3425 16th Ave. SE Naples, Florida 34117

Get the most affordable sailing charter packages in Southwest Florida when you book with Tropical Penguin Charters

Family Sailing Charters
& Endless Adventures

NAPLES, FT. MYERS, CAPE CORAL, MARCO ISLAND Tropical Penguin Charters White View Our sailing packages

Get the most affordable sailing charter packages in Southwest Florida when you book with Tropical Penguin Charters Tropical Penguin Charters

Sailing Charters
& Endless Adventures

Experience the most incredible selection of boats and yacht rentals professionally crewed by highly qualified personnel! BOOK A SAILING TOUR View Our Packages

Day & Sunset Sailing Tours

With amazing year-round weather, our 3-hour daytime sailing charter is perfect for anyone looking to enjoy a great day of sailing Southwest Florida.

All Day Sailing Charters

The 8 hour day sailing trip provides for ample time to relax and enjoy your time on the water with several options not available during the shorter trips.

Overnight Sailing + Kayaking

This trip destination is the Shark River Island area. 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.

Southwest Florida Sailboat Charters & Adventures

At Tropical Penguin Charters, we specialize in arranging memorable family & kid-friendly yacht charters and sailing vacation trips to destinations like The Florida Keys, Dry Tortugas, the Caribbean, and of course the backwaters of Marco Island, Florida. If you’re looking for your next adventure on the water, look no further than Tropical Penguin Charters. We’re here to help you cruise into your dream vacation.

Southwest Florida Sailboat Charters & Adventures

At Tropical Penguin Charters, we specialize in arranging memorable family & kid-friendly yacht charters and sailing vacation trips to destinations like The Florida Keys, Dry Tortugas, the Caribbean, and of course the backwaters of Marco Island, Florida. If you’re looking for your next adventure on the water, look no further than Tropical Penguin Charters. We’re here to help you cruise into your dream vacation.

Tropical Penguin Yacht Charters Sailing

Tropical Penguin Charters

Tropical Penguin Charters offers professional yacht charters services for private family cruises, sunset cruises, fishing charters, romantic getaways for two, and more. Set sail on our 42′ Catalina 42 MK II yacht by the day, weekend or week for your next adventure on the water.

CAPTAINED SAILING CHARTERS

We offer captained sailing charters that are fun, engaging, and memorable. If you just want to kick back and take in the experience, you can do that while allowing us to take care of everything, or you can do as much of the helm work and sail trim as you like under the Captain’s supervision and guidance.

TROPICAL ADVENTURES & WORLD-CLASS DESTINATIONS

Naples, Marco Island, Captiva, Sanibel, Ft Myers Beach, Dry Tortugas, Panther Key, Shark River, Florida Keys!

Our Sailing Charter Packages

We offer a variety of sailing charter packages to fit your budget and accommodate you, your family, and your guests. Enjoy a half-day or a full day on the water fishing, snorkeling, and sailing the paradise coast of Southwest Florida.

Special Savings Coupons

2d Reconnaissance Battalion Discount

Any 2d Recon Bn Association member will get one free full day sailing excursion and 50% off of any trip offered one time with proof of…

Educator’s Discount

Educators will receive an additional hour free-of-charge to any day sail trip booked, and 10% off any excursion

Police Officer’s/Firefighter’s Discount

Police officers and firefighters will receive an additional hour free-of-charge to any day sail trip booked, and 10% off any excursion.

Special Savings Coupons

2d Reconnaissance Battalion Discount

Any 2d Recon Bn Association member will get one free full day sailing excursion and 50% off of any trip offered one time with proof of…

Educator’s Discount

Educators will receive an additional hour free-of-charge to any day sail trip booked, and 10% off any excursion

Police Officer’s/Firefighter’s Discount

Police officers and firefighters will receive an additional hour free-of-charge to any day sail trip booked, and 10% off any excursion.

Featured Sailboat for Charter

Southwest Florida Family Sailing Charter by Tropical Penguin Charters

2001 Catalina 42 MK II - Athena

Sails at 42 Knots

3 Cabin Pullman Railroad Cabin

Separate Head in the Forward Cabin

Captained Sailing Charters

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.
Naples Florida Yacht Charters
key west yacht charters
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Your Charter Captain

Captain Dan Short
Captain Dan Short
Owner & Captain

Your Charter Captains

Captain Dan Short
Captain Dan Short
Owner & Captain

Interested in Chartering
Your Sailboat?

If you're a sailboat owner and you are considering offering it as a charter boat, please, contact us via phone or email to discuss how we can help you get started and make this a valuable opportunity.