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All listings in the United States

Awesome sailboat rentals in United States.

4.9

(8,362 Reviews)

Page 20 of 39 • 924 listings

Sailing in Marina · 14 guests

Enjoy a small group Shared Sunset Sailing Cruise in Cabo San Lucas

5.0

Superowner

Best of 2026

$60/hour

Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0

$940/hour

Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0

$250/hour

Sailing in Annapolis · 12 guests

Charter 42' Lagoon Catamaran in Annapolis, MD

5.0

$425/hour

Sailing in Nassau · 12 guests

50ft Luxury Catamaran – Rose Island, Gilligan’s Island & Green Cay

5.0

$1,375/hour

Sailing in Zona Comercial · 8 guests

Ultra Luxury 2023 51 ft Trimaran Experience in the Sea of Cortez

5.0

$359/hour

Sailing in Isla Mujeres · 10 guests

Sailboat Odyssey 46 Luxury Sailing In Cancun, Mexico

5.0

$217+/hour

Sailing in Cancún · 55 guests

Custom 45ft Sailing Catamaran with food and open bar

New

$561/hour

Sailing in Los Angeles · 6 guests

Sailboat tours in Port of Los Angeles (San Pedro)

5.0

$190/hour

Events in Cape Canaveral · 11 guests

''Razor's Edge'' Yacht Rental in Cape Canaveral, Fl

5.0

$382/hour

Events in Barrio Las Yaguitas · 60 guests

🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata

1.0

$170/hour

Powerboats in Isla Iguana · 20 guests

Private 45' Party Catamaran with Professional Bilingual Crew In Puerto Vallarta

New

$625/hour

Sailing in Dominican Republic · 65 guests

Private Catamaran to Bahia de las Aguilas Cabo Rojo

New

$1,450/hour

Sailing in Los Melones · 35 guests

Private 47ft Power Catamaran to Saona Island – Full-Day All-Inclusive Experience

New

$850/hour

Sailing in Guanacaste Province · 46 guests

Private Cruise aboard 65ft Sailing Catamaran Charter in Papagayo

New

$900/hour

Sailing in Playa Flamingo · 40 guests

Private Full-Day Catamaran Charter in Playa Flamingo

New

$800/hour

Sailing in La Cruz de Huanacaxtle · 10 guests

Private 34'Cruiser Charter Fit 10 Guests in Punta Mita

New

$350+/hour

Sailing in La Cruz de Huanacaxtle · 10 guests

Private 56ft Luxury Catamaran Charter in Punta Mita

New

$600+/hour

Sailing in Sosúa · 20 guests

Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar

New

$425/hour

Sailing in Sosúa · 10 guests

Puerto Plata Private Sunset Catamaran Cruise with Open Bar and BBQ

New

$260/hour

Sailing in Dominican Republic · 45 guests

Private 3-Hour Sunset Catamaran Cruise to Media Luna Pool

New

$1,100/hour

Powerboats in La Romana · 20 guests

Isla Saona 60ft Private Yacht – Full Day Luxury Tour

New

$1,820/day

Tours in Valle de Bravo · 5 guests

Sailing Lessons in Valle de Bravo

5.0

$89/hour

Powerboats in Oranjestad-West · 10 guests

Private 26ft Family Friendly Speedboat Charter in Aruba

New

$500/hour

Top Destinations Nearby

Sailing Reviews in United States

Lauren

Charter 42' Lagoon Catamaran in Annapolis, MD
We had an amazing day on the bay with Captain Adam! He was super communicative leading up to the trip, providing amazing instruction to make it as easy as possible to get aboard. While on board the vessel was very clean and comfortable and he and his team were knowledgeable about the area. Highly recommend! They’re lovely!
Ryankeisha

Private Group Sail and Snorkel Montego Bay
My crew and I really enjoyed our boat ride and the Excursions that went along with it. We had lots of fun and the captain, my co-captain, and crew were very entertaining and accommodating. The food was delicious and the drinks were continuously flowing. I will definitely come back and do it again.
ET
Erica

Ultra Luxury 2023 51 ft Trimaran Experience in the Sea of Cortez
Thank you for an unforgettable day visiting Isla Espiritu Santo! The crew aboard Lambo were truly what set this trip apart from any other. Armando was so attentive and always thinking 3 steps ahead to anticipate our wants and needs. They were professional, polished and efficient in everything they did from maneuvering the boat to setting up for lunch, and more. The boat was immaculate- in fantastic condition, which made for a comfortable ride and luxurious experience. We will definitely book again next time we visit La Paz!
FA
Fermin

Ultra Luxury 2023 51 ft Trimaran Experience in the Sea of Cortez
Gran servicio, trato y experiencia. 100% recomendado.
KC
Kevin

Charter 42' Lagoon Catamaran in Annapolis, MD
Adam Yearwood is a fantastic captain! His boat is beautiful and he is well organized. We did a team outing sailing around the Chesapeake and had an awesome time - I highly recommend working with Adam!
Ryan

Sailing Lessons in Valle de Bravo
Great experience. I sent a booking request overnight and got a response first thing in the morning. The captain was knowledgeable and professional. Spanish Language.