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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,496 Reviews)

Page 10 of 40 • 951 listings

LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE
Sailing in Isla Iguana · 15 guests

LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE

5.0
$265/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
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
Curacao Private Romantic Sunset Tour 2p
Sailing in Jan Thiel · 2 guests

Curacao Private Romantic Sunset Tour 2p

5.0
$250/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
Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package
Sailing in San Francisco · 20 guests

Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

5.0
Superowner
$750+/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
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
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
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
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
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/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
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
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
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
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
$40/hour
Sailing in Cancun and Isla Mujeres
Sailing in Cancún · 45 guests

Sailing in Cancun and Isla Mujeres

New
$272+/hour
50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys
Sailing in Marina · 40 guests

50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys

New
$720/hour
Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC
Sailing in Morehead City · 6 guests

Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC

5.0
$100/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
$315/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
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
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

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. 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!

  4. Vince

    Vince

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

    Highly recommend, Planned a surprised engagement, and Ted and Christy were awesome. Super accommodating, friendly, and went out of their way to make the experience very personal and fun. I wouldn’t want to experience a charter any other way.

  5. VL

    Vincent

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

    I booked a trip for my niece and nephew to scatter their mom's (my sister's) ashes. They were very pleased with the service, and it was a perfect day. Communication was fantastic, and the crew was very receptive to their needs. Don't hesitate to book with them!

  6. William

    William

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

    2nd sail w/ Rick & Deb. They are warm and entertaining hosts and their boat is a beauty. Wonderful sail last night and we were lucky to catch some wind and get up to 8 knots. A delicious charcuterie board was included. Highly recommend sailing the Artemis with Rick & Deb.