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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,461 Reviews)

Page 8 of 41 • 962 listings

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 49 guests

⛵️ Catamaran 49-Person Party Boat Includes: 1-Captain, 1-Mate and 1-Bartender

5.0
Superowner
$700+/hour
Sail San Diego Bay Aboard a French Yacht - Beer and Wine Included!
Sailing in San Diego · 6 guests

Sail San Diego Bay Aboard a French Yacht - Beer and Wine Included!

5.0
$450/hour
Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat
Sailing in Chicago · 6 guests

Come Sailing at Navy Pier Marina, Chicago - Beautiful 36' Catalina Sailboat

5.0
$225/hour
Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB
Sailing in Charleston · 6 guests

Private Luxury Sailing in the Charleston Harbor — Captain Included, BYOB

5.0
Superowner
$240/hour
Memorable Experience on this Leopard 47 Catamaran
Sailing in Isla Iguana · 25 guests

Memorable Experience on this Leopard 47 Catamaran

5.0
$325/hour
Full Day Sailing Potrero Guanacaste Province, Costa Rica
Sailing in Potrero · 12 guests

Full Day Sailing Potrero Guanacaste Province, Costa Rica

5.0
$200/hour
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
Beautiful Sea Ray Flybridge 45ft Available In Cabo San Lucas,
Events in Marina · 12 guests

Beautiful Sea Ray Flybridge 45ft Available In Cabo San Lucas,

5.0
$350/hour
3hr Classic Yacht Experience Montego Bay
Powerboats in Montego Bay · 35 guests

3hr Classic Yacht Experience Montego Bay

5.0
Superowner
$933/hour
60ft AIcon Yacht – Perfect for Luxury Day Trips
Events in Miami · 13 guests

60ft AIcon Yacht – Perfect for Luxury Day Trips

4.8
$350/hour
38' Sailing catamaran for parties / events in Long Beach! DISCOUNT WEEK DAYS
Sailing in Long Beach · 12 guests

38' Sailing catamaran for parties / events in Long Beach! DISCOUNT WEEK DAYS

5.0
Superowner
$169+/hour
3-hour exclusive Catamaran Sunrise or Sunset
Sailing in Isla Mujeres · 16 guests

3-hour exclusive Catamaran Sunrise or Sunset

4.9
Superowner
$262/hour
Incredible 36' Cruiser For Rent
Powerboats in Long Beach · 10 guests

Incredible 36' Cruiser For Rent

5.0
$149/hour
One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!
Events in Manhattan · 12 guests

One & Only - 52 Foot Luxury SeaRay Yacht, Brooklyn Bridge Park!

5.0
$475/hour
Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away
Sailing in Nuevo Vallarta · 18 guests

Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away

5.0
Superowner
Best of 2026
$263+/hour
Instant Book
Your own 42' Private Sailboat in Cabo
Sailing in Marina · 14 guests

Your own 42' Private Sailboat in Cabo

5.0
Superowner
Best of 2026
$255/hour
FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!
Sailing in San Francisco · 6 guests

FAST J/105 Sailing Yacht Charter Downtown San Francisco, California!

5.0
Superowner
$300+/hour
Sailing From Pompano Beach, FL
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL

4.6
Superowner
$125+/hour
Let's go Sailing in Miami!
Sailing in Miami · 6 guests

Let's go Sailing in Miami!

5.0
$45+/hour
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
Sailing in Manhattan · 6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
$300/hour
SeaDoo Switch Sport *5 ADULTS*
Powerboats in Texas · 9 guests

SeaDoo Switch Sport *5 ADULTS*

5.0
$100/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran
Sailing in San Miguel de Cozumel · 22 guests

Promo: 1 Hour Free Vip 40ft Lagoon Sailing Catamaran

5.0
Superowner
$250+/hour
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190/hour

Sailing Reviews in United States

  1. Peter

    Peter

    Sunfish Sailboat on Merrymeeting Lake in New Hampshire

    My wife and I had a great time taking out Matt’s Sunfish sailboat! He was there to greet us and help prepare the boat, and he had great recommendations for where in the lake to find the best sailing conditions. His sunfish is well maintained and sailed great. I would love to rent his Sunfish again next summer!

  2. DG

    Donald

    Memorable Experience on this Leopard 47 Catamaran

    Our group of 8 enjoyed a four-hour Puerto Vallarta cruise with Janette, Gabriel y Gabriel Jr, and Jose. They sailed us to a place where we could swim, dive off the boat, stand-up paddle board, and try our balance on the lilly pad. The teenage girls tanned themselves in style at the front of the boat. We enjoyed the views of the shore and the lovely breeze. Some of us enjoyed practicing our Espanol with the crew. At some point we were served delicious lunch at a table in the shade. Such a peaceful day. This was the favorite activity of the week-long vacation for many in our group. We highly recommend.

  3. Kevin

    Kevin

    Memorable Experience on this Leopard 47 Catamaran

    I think this is the 4th or 5th time we’ve booked with Hugo and this boat. Switched things up and did a sunset trip. We’re usually swimming or snorkeling generally jumping off the boat. Boat and crew are fantastic, see you again in a few months. Thanks!!

  4. RB

    Rachel

    Memorable Experience on this Leopard 47 Catamaran

    I booked this boat to celebrate a bachelorette and we had such an unmatched experience on the boat! The crew was amazing and so friendly. The boat was clean and spacious, there was enough space to lay out in the front and also be in the shade if needed. It was so great having everything arranged, it made it all easy and worry free. They helped me arrange transportation and additional food for the boat. We were taken on a ride to los arcos and a cove to swim in which was so fun. I would book this boat again. Everyone in our group had nothing but positive feedback. One of the crew members sang for us which was such a special treat! Book this trip!

  5. Dahlia

    Dahlia

    Memorable Experience on this Leopard 47 Catamaran

    We had such a blast!! What an amazing crew. The experience was incredible to see beautiful whales dolphins and tortuga just feet away. We loved the stop to snorkel and play on the water. Dancing in the bow was so much fun too. The food provided was great as well as fresh margaritas :)

  6. DJ

    Denny

    Memorable Experience on this Leopard 47 Catamaran

    You must book with Hugo and his crew. From the moment we arrived they provided outstanding service to all of us. The boat was better then the pictures!! The crew was very attentive and provided us with food and drink. They took us to Los Colomitos, a small cove with a private beach. We spent an hour or 2 at this location, and didn’t want to leave. They prepared chicken and steak fajitas that were delicious. They also made ceviche which was a hit with our group. One of the crew members played music and sang a couple of songs which was a real treat. Thank you all for such a fantastic boat trip!!!!