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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,434 Reviews)

Page 10 of 39928 listings

Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
Blue Oceans | Private Party Catamaran | Up to 12 Guests | San Diego Bay
Sailing in San Diego · 12 guests

Blue Oceans | Private Party Catamaran | Up to 12 Guests | San Diego Bay

5.0
$550+/hour
Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay
Sailing in Mayo · 6 guests

Hunter 42' Sailboat - Take a Charter or your Sailing Lessons on Chesapeake Bay

5.0
$150+/hour
49-Passenger Sailing Charter Catamaran at Navy Pier Marina
Sailing in Chicago · 49 guests

49-Passenger Sailing Charter Catamaran at Navy Pier Marina

New
$900/hour
Create Memories you will Cherish for Life on this 47' Luxury Sailboat!
Sailing in Newport Beach · 6 guests

Create Memories you will Cherish for Life on this 47' Luxury Sailboat!

5.0
Superowner
$225+/hour
38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
Sailing in Playa del Carmen · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

4.7
Superowner
Best of 2026
$420/hour
Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe
Sailing in Placer County · 4 guests

Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe

5.0
$200/hour
Shared Snorkeling & Sailing in Cabo San Lucas
Sailing in Marina · 12 guests

Shared Snorkeling & Sailing in Cabo San Lucas

5.0
Superowner
Best of 2026
$40/hour
Private Sailing Tour in San Diego up to 10 Guests
Sailing in San Diego · 10 guests

Private Sailing Tour in San Diego up to 10 Guests

5.0
$175+/hour
Limited Availability
Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!
Powerboats in South Carolina · 10 guests

Beautiful 24ft Bennington! Free Fuel, Delivery, Tube, And Life Vest!!!

5.0
$57/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
50' Party Boat Catamaran in Miami  - 4 Hour Minimum - Up to 42 Guests
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami - 4 Hour Minimum - Up to 42 Guests

4.8
$1,200/hour
Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.
Events in Gonzalo Guerrero · 35 guests

Lagoon 44’ with Open Bar and Full lunch. Visit El Cielo, Cozumel.

5.0
Superowner
$480/hour
Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago
Sailing in Chicago · 6 guests

Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

5.0
$210+/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
$325/hour
🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.
Events in Sosúa · 150 guests

🤩DELUXE BOAT FOR PRIVATE VIP BACHELORETTE/BIRTHDAY PARTY in Sosua Beach.

5.0
$425/hour
Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat
Sailing in Marina Mazatlán · 8 guests

Privat Sunset Sailing in Mazatlán, Sinaloa on 30ft Catalina Sailboat

5.0
$2,500/hour
$4400 | 49 Guests | 2hrs | Sailing Catamaran
Sailing in Washington · 49 guests

$4400 | 49 Guests | 2hrs | Sailing Catamaran

5.0
Superowner
$2,200/hour
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
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
$1,800/day
Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran
Sailing in San Pedro · 24 guests

Day Sailing Trip in San Pedro Aboard 42' Polynesian Catamaran

5.0
$400/hour
BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/hour
Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests

5.0
$199+/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.
Sailing in Tulum · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.

5.0
Superowner
Best of 2026
$450/hour

Sailing Reviews in United States

  1. TF

    Todd

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    This is the boat to book for a sweet sailing experience in Chicago. Super family friendly. Ocean-worthy vessel and Capt Bob and Gabby have been all over the hemisphere with it. They're more than willing to share as much knowledge as you'd like to know. I even pulled up the main sail! Bob and Gabby were great with our young children. Just wonderful people. Swimming spot they chose was excellent. If you're looking for the real deal, this is it. Loved hearing their stories about open ocean sailing and traversing the Caribbean Islands. Kids loved the aqua chair floaty. Worth every penny and more.

  2. RG

    Ryan

    Blue Oceans | Private Party Catamaran | Up to 12 Guests | San Diego Bay

    Amazing trip! First, the boat is beautiful. We had Captain Andy who was a great host. Helped us make a quick itinerary and we were on our way! Stopped for a swim before we headed back towards the harbor. I will be booking one of these trips again and would book this same one if I’m in San Diego.

  3. HC

    Hazel

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    Bob and his wife Gabby are amazing. We had so much fun with them. The boat is gorgeous and Bob is clearly a seasoned captain. Thanks again!

  4. sa

    steven

    Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

    It was an amazing experience! Everyone was nice and welcoming. Great flexibility and understanding. I would book this again!

  5. as

    apama

    Private Sailing Tour in San Diego up to 10 Guests

    Our captain had our charcuterie delivery and a cooler of ice ready and was a wonderful host as we "strolled" around.

  6. AS

    Andy

    Lets go sailing on a world class 40ft Pacific Seacraft Sailboat from Chicago

    What a wonderful time out on beautiful lake Michigan with Captain Bob! First time my family and I have been on a sailboat and we learned so much! The views of the city coupled with the hospitality onboard made it a day to remember for sure! A+ Highly recommend!