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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,474 Reviews)

Page 9 of 41 • 971 listings

Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190/hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
SeaDoo Switch Sport *5 ADULTS*
Powerboats in Texas · 9 guests

SeaDoo Switch Sport *5 ADULTS*

5.0
$100/hour
Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran
Sailing in San Miguel de Cozumel · 22 guests

Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran

5.0
Superowner
$250+/hour
Puget Sound Sailing Adventure on 32' Hunter Sailboat
Sailing in Seattle · 6 guests

Puget Sound Sailing Adventure on 32' Hunter Sailboat

5.0
$180/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

4.9
Superowner
$117+/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
42ft J Boat Sailing Yacht in Newport, Rhode Island
Sailing in Newport · 4 guests

42ft J Boat Sailing Yacht in Newport, Rhode Island

5.0
$260/hour
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$317/hour
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200+/hour
44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.
Sailing in Playa del Carmen · 35 guests

44' Leopard Catamaran All-Inclusive Charter in Playa del Carmen.

5.0
Superowner
Best of 2026
$520/hour
Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL
Sailing in Stuart · 13 guests

Lagoon 42 Sailing Catamaran for Up to 13 (12 + Charterer) Guests Near Stuart, FL

5.0
$354/hour
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour
Endeavour 40 Sailboat in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 12 guests

Endeavour 40 Sailboat in Puerto Vallarta, Mexico

5.0
$125+/hour
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
Day Sails and Sunset Cruises in Downtown St. Petersburg,  44' Morgan Sailboat
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises in Downtown St. Petersburg, 44' Morgan Sailboat

5.0
$206+/hour
Create Memories you will Cherish for Life on this 47' Luxury Sailboat!
Sailing in Newport Beach · 6 guests

Create Memories you will Cherish for Life on this 47' Luxury Sailboat!

5.0
Superowner
$225+/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2026
$50/hour
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/hour
Sunseeker 60ft Motor Yacht
Events in Cancún · 20 guests

Sunseeker 60ft Motor Yacht

4.8
$230/hour
Sailing Charters in Wilmington NC
Sailing in Wilmington · 6 guests

Sailing Charters in Wilmington NC

5.0
$178/hour
Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.
Events in Gonzalo Guerrero · 35 guests

Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.

5.0
Superowner
$480/hour
Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht
Sailing in San José del Cabo · 12 guests

Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht

5.0
$500+/hour

Sailing Reviews in United States

  1. Nick

    Nick

    Create Memories you will Cherish for Life on this 47' Luxury Sailboat!

    Absolutely incredible experience from start to finish! Our captain was professional, knowledgeable, and made the entire afternoon on the water unforgettable. The boat was beautiful, the atmosphere was perfect, and every detail was taken care of. Whether you’re looking for a relaxing cruise or an amazing day sailing, I couldn’t recommend this experience more. Hands down a 10/10 experience, and we can’t wait to do it again!

  2. MR

    Michele

    Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.

    I can't thank Diego enough. This listing does not show at all what he did for me and my group. I had 100 people and wanted to spend a day on cats, but didnt want to make myself crazy trying to plan it. Diego said I got this. He got me 3 catamarans, transportation, seamless planning, stayed in touch with me for almost a YEAR while planning. There was not one detail missed. He had not 1 but 2 staff at the port waiting for me and my group. They stayed until our cats were pulling away from the port amd were standing there again when we got back. The staff on all three cats went above and beyond. Never an empty cup, never a worry about safety, amazing food and they kept it all flowing flawlessly! For a group of 100 people to go this seamless, Diego and his team nailed it. You want fun and no worries, trust me on Diego and his team!

  3. Peter

    Peter

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    My wife and I had a great time taking out Matt’s Sunfish sailboat! He was there to greet us and help prepare the boat, and he had great recommendations for where in the lake to find the best sailing conditions. His sunfish is well maintained and sailed great. I would love to rent his Sunfish again next summer!

  4. JG

    Jen

    Well Appointed Beneteau 32, Folly Beach, SC

    Loved our sunset cruise with Greg for my friends birthday. Beautiful boat, scenery, and weather! It was so relaxing to sail, watch the dolphins and catch a gorgeous sunset on the water. Greg was super nice, took pics of our group, and made the trip more enjoyable with his easygoing personality. We would sail again with Greg anytime!

  5. Angela

    Angela

    Well Appointed Beneteau 32, Folly Beach, SC

    We cannot say enough about Greg! He’s knowledge of sailing, the area, and the ability to make you feel like you’re at home on his beautiful boat. Your mistake would be not having Greg as your captain! Thank you for a wonderful experience and look forward to the next time!!!!

  6. LW

    Lori

    Well Appointed Beneteau 32, Folly Beach, SC

    Captain Greg gave us the best experience for our first time sailing!! Not only was he extremely nice and fun, but very educational! The Water Music is a beautiful sail boat and we felt extremely safe on board with Captain Greg. The whole experience was relaxing with just absolutely stunning sunset views. We can't wait to go sailing again with Captain Greg!!