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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,498 Reviews)

Page 23 of 40 • 951 listings

Sail from Delray Beach to Lake Boca
Sailing in Delray Beach · 12 guests

Sail from Delray Beach to Lake Boca

1.0
Superowner
$125+/hour
40' Catamaran - Sail away
Sailing in Marina del Rey · 6 guests

40' Catamaran - Sail away

5.0
$400/hour
Sailing live aboard  Charter in Montego Bay, Jamaica
Sailing in Montego Bay · 15 guests

Sailing live aboard Charter in Montego Bay, Jamaica

5.0
$950/day
3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel
Powerboats in Sosúa · 15 guests

3-Hours Puerto Plata Private Catamaran Cruise with BBQ Drinks and Snorkel

New
$332/hour
Instant Book
45' Lagoon Luxury Catamaran Charter in Riviera Maya
Sailing in Puerto Aventuras · 30 guests

45' Lagoon Luxury Catamaran Charter in Riviera Maya

5.0
$371+/hour
Super Comfortable McClain 50 Sailing Catamaran
Events in Marina Vallarta · 20 guests

Super Comfortable McClain 50 Sailing Catamaran

New
Superowner
$349/hour
Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Afternoon Sail | Private 50ft Jeanneau Sun Odyssey Sailing Yacht in Charleston

New
$250/hour
Discover the magic of the sea | Westsail 43' Private Sailing Tours
Sailing in San Diego · 12 guests

Discover the magic of the sea | Westsail 43' Private Sailing Tours

New
$280/hour
Catalina 27 Sailboat Rental in Olga, Washington
Sailing in Anacortes · 6 guests

Catalina 27 Sailboat Rental in Olga, Washington

5.0
$90+/hour
Sunset Cruise on Cartagena Bay Aboard 48' Leopard Catamaran with DJ and Open Bar
Sailing in Cartagena · 30 guests

Sunset Cruise on Cartagena Bay Aboard 48' Leopard Catamaran with DJ and Open Bar

New
$120/hour
42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland
Sailing in Rock Hall · 6 guests

42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

5.0
$150+/hour
Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views
Powerboats in Folly Beach · 6 guests

Tiki Bar, Hoppin, Sandbars, Down Island Vibes with Barrier island views

New
Superowner
$150/hour
Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

5.0
$550/hour
45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay
Sailing in San Diego · 6 guests

45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

5.0
$550+/hour
Private 40ft Catamaran Charter to Rosario Islands, Cartagena
Sailing in Cartagena · 15 guests

Private 40ft Catamaran Charter to Rosario Islands, Cartagena

New
$3,799/day
Instant Book
Manuel Antonio Catamaran Private ''Spanish Dancer''
Sailing in Quepos · 12 guests

Manuel Antonio Catamaran Private ''Spanish Dancer''

5.0
$1,500/hour
Luxury 52 Catamaran With  AC - Price include 2 People
Sailing in Guna Yala Comarca · 8 guests

Luxury 52 Catamaran With AC - Price include 2 People

5.0
$2,700/day
🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️
Tours in Dominican Republic · 40 guests

🛥️🏝️ SAIL IN PUNTA CANA PRIVATE GROUPS 🛥️🏝️

New
Superowner
Best of 2026
$75/hour
Experience Maine on 65ft Classic Schooner Yacht
Sailing in Rockport · 30 guests

Experience Maine on 65ft Classic Schooner Yacht

5.0
$500/hour
Maxicat 65ft Private Party Catamaran in Cartagena
Sailing in Cartagena · 80 guests

Maxicat 65ft Private Party Catamaran in Cartagena

New
Superowner
$838/hour
$3000 HR  |15 Guests|Catamaran - Choptank River
Sailing in Maryland · 15 guests

$3000 HR |15 Guests|Catamaran - Choptank River

New
Superowner
$700/hour
Costa Rica Catamaran Private Sunset Tour with Drinks
Sailing in Tamarindo · 20 guests

Costa Rica Catamaran Private Sunset Tour with Drinks

New
$515/hour
Lagoon 45' All Inclusive From Tulum
Sailing in Tulum · 30 guests

Lagoon 45' All Inclusive From Tulum

New
Superowner
$634/hour
Private 63ft Luxury Catamaran in La Romana – Saona or Catalina – Up to 35 Guests
Sailing in La Romana · 35 guests

Private 63ft Luxury Catamaran in La Romana – Saona or Catalina – Up to 35 Guests

New
$570/hour
Instant Book

Sailing Reviews in United States

  1. DP

    Dawn

    Luxury 52 Catamaran With AC - Price include 2 People

    ⭐⭐⭐⭐⭐ An unforgettable experience in San Blas, Panama! The Italian-owned boat exceeded all expectations. The food was divine, reflecting true Italian finesse, and the service was impeccable. Every moment aboard was filled with warmth, comfort, and authentic hospitality. A must-try for anyone seeking a remarkable sailing adventure in paradise!

  2. AA

    Adam

    45' Hunter Deck Salon PRIVATE Luxury Sailing Yacht, San Diego Bay

    What can I say except a big thank you for the best experience I’ve had before! It’s been an adventure holiday and for me personally, an awakening. You gave it your all for me and it's been totally great. Your new friend, Adam.

  3. MS

    Michelle

    Catalina 27 Sailboat Rental in Olga, Washington

    Lots to learn of you're new at sailing. Great teacher. Guess over it until you get it. Did a wonderful job explaining everything. The who what when where and why's. Also gave us a great dinner ideas.

  4. MH

    Madeline

    Experience Maine on 65ft Classic Schooner Yacht

    It was an absolutely beautiful sail! The captain and crew were so personable, sweet and accommodating! Gorgeous day and a BREATHTAKING boat! 10000/10 would recommend

  5. LT

    Lloyd

    42 foot Captained Catalina Sailing Yacht Located In Rock Hall, Maryland

    Davis was our captain, he was great . Very informative and knowledgeable . We went on a 31/2 hour sail in the Chesapeake bay. Would definitely do it again

  6. Sreenivasan

    Sreenivasan

    Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

    Excellent sail boat and amazing crew. We had an unforgettable experience. The When & If… is a beauty! Thank you Capt. Seth & team of pirates :)..