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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,669 Reviews)

Page 25 of 451,076 listings

Learn To Sail On The Moose with Pearson Ensign Sailing Yacht!
Sailing in Brooklyn · 4 guests

Learn To Sail On The Moose with Pearson Ensign Sailing Yacht!

5.0
$180hour
38' Catalina Sailing Cruise in Chicago
Sailing in Chicago · 6 guests

38' Catalina Sailing Cruise in Chicago

5.0
$250hour
Catalina 270, The Channel Islands Great trip on the sailboat
Sailing in Newport Beach · 6 guests

Catalina 270, The Channel Islands Great trip on the sailboat

5.0
$122-$146hour
Fountain Pajot Astrea Luxury 42' Catamaran for Charter
Sailing in Toronto · 18 guests

Fountain Pajot Astrea Luxury 42' Catamaran for Charter

5.0
$1,000-$1,300hour
Searay Sundancer 60¨ in North Miami Beach, Florida
Events in Aventura · 12 guests

Searay Sundancer 60¨ in North Miami Beach, Florida

4.0
$400hour
27ft Catalina Sailing Yacht in Pacific Ocean!
Sailing in Marina del Rey · 6 guests

27ft Catalina Sailing Yacht in Pacific Ocean!

New
$115hour
Amazing Day On Catamaran 43 FT With Unlimited Open Bar Cancun and Isla Mujeres
Sailing in Cancún · 35 guests

Amazing Day On Catamaran 43 FT With Unlimited Open Bar Cancun and Isla Mujeres

New
$307hour
Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!
Events in Toronto · 15 guests

Stylish & Spacious‼️ Enjoy Toronto's One of a Kind 44ft Bayliner!

5.0
$365hour
42ft Sea Ray Motor Yacht Rental in Cabo San Lucas, Baja California Sur
Events in Marina · 10 guests

42ft Sea Ray Motor Yacht Rental in Cabo San Lucas, Baja California Sur

New
$250hour
Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida
Powerboats in Marco Island · 6 guests

Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida

5.0
$99hour
Tutrles, Snorkeling Beach day!
Powerboats in Nassau · 18 guests

Tutrles, Snorkeling Beach day!

New
$150person
Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay
Sailing in Montego Bay · 4 guests

Jeanneau Sun Odyssey for an Intimate Cruise in Montego Bay

New
$417hour
Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica
Sailing in Playa Flamingo · 45 guests

Charter 45ft Cruising Catamaran In Playa Flamingo, Costa Rica

5.0
$712hour
Luxury Catamaran 44 in Puerto Vallarta, Banderas Bay
Sailing in Marina Vallarta · 12 guests

Luxury Catamaran 44 in Puerto Vallarta, Banderas Bay

New
Superowner
Best of 2023
$439hour
3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests
Sailing in Nassau · 12 guests

3 courses dinner & sunset cruise on a luxury catamaran up to 12 guests

New
$300person
115' Cruising Luxury Schooner Charter in Noord, Aruba
Sailing in Oranjestad-West · 60 guests

115' Cruising Luxury Schooner Charter in Noord, Aruba

5.0
$1,590hour
Enjoy a 35' Sloop J/105 Sailing Charter in San Diego, California
Sailing in San Diego · 6 guests

Enjoy a 35' Sloop J/105 Sailing Charter in San Diego, California

5.0
$600day
Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions
Sailing in Fort Myers Beach · 12 guests

Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions

New
$300hour
Offshore Racing Boat for charter in San Francisco
Sailing in San Francisco · 4 guests

Offshore Racing Boat for charter in San Francisco

5.0
$125hour
🛥🥂VIP EXPERIENCE-Prívate Catamaran for bachelorette-birthday in Puerto Plata
Events in Barrio Las Yaguitas · 60 guests

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

New
Superowner
$59person
44ft Sea Ray Sundancer Motor Yacht Rental in Quintana Roo, Mexico
Events in Cancún · 14 guests

44ft Sea Ray Sundancer Motor Yacht Rental in Quintana Roo, Mexico

New
$400hour
Cruising Catamaran Charter in Cabarete, Dominican Republic
Sailing in Cabarete · 80 guests

Cruising Catamaran Charter in Cabarete, Dominican Republic

New
$75hour
Luxury Lagoon 45FT 2019 in La Cruz de Huanacaxtle
Sailing in La Cruz de Huanacaxtle · 14 guests

Luxury Lagoon 45FT 2019 in La Cruz de Huanacaxtle

New
$790hour
Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland
Sailing in Saint Michaels · 6 guests

Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

5.0
$250-$349hour

Sailing Reviews in United States

  1. Patricia

    Patricia

    Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida

    We had a great afternoon on the water with Jonallen. He was kind and courteous and knew all of the places to go for a good time. Even the teenagers in our group had a blast and they’re not always easy to please! It was an awesome experience and I’d recommend to anyone who’s looking for a fun time on the water.

  2. Robyn

    Robyn

    Bay Boat Dolphin/Shelling Adventures in Marco Island, Florida

    JonAllen is an outstanding young man with superior captain skills. Very accommodating from the moment we met him. Carried our items to the boat, offered towels, drinks and pleasant conversation. Extremely well versed in the areas water ways. We travel to the area many times per year and I am certain JonAllen will be hearing from us often. Absolutely will not be disappointed!

  3. Scott

    Scott

    Enjoy a 35' Sloop J/105 Sailing Charter in San Diego, California

    Awesome option to get a great San Diego sailing charter. We asked to get involved and received a valuable education with hands-on practical experience on how to improve sailing technique. JWorld and Collin our Captain delivered exactly what we hoped for in 4 hours of sailing. Already planning to stay in touch toward future sails!

  4. MN

    Michael

    Offshore Racing Boat for charter in San Francisco

    Fabulous trip, thank you for the well planned and executed trip. Fast, fun. Allowing us to be a part of the sailing was great. Thank you for the great day out Barry! We had a well timed day with sun and good wind. We sailed around Alcatraz, Great views of the city, and bridges. Perfect for what we wanted, a more minimal race experience with time at the till. Thank you very much!

  5. Pamela

    Pamela

    Charter 41ft S/Y Selina II Sloop in St. Michaels, Maryland

    We booked this experience for my husbands birthday and it was PERFECT! The Selina II IS STUNNING, and Captain Iris and her crew were absolutely wonderful. Captain Matt was fantastic! He took such good care of us while we sailed across the Chesapeake Bay and celebrated with a couple of glasses of delicious champagne! Look no further and book the Selina II, you won’t regret it, it’s absolutely worth it !!

  6. PL

    Paul

    Enjoy a 35' Sloop J/105 Sailing Charter in San Diego, California

    The whole team at J World was super communicative and nice. The process was super smooth. The J/105 we rented was well equipped and well maintained. David showed us around the boat and gave us some advice on where to sail to. We had a blast!