The Florida Keys offer a perfect blend of sun-soaked relaxation and exhilarating adventures, making it an ideal destination for a fun-filled vacation. From exploring vibrant coral reefs and historic sites to enjoying watersports and savoring fresh seafood, the Keys provide a diverse range of activities set against the backdrop of stunning tropical landscapes, ensuring there’s something for every type of traveler.

Here is our itinerary for 4 nights and 5 days in The Florida Keys!

Day 1: Arrive to Miami and pick up rental car.

Departure for the Florida Keys

After landing in Miami, we made our way to The Florida Keys, the ultimate tropical paradise. Our home for the night is the stunning Amara Cay Resort, a haven nestled in the heart of Islamorada.

Amara Cay Resort

Amara Cay Resort is a beachfront oasis that captures the laid-back essence of the Upper Keys. As the sun begins to dip below the horizon, we dine at Reel Catch, an onsite gem at Amara Cay Resort.

Day 2: Island Adventures and Underwater Wonders

We started the day with a leisurely breakfast, soaking in the island vibes at Amara Cay Resort.

We had an amazing experience playing ocean golf with the Albus Golf EcoBioBall, 100% safe, biodegradable, non-toxic, and filled with fish food. We fed the fish while practicing our swing and enjoying the ocean view.

12:30 p.m.: Dive/Snorkel Trip with Horizon Divers

Next, we embarked on an underwater adventure with Horizon Divers. We snorkeled and witnessed underwater shipwrecks, exotic fish, and vibrant coral reefs in the Upper Keys National Sanctuary.

Return to Property to Refresh

After our underwater escapade, we return to Amara Cay to refresh and rejuvenate for the evening ahead.

8 p.m.: Dinner at Chef Michael’s

Chef Michael’s promises a feast of freshly caught fish, creatively prepared with Florida Keys flair. Our experience at Chef Michael’s was exceptional, with the Lionfish appetizer, Hogfish, and Seafood Pasta all standing out as delicious highlights. The chef’s creativity and commitment to excellence made our visit a memorable culinary experience, and we eagerly anticipate returning for more culinary delights in the future.

Day 3: Key West Bound – Historic Explorations and Maritime Charm

Morning at Leisure on Property

Our morning started with a leisurely exploration of Amara Cay Resort, basking in the tranquility of Islamorada. Next, we checked out of the hotel and headed toward Key West.

10:30 a.m.: Breakfast at Robbie’s of Islamorada

On our way to Key West, we enjoyed a breakfast at Robbie’s, surrounded by the eclectic mix of outdoor shops and the thrill of tarpon feeding.

12:40 p.m.: Tram Ride to Pigeon Key

Our journey to Key West included a stop at Pigeon Key, a historically rich site with ties to the Florida Keys Over-Sea Railroad. The short train ride to Pigeon Key consists of a narration about the history of the island and the option to walk around the island to explore the museum. It is a family-friendly tour and great for all ages!

Check-in at The Perry Hotel Key West

We arrived in Key West and were welcomed to The Perry Hotel Key West, a boutique gem on Stock Island Marina.

Sunset Cruise with Danger Charters

As the sunset approaches we headed to our sailboat cruise with Danger Charters. This particular voyage sets itself apart from the others by being one of the only options that pairs wine tastings with light appetizers for a relaxing evening on the water. Along with unlimited wine, beer, and soda, nibble on a gourmet cheese buffet, summer sausages, crackers, and apples, as you watch the sun go down over Key West.

7 p.m.: Dinner at Matt’s Stock Island

After a beautiful evening on the water, we enjoyed the culinary delights of Matt’s Stock Island.

Day 4: Dolphin Watching and Key West Delights

8:45 a.m. – 12:30 p.m.: Dolphin Watch & Snorkel Tour with Honest Eco

A morning of eco-friendly adventure unfolds as we embarked on a dolphin watch and snorkel tour with Honest Eco. We even had extra time to kayak on the stunning blue waters.

2 p.m.: Lunch at Blue Heaven

After our aquatic escapade, we headed to Blue Heaven for a delightful lunch, surrounded by a century-old history of island entertainment.

Afternoon at Leisure Exploring Key West with VIP Pass

Our VIP Pass unlocks the doors to Key West’s iconic attractions, including the Lighthouse & Keeper’s Quarters and the Ernest Hemingway Home and Museum.

7 p.m.: Dinner at Milagro Restaurant and Bar

Our culinary journey continues at Milagro Restaurant and Bar, a hidden gem run by a husband-and-wife duo. Nestled off the beaten path, it promises a culinary experience tied to scratch-made food, art, and community.

Day 5: Farewell Key West

On our final morning in Key West we checked parasailing off of our bucket list with Sebago. Parasailing was a thrilling adventure that combines the excitement of flying with the serenity of being suspended high above the water. Secured to a parachute and tethered to a boat, we were gently lifted into the air, providing a breathtaking bird’s-eye view of the surrounding landscape and the vast expanse of the open sea.

3:31 p.m.: Depart Key West International

Our Florida Keys adventure concludes as we board our flight from Key West International, carrying memories of turquoise waters, historic sites, and the warmth of the southernmost paradise. It’s a place where relaxation meets adventure, and we will definitely be back in the future!