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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,476 Reviews)

Page 2 of 40 • 938 listings

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Sailing in Tisbury · 6 guests

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

5.0
Superowner
$355/hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$180/hour
Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0
$238+/hour
Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak
Sailing in Cancún · 25 guests

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak

5.0
$424/hour
Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
$85/hour
Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!
Powerboats in South Carolina · 10 guests

Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

5.0
$57/hour
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey
Sailing in Marina del Rey · 6 guests

Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

5.0
Superowner
Best of 2026
$150/hour
#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages

5.0
Superowner
$300/hour
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
$300+/hour
Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston
Sailing in Mount Pleasant · 12 guests

Sunset Sail | Private 50ft Luxury Sailing Yacht in Charleston

5.0
$250/hour
Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling
Sailing in Centro - Supmza. 001 · 15 guests

Private Catamaran Fun from Isla Mujeres | Open Bar & Snorkeling

4.9
Superowner
$188/hour
Beautiful 45’ Sailboat - Private Charter
Sailing in Madeira Beach · 6 guests

Beautiful 45’ Sailboat - Private Charter

5.0
$225/hour
Avalon Harbor's Only Sailing Charter
Sailing in Avalon · 6 guests

Avalon Harbor's Only Sailing Charter

5.0
$275+/hour
Beautiful Catalina 42 Sailboat In Puerto Vallarta, México
Sailing in Marina Vallarta · 12 guests

Beautiful Catalina 42 Sailboat In Puerto Vallarta, México

5.0
$130+/hour
Enjoy cruising the Montego Bay coastline  In a 46  feet Searay yacht
Events in Montego Bay · 16 guests

Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

4.9
Superowner
Best of 2026
$599/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

4.9
Superowner
Best of 2026
$450/hour
⛵️ Catamaran Party Boat 50' (49-Person)
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 50' (49-Person)

5.0
Superowner
$700+/hour
La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California
Sailing in Oceanside · 6 guests

La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California

5.0
$150/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0
$100+/hour
Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.9
Superowner
$700+/hour
Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo
Sailing in Tamarindo · 20 guests

Why Not Oceanic Experience- Luxury Fountaine Pajot 61 feet in Flamingo

5.0
$2,190/day

Sailing Reviews in United States

  1. DH

    Dianne

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    Booked for our Anniversary with my 2 kids and OMG it was an experience we will never ever forget! I wish we coulve stayed longer. It was spectacular, amazing beyond words! Gustavo made sure we are safe especially the kids! He is a gentle soul, very patient and welcoming. The boat was very clean and well equipped. Truly an experience everyone must try once in their life! Haha! I can’t get over it!!

  2. SL

    Saskia

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto and his wife provided a lovely sailing experience for myself and my elderly parents, and were so kind to help both of my parents on and off the boat with great care-- even assisting them to get back to our car. We really enjoyed our time out on the bay

  3. LH

    Laura

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Alberto and his wife were absolutely wonderful hosts. They were welcoming, attentive, and made sure every detail of our sailing trip felt effortless. We had the most perfect day on the water, beautiful views, great company, and an experience we’ll remember for a long time. Highly recommend their boat and hospitality.

  4. PS

    Patricia

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Alberto was great about communicating and flexible when we had to reschedule due to bad weather the first time. He and his wife hosted us, balancing chatting and talking with them and having our own time as friends. Definitely recommend and would book again

  5. VN

    Viridiana

    Beautiful Catalina 42 Sailboat In Puerto Vallarta, México

    This boat was everything and more than we expected. What truly made it more memorable was the crew. They take safety so serious. Two members in our party decided to swim with our life jackets to a private beach. They were tired out on the way back and I immediately informed the crew. Like Superman in water this man dove in with flippers and brought them back with such ease. They prepared fantastic food and drinks and made sure we had a great time ! I highly encourage you to book. We saw los arcos and did some snorkeling. I will definitely book again the next time we return !

  6. AR

    Alison

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We had such a fun experience with Captain Alberto and Grace. They were delightful company and the sailing was beautiful! Getting to steer and learn the ropes was an extra perk.