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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,254 Reviews)

Page 14 of 40950 listings

38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.
Sailing in Tulum · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.

5.0
Superowner
$420/hour
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
Luxury Lagoon 450 Sailing Catamaran in Oceanside
Sailing in Oceanside · 6 guests

Luxury Lagoon 450 Sailing Catamaran in Oceanside

5.0
$250/hour
Instant Book
Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!
Sailing in Clear Lake Shores · 6 guests

Irwin Center Cockpit 53ft Cruising Monohull in Clear Lake Shores!!

5.0
$180/hour
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
Sailing in Oyster Bay · 6 guests

Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

5.0
$190+/hour
Instant Book
Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia
Sailing in Cartagena · 18 guests

Lagoon 400 18 People Cruising Catamaran In Cartagena, Colombia

5.0
$1,600/day
Sail Miami! Beautiful Beneteau 43 Cruising Monohull
Sailing in Miami · 10 guests

Sail Miami! Beautiful Beneteau 43 Cruising Monohull

5.0
$170/hour
Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises
Sailing in Mount Pleasant · 12 guests

Charleston's Largest Private Luxury Sailing Yacht 50ft Windchaser Custom Cruises

New
$250/hour
LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE
Sailing in Isla Iguana · 15 guests

LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE

5.0
$265/hour
Instant Book
Jeanneau 39i Julia Sailing Yacht in NY Harbor
Sailing in Manhattan · 6 guests

Jeanneau 39i Julia Sailing Yacht in NY Harbor

5.0
$400/hour
Epic 42' Party Catamaran for Rent in Cabo San Lucas
Events in Marina · 30 guests

Epic 42' Party Catamaran for Rent in Cabo San Lucas

New
$550/hour
Experience premier service: NYC’s longest-running private sailing charter
Sailing in Manhattan · 6 guests

Experience premier service: NYC’s longest-running private sailing charter

5.0
$395/hour
41' Luxury Catamaran Private Sailing Adventure
Sailing in Zona Hotelera Norte · 25 guests

41' Luxury Catamaran Private Sailing Adventure

5.0
$381/hour
65ft Hatteras Luxury Motor Yacht up to 28 pax in Cancún, Quintana Roo
Events in Cancún · 28 guests

65ft Hatteras Luxury Motor Yacht up to 28 pax in Cancún, Quintana Roo

5.0
$299/hour
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0
$400+/hour
Lagoon 42 Yacht Catamaran in Punta Mita
Sailing in Punta de Mita · 20 guests

Lagoon 42 Yacht Catamaran in Punta Mita

New
Superowner
Best of 2025
$310+/hour
 Come Play and Sail Away Barnegat Bay!
Sailing in Lacey Township · 6 guests

Come Play and Sail Away Barnegat Bay!

5.0
$150/hour
ALL INCLUSIVE Charter the Sea Ray 55  Yacht in PUERTO AVENTURAS
Events in Puerto Aventuras · 22 guests

ALL INCLUSIVE Charter the Sea Ray 55 Yacht in PUERTO AVENTURAS

5.0
$440+/hour
4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun
Sailing in Isla Mujeres · 12 guests

4-Hour Sailing Catamaran for Rent in Punta Sam, Cancun

5.0
Superowner
Best of 2025
$196/hour
!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic
Events in La Romana · 100 guests

!!Best 2025 Winner !! Power Catamaran in La Romana, Dominican Republic

5.0
Superowner
Best of 2025
$60/hour
Celebrate your special event in style with a fun Cruise on SF Bay
Sailing in San Francisco · 28 guests

Celebrate your special event in style with a fun Cruise on SF Bay

5.0
Superowner
$650/hour
Instant Book
50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle
Sailing in Seattle · 47 guests

50' Pirate Ship Adventure Aboard Queen Anne's Revenge in Seattle

4.9
$1,050/hour
Join us on the 38' 2006 Hunter for Sunset Cruises and Catalina Island Sail Trips
Sailing in Long Beach · 6 guests

Join us on the 38' 2006 Hunter for Sunset Cruises and Catalina Island Sail Trips

5.0
$140/hour
The Best Boat For You And Your Friends NERO
Events in Miami · 13 guests

The Best Boat For You And Your Friends NERO

New
Superowner
$365+/hour

Sailing Reviews in United States

  1. Jordan

    Jordan

    Join us on the 38' 2006 Hunter for Sunset Cruises and Catalina Island Sail Trips

    I had the pleasure of booking with Lisa & Alex for a couple of hours on a beautiful sunset afternoon. I had a special moment I wanted to create, and they were both so encouraging and helpful with all my needs. They were flexible, communicative, and fun trip companions. Alex is a great captain, and Lisa helped me with taking pictures while we stayed in the moment. I would not have been able to bring my idea to life without them, and I would highly recommend them to anyone looking for a boat managed by some amazing people for any type of event, get-together, or hangout.

  2. KH

    Kareem

    LUXURY VIBES CATAMARAN 380 PUERTO VALLARTA - NUEVO NAYARIT-CRUZ HUANACAXTLE

    We had an absolutely lovely time. The staff were attentive kind and accommodating. The boat was immaculate and clean. The food beverages and service were top notch. Would absolutely join this boat and crew again. Thank you!

  3. JS

    Jen

    STARZ -Lagoon 42 Catamaran in Chesapeake Bay

    I highly recommend Chronic Sailing! We did a 4 hour charter out of Annapolis as a bachelorette party. Captain Steve and Sarah were so accommodating and made our time so memorable. We are so appreciative. They made everything so easy- from booking to sailing and making memories with us. The STARZ catamaran boat was incredible! It fit our big group comfortably and gave us a little bit of luxury as we lounged and enjoyed on the bay. Again, this was a great experience for all of us and I would love to use them again!

  4. Tal

    Tal

    Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

    From the moment we stepped aboard, it was clear this yacht was something special. Impeccably maintained with every detail thoughtfully cared for, the vessel was not only stunning but also incredibly comfortable and inviting. What truly set this experience apart was our captain. An absolute gem- professional, patient, and genuinely kind. John’s calm demeanor and warm personality created an atmosphere of ease and enjoyment throughout the entire time. Whether it was navigating the waters flawlessly or ensuring everyone felt safe and cared for, this captain went above and beyond. This was more than just a ride—it was a luxury experience wrapped in beauty, serenity, and top-tier hospitality. Highly recommend for anyone looking to create lasting memories on the water. We will definitely be back❤️

  5. RS

    Robert

    Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!

    Jonathan is a very personable and friendly guy. Would definitely book with him again.

  6. Anna Sofia

    Anna Sofia

    38' Luxury Catamaran All-Inclusive Cruise in Tulum Beach.

    Absolutely the most stunning day ever! The crew could not have been nicer, more professional, or more attentive. They made sure we had the absolute best time of our lives and had an unforgettable experience. Our drinks were always being refilled without even having to ask, everything was explained to us in English and Spanish, snorkelling was made very safe and enjoyable and the views were stunning. The food was made fresh by our on-board chef and it was absolutely delicious. Thank you for everything!