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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,462 Reviews)

Page 12 of 39932 listings

Epic 42ft Party Catamaran for Rent in Cabo San Lucas
Events in Marina · 30 guests

Epic 42ft Party Catamaran for Rent in Cabo San Lucas

5.0
$550/hour
🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.
Events in Sosúa · 150 guests

🛥🤩LUXURY YACHT PARTY SAILING AND Swimming in SOSUA, Puerto Plata.

4.4
$300/hour
Sailing Lessons with Chicago's #1 Rated Sailing School
Tours in Chicago · 6 guests

Sailing Lessons with Chicago's #1 Rated Sailing School

5.0
$175+/hour
41ft Metta Sailing Catamaran in Turks and Caicos Islands
Sailing in Leeward Settlement · 12 guests

41ft Metta Sailing Catamaran in Turks and Caicos Islands

5.0
$450/hour
Limited Availability
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
Welcome Aboard Optimystic! Create a beautiful memory on the water.
Sailing in Essex · 6 guests

Welcome Aboard Optimystic! Create a beautiful memory on the water.

5.0
$150/hour
Available in Puerto Plata  Private Yacht Experience: Beautiful Views book now
Powerboats in Puerto Plata · 100 guests

Available in Puerto Plata Private Yacht Experience: Beautiful Views book now

New
Superowner
Best of 2026
$50/hour
Bachelorette Party in Trimaran at Cabo San Lucas💃🏼🍾⛵️
Sailing in Marina · 50 guests

Bachelorette Party in Trimaran at Cabo San Lucas💃🏼🍾⛵️

5.0
Superowner
Best of 2026
$359/hour
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
Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica
Sailing in Tamarindo · 16 guests

Private Catamaran Tour and Snorkeling all-Inclusive, Tamarindo, Costa Rica

5.0
$320/hour
Sailing Sloop Hunter 40 in Puerto Vallarta
Sailing in Marina Vallarta · 12 guests

Sailing Sloop Hunter 40 in Puerto Vallarta

4.7
Superowner
$145/hour
Cancun Party Yacht 46ft Sea Ray Flybridge
Tours in Cancún · 15 guests

Cancun Party Yacht 46ft Sea Ray Flybridge

5.0
$260/hour
Instant Book
We Have Your 58' Sailing Ketch. Come Join Us On Clearlake / Galveston Bay Cruise
Sailing in Kemah · 12 guests

We Have Your 58' Sailing Ketch. Come Join Us On Clearlake / Galveston Bay Cruise

New
$199/hour
Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina
Sailing in Little River · 6 guests

Ocean Inlet Captained Charter onboard Beneteau 39 Sailboat in Little River, South Carolina

5.0
$150/hour
37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State
Sailing in Marina del Rey · 6 guests

37' Sailing Yacht in Marina Del Rey: Sail into a deep, Relaxed State

5.0
$200/hour
Lux Catamaran Fountaine Pajot 40ft
Sailing in Leeward Settlement · 10 guests

Lux Catamaran Fountaine Pajot 40ft

New
$714+/hour
6 passengers:  San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor
Sailing in San Diego · 6 guests

6 passengers: San Diego Bay Sport Catamaran Sail & Swim with With Expert Sailor

5.0
$220/hour
Luxury Sailing Experience on Robertson & Caine Leopard 40
Sailing in Saint Petersburg · 12 guests

Luxury Sailing Experience on Robertson & Caine Leopard 40

5.0
Superowner
$799+/hour
Private Sailboat Beneteau 42ft in Cabo, All-Inclusive
Sailing in Marina · 12 guests

Private Sailboat Beneteau 42ft in Cabo, All-Inclusive

5.0
$320/hour
Catmania Sailing Catamarans in Playa Mujeres, Cancun, Mexico.
Sailing in Isla Mujeres · 38 guests

Catmania Sailing Catamarans in Playa Mujeres, Cancun, Mexico.

5.0
Superowner
$262/hour
Captained Luxury Lagoon 560 Catamaran In The Bahamas
Sailing in Nassau · 25 guests

Captained Luxury Lagoon 560 Catamaran In The Bahamas

5.0
$1,050/hour
Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran
Sailing in Chicago · 13 guests

Chicago's Largest Chartered 38ft Lagoon Sailing Catamaran

5.0
$440/hour
41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.
Sailing in Whitehall · 6 guests

41ft Sailing Crusing Monohull Charter on ''White Lake'' Michigan, USA.

5.0
$140/hour
Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach
Sailing in West Palm Beach · 6 guests

Safe and Comfortable 42ft Fountaine Pajot catamaran sailing in West Palm Beach

5.0
$300/hour

Sailing Reviews in United States

  1. BF

    Barb

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Highly recommend sailing with Captain Charles on the Optimystic! Was like hanging out with an old friend. Beautiful boat and fun time!

  2. ET

    Ellan

    Captained Luxury Lagoon 560 Catamaran In The Bahamas

    Our large group of 21 with a mix of adults and kids had a great time! This was on our list for the Bahamas and it was the most epic part of our trip. We would highly recommend this company, if we are ever back, we already know who to call!

  3. EB

    Elias

    Welcome Aboard Optimystic! Create a beautiful memory on the water.

    Charles is fantastic, he and his wife went above and beyond to make everything go flawlessly, and the boat is gorgeous

  4. CA

    Caroline

    Experience premier service: NYC’s longest-running private sailing charter

    Beautiful boat with a professional and thoughtful team. We had a wonderful sail.

  5. Angela

    Angela

    Captained Luxury Lagoon 560 Catamaran In The Bahamas

    10/10 recommend. Crew was wonderful and food was excellent. Our group had an amazing time!

  6. TW

    Terry

    41ft Metta Sailing Catamaran in Turks and Caicos Islands

    A perfect day on the Metta. After messaging about our grandkids interests, the captain took us to the boat wreck to snorkel and then to a great coral reef! Snacks, drinks and gear were provided and they were very helpful. Last, we swam and played on the most beautiful beach and the kids saw iguanas! Great hosts! We will book the Metta again!