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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,469 Reviews)

Page 10 of 41 • 966 listings

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
DAYTRIP/SLEEP ON BOARD TO CATALINA
Sailing in Los Angeles · 12 guests

DAYTRIP/SLEEP ON BOARD TO CATALINA

4.9
Superowner
$199/hour
35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands
Sailing in Vancouver · 6 guests

35ft Classy Allmand Sailboat for Extended Charters in Vancouver and Gulf Islands

5.0
$129/hour
Private Party Catamaran | Up to 12 Guests | San Diego Bay
Sailing in San Diego · 12 guests

Private Party Catamaran | Up to 12 Guests | San Diego Bay

5.0
$550+/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2026
$50/hour
Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!
Sailing in Gloucester · 6 guests

Sail with us aboard our 64’ sailing yacht Artemis. Gloucester MA. Meal included!

5.0
$250/hour
Sail in Modern Luxury Beneteau Oceanis 37 Yacht
Sailing in Oceanside · 6 guests

Sail in Modern Luxury Beneteau Oceanis 37 Yacht

5.0
$200/hour
34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

34ft Pacific Seacraft Sailboat for full day Trip in Santa Marta, Magdalena

5.0
$100/hour
38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
Sailing in Playa del Carmen · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

4.7
Superowner
Best of 2026
$420/hour
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/hour
Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
Events in San Francisco · 49 guests

Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

5.0
Superowner
$1,467/hour
Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure
Sailing in Potrero · 12 guests

Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure

5.0
$165/hour
28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!
Sailing in Marina del Rey · 8 guests

28' Party Catamaran with Trampoline for Bay Sails & Sunset Cruises!

4.8
$250+/hour
2hr Day Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Day Sail from the port of South Haven Mi. on a Catalina 36

5.0
$175/hour
Shared Snorkeling & Sailing in Cabo San Lucas
Sailing in Marina · 12 guests

Shared Snorkeling & Sailing in Cabo San Lucas

5.0
Superowner
Best of 2026
$28/hour
Set Sail on a classic 36' S2 in Chicago for up to 6 Guests
Sailing in Chicago · 6 guests

Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

5.0
$200/hour
Sailing in Cancun and Isla Mujeres
Sailing in Cancún · 45 guests

Sailing in Cancun and Isla Mujeres

New
$269+/hour
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
Sailing in San Diego · 6 guests

San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

4.7
$54/hour
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$322/hour
50' Party Boat Catamaran in Miami  - 4 Hour Minimum - Up to 42 Guests
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami - 4 Hour Minimum - Up to 42 Guests

4.8
$1,200/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe
Sailing in Placer County · 4 guests

Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe

5.0
$200/hour

Sailing Reviews in United States

  1. 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!

  2. Ashley

    Ashley

    Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

    We had an absolutely incredible time on our catamaran charter with Captain David! He truly went above and beyond to make our birthday celebration memorable. The highlight of the trip was when he sang each of us a unique, personalized happy birthday song, it was such a thoughtful and fun touch that we will never forget. If you want a captain who is professional, attentive, and knows how to make an experience truly special, book with Captain David. Highly recommended!

  3. RG

    Ryan

    Private Party Catamaran | Up to 12 Guests | San Diego Bay

    Amazing trip! First, the boat is beautiful. We had Captain Andy who was a great host. Helped us make a quick itinerary and we were on our way! Stopped for a swim before we headed back towards the harbor. I will be booking one of these trips again and would book this same one if I’m in San Diego.

  4. JK

    James

    Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

    Ted was the captain of the boat and was excellent. He made our ride very enjoyable and stayed out for the fireworks at the end which was amazing. Kids loved the experience too!

  5. BS

    Brooke

    Sailing Charters in Wilmington NC

    Oliver is an amazing captain! My husband and I celebrated our anniversary aboard Oliver’s sailboat and it was an amazing experience. He’s extremely personable, knowledgeable, and safe! We loved having the opportunity to help steer, put sails up, and dock the boat. We also loved the relaxing moments where we could soak up the sun and the view! We will definitely be booking other Oliver again and highly suggest him for anyone looking to do a boat ride in Wilmington. This is a must do!!

  6. JK

    Jorn

    Sailing Charters in Wilmington NC

    I would recommend this to anyone that would like the experience and feeling of being on a sailboat in a safe and peaceful manner. Captain Oliver was knowledgeable and a very pleasant person. More wind would have been appreciated but who’s in control of that.