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
(7,413 Reviews)

Page 13 of 38891 listings

35' Beneteau Sailing Yacht For Rent Newport (MAP: 2022-32)
Sailing in Newport Beach · 10 guests

35' Beneteau Sailing Yacht For Rent Newport (MAP: 2022-32)

5.0
$100+/hour
San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat
Sailing in San Diego · 8 guests

San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat

5.0
$300/hour
AMAR IS THE WAY TO ENJOY
Events in Miami · 13 guests

AMAR IS THE WAY TO ENJOY

5.0
Superowner
$400+/hour
Premium Sunset Sailing on a True WestSail 43ft Yacht
Sailing in San Diego · 6 guests

Premium Sunset Sailing on a True WestSail 43ft Yacht

5.0
$200/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
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
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
Lagoon Basileus 42 Catamaran in Puerto Vallarta
Sailing in Isla Iguana · 20 guests

Lagoon Basileus 42 Catamaran in Puerto Vallarta

New
$290/hour
 SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN
Sailing in Annapolis · 12 guests

SWEET & SALTY FOUNTAINE PAJOT HELIA 44 CATAMARAN

5.0
$400+/hour
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
41' Luxury Catamaran Private Sailing Adventure
Sailing in Zona Hotelera Norte · 25 guests

41' Luxury Catamaran Private Sailing Adventure

5.0
$379/hour
65ft Hatteras to 28 pax Free pick up transportation Hotel marina one way
Events in Cancún · 28 guests

65ft Hatteras to 28 pax Free pick up transportation Hotel marina one way

5.0
$325/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
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
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
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
STARZ -Lagoon 42 Catamaran in Chesapeake Bay
Sailing in Annapolis · 13 guests

STARZ -Lagoon 42 Catamaran in Chesapeake Bay

5.0
$400+/hour
Sail Miami! Beautiful Beneteau 43 Cruising Monohull
Sailing in Miami · 10 guests

Sail Miami! Beautiful Beneteau 43 Cruising Monohull

5.0
$170/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
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
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
Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis
Sailing in Port Washington · 6 guests

Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

5.0
$169+/hour
Shopping Tour to Isla Mujeres, Everyday 12:30 (Shared Basis)
Sailing in Isla Mujeres · 30 guests

Shopping Tour to Isla Mujeres, Everyday 12:30 (Shared Basis)

5.0
Superowner
Best of 2025
$395/hour

Sailing Reviews in United States

  1. RM

    Richard

    San Diego Sunset & Sunshine Sailing Tour on our Catalina 36 MK1 Sailboat

    Everyone, if you think twice don’t. Captain Dewayne is extremely accommodating and provided the wife and I with a 1 of 1 experience. We will be back to sail with you again. Thank you. We are so grateful.

  2. 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!

  3. Tawny

    Tawny

    Premium Sunset Sailing on a True WestSail 43ft Yacht

    Great experience on a steady and comfortable sail boat

  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. MR

    Matthew

    Sailing Long Island Sound with Captain Steve onboard 34ft Beneteau Oceanis

    We had a great time sailing out of Port Washington with Steven! Got to sail around the harbor to see some cool houses in Great Neck, the old lighthouse, and views of New York City in the distance. Steven was very communicative and a great captain for the morning! Would do again!

  6. BS

    Bianca

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

    Captain Jim was such a personable and kind man who gave us the most beautiful afternoon on the Barefoot Babe. He taught us out to sail the boat and so much more, wish we could have stayed on for hours. It was amazing and I would definitely rent from him again if I am ever back in Houston.