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All listings in the United States

Awesome sailboat rentals in United States.

4.9
(8,442 Reviews)

Page 10 of 40 • 949 listings

2hr Day Sail from the port of South Haven Mi. on a Catalina 36
Sailing in South Haven · 6 guests

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

5.0
$175/hour
Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure
Sailing in Potrero · 12 guests

Private Sailing Tour Flamingo, Guanacaste - Unforgettable Ocean Adventure

5.0
$165/hour
38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.
Sailing in Playa del Carmen · 15 guests

38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

4.7
Superowner
Best of 2026
$420/hour
Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat
Sailing in Saint Pete Beach · 6 guests

Sunset, Hour and Day Sailing Tours in St. Pete Beach - 30ft Dufour Sailboat

5.0
$110/hour
Sunset Sail in Bay of Santa Marta, Magdalena
Sailing in Santa Marta · 12 guests

Sunset Sail in Bay of Santa Marta, Magdalena

5.0
$125/hour
Create Memories you will Cherish for Life on this 47' Luxury Sailboat!
Sailing in Newport Beach · 6 guests

Create Memories you will Cherish for Life on this 47' Luxury Sailboat!

5.0
Superowner
$225+/hour
Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers
Events in San Francisco · 49 guests

Sailing Charter On 72' Tall Ship on SF Bay, California- up to 49 passengers

5.0
Superowner
$1,467/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
$30/hour
Set Sail on a classic 36' S2 in Chicago for up to 6 Guests
Sailing in Chicago · 6 guests

Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

5.0
$200/hour
San Diego Catamaran Charter | Private Harbor Cruises or Sunset Sail - 12 guests
Sailing in San Diego · 12 guests

San Diego Catamaran Charter | Private Harbor Cruises or Sunset Sail - 12 guests

5.0
$350+/hour
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
Sailing in Cancun and Isla Mujeres
Sailing in Cancún · 45 guests

Sailing in Cancun and Isla Mujeres

New
$271+/hour
50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys
Sailing in Marina · 40 guests

50' Spacious Catamaran for Fun & Adventure – Food, Drinks & Water Toys

New
$720/hour
Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC
Sailing in Morehead City · 6 guests

Charter our J-35 Sailboat, Blue Mind @ Northwest Creek Marina in New Bern NC

5.0
$100/hour
Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind
Sailing in Prince Edward · 12 guests

Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

4.9
$317/hour
Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe
Sailing in Placer County · 4 guests

Sail a Melges 24 Race Boat for 3 hours on Lake Tahoe

5.0
$200/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
50' Party Boat Catamaran in Miami  - 4 Hour Minimum - Up to 42 Guests
Sailing in Miami Beach · 42 guests

50' Party Boat Catamaran in Miami - 4 Hour Minimum - Up to 42 Guests

4.8
$1,200/hour
Private Sailing Tour in San Diego up to 10 Guests
Sailing in San Diego · 10 guests

Private Sailing Tour in San Diego up to 10 Guests

5.0
$175+/hour
Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena
Sailing in Cartagena · 23 guests

Captained Charter on Lagoon 440 Cruising Catamaran in Cartagena

4.9
$1,800/day
San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp
Sailing in San Diego · 6 guests

San Diego Bay 2.5 Hour Catamaran Sailing Tour - Small Group 6 or less @$99pp

4.7
$54/hour
Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests
Sailing in Oakville · 5 guests

Hunter 43 Sailing Yacht in Oakville, Ontario for 5 Guests

5.0
$194+/hour
40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.
Sailing in Tulum · 20 guests

40' Leopard Luxury Catamaran All-Inclusive Charter in Tulum Beach.

5.0
Superowner
Best of 2026
$450/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

Sailing Reviews in United States

  1. Ashley

    Ashley

    Private Sailing Charters Aboard a 40ft Trimaran – Explore PEC by Wind

    We had an absolutely incredible time on our catamaran charter with Captain David! He truly went above and beyond to make our birthday celebration memorable. The highlight of the trip was when he sang each of us a unique, personalized happy birthday song, it was such a thoughtful and fun touch that we will never forget. If you want a captain who is professional, attentive, and knows how to make an experience truly special, book with Captain David. Highly recommended!

  2. JK

    James

    Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

    Ted was the captain of the boat and was excellent. He made our ride very enjoyable and stayed out for the fireworks at the end which was amazing. Kids loved the experience too!

  3. Vince

    Vince

    Set Sail on a classic 36' S2 in Chicago for up to 6 Guests

    Highly recommend, Planned a surprised engagement, and Ted and Christy were awesome. Super accommodating, friendly, and went out of their way to make the experience very personal and fun. I wouldn’t want to experience a charter any other way.

  4. Taylor

    Taylor

    38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

    At the end of February 2025, my fiancé and I planned a combined bachelor/bachelorette party to Playa Del Carmen. We booked a catamaran for 9 people with Riviera Elite and can’t explain how great of an experience we had. The boat tour was originally scheduled for a Friday but due to the weather, the marina closed and boats were not allowed out on the water. Immediately, Riviera Elite contacted me and explained the situation and gave me an option to refund my money or reschedule for a future date. I am so grateful we rescheduled! Our experience was one to remember. We met a crew member at the Puerto Adventuras marina for check-in. Shortly after we were taken to the catamaran where we greeted the other 4 crew members. The catamaran was gorgeous and very spacious! Could have fit 20 people if we needed it to. They had Tequila Sunrise drinks and welcome appetizers waiting for us when we arrived. The workers made all of us feel at home and very safe. The crew first did a safety meeting to go over the boat protocols as well as specify which restrooms are for the males and which ones are for the females. Then they explained we had 2 options to choose from for the day. One, to go to the InHa reef and snorkel, but that it would take us 1 hour to get there and 1 hour back, leaving about 2 hours of free time. Or go to a sandbar inlet called La Bocana to party. We really wanted to snorkel, so we chose option A. The ride out to the reef was breathtaking. The weather could not have been more amazing with the water as still as can be. The catamaran was extremely sturdy, not one of us got seasick the entire day. Took about an hour to get to the reef as stated, where we all grabbed snorkel gear provided by the boat. We were able to see all different types of coral, fish and stingrays. Such a cool experience and beautiful at that. Once we finished snorkeling we hopped back on board the catamaran to an amazing assortment of fish and shrimp ceviche plus guacamole and chips. YUM! After we hung out and listened to some music at the reef we started to head back to the marina. On our way back to shore, 2 dolphins began following the boat for a good 10 minutes. It was magical! The entire day went off without a hitch. I highly recommend taking a boat/catamaran tour with Riviera Elite. They were one of the highlights of the trip to Mexico. Absolutely 100% would go on another trip with that crew. They even had a profession photographer on board as one of the crew members documenting the entire day. We ended up purchasing the photos and to our surprise he even had an underwater camera and snapped photos of us and the reefs below. We were mind blown! Please take a trip with Riviera Elite. You will not be disappointed at all! The best experience! And this is coming from folks in California who are used to beautiful beaches.

  5. SB

    Sarah

    38' Luxury Catamaran All-Inclusive Cruise in Playa del Carmen.

    Crew were brilliant. We arrived a little earlier rhan the agreed time (6.55 vs 7pm) bur had also left about 5-10 mins earlier so probably evened out. Food was amazing, setvice great. Water visibility was low snorkelling thanks to hurricane Ian (outside staff control). Spots were great though, just weather challenges in the lead up

  6. Diana

    Diana

    Create Memories you will Cherish for Life on this 47' Luxury Sailboat!

    Wonderful Father's Day sailing trip with Captain Dale and Danielle! Can not say enough and will totally book another day with them on this sailboat! All 6 of us had such a wonderful time. I really wanted to see dolphins on this trip and Captain Dale said that he had the dolphins on his payroll, well he has one heck of a payroll as hundreds showed up! We took a 4 hour trip which was just prefect, well maybe I would add one more hour! Diana