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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,341 Reviews)

Page 2 of 39915 listings

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak
Sailing in Cancún · 25 guests

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak

5.0
$430/hour
Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur
Sailing in Zona Comercial · 6 guests

Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur

5.0
$120/hour
34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas
Events in Marina · 8 guests

34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas

5.0
$190/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat
Powerboats in Iona · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0
$100+/hour
Luxury Catamaran Leopard 48 in Santa Marta Colombia
Sailing in Santa Marta · 10 guests

Luxury Catamaran Leopard 48 in Santa Marta Colombia

5.0
$150/hour
#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages

5.0
Superowner
$300/hour
Limited Availability
Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0
$238+/hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
$300+/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
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

5.0
Superowner
Best of 2026
$450/hour
30ft Sailing Yatch. Real & Unique Sailing in Mazatlán
Sailing in Marina Mazatlán · 8 guests

30ft Sailing Yatch. Real & Unique Sailing in Mazatlán

5.0
$2,000/hour
Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo
Sailing in Tamarindo · 20 guests

Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

5.0
$2,190/day
Limited Availability
Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!
Powerboats in South Carolina · 10 guests

Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

5.0
$57/hour
La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California
Sailing in Oceanside · 6 guests

La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California

5.0
$150/hour
Enjoy cruising the Montego Bay coastline  In a 46  feet Searay yacht
Events in Montego Bay · 16 guests

Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

4.9
Superowner
Best of 2026
$599/hour
Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta
Sailing in Marina Vallarta · 13 guests

Beautiful 40ft Hunter Sailboat — Enjoy Adventure & Sea Breeze in Puerto Vallarta

4.7
$130/hour
Beautiful Catalina 42 Sailboat In Puerto Vallarta, México
Sailing in Marina Vallarta · 12 guests

Beautiful Catalina 42 Sailboat In Puerto Vallarta, México

5.0
$130+/hour
Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.9
Superowner
$700+/hour
Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling
Sailing in Centro - Supmza. 001 · 15 guests

Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling

4.9
Superowner
$188/hour
Charter this beautiful Catalina from Milwaukee, WI - Captain Included
Sailing in Milwaukee · 6 guests

Charter this beautiful Catalina from Milwaukee, WI - Captain Included

4.9
$150/hour
Spacious, fast 80 foot sailboat
Events in Nuevo Vallarta · 40 guests

Spacious, fast 80 foot sailboat

5.0
$275/hour
Luxury Catamaran Lagoon 52' Capacity up to 40
Powerboats in Cartagena · 40 guests

Luxury Catamaran Lagoon 52' Capacity up to 40

5.0
Superowner
$325/hour
Limited Availability
All-Inclusive Private 42’ Trimaran in Los Cabos
Sailing in Marina · 50 guests

All-Inclusive Private 42’ Trimaran in Los Cabos

4.8
Superowner
Best of 2026
$379/hour

Sailing Reviews in United States

  1. Doug

    Doug

    Charter this beautiful Catalina from Milwaukee, WI - Captain Included

    Patrik did a great job getting us out on the water. There was a storm coming in and we had to cut the sail a little short but the winds did not disappoint. Great tour of the harbor and the city skyline. Patrik let us take the helm and experience sailing on the lake. Wish we had more time but better to be safe and dry.

  2. Kimberly

    Kimberly

    Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

    It was such a pleasure meeting Dedrick in person. Very kind. Shadika and crew were phenomenal!! I reserved this yacht for my 50th birthday celebration,and the crew went above and beyond to ensure that this was an unforgettable experience! From food (wings were BOMB), to drink, fruit, and attentiveness, everything was great! You can’t go wrong with Deidrick and crew!

  3. CF

    Carlos

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Captain Marco was absolutely amazing! He was incredibly attentive to our entire group throughout our birthday party celebration and truly went above and beyond. His energy and hospitality made it such a special and memorable day for all of us. We would definitely recommend him to anyone looking for a perfect day on the water and we are already planning our future boat adventures with him!

  4. MB

    Michele

    Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

    Used this company for a Birthday celebration. Had an awesome time on the yacht. The staff, Deidrick, and Shadika was friendly, fun, and very accommodating. The food was delicious and we had such a fun time. The yacht is nice and we will definitely be back. I highly recommend.

  5. NN

    Natalie

    All-Inclusive Private 42’ Trimaran in Los Cabos

    My group of 19 had so much fun on this private excursion! One thing that stood out what how extremely kind and attentive the staff was. The bartender, driver, coordinator, photographer, etc. were all so nice and made sure we were safe and having fun. However a tip from me would be to not party too hard the night before because half of our group was so hungover and seasick LOL. Despite that, we still had so much fun making memories in the water. Food and drinks were great! There is a photographer on board who was very kind but there is an additional charge for photos/drone footage which we unfortunately did not purchase because it was out of budget. There are also some jelly fish in the water that some of my friends got stung by. The staff was helpful to spray some unknown liquid on the stings to prevent it from getting worse. Overall through the hangover, I still had a great time thanks to Big Mike Adventures!!!

  6. SG

    Stacey

    Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

    We had a great experience! The boat was clean and well taken care of. All 10 of us fit just fine and the kids had fun tuning. Communication was great and everything went smoothly. Would definitely recommend!