3425 16th Ave. SE Naples, Florida 34117

Sailing Packages

Sailing Packages

3 HOUR DAY OR SUNSET SAIL - $425

DAYTIME & SUNSET SAILING TOURS AVAILABLE!

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. Enjoy the blue skies, warm weather, and active wildlife. Enjoy a great day of sailing while taking in the sights of beautiful Southwest Florida from a different point of view.

 Duration: 3 Hours
Price:  $425 (Approx. $70 Per Person)
Guests: 6 Guests Maximum

HALF DAY SAILING CHARTER - $525

RELAX ON A 4 HOUR TOUR OF SOUTHWEST FL.

Sunset Charters leave the dock at approximately 2 and a half hours before sunset. During the trip through Naples Bay, you will enjoy viewing some of the historic mansions of the Port Royal community. One of the highlights of your trip will be the regional wildlife you will enjoy viewings, such as ospreys, egrets, herons, pelicans, cormorants, and anhingas. You will most likely see dolphins from one of the local pods- and if you’re really lucky- maybe manatees or even a sea turtle. Water, sodas, and snacks included. Feel free to bring your favorite adult beverages.

 Duration: 4 Hours
Price:  $525 (Approx. $87 Per Person)
Guests: 6 Guests Maximum

FULL DAY SAILING CHARTER - $800

YOU'LL HAVE ALL DAY TO SOAK UP THE FUN

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.  You can stop off Keewaydin Island to enjoy some swimming and lounging in the waters and shelling on the island only accessible by boat.  You can also choose between enjoying an extended cruise off the coast of Marco Island or north towards Ft Myers Beach.

 Duration: 8 Hours
Price:  $800 (Approx. $133 Per Person)
Guests: 6 Guests Maximum

OVERNIGHT + KAYAKING EXCURSIONS - $3000

SAILING + KAYAKING UNDER THE STARS

Excursion 1- 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 area of the Everglades. This trip departs Friday afternoon and returns Sunday afternoon. En route, we will see the dome houses and numerous islands with white-sand beaches for you to explore.

 Duration: Overnight Excursion
Price:  $3000 ($500 Per Person)
Guests: 6 Guests Maximum

 

You are welcome to bring your own adult beverages.
All water bottles, non-alcoholic drinks, and light snacks are complimentary.

Our sailing packages are great for kids!

Call for private & larger corporate chartering prices. We have overnight tours with flexible departure times.
We’re happy to extend the length of your tour per your request.

NEED A LONGER TOUR OR HAVE A QUESTION? CALL 239-963-6770

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
Tropical Penguin Sailing Charters Sailing
Southwest Florida Family Sailing Charter by Tropical Penguin Charters
3
4
8
2
7
1
6
5
9
10
Tropical Penguin Charters Sailboat Charters
Tropical Penguin Charters Sailboat Charters (7)
Tropical Penguin Charters Sailboat Charters
Naples, Florida Tropical Penguin Charters
6
Naples Family Yacht Charter
Tropical Penguin Charters Destinations
Tropical Penguin Sailing Charters Sailing
Tropical Penguin Charters Sailboat Charters
5
21
13
12
16
15
14
18
17
20
19
22
previous arrowprevious arrow
next arrownext arrow
3
4
8
2
7
1
6
5
9
10
Tropical Penguin Charters Sailboat Charters
Tropical Penguin Charters Sailboat Charters (7)
Tropical Penguin Charters Sailboat Charters
Naples, Florida Tropical Penguin Charters
6
Naples Family Yacht Charter
Tropical Penguin Charters Destinations
Tropical Penguin Sailing Charters Sailing
Tropical Penguin Charters Sailboat Charters
5
21
13
12
16
15
14
18
17
20
19
22
previous arrow
next arrow

Your Charter Captains

Captain Dan Short
Captain Dan Short
Owner & Captain