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 for you and your group.
Day 1 | Naples
Naples is a destination that has many five-star resorts and top-notch golf courses. Miles beaches with calm water and soft white sand embrace this coastal city. Before departing for Cape Romano, browse high-end boutiques such as Petunias of Naples or Rouze. Enjoy lunch at Captain & Krewe or The Cafe.
As you make 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 famous for fishing and boating, and 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 area’s rugged beauty. If you want to feel at the world’s edge, this is your place.
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.
Once you arrive at Fort Jefferson National Park, spend the day exploring. The Civil War-era Fort Jefferson, one of the most significant masonry structures in the Western Hemisphere, is the remote park’s awe-inspiring centerpiece. This is a fantastic place for jet skiing, paddle boarding, fishing, and snorkeling.
Note that the fort is ancient, 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.
Spend the afternoon browsing eclectic shops and visiting museums to learn about Key West’s colorful past. Bar hopping on Duval Street is another popular activity!
Take a hike, 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. 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.
Frequently asked questions
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Yes, most itineraries include daily boat trips to nearby islands, usually with beach chairs, sunshade, snorkeling gear, and a cooler lunch provided. Popular day-trip spots include Francisquí, Madrisquí, Crasquí, and Cayo de Agua
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Yes, the crew will work with you to plan an itinerary that suits your interests and preferences.
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Yes, most charter itineraries remain flexible, allowing changes based on weather conditions, your preferences, and the captain’s recommendations. However, major route changes should consider fuel capacity and port availability.
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Yes, you can use them during your charter. However, availability may vary depending on the yacht, so it’s advisable to check with the charter company beforehand.
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Many yacht charters are family-friendly and offer amenities and activities suitable for children of all ages, but it’s always best to check with the charter company beforehand.
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Yes, there are, depending on the time of the year and the yacht charter destination.
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One of the first FAQs about luxury yacht charters is their affordability. Yes, you can afford a yachting vacation. Prices for private yacht chartering vary remarkably based on factors such as:
- The type of charter yacht
- The size of the charter yacht
- The number of guests in your group
- The location of the yacht charter destination
- The rates may also differ from the low-season and high-peak seasons
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Guests booking an 8-day charter will only pay for 7 days, essentially receiving an extra day of luxury cruising at no additional charge. This offer applies to selected Mediterranean itineraries.
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The minimum length of charter is a half-day cruise that lasts 4-5 hours.
Of course, more extended charter options are available as well, depending on the preferences and needs of the guests.
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Water sports availability depends on the yacht:
- Most luxury yachts include basic equipment
- Typical complimentary activities:
- Snorkeling
- Paddleboarding
- Kayaking
- Additional water sports may incur extra charges:
- Jet skiing
- Scuba diving
- Specialized equipment rental
