3425 16th Ave. SE Naples, Florida 34117

Sailing Charter Rates

3 HR Daytime or Sunset Sail​

3 Hour Charter
$425
All trips are for up to a maximum of 6 guests

Half Day Sailing Charter

4 Hour Charter
$525
All trips are for up to a maximum of 6 guests

Full Day Sailing Charter

8 Hour Sailing Charter
$800
All trips are for up to a maximum of 6 guests

Overnight Kayaking Excursion 1

Excursion from Naples to Shark River Island (Package 1)
$3000
We will depart Naples at approximately noon through Gordon’s Pass, then turn south past Marco Island, Cape Romano, and into the 10,000 Islands area of the Everglades. All trips are for up to a maximum of 6 guests

Overnight Kayaking Excursion 2

Excursion from Naples to Gordon's Pass (Package 2)
$3000
This trip will depart Naples at approximately noon through Gordon’s Pass, and head north past Fort Myers Beach and Sanibel Island to the north part of Captiva Island. All trips are for up to a maximum of 6 guests

Special Discounts

As veterans ourselves, we are offering all veterans a special discount.
Police officers and firefighters will receive an additional hour free-of-charge to any day sail trip booked, and 10% off any excursion.

3 HR Daytime or Sunset Sail​

3 Hour Charter
$425
All trips are for up to a maximum of 6 guests

Half Day Sailing Charter

4 Hour Charter
$525
All trips are for up to a maximum of 6 guests

Full Day Sailing Charter

8 Hour Sailing Charter
$800
All trips are for up to a maximum of 6 guests

Overnight Kayaking Excursions

Excursion from Naples to Shark River Island (Package 1)
$3000
We will depart Naples at approximately noon through Gordon’s Pass, then turn south past Marco Island, Cape Romano, and into the 10,000 Islands area of the Everglades. All trips are for up to a maximum of 6 guests

Overnight Kayaking Excursions

Excursion from Naples to Gordon's Pass (Package 2)
$3000
This trip will depart Naples at approximately noon through Gordon’s Pass, and head north past Fort Myers Beach and Sanibel Island to the north part of Captiva Island. All trips are for up to a maximum of 6 guests

Special Discounts

As veterans ourselves, we are offering all veterans a special discount.
Police officers and firefighters will receive an additional hour free-of-charge to any day sail trip booked, and 10% off any excursion.

Sailing Charters Booking Details

A 10% deposit is required to guarantee your sailing trip reservation. The remaining balance is to be paid directly to the charter operator on or prior to your trip date.

You can cancel or change your booking free of charge up to 48 hours before your sailing adventure.

If the captain cannot run the trip due to unsafe weather conditions, your booking can be moved to another date or canceled, free of charge.

Sailing Charters Booking Details

A 10% deposit is required to guarantee your sailing trip reservation. The remaining balance is to be paid directly to the charter operator on or prior to your trip date.

You can cancel or change your booking free of charge up to 48 hours before your sailing adventure.

If the captain cannot run the trip due to unsafe weather conditions, your booking can be moved to another date or canceled, free of charge.

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Photo Gallery

Sail into the night on our over-the-night sailing & kayaking charter throughout Southwest Florida. Contact Tropical Penguin Charters to book your over-the-night excursion today.
The Catalina is a beautiful, luxury sailboat chartered by Tropical Penguin Charters
Set sail on a 3 hour daytime or sunset charter on our Catalina sailboat. Sail the paradise coast of Southwest Florida with friends, family, or a romantic getaway.
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Your Charter Captains

Captain Dan Short
Captain Dan Short
Owner & Captain