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Find Sailing Charters Near You

4.9
(4,656 Reviews)

Page 10 of 10240 listings

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
''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
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
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
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

4.5
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
Instant Book
Sail from Boynton Beach to Lake Boca - $200/Hour - $33.33/Person
Sailing in Boynton Beach · 12 guests

Sail from Boynton Beach to Lake Boca - $200/Hour - $33.33/Person

New
Superowner
$126+/hour
50ft Catamaran Charter with Water Toys -Boca Raton, FL
Sailing in Boca Raton · 12 guests

50ft Catamaran Charter with Water Toys -Boca Raton, FL

5.0
Snoozed - Active 03 Nov 2025
Lagoon 42' Private Sailing Adventure in Florida with Captain Eric
Sailing in Deerfield Beach · 8 guests

Lagoon 42' Private Sailing Adventure in Florida with Captain Eric

5.0
$300/hour
30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida
Powerboats in Deerfield Beach · 10 guests

30 foot Jupiter Center Console Rental in Fort Lauderdale, Florida

5.0
$200/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
Sailing From Pompano Beach, FL - $200/Hour - $33.33/Person
Sailing in Pompano Beach · 12 guests

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

4.5
Superowner
$125+/hour
Brand new 200HP bayliner VR5
Powerboats in Texas · 7 guests

Brand new 200HP bayliner VR5

5.0
$110/hour
Bali Catspace 40 ft Catamaran in Ft Lauderdale for charter to Florida Keys
Sailing in Fort Lauderdale · 12 guests

Bali Catspace 40 ft Catamaran in Ft Lauderdale for charter to Florida Keys

New
$1,400/day
Fort Lauderdale Bahamas Sailing Charters
Sailing in Fort Lauderdale · 6 guests

Fort Lauderdale Bahamas Sailing Charters

5.0
$130+/hour
21ft Sun Tracker 20 Party Barge {Catch a Vibe}
Powerboats in Fort Lauderdale · 6 guests

21ft Sun Tracker 20 Party Barge {Catch a Vibe}

5.0
$100/hour
Luxury Lagoon 450 Catamaran in Key West
Sailing in Fort Lauderdale · 8 guests

Luxury Lagoon 450 Catamaran in Key West

New
$600+/hour
Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max
Powerboats in Fort Lauderdale · 6 guests

Fll Sun Deck 24' Final Price No Hidden Fees 10ppl max

4.8
Superowner
$113+/hour
Instant Book
Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida
Tours in Fort Lauderdale · 6 guests

Sailing Charter On 39' Catalina Sailboat In Fort Lauderdale, Florida

5.0
Superowner
$119+/hour
40 ft Jeanneau Sloop Charter in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

40 ft Jeanneau Sloop Charter in Fort Lauderdale

5.0
$109+/hour
2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale
Sailing in Fort Lauderdale · 6 guests

2 Hour Sunset River Cruise for up to 6 people in Fort Lauderdale

5.0
$150/hour

Local Sailing Reviews

  1. ES

    Emily

    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

    Captain Bill is professional, prompt, knowledgeable, and fun! Highly recommend booking with Captain Bill whether it’s a pleasure cruise or making your boyfriend’s dream come true by going ocean sailing. Captain Bill is amendable and very generous with letting us operate the boat. Thank you Captain Bill!

  2. CM

    Chris

    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

    Bill was great! There was regular, clear communication leading up to bareboat charter. He was also extremely accommodating as we made itinerary adjustment based on weather. He also provided helpful local knowledge during briefing to ensure safe and fun charter. Lorikeet is well maintained with up to date electronics and in excellent shape. I hope to return for future trips! Thanks Bill

  3. Anthony

    Anthony

    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

    Great overnight charter! Spent the day sailing the Atlantic followed by an evening of dining and nightlife in West Palm Beach. Bill was very thorough in making sure everything was prepared for an overnight charter. I will be doing another overnighter again!

  4. BC

    Bob

    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

    Captain Bill was very prepared, on time and helpful. The vessel was in excellent condition with all the gadgets, electronics and bells and whistles anyone would want. Boat handles well. Captain Bill is pleasant, easy to get along with and good company. Would highly recommend this charter without hesitation. Looking forward to next time.

  5. ds

    dave

    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

    My wife and I had a great trip celebrating our 30th anniversary. Bill was great to sail with and the boat was beautiful. We went out on the open ocean for a bit, but then headed to the inter-coastal waterway as the seas were pretty rough. We will absolutely be back again.

  6. BU

    Brian

    Enjoy a memorable sailing experience aboard this beautiful Jeanneau 389

    Bill’s boat is a beautiful and well equipped vessel. He was a great host and communicator and very accommodating. I soloed the boat for two days in the ICW and she handled great with all tacking lines brought aft to the twin helms. All the clutches for halyards and furlers were well marked. It’s a furling main which was my first experience with that system and with a little coaching from Bill I had no problem understanding the the proper method for operating it and avoiding any snags. The B&G GPS was accurate and local charts kept us within the 6’ draft when navigating the sometimes narrow sailing area in the Lake Worth ICW. We didn’t use the below deck accommodations much but the interior was beautiful with enough headroom, well cared for and clean. We look forward to using Bill’s boat again for a longer passage.