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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,392 Reviews)

Page 2 of 39914 listings

Manhattan Luxury Sailboat - 40' Hinckley Sailboat
Sailing in Manhattan · 6 guests

Manhattan Luxury Sailboat - 40' Hinckley Sailboat

5.0
$300/hour
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
$180/hour
Captained 42' Sailing Catamaran with 3 cabins and all the toys
Sailing in Key West · 6 guests

Captained 42' Sailing Catamaran with 3 cabins and all the toys

5.0
$320/hour
Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin
Sailing in Shalimar · 6 guests

Stiletto 30 Catamaran for Dolphin Watching, Sunsets, Snorkeling in Destin

5.0
$150/hour
40' Luxury Catamaran in Cozumel -
Sailing in San Miguel de Cozumel · 22 guests

40' Luxury Catamaran in Cozumel -

5.0
Superowner
$273+/hour
Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht
Sailing in San José del Cabo · 12 guests

Private Catamaran Charter in Los Cabos | 46ft Nautitech Sailing Yacht

5.0
$500+/hour
Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT
Sailing in Norwalk · 12 guests

Hunter Marine Passage 450 - Sail from Norwalk/Westport, CT

4.7
Superowner
$200/hour
Sail From Northport or Huntington, NY
Sailing in Huntington · 12 guests

Sail From Northport or Huntington, NY

4.8
Superowner
$150/hour
Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak
Sailing in Cancún · 25 guests

Luxury 45' Bali Vessel for VIP Groups | Chef Open Bar Grill Lobster Steak

5.0
$440/hour
34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas
Events in Marina · 8 guests

34ft Brown Sea Ray Sundancer Motor Yacht Rental in Cabo San Lucas

5.0
$190/hour
Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete
Sailing in Saint Petersburg · 6 guests

Luxury Bali 4.2 Catamaran | All-Inclusive Private Charters in St. Pete

5.0
$238+/hour
Luxury Catamaran Leopard 48 in Santa Marta Colombia
Sailing in Santa Marta · 10 guests

Luxury Catamaran Leopard 48 in Santa Marta Colombia

5.0
$150/hour
Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat
Powerboats in Iona · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained 24' Hurricane Deck Boat

5.0
$100+/hour
41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing
Sailing in Sag Harbor · 12 guests

41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

5.0
$750+/hour
Instant Book
#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages
Sailing in Manhattan · 6 guests

#1 Manhattan Sailboat! Champagne & Catering & Special Occasion Packages

5.0
Superowner
$300/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
$225+/hour
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
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Saint Petersburg · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
$300+/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
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
Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur
Sailing in Zona Comercial · 6 guests

Fully Equipped Bavaria 46 Cruiser in La Paz, Baja California Sur

5.0
$120/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.
Sailing in Puerto Aventuras · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Riviera Maya.

5.0
Superowner
Best of 2026
$450/hour
Enjoy cruising the Montego Bay coastline  In a 46  feet Searay yacht
Events in Montego Bay · 16 guests

Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

4.9
Superowner
Best of 2026
$599/hour
⛵️ Catamaran Party Boat 50' (49-Person)
Sailing in Miami Beach · 42 guests

⛵️ Catamaran Party Boat 50' (49-Person)

5.0
Superowner
$700+/hour

Sailing Reviews in United States

  1. ST

    Sabrina

    41' Beautiful sailing catamaran, perfect for lounging, swimming, and sailing

    This was actually the best day of my life. I had my bachelorette and the boat was so incredible, Brian and his partner are amazing hosts and their boat is so gorgeous and special. They were flexible with the hours and very accommodating. Would love to rebook !!

  2. AJ

    Aaron

    Sail From Northport or Huntington, NY

    Great captain, great experience. First time sailing for me and felt as comfortable as ever. Seamlessly kept me informed on the goings on with sailing so I felt at peace knowing what was happening. The boat was comfortable and safe. Captain mark was accommodating and friendly, good heart, good vibes! You'd be lucky to Have Captain Mark!

  3. Rafi

    Rafi

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    You must book with Gustavo, he is the best!!! His sailboat was absolutely perfect for our family birthday trip. He was extremely knowledgeable about the boat, and took a lot of care into his passengers. We sailed in the open waters and it was beautiful. He was such a positive person and great to have around. Book with Gustavo!!

  4. SF

    Sierra

    38-ft Hunter 376 Sailing Adventure in Annapolis

    Captain Alberto and Grace were incredibly welcoming and accommodating during our time on their boat. Captain Alberto taught us all about sailing and we really enjoyed being involved with helping sail the boat. My friend group had such a great time; would recommend! We will definitely be back!

  5. Kimberly

    Kimberly

    Enjoy cruising the Montego Bay coastline In a 46 feet Searay yacht

    It was such a pleasure meeting Dedrick in person. Very kind. Shadika and crew were phenomenal!! I reserved this yacht for my 50th birthday celebration,and the crew went above and beyond to ensure that this was an unforgettable experience! From food (wings were BOMB), to drink, fruit, and attentiveness, everything was great! You can’t go wrong with Deidrick and crew!

  6. Ara

    Ara

    Pearson 323 Day Sailing Cruising Adventure in Marina Del Rey

    We had a lovely day out on the water with Gustavo. He is very passionate about sailing and shared this passion with us. It was very easy to book with him and would definitely book again!