Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,469 Reviews)

Page 6 of 39933 listings

Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!
Sailing in Marina del Rey · 12 guests

Hudson 58ft Sailing Vessel - Enjoy The Classic Sailing Experience With Us!

4.8
$275+/hour
Exclusive Sailing Boat
Sailing in Marina Vallarta · 15 guests

Exclusive Sailing Boat

5.0
Superowner
Best of 2026
$80+/hour
Fountaine Pajot Great Sailing Catamaran for up to 25 people!
Sailing in Cartagena · 25 guests

Fountaine Pajot Great Sailing Catamaran for up to 25 people!

4.6
Superowner
$1,600/day
32ft Classic Sailing Charter on Swedish Sloop for 6 Guests
Sailing in Rockland · 6 guests

32ft Classic Sailing Charter on Swedish Sloop for 6 Guests

5.0
$150/hour
🛥️ Make It a Yacht Day – Your Private 45ft VIP Yacht Experience in Aruba
Events in Oranjestad-East · 12 guests

🛥️ Make It a Yacht Day – Your Private 45ft VIP Yacht Experience in Aruba

5.0
$575/hour
44' Luxury Cruiser Sailboat Charter  | San Francisco Bay
Sailing in Alameda · 6 guests

44' Luxury Cruiser Sailboat Charter | San Francisco Bay

5.0
$159/hour
Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor
Sailing in Chicago · 3 guests

Beautiful Ranger 22 Sailboat for rent in Chicago's Monroe Harbor

4.9
$107+/hour
Caribbean Vibez on a Brooklyn Sailboat
Sailing in Brooklyn · 4 guests

Caribbean Vibez on a Brooklyn Sailboat

5.0
Superowner
$191/hour
Limited Availability
AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch
Sailing in Annapolis · 6 guests

AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

5.0
$200+/hour
Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur
Sailing in Zona Comercial · 6 guests

Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur

5.0
$120/hour
⛵️  MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)
Sailing in Miami Beach · 49 guests

⛵️ MARIAH — 60’ CATAMARAN (UP TO 49 GUESTS)

5.0
Superowner
$700+/hour
56' SeaRay Yacht in New York!
Events in Brooklyn · 12 guests

56' SeaRay Yacht in New York!

4.8
$475/hour
42ft Catalina MkII Sailing Yacht in The San Diego Bay, California
Sailing in San Diego · 6 guests

42ft Catalina MkII Sailing Yacht in The San Diego Bay, California

5.0
$285/hour
Sail San Diego Bay Aboard a French Yacht - Beer and Wine Included!
Sailing in San Diego · 6 guests

Sail San Diego Bay Aboard a French Yacht - Beer and Wine Included!

5.0
$450/hour
Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests
Sailing in Chicago · 10 guests

Private Jeanneau Sun Odyssey 37ft Sailboat Chicago Cruise with 10 Guests

5.0
Superowner
$250/hour
Instant Book
47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay
Sailing in Seabrook · 12 guests

47' Leopard Sailing Catamaran on Clear Lake/Galveston Bay

5.0
$300/hour
81' Sailboat | Hot Tub + Full Water Toys | Up to 50 Guests
Sailing in Marina Vallarta · 50 guests

81' Sailboat | Hot Tub + Full Water Toys | Up to 50 Guests

New
$603/hour
42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)
Sailing in Sag Harbor · 6 guests

42' Catalina Sailing Yacht in the Hamptons - For a perfect day on the water /)

5.0
$312+/hour
Newport Harbor Sailing Adventure
Sailing in Newport Beach · 6 guests

Newport Harbor Sailing Adventure

5.0
$133/hour
40' Sea Ray Sundancer All-Inclusive Yacht Charter in Riviera Maya.
Events in Puerto Aventuras · 12 guests

40' Sea Ray Sundancer All-Inclusive Yacht Charter in Riviera Maya.

5.0
Superowner
Best of 2026
$350/hour
Private Harbor Cruise in Newport Beach, California
Tours in Newport Beach · 4 guests

Private Harbor Cruise in Newport Beach, California

5.0
$200/hour
Suncatcher 22ft Family Pontoon!
Powerboats in Montana · 8 guests

Suncatcher 22ft Family Pontoon!

5.0
$65/hour
Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California
Sailing in Marina del Rey · 12 guests

Stunning 46' Bali Cruising Catamaran Charter in Marina del Rey, California

5.0
Superowner
$650/hour
Lovely Catalina 36 Sailboat in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Lovely Catalina 36 Sailboat in Puerto Vallarta

5.0
Superowner
$155/hour

Sailing Reviews in United States

  1. KG

    Kathleen

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

    Highly highly recommend booking with Stephen! We had friends coming to visit from out of town and we had the most wonderful charter. Stephen was an excellent captain and very kind host. The boat itself is very cool, with plenty of room to hang on the bow (and a clean bathroom!). Can’t say enough about what a great time we had!!

  2. RB

    Richard

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

    Not sure I can say enough about how absolutely incredible our experience was with Steve. Boat was perfect. Communication was perfect. But the experience was incredible! He took my wife, two sons and I out to the Wednesday night races in Annapolis, and we got to engage right into the races, feel the speed of the boats, see the tight turns, and it’s an experience my sons will not forget. Can’t recommend highly enough.

  3. ST

    Shaddy

    56' SeaRay Yacht in New York!

    We had an incredible experience aboard Encore with Captain Max! I booked the boat for my engagement, and when rain threatened our original date, Max was extremely understanding and worked with me to move the reservation so the moment could still be everything I had planned. He was communicative, flexible, and genuinely invested in helping make the occasion special. The boat was beautiful, clean, comfortable, and exactly as advertised. Once we were aboard, Max made us feel completely at ease and gave us the perfect experience on the water. This was one of the most important and memorable days of our lives, and Max played a huge role in making it happen. I truly appreciate how accommodating he was throughout the entire process. I couldn’t recommend Captain Max and Encore more highly!

  4. TA

    Ty

    Suncatcher 22ft Family Pontoon!

    We had a great experience renting this pontoon. The host was incredibly accommodating, flexible, and communicative from start to finish. The listing was exactly as advertised, and everything on the boat worked perfectly. The pickup and dropoff was easy. We’d definitely rent from them again!

  5. LF

    Linda

    AnnapolisBoatExperiences presents an Exclusive Sail on its Classic 37' Ketch

    Stephen was wonderful! A few days before our sailing trip, the weather forecast looked questionable, but he stayed in touch the entire time, offering to start earlier or even reschedule for a different day if needed. He was incredibly flexible and genuinely wanted to make sure we had the best possible experience. Thanks to his communication and commitment, we had a fantastic trip. I highly recommend sailing with Stephen!

  6. NC

    Noah

    Newport Harbor Sailing Adventure

    Captain Andrew provides a lovely charter experience! It was at once both relaxing and adventurous. He’s extremely knowledgeable and professional. Can’t wait to book another charter!