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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,466 Reviews)

Page 11 of 41 • 964 listings

Private Sailing Tour in San Diego up to 10 Guests
Sailing in San Diego · 10 guests

Private Sailing Tour in San Diego up to 10 Guests

5.0
$175+/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys
Sailing in Marina · 40 guests

50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys

New
$720/hour
Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC
Sailing in Morehead City · 6 guests

Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC

5.0
$100/hour
Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package
Sailing in San Francisco · 20 guests

Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

5.0
Superowner
$750+/hour
Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests

5.0
$197+/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.
Sailing in Tulum · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.

5.0
Superowner
Best of 2026
$450/hour
Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran
Sailing in San Pedro · 24 guests

Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran

5.0
$400/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
🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
Events in Sosúa · 150 guests

🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

5.0
$425/hour
Luxury Italian Sailing Yacht on the Puget Sound — Seattle
Sailing in Seattle · 6 guests

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

5.0
$349+/hour
BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/hour
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
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
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
$483+/hour
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
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
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
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
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
$4000 | 49 Guests | 2hrs | Annapolis
Sailing in Annapolis · 49 guests

$4000 | 49 Guests | 2hrs | Annapolis

5.0
Superowner
$2,200/hour
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
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
Bali 43 Complete comfort Catamaran
Sailing in Marina del Rey · 12 guests

Bali 43 Complete comfort Catamaran

5.0
$400/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. LD

    Lucy

    Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

    We had a beautiful day on the bay with Drew and Garrett who are both accomplished sailors and considerate hosts. Everyone felt comfortable and taken care of and I would highly recommend them to anyone looking for a day on the water with local experts. It was a gorgeous day and reminded us why we are so lucky to live here!

  4. RE

    REGINALD

    Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests

    I will definitely be a repeat customer. Beautiful experience with the wind in the sails and the silence on the water. If you want to enjoy the scenic views of nature then there is nothing better than riding over the water using only the wind. David made it easy for the whole family.

  5. BC

    Bismark

    40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.

    We had an amazing day today as a family! The entire team was excellent—very friendly and attentive. A big shoutout to Pablo, he’s truly the best! He made sure everyone felt comfortable and was always checking in on us with a great attitude. We highly recommend this experience!

  6. AR

    Aurora

    40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.

    I highly recommend Mikael’s company. We had an amazing 5hr trip around Tulum, had a nice lunch and had a great time while snorkeling. We were a family of five with one teen that enjoyed the scenery. The crew led by Pablo were responsive, respectful and knowledgeable. We upgraded our food options and Fernanda, the chef, prepared a delicious meal that we all enjoyed. Good value for the amenities and service. When back to Tulum, we will book with them.