Naples to Key West to Naples

Enjoy Florida’s scenic west coast on your Naples to Key West to Naples yacht charter itinerary. This is only one example of an itinerary you may enjoy. We will work with you and your yacht’s captain and crew to make a custom plan just for you and your group.

Day 1: Naples

Naples is a destination that has many five-star resorts and top-notch golf courses. Miles of beaches with calm water and soft white sand embrace this coastal city. Before departing for Cape Romano, spend some time browsing high-end boutiques such as Petunias of Naples or Rouze. Enjoy lunch at Captain & Krewe or The Cafe.

As you make your way to your next stop, keep your eye out for manatees. They love the warm water close to shore.

Day 2: Cape Romano

Cape Romano is a nature reserve that’s popular for fishing and boating. It’s also known for a group of unique abandoned dome houses. Explore the area in a kayak, fish, look for shells, and view the native wildlife including shorebirds and dolphins.

Its natural environment and isolation make Cape Romano seem otherworldly. Each year, thousands of migratory birds land in the area, making its ecosystem extremely important.

The beaches here are pristine and largely uninhabited. Soak up the sunshine, go swimming, and observe the local wildlife. Walk from one sandbar to another, enjoying the sun and the rugged beauty of the area. If you really want to feel like you’re at the edge of the world, then this is the place for you.

Days 3 and 4: Dry Tortugas (2 Days)

The Dry Tortugas National Park consists of seven tiny coral-and-sand islands. Visitors can only reach the park by private boat, ferry, or seaplane.

florida yacht charter fort jefferson
Fort Jefferson. Photo by Andy Newman/Florida Keys News Bureau.

Once you arrive at Fort Jefferson National Park, spend the day exploring. The Civil War-era Fort Jefferson, one of the largest masonry structures in the Western Hemisphere, is the remote park’s awe-inspiring centerpiece. This is a fantastic place for activities such as jet skiing, paddle boarding, fishing, and snorkeling.

Note that the fort is very old and you should be cautious when exploring. Sturdy, closed-toe shoes are best for walking in this area.

Days 5 and 6: Key West (2 Days)

Arrive at Key West, FL, the southernmost city in the continental United States.

Naples to Key West to Naples
Key West, Florida. Photo by Rob O’Neal/Florida Keys News Bureau.

Spend the afternoon browsing eclectic shops and visiting some of the museums to learn about Key West’s colorful past. Bar hopping on Duval Street is another popular activity!

Take a hike and visit the shipwreck museum and learn about all the shipwrecks in the area. Visit the Ernest Hemingway Home, home to famed author Ernest Hemingway. He wrote many of his novels in Key West. In fact, some believe the saloon at what is now Captain Tony’s was the inspiration for a bar Hemingway called “Freddy’s” in his Key West novel To Have and Have Not.

Have your picture taken at the Southernmost point. Then, after a day of seeing the sights, make your way to Mallory Square. Here the sunset festival happens every night and kicks off about an hour before sunset. Enjoy local foods and watch fun street performers.

Day 7: Naples

Return to Naples. If you have time, visit Naples Zoo at Caribbean Gardens or take a guided kayak tour. Other places to visit include East West Fine Art, Historic Palm Cottage, or Naples Pier.

Browse our Naples to Key West to Naples Yacht Charter Boats below or contact us now to start planning.

Florida Yacht Charter Boats for a Naples to Key West to Naples Itinerary

STARSHIP 185'
Scuba  Scuba Diving On Board
STARSHIP 185'
6 Cabins Year/Rebuilt: 2001
$275,000 - $315,000 /wk 185.00 Ft Power
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ASPEN ALTERNATIVE
ASPEN ALTERNATIVE
5 Cabins Year/Rebuilt: 2010
$199,000 - $220,000 /wk 164.00 Ft Power
View ASPEN ALTERNATIVE
REMEMBER WHEN
Scuba  Scuba Diving On Board
REMEMBER WHEN
6 Cabins Year/Rebuilt: 2011
$230,000 /wk 162.00 Ft Power
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