Find awesome sailboat rentals and sailing charters for any travel destination.

4876 reviews worldwide.
1 - 18 of 7,613 listings
38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA
hour$150
United StatesPotomac River
Super Owner6 guests

38' Hunter 376 Cruising Monohull in Annapolis, Maryland, USA

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark
hour$145
United StatesCaliforniaMarina del Rey
Super Owner6 guests

Beneteau 40 Cruising Monohull in Marina del Rey with Captain Mark

Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii
hour$350
United StatesHawaiiO‘ahu
Super Owner12 guests

Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

Caribbean Vibez on a Brooklyn Sailboat
hour$179
United StatesNew YorkLong Island
Super Owner4 guests

Caribbean Vibez on a Brooklyn Sailboat

37' Luxury Sailboat with Captain
hour$275
United StatesLake Michigan
Super Owner6 guests

37' Luxury Sailboat with Captain

Cruise In Style On Roomy Sailboat - 36' Catalina
hour$145
United StatesCaliforniaMarina del Rey
Super Owner6 guests

Cruise In Style On Roomy Sailboat - 36' Catalina

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
hour$180
United StatesLake Michigan
Super Owner6 guests

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

38’ Morgan Sailboat Rental in Miami Beach, Florida
hour$175
United StatesFloridaMiami Beach
Super Owner6 guests

38’ Morgan Sailboat Rental in Miami Beach, Florida

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland
hour$150
United StatesChesapeake Bay
Super Owner6 guests

Beneteau Oceanis 50 Cruising Yacht in Rock Hall, Maryland

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
hour$125
United StatesFloridaFort Lauderdale
Super Owner6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

Charter 55ft Irwin Sailboat in Marina del Rey, California. PLEASE READ THE PRICES UNDER
hour$275
United StatesCaliforniaMarina del Rey
Super Owner12 guests

Charter 55ft Irwin Sailboat in Marina del Rey, California. PLEASE READ THE PRICES UNDER

#1 Manhattan Luxury Sailboat | 5-Star Accommodations | Champagne & Catering Packages
hour$325
United StatesNew YorkLong Island
Super Owner6 guests

#1 Manhattan Luxury Sailboat | 5-Star Accommodations | Champagne & Catering Packages

32' Ericson Racer/Cruiser Sailboat Charter in Long Beach, California
hour$200
United StatesCaliforniaLong Beach
Super Owner6 guests

32' Ericson Racer/Cruiser Sailboat Charter in Long Beach, California

42 Sailing Monohull Tours in Sausalito
hour$175
United StatesCaliforniaSausalito
Super Owner4 guests

42 Sailing Monohull Tours in Sausalito

Beneteau First 43 ft Monohull in Kewalo Habour Honolulu, Hawaii
hour$195
United StatesHawaiiO‘ahu
Super Owner12 guests

Beneteau First 43 ft Monohull in Kewalo Habour Honolulu, Hawaii

Islander 36' Sailboat for Charter in Nuevo Vallarta, Nayarit
hour$95
MexicoNayaritNuevo Vallarta
Super Owner6 guests

Islander 36' Sailboat for Charter in Nuevo Vallarta, Nayarit

Fountain Pajot 40ft Cruising Catamaran rental in Cancún
hour$215
MexicoQuintana RooCancún
Super Owner30 guests

Fountain Pajot 40ft Cruising Catamaran rental in Cancún

7,000+ results

Set sail with the best sailboat rentals and charters around the world.

Hit the open water in style on a sailboat rental or sailing charter. You can rent or charter a sailboat with or without a captain. Enjoy exploring the water by wind power. Most larger sailboats (typically 18+ feet) also use an engine for longer sailing trips. From hourly, half-day, full-day or multi-day sailing excursions, you are sure to create memories that will last a lifetime.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safety checks on each rental transaction.

Search for the perfect experience now and book your dream day out on the water.

Things to consider when booking a sailboat rental or charter.

  • Sailboats range in size and carrying capacity, so check with the captain to make sure the boat you pick will meet your needs.
  • If you want to learn some sailing techniques, ask about instruction or lessons while you're onboard.
  • Any doubts about booking your sailing adventure? No problem! Simply message the captain and ask any questions you may have.

GetMyBoat customer reviews for Boat Rentals worldwide.

  1. RW
    Randy
    42 Sailing Monohull Tours in Sausalito

    Rick was a fantastic host. He had the boat rigged and ready to go upon our arrival. His pre-trip communication was spot on, letting us know what to expect weather-wise, as well as what we would experience out on the bay. Everything went according to plan and we had a marvelous time. I highly recommend a cruise on General Storm. Thanks again Rick, can’t wait to get here again.

  2. NP
    Newsha
    Cruise In Style On Roomy Sailboat - 36' Catalina

    I had a friend visiting from out of town and booked a 4-hour sunset sail with Jared for our group of six. Jared was wonderful in communication, planning and as a captain and a human. He made the experience for us super fun, took great pictures from us and was an aware and awesome captain taking great care of us. I can't wait to book my next sail with him.

  3. KS
    Kendall
    Cruise In Style On Roomy Sailboat - 36' Catalina

    Jared was a phenomenal captain! His boat was comfortable and very well equipped! We were able to bring our own food and drinks and he provided pillows/blankets. He was very knowledgeable of the best sailing routes and was an amazing conversationalist! I could not recommend him enough!

  4. AT
    Arline
    Caribbean Vibez on a Brooklyn Sailboat

    Thank you Johnny for a wonderful day! It was cloudy and high chance of rain on the day of our initial booking but he changed it to accommodate the weather and our safety. He was great! He was calm just like the waves. Johnny is a great captain. He provided his speaker so we felt comfortable on his vessel. He made us feel at home and we would definitely book again. Please book with Johnny too!

  5. GM
    Gerald
    37' Luxury Sailboat with Captain

    We had an awesome experience on Dragonfly. Greg arrived on time to pick us up and we immediately headed out onto the lake. Greg listened to what we needed as a new sailing couple and really delivered. Greg is extremely knowledgeable and a good teacher. We had a lot of fun, highly recommend Greg and Cait. We will be back aboard the next time we're in Chicago.

  6. JT
    Jennie
    Sailing Charter On 48' Custom Made Sailing Catamaran In Honolulu, Hawaii

    Our group reserved the boat for 2-7pm which was perfect, as they said the sea turtles tend to leave around 3pm and we were able to see the sunset as well. We had excellent views of Diamond head and Waikiki, and they stopped at a few places so we could get out and swim. The crew was really nice and were happy to chat with us about the local fish and turtles. We would definitely love to rent the boat again when we come back to Hawaii!