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Find Sailing Charters Near You

4.9
(4,499 Reviews)

Page 9 of 10240 listings

Sunset Sails: Explore the Open Waters of Tampa, Florida
Sailing in Tampa · 6 guests

Sunset Sails: Explore the Open Waters of Tampa, Florida

5.0
$175/hour
Instant Book
55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida
Events in Tampa · 13 guests

55ft "Poseidon SR" Sea Ray Flybridge Power MegaYacht Charter in Tampa, Florida

New
$801/hour
Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht
Sailing in Saint Petersburg · 6 guests

Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

5.0
$205+/hour
2017 Robertson and Caine Leopard 40 - Luxury Catamaran
Sailing in Treasure Island · 12 guests

2017 Robertson and Caine Leopard 40 - Luxury Catamaran

5.0
Superowner
Best of 2025
$300+/hour
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Treasure Island · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

New
Superowner
Best of 2025
$315+/hour
Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!
Sailing in Treasure Island · 28 guests

Set Sail aboard the Most Photographed Boat in the Tampa Bay Region!

New
$695/hour
Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul
Sailing in Stuart · 6 guests

Leopard 40 Cruising Catamaran for Up to 6 People in Stuart, FL with Captain Paul

5.0
$225/hour
Instant Book
44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL
Sailing in Palmetto · 13 guests

44ft Aquila "A Lil Bit Nauti" Yacht Charter in Palmetto, FL

New
$590/hour
''Remarkable I'' 54ft Aquila Powercat Rental in Palmetto, Florida
Sailing in Palmetto · 13 guests

''Remarkable I'' 54ft Aquila Powercat Rental in Palmetto, Florida

New
$1,147/hour
Hunter 336 Sailing Yacht Charter in Palm Beach, Florida
Sailing in North Palm Beach · 4 guests

Hunter 336 Sailing Yacht Charter in Palm Beach, Florida

New
$125/hour
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
Instant Book
42' Wanderlust - The Best Sailing Cat in the Market
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market

New
$449+/hour
Instant Book
''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida
Events in Sarasota · 13 guests

''Aloan at Last''r Mega Yacht Rental in Sarasota, Florida

New
$1,690/hour
Palm Beach FL: Private sailing, sighting-seeing and swimming with Capt Eric
Sailing in Palm Beach Shores · 6 guests

Palm Beach FL: Private sailing, sighting-seeing and swimming with Capt Eric

5.0
$300/hour
Instant Book
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$436/hour
"Thea Marie" Yacht Charter in Riviera Beach, FL
Sailing in Riviera Beach · 49 guests

"Thea Marie" Yacht Charter in Riviera Beach, FL

New
$1,288/hour
ALL INCLUDED | 35ft Luxury Scarab Sportster Sport Boat
Powerboats in West Palm Beach · 12 guests

ALL INCLUDED | 35ft Luxury Scarab Sportster Sport Boat

5.0
$280/hour
Instant Book
Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389
Sailing in West Palm Beach · 8 guests

Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

5.0
$105+/hour
44' Catamaran Party Boat In Grand Bahamas Island
Sailing in Bell Channel Bay · 45 guests

44' Catamaran Party Boat In Grand Bahamas Island

4.5
$140/hour
63' Catamaran - Luxury sailing for large groups!
Sailing in West Palm Beach · 40 guests

63' Catamaran - Luxury sailing for large groups!

New
$833/hour
Hakuna Matata - Party Catamaran in South Florida
Powerboats in West Palm Beach · 43 guests

Hakuna Matata - Party Catamaran in South Florida

New
$1,000/hour
Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida
Sailing in West Palm Beach · 12 guests

Private Luxury Lagoon Catamaran Charter in West Palm Beach, Florida

5.0
Snoozed - Active 24 Jul 2025
Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person
Sailing in West Palm Beach · 12 guests

Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person

4.8
Superowner
$125+/hour
Classic 1970 Sail Yacht
Sailing in West Palm Beach · 4 guests

Classic 1970 Sail Yacht

2.0
$900/hour

Local Sailing Reviews

  1. Madelyn

    Madelyn

    Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person

    Captain Mark was very welcoming and talkative! he kept us entertained with jokes and stories. it was slightly chill that day but they had an enclosure that kept us toasty!!!

  2. MT

    Mary

    Sunset Sails: Explore the Open Waters of Tampa, Florida

    Had a great time!! Definitely worth it.

  3. RB

    Russell

    Sailing From West Palm Beach, FL - $200/Hour - $33.33/Person

    Captain Mark is very knowledgeable and personable. He tailored our itinerary to our requests. His boat is comfortable and sails well. Highly recommended.

  4. Leah

    Leah

    Sunset Sails: Explore the Open Waters of Tampa, Florida

    Such an amazing experience! From the day I inquired to the moment we got off the boat , Arlo was a great person and made the experience unforgettable! Highly recommend, you won’t regret it and you’ll have the best memories to hold on to. Thank you again!

  5. JR

    Jeremy

    Sunset Sails: Explore the Open Waters of Tampa, Florida

    Whether you’re considering your first adventure out at sea or perhaps taken a few adventures, Arlo is your guy for a great sailing experience, kind heartedness, and very experienced in boats and adventures out at sea. He ensured that we were taken care of, well attended, and was an excellent host. I highly recommend Arlo. He gave a great experience.

  6. Robert

    Robert

    Day Sails and Sunset Cruises - Downtown St. Petersburg, FL - 44' Yacht

    If you're looking for a professional to take you sailing but you don't want it to feel like a tour boat, take a ride on Nick's personal boat. Bring along something cold to drink and enjoy the peace and quiet of being out on the water. My only regret is I should have made it a full day