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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,233 Reviews)

Page 11 of 40949 listings

Sailing From Pompano Beach, FL - $200/Hour - $33.33/Person
Sailing in Pompano Beach · 12 guests

Sailing From Pompano Beach, FL - $200/Hour - $33.33/Person

4.5
Superowner
$125+/hour
Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena
Sailing in Cartagena · 23 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

4.9
$1,650/day
Personalized Luxury Catamaran Getaways on 47ft Fountaine Pajot
Sailing in Nuevo Vallarta · 12 guests

Personalized Luxury Catamaran Getaways on 47ft Fountaine Pajot

New
$823/hour
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$326/hour
Instant Book
Let's Go Sail in Gloucester Point, Virginia
Sailing in Gloucester Point · 6 guests

Let's Go Sail in Gloucester Point, Virginia

5.0
Superowner
$117+/hour
Set Sail with 36' Sailing Boat in Downtown, Chicago
Sailing in Chicago · 6 guests

Set Sail with 36' Sailing Boat in Downtown, Chicago

5.0
$225/hour
Marlowe Hunter 33’ Sailing in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

Marlowe Hunter 33’ Sailing in Fort Lauderdale

5.0
$90+/hour
The nicest Charter Sailing Yacht in the West - Downtown San Francisco
Sailing in San Francisco · 20 guests

The nicest Charter Sailing Yacht in the West - Downtown San Francisco

4.9
$750+/hour
Instant Book
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Instant Book
50' Party Boat Catamaran in Miami ($1,200  PER HOUR)
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami ($1,200 PER HOUR)

4.8
$1,100/hour
🥂AMAZING PRIVATE YACHT🥂
Powerboats in La Romana · 50 guests

🥂AMAZING PRIVATE YACHT🥂

5.0
Superowner
Best of 2025
$50/hour
Impressive 56' Sailing Yacht in Nassau! Private charters & small group cruises.
Sailing in Nassau · 26 guests

Impressive 56' Sailing Yacht in Nassau! Private charters & small group cruises.

4.4
$607+/hour
41' Morgan Classic Sloop in Muskegon, Michigan!!!
Sailing in Muskegon · 6 guests

41' Morgan Classic Sloop in Muskegon, Michigan!!!

5.0
$100/hour
Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia
Sailing in Kilmarnock · 4 guests

Chesapeake Bay Sailing (w/ Captain) - 33' Cape Dory - Kilmarnock, Virginia

5.0
$15+/hour
Leopard 51 with flybridge in Tulúm
Powerboats in Tulum · 25 guests

Leopard 51 with flybridge in Tulúm

5.0
Superowner
$627/hour
Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC
Sailing in Manhattan · 6 guests

Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

5.0
$300/hour
Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands
Sailing in George Town · 20 guests

Luxury Beneteau Sense 55 Sailing Yacht Rental in George Town, Cayman Islands

5.0
$425/hour
Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul
Sailing in Stuart · 6 guests

Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul

5.0
$225/hour
Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.
Sailing in Nassau · 12 guests

Beautiful 41' Sailing Yacht in Nassau! Small group cruises & private charters.

4.7
$252+/hour
Hunter 43 Sailing Yacht in Oakville, Ontario
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario

5.0
$272/hour
Beneteau Modern Premium Sailboat from San Francisco
Sailing in San Francisco · 6 guests

Beneteau Modern Premium Sailboat from San Francisco

5.0
$220+/hour
Instant Book
34' Hunter Cruising Monohull In Rock Hall, Maryland United States
Sailing in Rock Hall · 4 guests

34' Hunter Cruising Monohull In Rock Hall, Maryland United States

4.6
$275+/night
Luxury Sail into a Deep, Relaxed State
Sailing in Marina del Rey · 6 guests

Luxury Sail into a Deep, Relaxed State

5.0
$200/hour
Instant Book
Sailing Sloop Hunter 40 in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Sailing Sloop Hunter 40 in Puerto Vallarta

4.7
Superowner
Best of 2025
$130/hour

Sailing Reviews in United States

  1. Kenderick

    Kenderick

    Luxury Sail into a Deep, Relaxed State

    I had an amazing experience Sailing with Matthew! From start to finish, everything was smooth and easy. The boat was beautiful, clean, and comfortable, and the entire day out on the water in the Marina was absolutely perfect. Matthew was professional, welcoming, and made sure we had everything we needed to enjoy the trip. It was such a memorable and relaxing day, and I can’t wait to book again. Highly recommend!

  2. Evan

    Evan

    Amazing Sailing Trip in NYC !!! The Most beautiful Sailboat in NYC

    Captain Paul and his wife, Melissa, were absolutely wonderful. I spent my birthday on their gorgeous sailboat with a group of friends, and we had the best day! The boat itself was stunning and Paul and Melissa went above and beyond to make our day perfect.

  3. KP

    Kendra

    Hunter 43 Sailing Yacht in Oakville, Ontario

    We had a great time on Dave’s boat! He recommended a beach area where we could anchor and swim around and let the kids get involved with the sailing when they asked. Very friendly and the boat was exactly what we expected.

  4. FC

    Fionnella

    Hunter 43 Sailing Yacht in Oakville, Ontario

    Great experience. Competent captain who is flexible with the itinerary. Enjoyed our 3 hour sail.

  5. LP

    Leeann

    Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

    Oleg was an awesome captain! He went above and beyond to accommodate us!

  6. ED

    Ethan

    Hunter 43 Sailing Yacht in Oakville, Ontario

    David was nothing but nice and the whole experience was beyond our expectations! Strongly recommend for anyone to unwind and rest in the calmness of Lake Ontario.