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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

Hunter 336 Sailboat! Relaxing Sailing Palm Beach
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailboat! Relaxing Sailing Palm Beach

5.0
$120/hour
36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers
Sailing in San Miguel de Cozumel · 15 guests

36' Private Catamaran Charter in Cozumel | Perfect for Cruise Passengers

5.0
$310/hour
⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 42-people Includes: 1-Captain, 1-Mate and 1-Bartender

3.0
Superowner
$700+/hour
Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain
Sailing in Chicago · 6 guests

Private 38' Catalina Sailing Catamaran Charter for up to 7 Person with Captain

5.0
$450/hour
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
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
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
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
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
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
33ft The Key West's Most Versatile Sailboat! (With Captain Only)
Sailing in Key West · 12 guests

33ft The Key West's Most Versatile Sailboat! (With Captain Only)

4.6
$199+/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
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

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. 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!

  5. MT

    Michelle

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    We had the absolute best time with Gerald. From the moment we stepped on the boat, we were treated like family. His kindness, generosity, and genuine spirit made the entire experience feel so special. What stood out most was not only how much fun we had, but how it truly felt like we made a new friend. Gerald’s knowledge of the area is expert level, and he shared so many great insights that made the day even more enjoyable. This was such a memorable experience for our group, and we cannot recommend him enough. We will absolutely be back.

  6. AK

    ALEXANDER

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    Excellent experience from first contact until and beyond offboarding. Very family friendly. Definitely 5* experience. Will book again next time. The trip from the pier to the Atlantic is a great experience by itself. Sailing on the ocean is a dream come true. Enjoy!