sag Harbor, New York
Events in Sag Harbor · 12 guests

62' Pershing + 2 Seabobs Yacht Charter in Sag Harbor, New York

New
$2,384/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
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
$1,482/hour
2025 Dorrien Yachts 160T 1/1 -- Exclusive Luxury Charter
Powerboats in Sag Harbor · 5 guests

2025 Dorrien Yachts 160T 1/1 -- Exclusive Luxury Charter

New
$295/hour
Luxury 37’ EdgeWater 370CC Charter – Sag Harbor | Sunset Cruises & Montauk Trips
Powerboats in Sag Harbor · 12 guests

Luxury 37’ EdgeWater 370CC Charter – Sag Harbor | Sunset Cruises & Montauk Trips

New
$750+/hour
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
Sail the glamorous Hamptons in a 58ft Catana luxury catamaran
Sailing in Sag Harbor · 12 guests

Sail the glamorous Hamptons in a 58ft Catana luxury catamaran

New
$750/hour
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
$310+/hour
Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran
Sailing in Sag Harbor · 25 guests

Enjoy the Hamptons waters on wonderful and unique Classic 45' Mahogany Trimaran

5.0
$900+/hour
Brand New Convertible Riva 76 Bahamas Motor Yacht - NY
Events in Sag Harbor · 12 guests

Brand New Convertible Riva 76 Bahamas Motor Yacht - NY

New
$2,584+/hour

Old Lyme Reviews

  1. ST

    Sabrina

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    This was actually the best day of my life. I had my bachelorette and the boat was so incredible, Brian and his partner are amazing hosts and their boat is so gorgeous and special. They were flexible with the hours and very accommodating. Would love to rebook !!

  2. Charla

    Charla

    40ft Silverton Convertible Flybridge Yacht in Southold, New York

    They are so fun and easy to work with. It’s like renting a friend with a boat! Will definitely book again soon!

  3. DK

    Dmitri

    Charter 36ft Sloop In Westbrook, Connecticut

    We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!

  4. CV

    Cheryl

    Sea Ray 39ft Yacht Charter in Deep River. A great day on the water !

    Rob and mellie were amazing, they made our boat excursion for a 40th bday extra special, with so many great touches. Mellie was so great helping with our theme and putting together food and drinks for us. She went above and beyond. Rob was great at communicating with me during the whole planning process and answered all my questions . We never felt rushed and they made sure we had good time , we will be booking again next summer , can't wait !!!!

  5. Gonzalo

    Gonzalo

    84ft Azimut – Luxury Yacht + Jet Skis, Seabobs & Jacuzzi

    I want to thank Frank, Captain Allan, and his crew for a wonderful day on the yacht. Communication was perfect; they always answered all our questions promptly, and the captain and crew were very attentive to all our needs. A perfect trip. Thank you so much for everything. We really enjoyed the ride, the jet ski, the Seabob, and the jacuzzi

  6. EC

    Emily

    42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

    Nate and Jaime were the absolute best from start to finish! Super great communication and excellent service - loved the swimming spot and how knowledgeable Nate was about the area and other boats. Exceeded our expectations, will definitely book with Nate again!