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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,466 Reviews)

Page 4 of 41 • 964 listings

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!
Sailing in Richmond · 6 guests

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

5.0
$162+/hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark
Sailing in Marina del Rey · 6 guests

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

5.0
Superowner
Best of 2026
$150/hour
North Lake Tahoe 33ft Hobie Yacht 3 Hour Sailing Experience
Sailing in Placer County · 6 guests

North Lake Tahoe 33ft Hobie Yacht 3 Hour Sailing Experience

4.9
$233/hour
Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat
Sailing in Newport · 6 guests

Explore Newport Harbor on a Luxurious Beneteau Sense 55 Sailboat

5.0
$400/hour
Sail Away Private Day Trip: all inclusive with Snorkelling ...and Island Hop!
Sailing in San Pedro · 24 guests

Sail Away Private Day Trip: all inclusive with Snorkelling ...and Island Hop!

4.9
$275+/hour
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

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

5.0
$200/hour
Private 44ft Trimaran in Los Cabos for 50 Guests
Sailing in Juárez · 50 guests

Private 44ft Trimaran in Los Cabos for 50 Guests

5.0
Superowner
Best of 2026
$250/hour
Schock 35' Cruiser Sailboat in San Francisco Bay
Sailing in Alameda · 6 guests

Schock 35' Cruiser Sailboat in San Francisco Bay

5.0
$99/hour
12 passengers:  Explore San Diego Bay on a Luxury Sailing Catamaran
Sailing in San Diego · 12 guests

12 passengers: Explore San Diego Bay on a Luxury Sailing Catamaran

5.0
$330/hour
55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.
Sailing in Marina del Rey · 12 guests

55ft Hudson sailboat in Marina del Rey. Your private group. Best Choice in L.A.

5.0
Superowner
Best of 2026
$185+/hour
Private 38' Hunter Sailing boat in Cabo San Lucas
Sailing in Marina · 12 guests

Private 38' Hunter Sailing boat in Cabo San Lucas

4.9
Superowner
Best of 2026
$193/hour
All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas
Sailing in Marina · 50 guests

All Inclusive 42-ft Private Trimaran for Snorkeling Adventures in Cabo San Lucas

5.0
Superowner
Best of 2026
$367/hour
Rent a 5 person Daysailer in Valle de Bravo, Mexico
Sailing in Valle de Bravo · 5 guests

Rent a 5 person Daysailer in Valle de Bravo, Mexico

5.0
$59/hour
Luxury Leopard 38 Catamaran located in Downtown Miami
Sailing in Miami · 12 guests

Luxury Leopard 38 Catamaran located in Downtown Miami

5.0
$219+/hour
36' Catalina Sailboat for LA Coastal Sailing | Santa Monica - Malibu - Catalina
Sailing in Marina del Rey · 6 guests

36' Catalina Sailboat for LA Coastal Sailing | Santa Monica - Malibu - Catalina

New
$90/hour
Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo
Sailing in Valle de Bravo · 16 guests

Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo

5.0
$161/hour
Private Catamaran Escape for 2–6 Guests – Celebrate Your Way
Sailing in Marina · 6 guests

Private Catamaran Escape for 2–6 Guests – Celebrate Your Way

4.8
Superowner
$170/hour
Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 8 guests

Sailing Charter On 35' Ericson Sloop In Puerto Vallarta, Mexico

5.0
Superowner
$119+/hour
Beautiful Classic Sailboat in Marina Del Rey
Sailing in Marina del Rey · 10 guests

Beautiful Classic Sailboat in Marina Del Rey

5.0
$170+/hour
The Wanderlust Ultimate Catamaran Adventure
Sailing in Nassau · 12 guests

The Wanderlust Ultimate Catamaran Adventure

5.0
$627/hour
55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!
Sailing in Marina del Rey · 12 guests

55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

4.9
Superowner
Best of 2026
$185+/hour
Come sail away on this Jeanneau 58' Sailboat in San Diego
Sailing in San Diego · 6 guests

Come sail away on this Jeanneau 58' Sailboat in San Diego

4.8
$400/hour
Wild Cat 35 Sailing Catamaran Charter starting fare up to 12 people.
Sailing in Isla Mujeres · 26 guests

Wild Cat 35 Sailing Catamaran Charter starting fare up to 12 people.

4.8
Superowner
$169+/hour

Sailing Reviews in United States

  1. AH

    Amit

    Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

    Jan was an excellent captain, he helped plan a surprise proposal and was a big reason why the day turned out so well. He’s very professional, easy to work with. The boat is quite nice as well, with space to comfortably sit in front and truly take in the sites that the bay has to offer. Could not recommend Captain Jan and his boat enough

  2. SF

    Sarah

    55ft Irwin Sailboat in Marina del Rey, YOUR PRIVATE GROUP BEST CHOICE IN L.A.!

    We had such an amazing time out on the water, sailing a bit of the coast and then docking to jump in. Captain was communicative, professional and a total joy! The boat was spacious enough that our group of 11 could spread out in different areas. This was the final activity of a 3-day retreat and many folks named this as their top moment of the weekend! Whether you're visiting or are local and want a special way to experience the water, I highly recommend. Thanks Captain!!

  3. JA

    Juliet

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    We had a really wonderful time sailing to Catalina Island with Captain Mark (2 nights, 4 adults). Captain Mark made us feel super comfortable throughout the trip and put a lot of care into teaching us about sailing and cooking meals. He really went above and beyond. We had fun relaxing on the boat and swimming and snorkeling in the crystal clear waters of Catalina. But you can’t beat drinking coffee and eating a hot breakfast in Emerald Bay, watching the sea life and fellow sailers start their days. I’ll definitely book another trip with Captain Mark!

  4. Evelyn

    Evelyn

    Come sail away on this Jeanneau 58' Sailboat in San Diego

    An unforgettable way to see San Diego! Julie was amazing! My cousin was visiting from Chicago and wanted to experience San Diego from the water, and this was the perfect way to do it. The boat was perfect, the views were beautiful, and we even got to see seals up close. It was a bit chilly the day we sailed, but the crew thought of everything, with warm blankets and comfy chairs so we could relax on the deck. Julie made the whole experience special, and I'd recommend booking with her to anyone!

  5. Jen

    Jen

    Cal 36 Sailboat Rental in Marblehead, Massachusetts

    My sister and I had a wonderful time with Captain Allan and we had perfect weather all day. He was very knowledgable about the local area and a very skilled captain, making us feel comfortable throughout the whole experience. We played music and had such a great time talking with him. Would absolutely recommend and definitely use Captain Allan again.

  6. HK

    Hemina

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    Mark was a wonderful captain! We had so much fun and his boat is amazing too. Highly recommended! Thanks Mark!! We will definitely be going sailing with you again.