Five Days of Discovery in the Florida Keys

Come along for a five-day journey exploring the Florida Keys. Here are the best places to stay, unforgettable experiences, and the best food.

Follow me on a five-day journey exploring three enchanting islands in the Florida Keys: Key Largo, Islamorada, and Key West. Spend your nights in exceptional boutique accommodations, experience exciting adventures, and dine on delicious island food.

Day 1 in the Florida Keys

Make your first stop at the Florida Keys Visitor Center in Key Largo. Speak with David Shine, a longtime resident and expert in everything Florida Keys. The Center offers numerous pamphlets and a public restroom for travelers.

Enjoy a Luxury Stay at Casa Morada

It takes about two hours to drive from Miami to Casa Morada, a luxury boutique hotel in Islamorada. On my way, I picked up a “colada” and an authentic Cuban coffee at The Juice House. I ordered the petite cup. The texture is extremely thick but delicious and gave me a significant caffeine boost.

Casa Morada is a privately owned hotel with 16 well-appointed suites set amongst lush gardens on the bayside of the island. Guests can take part in numerous water activities, enjoy yoga sessions on the pier, savor complimentary breakfast each morning, and lounge on the hotel’s exclusive island featuring a pool and the Sunset Gazebo bar.

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Casa Morada Hotel. Photo courtesy of Casa Morada

Casa Morada Tours is owned and operated by Captain Bill Todd and his wife Elle Summer. The couple offers private and small group eco, snorkeling, and sailing tours. I spent the early part of the evening with Captain Bill and Elle on one of their fabulous sunset sailings on the So Sister, a reproduction of a small skipjack sailboat.

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Sailing with Casa Morada Tours. Photo by Tracy Ellen Beard

Dining at Chef Michael’s

Not far from Casa Morada is Chef Michael’s. The chef serves inspired Florida Keys cuisine highlighting fresh-caught fish. I ordered the day’s special ceviche featuring pink Key West shrimp and Florida lobster in a coconut key lime sauce and the triple-fish special as an entrée. When traveling, I enjoy tasting the local specialties, so it seemed appropriate to try the key lime pie for dessert. It was fabulous.

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Ceviche at Chef Michael’s. Photo by Tracy Ellen Beard

Day 2 in the Florida Keys

We experienced so much during our first day, but there was so much more to explore during our time in the Florida Keys.

John Pennekamp Coral Reef State Park

Enjoy a quick continental breakfast on the Seaview Terrace overlooking Florida Bay at the hotel, and then head to John Pennekamp Coral Reef State Park in Key Largo, the first undersea park in the country. Take a boat to Key Largo Dry Rocks and snorkel out to see the “Christ of the Deep” statue.

The waters are clear, and snorkelers can see giant barracudas, rainbow fish, blue tang fish, sergeant major fish with their yellow and black stripes, and Nassau groupers. I loved how the purple, gold, and green plants rooted in the coral reef swayed back and forth with the waves.

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Snorkeling at JohnPennekamp Coral Reef State Park. Photo by Tracy Ellen Beard

Returning to the dock, we traveled through beautiful mangroves on our way to our next stop.

Local Brews at Florida Keys Brewing Co.

Before heading to dinner, stop at nearby Florida Keys Brewing Co. owned by Craig and Cheryl. It is common to find a band playing music outside on the patio of this local watering hole. Tell Rio about your personal beer preferences, and she will do a fabulous job selecting a tasty flight for you to sample.

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Florida Keys Brewing Co. Photo by Tracy Ellen Beard

Dinner at The Square Grouper in the Florida Keys

Square Grouper is great for a late dinner. The restaurant has only been open for a few months, and it is close to the hotel. The Signature Key Lime Martini is a must-try. It’s made with fresh key lime, Smirnoff vanilla vodka, and house-made key lime curd with a graham cracker rim. The yellowfin tuna with avocado eggrolls and the Asian dipping sauce is scrumptious. The capitelli pasta, shrimp, and asparagus with the key lime butter are fantastic.

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Key Lime Martini at the Square Grouper. Photo by Tracy Ellen Beard

Day 3 in the Florida Keys

Another magical day in paradise! We were ready to begin exploring after another relaxing evening in the Florida Keys.

Places to Stop on the Drive through the Florida Keys

After another light breakfast, it is time to travel farther south. Stop on Marathon Island and visit the Marathon Wild Bird Center. The purpose of the Center is to rescue, rehabilitate, and release migratory and resident birds when they become injured, sick, or orphaned. Give yourself an hour or two for hiking the Center grounds.

The Lighthouse Grill at Faro Blanco is a lovely place for a leisurely lunch. Sit outside on the patio and look out over the pool at the lovely view of the ocean and the lighthouse. The smoked pineapple margarita and fresh grilled fish tacos are worth the visit.

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Smoked pineapple margarita at Lighthouse Grill at Faro Blanco in the Florida Keys. Photo by Tracy Ellen Beard

The Marquesa Hotel in Key West

The Marquesa Hotel lies in the central historic district of Old Town Key West. The hotel boasts a courtyard with two swimming pools enclosed in a lush garden. The remodeled 1884 “conch” houses feature a front porch with ceiling fans, chairs, and a table. It is the ideal setting for an evening glass of bubbly or a steaming cup of coffee in the morning.

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Marquesa Courtyard view framed by palms. Photo courtesy of Marquesa Hotel

Before my dinner, I wandered the energetic streets of Old Town Key West. People milled about, and music filled the air. The area reminded me of a quieter version of the French Quarter in New Orleans. I was drawn into the Two Friends Patio Restaurant by Ericson Holt’s incredible piano music. I could only stay for a song or two, but I discovered that he was playing at “The Dirty Pig” later that evening.

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Singer and musician Ericson Holt. Photo by Tracy Ellen Beard

The hotel’s restaurant, Café Marquesa, is a high-end dining establishment with white linen tablecloths and a unique mural in front of the open kitchen. The she-crab soup enhanced with sherry is decadent, and the beef tenderloin comes with a classic béarnaise and delicious smashed red potatoes mixed with Crème Fraîche.

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Beef tenderloin at Café Marquesa. Photo by Tracy Ellen Beard

Extraordinary Music in Key West

After a delicious dinner, I walked the half-mile to “The Dirty Pig” BBQ restaurant, passing beautiful white houses with stunning porches and balconies. The Dirty Pig, owned by Kim and Dan, is new. It is off the beaten path; but if you love BBQ, follow your nose and you will find this quaint little place.

The bartenders are personable, and they make magnificent lemon drops. I spent the remainder of the evening listening to Ericson Holt’s version of blues, rock, and New Orleans jive. Ericson was kind enough to spend his breaks chatting with me about his exciting music career.

Day 4 in the Florida Keys

We have had three days of amazing driving, sightseeing, and dining in the Florida Keys and were determined to experience everything possible for our remaining two days.

Enjoying Local Food and Activities

With so much to do, it is a smart idea to start with a filling breakfast at the Cuban Coffee Queen. The sunrise sandwich comes with a fried egg, cheese, and Cuban pulled pork on a Cuban roll. Pair it with a small Cuban coffee. The half sandwich was plenty for me. This open-air, walk-up coffee shop was super cute.

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Cuban Coffee Queen is a great place to start the day. Photo by Tracy Ellen Beard

I drove a few miles to Lazy Dog to go kayaking on the Atlantic side of the island. Heather, my guide, took out a group of ten people.  We paddled through the mangroves, and Heather pointed out nursing sharks, tree crabs, a sea hare, and an upside-down jellyfish whose sting doesn’t hurt.

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Kayaking with Lazy Dog. Photo by Tracy Ellen Beard

Later, I returned to the Dirty Pig for lunch where I enjoyed a brisket sandwich with bourbon sauce and bacon mashed potatoes. Both were amazing.

Take a ride on the Conch Tour Train to see more of the downtown area and to learn more about the history of the city. It is a hop-on-hop-off train, so you can get off where you’d like to explore and then get back on later.

Stop at the Key West Aquarium and the Shipwreck Treasure Museum. The Aquarium is small but great for kids, and the Museum is quite fascinating. Several videos narrated by wreckers—people who scavenge the loot from shipwrecks—play continuously as you walk throughout the Museum. These videos describe how they work and what they collected from crashes on the nearby reef.

Book a Wind & Wine Key West Sunset Sail with Danger Charters. They offer several fun sailing options with a maximum of 25 people. During my trip, we sailed south of the island and watched the sun go down. We sampled eight wines, a few beers, and several tasty appetizers.

You can also go on fishing or diving excursions through Key West Yacht Rentals, where they take you to the best sites to enjoy this experience.

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Wind and Wine Key West Sunset Sail with Danger Charters. Photo by Tracy Ellen Beard

After sailing, walk over to Hot Tin Roof for a late dinner. The grilled asparagus with a sunny-side-up egg, Manchego cheese, and caramelized shallots are excellent. The Key West Pink Shrimp and Scallops with mascarpone tasso risotto is spicy and pairs well with a glass of Kim Crawford Sauvignon Blanc from New Zealand.

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Grilled asparagus at the Hot Tin Roof. Photo by Tracy Ellen Beard

Day 5 in the Florida Keys

It was our final day in the Florida Keys. We had more to see so we could make the most of our day in paradise.

Informative Sites in the Florida Keys

Begin the morning with a walk to Kermit’s Key West Key Lime Shoppe; yes, everything is green, including Kermit, the owner. He dresses in solid bright green. Order a colada and the Cuban coffee and try the pancakes with key lime syrup. The coffee is excellent, the pancakes are dense but tasty, and the key lime syrup is spectacular.

As a writer, I was compelled to tour the Ernest Hemingway Home & Museum. Mr. Hemingway lived in Key West for more than ten years.  It was exciting to listen to the stories that the tour guide shared about Hemingway’s life and about the books he wrote while living at the stunning residence. Possible descendants of Hemingway’s famous six-toed cat Snow White still roam the grounds.

My last stop on the journey was The Key West Butterfly & Nature Conservatory. The Conservatory showcases an exciting collection of vibrant-colored birds, spectacular butterflies, and extraordinary plant life.

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Flamingo at the Key West Butterfly & Nature Conservatory. Photo by Tracy Ellen Beard

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When You Visit the Florida Keys

Follow all or some of my five-day trip planner to The Florida Keys. The vibe is relaxed and carefree. If you require any additional information regarding things to do or other places to stay, contact the Florida Keys Visitor Website. Be sure to check out more on Wander for what to do when you visit Florida.

Take a 5-day journey exploring three enchanting islands in the Florida Keys: Key Largo, Islamorada, and Key West. Spend your nights in exceptional boutique accommodations, experience exciting adventures, and dine on delicious island food. #KeyWest #Florida #KeyLargo #Islamorada #Beaches #BeachHoliday #Adventure


Written by Tracy Ellen Beard

Tracy Ellen Beard, Wander With Wonder Senior Editor, is a freelance writer, editor, and photographer based in Longview, Washington. She is an avid traveler, wine connoisseur, foodie, hiker, cyclist, and kayaker. Tracy is the “Out and About” columnist for the Columbia River Reader and writes monthly for Upscale Living Magazine. She also contributes regularly to LuxeGetaways, Northwest Travel & Life, Country, Country Extra, and several other magazines. Her stories focus on luxury and adventure travel, fine dining, wine, libations, road trips, and recipes. Tracy shares a unique perspective on the world from her personal journeys and the excursions she took as the founder and past president of an international children’s nonprofit. Her twenty years of experience writing in various genres, and her culinary training in San Francisco, California, have added to her knowledge and expertise.

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