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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,467 Reviews)

Page 20 of 41 • 964 listings

Gorgeous 42' Bali Catamaran in Marina del Rey
Sailing in Marina del Rey · 12 guests

Gorgeous 42' Bali Catamaran in Marina del Rey

New
Superowner
$575/hour
45’ Leopard 2020 Cruising Catamaran in Cancun - Isla Mujeres!
Sailing in Cancún · 18 guests

45’ Leopard 2020 Cruising Catamaran in Cancun - Isla Mujeres!

5.0
Superowner
$515/hour
Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia
Sailing in Cartagena · 60 guests

Charter the Maxicat 65 Sailing Catamaran in Cartagena, Colombia

5.0
$3,500/day
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
Aicon 67 Fly  – Elite Luxury Yacht Experience
Events in Miami · 13 guests

Aicon 67 Fly – Elite Luxury Yacht Experience

New
$350/hour
La Paz Island Adventure Sailing Cruiser
Sailing in Zona Comercial · 8 guests

La Paz Island Adventure Sailing Cruiser

5.0
$235/hour
Rosario Islands Private Cruise – 40ft Catamaran from Cartagena
Powerboats in Cartagena · 15 guests

Rosario Islands Private Cruise – 40ft Catamaran from Cartagena

New
$4,999/day
Instant Book
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
Sailing Charter, 42 ft Cutter Ketch snorkeling, scuba. Roatan Honduras
Sailing in Bay Islands Department · 6 guests

Sailing Charter, 42 ft Cutter Ketch snorkeling, scuba. Roatan Honduras

5.0
$600/day
44ft Private Leopard Catamaran in Puerto Aventuras – Up to 35 Guests
Sailing in Puerto Aventuras · 35 guests

44ft Private Leopard Catamaran in Puerto Aventuras – Up to 35 Guests

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

35.5' Hunter-Legend Cruising Monohull

5.0
$125/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
Limited Availability
Ultra Luxury 2023 51 ft Trimaran Experience in the Sea of Cortez
Sailing in Zona Comercial · 8 guests

Ultra Luxury 2023 51 ft Trimaran Experience in the Sea of Cortez

5.0
$359/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
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
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
46ft Catamaran – Gulf of Papagayo Charter w/ Captain & Snorkeling
Sailing in Guanacaste Province · 30 guests

46ft Catamaran – Gulf of Papagayo Charter w/ Captain & Snorkeling

New
$840+/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 38ft Fountaine Pajot Athen Morning Sailing Catamaran in San Juan del Sur
Sailing in San Juan del Sur · 25 guests

Private 38ft Fountaine Pajot Athen Morning Sailing Catamaran in San Juan del Sur

New
$163/hour
Private 38ft Sunset Sailing Catamaran Charter — San Juan del Sur
Sailing in San Juan del Sur · 25 guests

Private 38ft Sunset Sailing Catamaran Charter — San Juan del Sur

New
$160/hour

Sailing Reviews in United States

  1. TF

    Tricia

    Sailing Charter, 42 ft Cutter Ketch snorkeling, scuba. Roatan Honduras

    My husband and I sailed with Captain John in August 2026, and it was an incredible experience! John put together a wonderful three-day private itinerary for us, including all the meals and snacks we enjoyed along the way. Since neither of us had ever sailed before, John was kind enough to show us the “ropes” 🙂 and made us feel comfortable and involved throughout the trip. From amazing snorkeling spots to fresh seafood dinners, every part of the experience was relaxing, memorable, and truly special. We couldn’t have asked for a better sailing experience and highly recommend Captain John to anyone looking for a fun, relaxing, and personalized adventure!

  2. 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.

  3. 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.

  4. ET

    Erica

    Ultra Luxury 2023 51 ft Trimaran Experience in the Sea of Cortez

    Thank you for an unforgettable day visiting Isla Espiritu Santo! The crew aboard Lambo were truly what set this trip apart from any other. Armando was so attentive and always thinking 3 steps ahead to anticipate our wants and needs. They were professional, polished and efficient in everything they did from maneuvering the boat to setting up for lunch, and more. The boat was immaculate- in fantastic condition, which made for a comfortable ride and luxurious experience. We will definitely book again next time we visit La Paz!

  5. 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!

  6. 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.