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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,476 Reviews)

Page 11 of 40 • 938 listings

Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat

5.0
$2,500/hour
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
Wedding Groups Best Seller 82ft Luxury Catamaran with Open Bar Unlimited
Sailing in Isla Mujeres · 140 guests

Wedding Groups Best Seller 82ft Luxury Catamaran with Open Bar Unlimited

5.0
$509+/hour
San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
Sailing in San Diego · 6 guests

San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

4.7
$54/hour
2015 Sailing Yacht Catamaran Leopard 44 in Puerto Vallarta
Sailing in Marina Vallarta · 15 guests

2015 Sailing Yacht Catamaran Leopard 44 in Puerto Vallarta

5.0
$340+/hour
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
$159+/hour
Luxury Sail into a Deep, Relaxed State
Sailing in Marina del Rey · 6 guests

Luxury Sail into a Deep, Relaxed State

5.0
$200/hour
Amazing Sailing Catamaran for Charter in Cabo San Lucas, Mexico
Sailing in Ildefonso Green · 10 guests

Amazing Sailing Catamaran for Charter in Cabo San Lucas, Mexico

5.0
$550/hour
The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Sailing in San Francisco · 20 guests

The nicest Charter Sailing Yacht in the West - Downtown San Francisco

4.9
Superowner
$750+/hour
Instant Book
Enjoy an Excursion in Cabo San Lucas, Mexico on this Sailing Catamaran
Sailing in Ildefonso Green · 12 guests

Enjoy an Excursion in Cabo San Lucas, Mexico on this Sailing Catamaran

5.0
$330+/hour
Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht
Sailing in Port Washington · 12 guests

Sail From Port Washington, NY with Hunter Passage 456 Sailing Yacht

4.8
Superowner
$219/hour
Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.
Sailing in Nassau · 12 guests

Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.

4.7
$252+/hour
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
Gorgeous Luxurious 50ft Sailing Catamaran in Cancún & Isla Mujeres - Open Bar
Sailing in Cancún · 30 guests

Gorgeous Luxurious 50ft Sailing Catamaran in Cancún & Isla Mujeres - Open Bar

5.0
$318/hour
Beneteau Oceanis 41 for sailing adventures in San Blas Islands
Sailing in Guna Yala Comarca · 3 guests

Beneteau Oceanis 41 for sailing adventures in San Blas Islands

New
$700/day
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
2022 Chaparral 23' SSI  - Get up to 6 captained up and down the Potomac River
Powerboats in Fort Washington · 6 guests

2022 Chaparral 23' SSI - Get up to 6 captained up and down the Potomac River

5.0
$150+/hour
Limited Availability
NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA
Sailing in Los Angeles · 12 guests

NIGHT ON BOARD on a 38' sailing catamaran IN SAN PEDRO OR CATALINA

5.0
Superowner
$169+/hour
ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura
Sailing in Nassau · 40 guests

ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

5.0
$960/hour
Bachelorette Party in Trimaran at Cabo San Lucas💃🏼🍾⛵️
Sailing in Marina · 50 guests

Bachelorette Party in Trimaran at Cabo San Lucas💃🏼🍾⛵️

5.0
Superowner
Best of 2026
$359/hour
Stunning 56' Sailing Yacht in Nassau! Up to 26 guests.
Sailing in Nassau · 26 guests

Stunning 56' Sailing Yacht in Nassau! Up to 26 guests.

4.4
$607+/hour
Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour
36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers
Sailing in San Miguel de Cozumel · 15 guests

36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers

5.0
$310/hour
⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
$700+/hour

Sailing Reviews in United States

  1. Rudolf

    Rudolf

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles and his wife are amazing people who went above and beyond to offer us an amazing sailing experience all while teaching us about the various aspects of boating life. Book them for your next adventure, you won’t be disappointed.

  2. BF

    Barb

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Highly recommend sailing with Captain Charles on the Optimystic! Was like hanging out with an old friend. Beautiful boat and fun time!

  3. RM

    Richard

    ALL INCLUSIVE luxury day and overnight charter on the sailing catamaran Amura

    The Amura was the highlight of our time in the Bahamas! The communication was clear, and time at sea was fantastic. The boat had all the toys that our family could want. Captain Dan and crew make for a really enjoyable day. Also the food was incredible, come hungry!

  4. EB

    Elias

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles is fantastic, he and his wife went above and beyond to make everything go flawlessly, and the boat is gorgeous

  5. JR

    James

    43' Sailboat, Bristol RI & Beyond

    Captain Francis is very personable, and a great host on the water. He has taken very good care of his yacht, which is comfortable, ample in space and comfort, and everything operates as expected. He has a warm and laid-back demeanor, which makes for a very nice chemistry while sailing. Overall an A+.

  6. 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!!!