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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,245 Reviews)

Page 3 of 40950 listings

30ft Sailing Yatch. Real & Unique Sailing in Mazatlán
Sailing in Marina Mazatlán · 8 guests

30ft Sailing Yatch. Real & Unique Sailing in Mazatlán

5.0
$108/hour
Safe & solid sailing catamaran - Green power! Stunning beauty & great location!
Sailing in Richmond · 6 guests

Safe & solid sailing catamaran - Green power! Stunning beauty & great location!

5.0
$162+/hour
52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana
Sailing in New Orleans · 6 guests

52ft Shannon Cruising Monohull Rental in Lake Pontchartrain, Louisiana

5.0
$110/hour
Avalon Harbor's Only Sailing Charter
Sailing in Avalon · 6 guests

Avalon Harbor's Only Sailing Charter

5.0
$275+/hour
Sailing is unique in Puerto Vallarta on board the Catalina 42 Sailing Yacht!
Sailing in Marina Vallarta · 12 guests

Sailing is unique in Puerto Vallarta on board the Catalina 42 Sailing Yacht!

5.0
Superowner
Best of 2025
$120/hour
High end Catamaran, Luxury Private Party in Cabo San Lucas. Captain &  crew inc
Powerboats in Marina · 50 guests

High end Catamaran, Luxury Private Party in Cabo San Lucas. Captain & crew inc

5.0
Superowner
$600/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
38-ft Hunter 376 Sailing Adventure in Annapolis
Sailing in Annapolis · 6 guests

38-ft Hunter 376 Sailing Adventure in Annapolis

5.0
Superowner
$100+/hour
Instant Book
43' Balize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur
Sailing in Marina · 20 guests

43' Balize Catamaran Yacht Charter in Cabo San Lucas Baja, California Sur

5.0
$544+/hour
Instant Book
Elegant 43ft Catamaran: Experience Boston Harbor in Style!
Sailing in Boston · 6 guests

Elegant 43ft Catamaran: Experience Boston Harbor in Style!

5.0
$313+/hour
50ft Catamaran Charter with Water Toys -Boca Raton, FL
Sailing in Boca Raton · 12 guests

50ft Catamaran Charter with Water Toys -Boca Raton, FL

5.0
$350/hour
Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois
Sailing in Chicago · 6 guests

Captained Charter this 36' C & C Cruising Monohull in Chicago, Illinois

5.0
Superowner
$220/hour
Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia
Sailing in Cartagena · 16 guests

Charter the 36' Fountaine Pajot Tobago Cruising Catamaran in Cartagena, Colombia

4.8
Superowner
Best of 2025
$870/day
PRIVATE CATAMARAN ⛵️ STARTING ON ISLA MUJERES 🏝️
Sailing in Centro - Supmza. 001 · 15 guests

PRIVATE CATAMARAN ⛵️ STARTING ON ISLA MUJERES 🏝️

4.8
Superowner
Best of 2025
$188/hour
 CATAMARAN/DOLPHIN SAIL  FOLLY BEACH SC
Sailing in Folly Beach · 6 guests

CATAMARAN/DOLPHIN SAIL FOLLY BEACH SC

5.0
Best of 2025
$190/hour
Luxury 35 ft catamaran with premium open bar and food included
Sailing in Marina · 8 guests

Luxury 35 ft catamaran with premium open bar and food included

5.0
Superowner
$568/hour
Lovely Catalina 36 Sailboat in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Lovely Catalina 36 Sailboat in Puerto Vallarta

5.0
Superowner
Best of 2025
$155/hour
2019 Lagoon 450F Sailing Catamaran Yacht in Puerto Vallarta, Mexico
Sailing in Marina Vallarta · 17 guests

2019 Lagoon 450F Sailing Catamaran Yacht in Puerto Vallarta, Mexico

5.0
$370+/hour
La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California
Sailing in Oceanside · 6 guests

La Bella Vita Hunter Sloop Sailing Trips in Oceanside, California

5.0
$150/hour
Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo
Sailing in Valle de Bravo · 16 guests

Catalina 36 Sailing Yacht Charter Mazingon in Valle de Bravo

5.0
Best of 2025
$162/hour
Cal 36 Sailboat Rental in Marblehead, Massachusetts
Sailing in Marblehead · 6 guests

Cal 36 Sailboat Rental in Marblehead, Massachusetts

5.0
$165/hour
All-Inclusive Private 42’ Trimaran in Los Cabos
Sailing in Marina · 50 guests

All-Inclusive Private 42’ Trimaran in Los Cabos

4.8
Best of 2025
$379/hour
The Midnight Sun,  Affordable Luxury  motor yacht
Events in Oranjestad-East · 15 guests

The Midnight Sun, Affordable Luxury motor yacht

5.0
Superowner
Best of 2025
$450/hour
Instant Book
The Ultimate Catamaran Party Boat | Up to 49 Passengers!
Events in Miami · 49 guests

The Ultimate Catamaran Party Boat | Up to 49 Passengers!

4.8
Superowner
Best of 2025
$800/hour
Instant Book

Sailing Reviews in United States

  1. CL

    Cong

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    I had a fantastic evening on this beautiful catamaran with a successful proposal to my now fiancee with sunset. Alex was so professional and accommodating, which led to the success. He was fast to respond, accommodating my date change request due to the weather forecast change even though it was within five days. Alex also coordinated well with my photographer, allowing him to board early before picking us up, which kept the proposal a surprise.

  2. Mike

    Mike

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    Perfect way to spend a day in Boston Harbor. The crew was so incredible and took amazing care of us. They had everything we would need, including snacks and towels (we usually bring our own, but totally didn't need to!). Would 100% recommend for a relaxing time on the water!

  3. AP

    Andrea

    38-ft Hunter 376 Sailing Adventure in Annapolis

    This was our crew’s second trip with Capt Alberto and was a second great experience. Capt Alberto shares his passion for sailing and teaching sailing! Capt and Grace are incredibly kind and make a great day spent out on the bay!

  4. TS

    Thomas

    Avalon Harbor's Only Sailing Charter

    This was an absolutely beautiful tour on an incredible sailboat. We toured the island and also were able to snorkel as the boat was equipped with plenty of masks and snorkels. Raphael was such a fantastic captain teaching us all of the history of Catalina. Totally recommend this experience!!!!! Thank you!

  5. OO

    Olivia

    Elegant 43ft Catamaran: Experience Boston Harbor in Style!

    We had the best time on the boat with Alex, the boat was perfect, plenty of room to move around. The views were stunning, everything went so smooth from the pickup to departure. They accommodated us with everything we needed. Alex and his mate were super knowledgeable and friendly. We had the best time with them and can’t wait to book again’

  6. Lisa

    Lisa

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Thank you so much Captain Alberto & Grace. We had a fabulous time and enjoyed learning about sailing. Thanks for trusting us to help steer and tack the boat. We had so much fun. You are a great teacher. We wish we could have stayed out longer.