Cookies!

We use cookies to improve your browsing experience. By continuing to browse or closing this banner, you agree to our use of cookies. Find out more about our cookies policy here.

All listings in the United States

Awesome sailboat rentals in United States.

4.9
(7,834 Reviews)

Page 4 of 38906 listings

Privat Sunset  Sailing
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing

5.0
$133/hour
Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away
Sailing in Nuevo Vallarta · 18 guests

Lagoon 40 in Nuevo Vallarta. Sip Margaritas, Relax, and Sail the day away

5.0
Superowner
Best of 2025
$238+/hour
Instant Book
Sailing Adventure Aboard 44' Hunter Sailboat
Sailing in New Castle · 6 guests

Sailing Adventure Aboard 44' Hunter Sailboat

5.0
$175+/hour
Fun time Jet Ski Rental at Lake Norman near Charlotte, NC
Water Sports in Cornelius · 8 guests

Fun time Jet Ski Rental at Lake Norman near Charlotte, NC

4.9
$84+/hour
Instant Book
Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY - $200/Hour - $33.33/Per Person

5.0
Superowner
$150/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
$138+/hour
Instant Book
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
$220/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
All-Inclusive Private 42’ Trimaran in Los Cabos
Sailing in Marina · 50 guests

All-Inclusive Private 42’ Trimaran in Los Cabos

4.8
Best of 2025
$379/hour
Instant Book
The Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

The Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.8
Superowner
Best of 2025
$900/hour
Instant Book
Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht
Sailing in Newport · 6 guests

Spectacular Sailing in Newport, RI Aboard our 36' Catalina Sailing Yacht

5.0
$200/hour
JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!
Sailing in Annapolis · 12 guests

JEHM of the SEA 2014 CATALINA 445 Sailboat for Amazing Day in Chesapeake Bay!

5.0
$250+/hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$150/hour
Luxury 35 ft catamaran with premium open bar and food included
Sailing in Marina · 8 guests

Luxury 35 ft catamaran with premium open bar and food included

5.0
Superowner
$568/hour
Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark
Sailing in Marina del Rey · 6 guests

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

5.0
Superowner
$125+/hour
Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,
Events in Marina · 12 guests

Beautiful Sea Ray Flybridge 45 ft Available In Cabo San Lucas,

5.0
$350/hour
LUXURY 44FT CATAMARAN ⛵️ SAILING TO ISLA MUJERES 🏝️
Sailing in Cancún · 40 guests

LUXURY 44FT CATAMARAN ⛵️ SAILING TO ISLA MUJERES 🏝️

5.0
Superowner
Best of 2025
$300/hour
2.5hr Catamaran Experience Montego Bay
Events in Montego Bay · 30 guests

2.5hr Catamaran Experience Montego Bay

5.0
Superowner
Best of 2025
$995/hour
Private Cruise onboard Hunter Legend Sailboat in Chicago
Sailing in Chicago · 6 guests

Private Cruise onboard Hunter Legend Sailboat in Chicago

5.0
Best of 2025
$200/hour
Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México
Sailing in Marina Vallarta · 20 guests

Lagoon 38 Beautiful Sailing Catamaran in Puerto Vallarta, México

5.0
$265/hour
27 Foot Sailboat for a Day of Fun in the Sun in Toronto
Sailing in Toronto · 6 guests

27 Foot Sailboat for a Day of Fun in the Sun in Toronto

5.0
$91+/hour
SeaRay 320 Yacht Charter in Cabo San Lucas
Events in Marina · 8 guests

SeaRay 320 Yacht Charter in Cabo San Lucas

4.9
$180/hour
Instant Book
Luxury 42ft Sea Ray Motor Yacht Charter for up to 8 people in Cancun
Events in Cancún · 8 guests

Luxury 42ft Sea Ray Motor Yacht Charter for up to 8 people in Cancun

5.0
$133/hour
Instant Book
Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0
$205+/hour

Sailing Reviews in United States

  1. TD

    Theresa

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    We had the best time on Mark’s sailboat for our friend’s bachelorette! From start to finish, Mark took such great care of us - always checking in to make sure we were comfortable and having fun. When one of the girls started feeling seasick, he quickly and calmly navigated us to smoother waters so she could feel better. He was so thoughtful, easygoing, and genuinely fun to chat with. Communication was seamless the entire time, and everything ran smoothly. We all left super happy and would highly recommend booking with Mark if you're looking for an amazing day on the water!

  2. AA

    Armine

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    Captain Mark provided an absolutely fantastic sailing experience! He was incredibly professional, polite, and so genuinely nice. We loved hearing his stories, and he had a wonderful way of making our entire family feel completely at ease. He was especially great with the kids, even sharing some hilarious dad jokes that had everyone laughing. We had such a memorable and fun time – highly recommend!

  3. GA

    Giselle

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Capt. Alberto and Graciela, the best! We had a great time and enjoyed learning about sailing with them. Everything was as described and much better. You’ll have a great time too! ⛵️☀️🩵

  4. Justine

    Justine

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    Wow what an amazing experience! I can’t believe the adventure we had sailing with Mark. His boat is beautiful and easy to move around and take up space. He offered us drinks and shared space for our added snacks. I didn’t have to bring my speaker because he had already thought ahead. He let my little cousins sail and inspired them to think bigger about the future and what is possible if they dream and choose for themselves to do so. I can not begin to describe how grateful I am for this beautiful memory co created on marks boat with my aunt, uncle and cousins on a very special occasion for us. This is the boat you want to book. So stop scrolling and submit your request to book! Look no further you have found the best option here 💖

  5. KS

    Kyli

    Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

    We had the best day on the water thanks to Captain Mark! He was incredibly friendly, easygoing, and made the whole experience feel effortless. From the moment we stepped on board, he made us feel welcome and at ease — super conversational, attentive, and just great energy all around. Whether you’re looking to relax, explore, or celebrate, Mark is the kind of captain who makes it all flow smoothly. Highly recommend for anyone looking for a seamless and fun boating day!

  6. Marie

    Marie

    38-ft Hunter 376 Sailing Adventure in Annapolis

    We thoroughly enjoyed our time with Alberto and his wife, Grace. Alberto is a delight to sail with - we learned so much from him. Grace is so lovely and gracious. We sailed around Annapolis during Memorial Day weekend and the weather was perfect. Alberto was very accommodating and friendly. We hope to see you again soon!