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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,496 Reviews)

Page 11 of 40 • 951 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
Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena
Sailing in Cartagena · 23 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

4.9
$1,800/day
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
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
$193+/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
🤩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
Private Party Catamaran | Up to 12 Guests | San Diego Bay
Sailing in San Diego · 12 guests

Private Party Catamaran | Up to 12 Guests | San Diego Bay

5.0
$550+/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
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
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
$159+/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
BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/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
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
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
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
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
$489+/hour
$4400 | 49 Guests | 2hrs | Sailing Catamaran
Sailing in Annapolis · 49 guests

$4400 | 49 Guests | 2hrs | Sailing Catamaran

5.0
Superowner
$2,200/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
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
Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!
Sailing in San Diego · 6 guests

Discover, Explore, Experience San Diego - Setting sail is the ultimate serenity!

New
$225/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. RG

    Ryan

    Private Party Catamaran | Up to 12 Guests | San Diego Bay

    Amazing trip! First, the boat is beautiful. We had Captain Andy who was a great host. Helped us make a quick itinerary and we were on our way! Stopped for a swim before we headed back towards the harbor. I will be booking one of these trips again and would book this same one if I’m in San Diego.

  3. 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!

  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. TJ

    Tushar

    Luxury Italian Sailing Yacht on the Puget Sound — Seattle

    Everything was perfect, Matt and JB made sure we had the perfect day! They made our day even more special, and were super accommodating and helpful, the perfect crew to sail with. As for the boat, Serafina is hands down the best boat on GetMyBoat, it is beautiful and very unique, it’s classy and we had a great time sailing.