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All listings near me

Find Sailing Charters Near You

4.9
(4,647 Reviews)

Page 9 of 10240 listings

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
$206+/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
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
Best of 2025
Snoozed - Active 17 Nov 2025
Luxurious 40ft Leopard Catamaran - Captain Included
Sailing in Saint Petersburg · 6 guests

Luxurious 40ft Leopard Catamaran - Captain Included

5.0
Superowner
Best of 2025
$315+/hour
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
42' Wanderlust - The Best Sailing Cat in the Market - Sarasota
Sailing in Sarasota · 12 guests

42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

5.0
$499+/hour
''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
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
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
Sail aboard this beautiful Jeanneau 389
Sailing in Riviera Beach · 8 guests

Sail aboard this beautiful Jeanneau 389

5.0
$105+/hour
Parasailing Adventure in West Palm Beach
Adventures in Riviera Beach · 12 guests

Parasailing Adventure in West Palm Beach

New
$99/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
Cabbage Key, Captiva Day Trip 1-6 people Captained
Powerboats in Cape Coral · 6 guests

Cabbage Key, Captiva Day Trip 1-6 people Captained

5.0
$95+/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
''Valentine'' Sea Ray SDX Series Deck Boat Rental  in Fort Myers, Florida
Powerboats in Fort Myers · 12 guests

''Valentine'' Sea Ray SDX Series Deck Boat Rental in Fort Myers, Florida

New
$535/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
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 31 Jul 2026
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
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

New
$300/hour
Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL
Sailing in West Palm Beach · 12 guests

Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL

4.6
Superowner
$125+/hour
Classic 1970 Sail Yacht
Sailing in West Palm Beach · 4 guests

Classic 1970 Sail Yacht

2.0
$900/hour
Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions
Sailing in Fort Myers Beach · 12 guests

Catamaran 48 foot luxury sailing cat daily, over night and weekly Excursions

5.0
$300/hour
Sail from Boynton Beach to Lake Boca
Sailing in Boynton Beach · 12 guests

Sail from Boynton Beach to Lake Boca

New
Superowner
$126+/hour

Local Sailing Reviews

  1. SG

    Steven

    Hunter Passage 456 Yacht - Sailing From West Palm Beach, FL

    Captain Mark is an excellent host and terrific sailor. His boat is beautiful and in great shape. He’s a great storyteller and it’s a pleasure to be in his company. I look forward to future voyages with him.

  2. FG

    Frank

    42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

    Thank you for such an amazing and memorable time. Our family had a blast. It was exactly what we were looking for! Boat was gorgeous and the staff was attentive, friendly and knowledgeable ! Anyone looking to charter, you guys will be our go to recommendation for sure!

  3. KC

    Krysten

    2017 Robertson and Caine Leopard 40 - Luxury Catamaran

    Our party had a wonderful time. It was a very pleasant sail and we pulled up to a near by beach where we could swim. The vessel is very spacious and clean. We felt safe as well. We would definitely sail again!

  4. CW

    Carly

    Hunter 336 Sailboat! Relaxing Sailing Palm Beach

    I rented the boat for and engagement photo shoot. The weather this time of year was very unpredictable and rainy, but Captain Gerald was great to work with and so funny. He made the day really enjoyable. Lovely boat and nice time, highly recommend!

  5. Mandy

    Mandy

    42' Wanderlust - The Best Sailing Cat in the Market - Sarasota

    Wonderful day, wonderful boat. The memories our family made together was priceless.

  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