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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,498 Reviews)

Page 20 of 40 • 951 listings

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
$160/hour
Jeanneau 49 Sailing Charter in Channel Islands Harbor, Oxnard CA
Sailing in Oxnard · 6 guests

Jeanneau 49 Sailing Charter in Channel Islands Harbor, Oxnard CA

5.0
$363+/hour
65ft Sailing Catamaran in Playa del Coco
Sailing in Coco · 70 guests

65ft Sailing Catamaran in Playa del Coco

5.0
$532/hour
72ft Mega Power Catamaran 'Canuwa II' | Private Events Up to 150 Pax
Powerboats in Nuevo Vallarta · 55 guests

72ft Mega Power Catamaran 'Canuwa II' | Private Events Up to 150 Pax

5.0
$1,032+/hour
Beautiful J/109 - Luxury and Fast! Downtown San Francisco at South Beach Harbor
Sailing in San Francisco · 6 guests

Beautiful J/109 - Luxury and Fast! Downtown San Francisco at South Beach Harbor

New
Superowner
$350+/hour
Captained 80' Sailing Schooner Charter In Key West, Florida
Sailing in Key West · 32 guests

Captained 80' Sailing Schooner Charter In Key West, Florida

5.0
$475+/hour
35.5' Hunter-Legend Cruising Monohull
Sailing in Oakland · 6 guests

35.5' Hunter-Legend Cruising Monohull

5.0
$125/hour
Catamaran Lose 50 Country House La Romana
Sailing in La Romana · 20 guests

Catamaran Lose 50 Country House La Romana

New
$2,088/day
53' Leopard Power Catamaran – Private Bahamas Day Charter
Sailing in Nassau · 15 guests

53' Leopard Power Catamaran – Private Bahamas Day Charter

5.0
$1,160+/hour
42ft Catamaran Charter in Cancun for up to 30 Guests
Sailing in Cancún · 30 guests

42ft Catamaran Charter in Cancun for up to 30 Guests

New
Superowner
$275+/hour
Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience
Sailing in Sag Harbor · 41 guests

Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

5.0
$1,100+/hour
Private Group Sail and Snorkel Montego Bay
Sailing in Montego Bay · 30 guests

Private Group Sail and Snorkel Montego Bay

5.0
$940/hour
Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!
Powerboats in Sosúa · 80 guests

Puerto Plata Boat Budget-Friendly B-day Party Charter with Deals!

New
Superowner
Best of 2026
$50/hour
Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar
Sailing in Sosúa · 20 guests

Puerto Plata Party Catamaran Jacuzzi Slide Barbecue and Bar

New
$425/hour
Instant Book
Private 42ft Speedboat Cartagena on Rosario Islands & Cholón
Powerboats in Cartagena · 18 guests

Private 42ft Speedboat Cartagena on Rosario Islands & Cholón

New
$225/hour
Private 45ft Catamaran — Rosario Islands & Cartagena
Sailing in Cartagena · 40 guests

Private 45ft Catamaran — Rosario Islands & Cartagena

New
$4,999/day
Belize Shore Excursion: Private Catamaran & Snorkel
Sailing in Belize City · 25 guests

Belize Shore Excursion: Private Catamaran & Snorkel

New
$660/hour
Private 2.5 Hour Glass-Bottom Boat Tour with Cabo Arch & Snorkeling
Powerboats in Marina · 12 guests

Private 2.5 Hour Glass-Bottom Boat Tour with Cabo Arch & Snorkeling

New
$150/hour
Private Snorkeling & Fishing Tour with Beach BBQ, San Pedro
Sailing in San Pedro · 4 guests

Private Snorkeling & Fishing Tour with Beach BBQ, San Pedro

New
$235/hour
Private 26ft Family Friendly Speedboat Charter in Aruba
Powerboats in Oranjestad-West · 10 guests

Private 26ft Family Friendly Speedboat Charter in Aruba

New
$200/hour
Instant Book
Private 42-Foot Sailing Catamaran Charter in Bocas del Toro
Sailing in Bocas del Toro Province · 22 guests

Private 42-Foot Sailing Catamaran Charter in Bocas del Toro

New
$199/hour
Private 51ft Power Catamaran Charter from Tamarindo
Powerboats in Tamarindo · 18 guests

Private 51ft Power Catamaran Charter from Tamarindo

New
$975+/hour
Isla Saona 60ft Private Yacht –  Full Day Luxury Tour
Powerboats in La Romana · 20 guests

Isla Saona 60ft Private Yacht – Full Day Luxury Tour

New
$1,820/day
Instant Book
Private Cruise aboard 65ft Sailing Catamaran Charter in Papagayo
Sailing in Guanacaste Province · 46 guests

Private Cruise aboard 65ft Sailing Catamaran Charter in Papagayo

New
$900+/hour

Sailing Reviews in United States

  1. WB

    Wayne

    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

    I really appreciate how Captain Nina accommodated me last minute after I had a lesson scheduled at a sailing school. Saved my plans for the weekend. She did a great job adjusting the experience to my level, and keeping the whole time chill and conversational.

  2. Cherie

    Cherie

    65ft Sailing Catamaran in Playa del Coco

    I had a great trip. Everything was a smooth process and I was able to book on a last minute whim. Jeff was very responsive and helpful throughout the booking. The staff chartering the catamaran were all amazing and I would highly recommend this company to anyone looking to get out on the water in Costa Rica.

  3. Mayuri

    Mayuri

    Sag Harbor 73ft Luxuriously Custom Schooner Private Sailing Experience

    If you are looking for an amazing time, do not hesitate booking the Luna! Toby and his staff take care of you every step of the way. The boat is well equipped with servingware, water, and ice for your event. Fun bean bags are plenty aboard. Our guests enjoyed the awning and swim spot on a hot day, as well. Just a fabulous experience from start to finish!

  4. Ryankeisha

    Ryankeisha

    Private Group Sail and Snorkel Montego Bay

    My crew and I really enjoyed our boat ride and the Excursions that went along with it. We had lots of fun and the captain, my co-captain, and crew were very entertaining and accommodating. The food was delicious and the drinks were continuously flowing. I will definitely come back and do it again.

  5. DF

    Dalila

    35.5' Hunter-Legend Cruising Monohull

    Here’s a more understated version: Mary was easy to communicate with and everything went smoothly. The fleet was in good condition, and we had a great experience overall. We’d be happy to charter with her again!

  6. GR

    Gillean

    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

    Nina was great, and the sail was so relaxing and peaceful. Not too many powerboats out like you see on so many other lakes, so it was smooth sailing all the way. I’d highly recommend a sail with Captain Nina on this lovely lake.