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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,289 Reviews)

Page 8 of 39925 listings

BEST IN CLASS All Inclusive Catamaran Charters
Sailing in Nassau · 20 guests

BEST IN CLASS All Inclusive Catamaran Charters

5.0
$1,080/hour
Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia
Sailing in Gloucester Point · 6 guests

Charter 32' Modern Hunter Sailboat In Gloucester, Point Virginia

5.0
Superowner
$125/hour
High Demand
Charter a 31' Pearson Cruising Sloop, Chicago
Sailing in Chicago · 6 guests

Charter a 31' Pearson Cruising Sloop, Chicago

4.5
$200+/hour
Limited Availability
Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package
Sailing in San Francisco · 20 guests

Nicest Certified 53' Santa Cruz Sailing Yacht on the West Coast - 20 Pax Package

5.0
Superowner
$750+/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
Limited Availability
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

5.0
$50/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
High Demand
San Diego Bay Sailing Experience
Sailing in San Diego · 12 guests

San Diego Bay Sailing Experience

5.0
$450/hour
2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

2hr Sunset Sail from the port of South Haven Mi. on a Catalina 36

5.0
$200/hour
Limited Availability
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
Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!
Sailing in Manhattan · 6 guests

Sail NYC's skyline aboard the Genesis, a beautiful classic sailboat!

5.0
$317/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
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
Luxury Italian Sailing Yacht on the Puget Sound — Seattle
Sailing in Seattle · 6 guests

Luxury Italian Sailing Yacht on the Puget Sound — Seattle

5.0
$374+/hour
High Demand
Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!
Events in Miami · 13 guests

Sea Ray Sundancer 38ft – Classic Luxury Cruise in Miami!

5.0
$100/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/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
High Demand
Well Appointed Beneteau 32, Folly Beach, SC
Sailing in Folly Beach · 6 guests

Well Appointed Beneteau 32, Folly Beach, SC

5.0
$190/hour
Wedding Groups Best Seller 82ft Luxury Catamaran with Open Bar Unlimited
Sailing in Isla Mujeres · 140 guests

Wedding Groups Best Seller 82ft Luxury Catamaran with Open Bar Unlimited

5.0
$515+/hour
Sunfish Sailboat on Merrymeeting Lake in New Hampshire
Sailing in New Durham · 2 guests

Sunfish Sailboat on Merrymeeting Lake in New Hampshire

5.0
$61+/day
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
Limited Availability
Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12
Sailing in San Francisco · 12 guests

Fully Crewed, All Inclusive Private Luxury Experience for 2 to 12

5.0
$876+/hour
Limited Availability
Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey
Sailing in Marina del Rey · 6 guests

Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

5.0
Superowner
Best of 2026
$150/hour
MAXUM 46' YACHT FOR RENT IN VANCOUVER
Events in Vancouver · 12 guests

MAXUM 46' YACHT FOR RENT IN VANCOUVER

5.0
$352/hour

Sailing Reviews in United States

  1. Geoffrey

    Geoffrey

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

    Icarus is a great boat and very well equipped. The sails and everything else on the vessel are in great shape and the fact it only draws 4' 6" is perfect for the Chesapeake. I spent a week on Icarus and everything worked well. The value of chartering Icarus is undeniable. I plan to charter Icarus again. Icarus has a lot of sail area, so if the winds are strong douse the headsail early.

  2. SK

    Scott

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    My family had a great trip out of MDR with Gustavo - he's a pro captain and has a lovely boat. He talked to all of us with ease and explained everything to us and showed us how to sail, helped us take pictures. We did 2 hours since that's all we had time for, but was just enough to sail from MDR up to the SM pier and back down. We saw some dolphins, sea lions and pelicans. If you want a friendly and easy to sail with captain and experience look no further than with Gustavo!

  3. LM

    Lauren

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    We rented Gustavo’s boat for two adults, two teenagers and two kids and we had a blast! It was a beautiful day and Gustavo took us out on the open water in his beautiful boat and even taught us things about how to sail. We loved his energy and expertise. Would absolutely book with him again!

  4. JP

    Jenny

    Charter 38' Pearson Cruising Monohull in Mamaroneck, New York

    I can’t say enough about how great this experience was! I celebrated my birthday, and it will definitely be one of the most memorable ones. The boat was beautiful, clean, and spacious. The best part was having Captain Rick on board. He was knowledgeable, kind, and made us feel very comfortable the entire time. He showed us around, shared interesting information, and made sure we had a smooth and relaxing sailing trip. Truly an unforgettable experience!

  5. Louis

    Louis

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    Can’t recommend Gustavo and the boat enough. On time, reliable, and not only knows exactly what he’s doing but happy to explain it all to you. Really great experience

  6. RK

    Richard

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

    Our group of four had a great three days onboard the Icarus. The boat was easy to sail and operate. No problems motoring around in the marinas, steers easy in reverse too. Jim was a great host, very responsive and knowledgeable. Highly recommend his boat to sail the Chesapeake!