Sarah’s Magical Florida Keys Itinerary

7 Days/8 Nights

The Florida Keys are a magical place that feels like an exotic country with the conveniences and accessibility of the US. The Keys are islands of mangroves with spectacular beaches and turquoise waters, rivaling those of the South Pacific. The gentle breezes keep mosquitos at bay and the relaxed atmosphere, along with comfortable temperatures, creates a true paradise. The Keys are renowned for excellent restaurants, eco-tourism, wildlife, live music and world-class fishing. This suggested itinerary will take you through the best that the Keys have to offer while traveling and relaxing on your private yacht.

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Day One

Embark in Miami and head for Key Largo (3 hours).

Have dinner at Skipper’s Dockside, a classic Keys outdoor dining experience. Enjoy local snapper and Key Lime pie as you become acquainted with the atmosphere of the Keys. Take in the sunset and the steel drum band and be transported into your vacation.

Slice of Key lime pie on a plate with red berry sauce, whipped cream and menus
Key lime pie is an iconic American dessert. Find your favorite slice.

Day Two

Enjoy the afternoon exploring John Pennekamp Coral Reef State Park, the first undersea park in the U.S.

Explore the extensive coral reefs, beautiful tropical fish and occasional sea turtle. The park’s crystal-clear waters are enjoyed by novice snorkelers and experienced divers, alike. On land, Pennekamp offers stunning beaches and boardwalk trails among the sprawling mangrove forest.

Pennekamp State Park

In the early evening, depart for Islamorada (2 hours) and drop anchor for dinner at Upper Matecumbe Key. Bask in the ambiance and sample gourmet fare at the Cheeca Lodge and Spa, a famous favorite of President George H.W. Bush while his family ran fishing tournaments in the Keys. Use your yacht’s tender to arrive in style at the Lodge’s dock, the longest in the Keys.

Turtle underwater close-up
Sea turtle, close up and personal
Dock with palm trees at Cheeca Lodge and Spa in Upper Mattecumbe Key, Florida
Dock with palm trees at Cheeca Lodge and Spa in Upper Mattecumbe Key, Florida
Entrance to Cheeca Lodge and Spa in Upper Mattecumbe Key, Florida
Entrance to Cheeca Lodge and Spa in Upper Mattecumbe Key, Florida

Day Three

Islamorada is a series of islands and is known as the “fishing capital of the world.”

The islands are a destination for elite and casual fishing, specifically famous for the unique sport of bonefishing. Enjoy a day of fishing or a round of golf at the Cheeca. In the evening, head for beautiful outdoor dinner at Morada Bay and their famous fresh stone crab and calamari. Morada Bay is the best al fresco dining in Islamorada and is located on a bayside beach with iconic sunsets and local live music. This is also the place to be for the best full moon party in the Keys.

Day Four

Islamorada’s ecotourism

Many of Islamorada’s islands are uninhabited, which makes for incredible ecotourism. We recommend spending the morning using your yacht’s tender to travel the winding canals and explore the various islands of pelicans, frigate birds and iguanas.

If you’re traveling with children, the Theater of the Sea is a famous destination for swimming with the dolphins and interacting with local sea life. Have an adventurous afternoon jet skiing then head to Pierre’s restaurant for dinner, the finest dining in the Keys. Enjoy the local catch of the day, fine wine and a Cuban cigar on the balcony at sunset.

Day Five

As you head down the Keys (2 hours), spend the day at Bahia Honda State Park, one of the most beautiful beaches in North America.

A true island paradise, Bahia Honda has crystal-blue waters and soft, white sand. There are coral reefs to explore and this is the place to use the toys available on your yacht. Relax and take in the view from deck as you head for an evening at Hawk’s Cay Resort on Duck Key. This family-friendly, yet elegant, resort has many dining options and bustling nightlife.

Day Six

Head to Key West, the cultural center of the Florida Keys.

There are countless dining and shopping options on Key West. Take a trolley tour of the island and explore Hemingway’s house (with the famous Hemingway cats), the lighthouse, and have a wonderful dinner on Duval Street. Experience local flavor at the Blue Heaven restaurant with its sand floors and Key West’s famous feral chickens clucking about.

Quick doses of joy can be had at the Key West Butterfly and Nature Conservatory. Walk among hundreds of “flowers of the sky”, tropical plants, and their celebrity flamingos, Rhett and Scarlett.

Enjoy the evening in the southernmost part of the continental US and catch a glimpse of the elusive “green flash” at the nightly sunset festival in Mallory Square.

Gate to popular Key West, Florida restaurant Blue Heaven at night
Gate to popular Key West, Florida restaurant Blue Heaven at night
Sultry Florida sunset on the water w boat, dock and palm trees
A sultry Florida sunset on the water

Day Seven

Head back to Miami, enjoying the luxuries of the yacht along the way.

Take in the tranquility of the aquamarine seas as you end your beautiful vacation in the Keys.

Day Eight

Disembark in Miami.

Meet Sarah Nottage, our Florida Keys Expert

Charter Manager, Sarah Nottage, is also Carol Kent Yacht Charter International’s expert on the Florida Keys. Lucky Sarah has traveled to the Keys since she was a child and has deep local knowledge of this beautiful part of the world.

You can learn more about Sarah HERE. To find out all about all things about Florida Keys yacht vacations, you can contact Sarah by email or call +1 781 631 1800.

Purple sunset with palm trees at Mooring Village beach Photo©2020SarahNottage
Purple sunset with palm trees at Mooring Village beach Photo©2020SarahNottage
Moorings Village beach on Islamorada in the Florida Keys Photo©2020SarahNottage
Moorings Village beach on Islamorada in the Florida Keys Photo©2020SarahNottage