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Florida Keys Itinerary: The Ultimate 5-Day Trip

Florida Keys Itinerary: The Ultimate 5-Day Trip

Oh the Florida Keys…

Full of so much natural beauty, rich history, and no shortage of great activities, there are many great ways to experience this unique destination. Key Largo, Islamorada, Marathon, heck you could easily spend a week in Key West alone! But in our opinion, the best way to experience the magic of the Florida Keys is too see them all by taking a road trip.

Behold, our ultimate 5-day itinerary through the Florida Keys!


When travelling to The Keys, you’ve got several options to get there including flying to Miami International, Key West International, as well as several cruise options from other locations in Florida. We arrived early in the morning in Miami, rented a car, and drove about an hour and a half south to the top of The Keys.

Our first stop on our Florida Keys itinerary was John Pennekamp Coral Reef State Park. Located just past Key Largo, John Pennekamp is the first undersea park in the US and covers roughly 70 square miles of mangroves, coral reefs, and wildlife. We were truly impressed with how well managed the park is and the passion that the park employees have for protecting and sharing its natural wonder.

They offer various activities such as snorkeling, scuba, glass-bottom boat tours, as well as boat and kayak rentals. We opted for the snorkeling tour, which takes you on a half-hour boat ride out to the reef. During the boat ride, our tour leaders Doug and Dean did a great job of providing us with background on the park, what types of wildlife we might see out there, a safety briefing, several great nautical jokes, and even a snorkeling lesson for those who were first-timers.

At the reef, we saw countless tropical fish, colorful coral, someone even saw a sea turtle! We also got to check out the famous “Famous Christ of the Deep” statue, which was super cool to see. Overall this was a fantastic way to spend an afternoon, we can’t say enough about how great our guides were!

After working up an appetite snorkelling we checked into our room for the night at The Fisher Inn Resort to freshen up for dinner. Very recently renovated, the Fisher Inn is a modern, stylish and comfortable place right on water with various activities and boat access available. We loved what they’ve done with the place! An ideal spot to stay in Islamorada.


An unassuming spot right off the highway, Robbie’s offers an eclectic mix of outdoor shops, food vendors and, our personal favorite, tarpon feeding. For those who don’t know, tarpon are MASSIVE sport fish that are spectacular to see swimming around and launching out of the water. What’s also cool about them is that they don’t have teeth, so you can buy a bucket of fish and feed the giants hanging out by the dock at Robbie’s.

It’s a bit adrenaline-pumping at first as these huge mouths come out of the water snatching the fish right out of your hands, but it’s unlike anything else. We liked it so much we got another two buckets of fish! Just watch out for the pesky pelicans 😛 Oh, and we saw a manatee come right up to the edge of the dock! It was wild.

After watching these giant creatures feed for so long, we started to get hungry ourselves, so we went for brunch at Robbie’s Marina restaurant, The Hungry Tarpon. A fantastic spot with amazing breakfast, we opted for the “alligator reef” Mexican scramble and the lobster frittata with hollandaise sauce (OMGGG wow!).

If you’re spending any time in Islamorada, Robbie’s Marina and The Hungry Tarpon are an absolute must.

We departed Robbie’s around noon and made our way down to Key West.

Upon arrival in Key West, we checked in to our home for the next three days, The Southernmost Beach Resort. An absolutely immaculate resort, we could not have imagined a better place to stay in Key West. Located at the quiet end of Duval Street, The Southernmost Beach Resort features fantastic rooms, beaches, pools, and bars and is the perfect spot for couples or families looking to stay in a more tranquil part of Key West. They also offer bike rentals which we found to be the best way to get around Key West.

We stayed in the historic and beautiful La Mer House, in a gorgeous King room. Our house hosts made us feel extremely welcome and made sure that we had an exceptional stay. La Mer and Dewey house offer an exclusive breakfast spread every morning, and relaxing, delightful refreshments every afternoon. There was always a delicious selection of cheeses, deli meats, fresh fruit, and sweets, as well as a made-to-order chef’s special at breakfast. This is was a great time to recharge and relax, as well as socialize with our hosts and the other guests.

After our afternoon refreshments, we headed to the docks to hop aboard The Wind & Wine Sunset Sail with Danger Charters. Note: we were able to call and book this tour just a few hours in advance, but for most tours, it is recommended to book most tours 24 hours in advance to guarantee a spot, especially during the busy seasons.

Contrary to what you may assume from the name, Danger Charters offers an exceptionally relaxing sunset sail. What’s unique about them is that they offer a wine tasting while you sail! We sampled 8 different wines and various gourmet appetizers as we sailed and enjoyed the sunset. The crew was exceptional, ensuring that we were always taken care of, sharing interesting tidbits and anecdotes about The Keys, and engaging in great conversation. They also offer craft beers and non-alcoholic drinks for any non-wine drinkers.

The sunsets of Key West are truly spectacular and we would recommend seeing at least one of them from a sunset cruise.


On day three, we checked off a bucket list item, The Dry Tortugas! Located 70 miles off the coast of Key West, Dry Tortugas National Park is famous for its spectacular waters and its prize historic feature, Fort Jefferson.

You can explore Fort Jefferson and the Dry Tortugas via a day-trip offered by Yankee Freedom. Trips depart from Key West daily aboard a large 250 passenger ocean-going catamaran that takes about 2 hours to make the crossing. Be warned that if there are strong winds, the seas can get quite rough, so be sure to check current conditions and take any necessary precautions to prevent motion sickness.

Along the way, the wonderful staff provided us with information on the geography and history of the area. Our lead guide, Hollywood, talked about the dynamic nature of the Tortugas and the key roles that they played for sailors in the early years of the US. He also pointed out some real-life treasure hunters who were searching for the remaining $600,000,000 treasure of two Spanish Galleons that went down in the area.

About an hour and half into the crossing, Fort Jefferson appears on the horizon. As you approach this immense structure in the middle of nowhere, one question comes pops into everyone’s mind, “Why on earth is this thing here??” Well, Hollywood explained everything once inside the fort, but you’ll have to visit yourself to find out 😉

Fort Jefferson is chilling. As you walk the moat around it or view the spectacular waters from atop its three story high roof, you really appreciate how much work went into building this spectacle and imagine what life would have been for fort dwellers. I can’t speak highly enough about how incredible exploring the fort and the islands was, and I’d love to go back and camp on the island for a night or two next time. Imagine the stars!

After a few hours exploring the Dry Tortugas, we reboarded the Yankee Freedom III and made our way back to Key West.

We made it back just in time to catch the sunset from Bistro 245 at Margaritaville Resort. As I mentioned before, Key West sunsets cannot be missed!

Bistro 245 is right next to sunset square and the upstairs bar is a great place to get a view above the crowds and enjoy the end of the day with a margarita in hand. The crowds tend to leave once the sun goes down, but make sure to stay a little longer as the best part of the sunset usually happens 10-15 minutes after the sun goes below the horizon.

For dinner on day three, we hopped in the car and drove up to a local favorite, Matt’s Stock Island Kitchen & Bar. Their aptly anointed “American coastal comfort food” features gourmet takes on the classics and fresh seafood all in a great location that earned them OpenTable’s 2018 Diners’ Choice Award for best ambiance. We highly recommend the crab beignets (uhh, yes please!!) and the black grouper.


Latitudes is an absolute treat. Located on Sunset Key –  just a 6-minute complimentary ferry ride across from Key West – Latitudes and its executive chef Jerry Crocker offer a “work of art” menu that incorporates fresh locally sourced fish and tropical fruits, all in a spectacular setting. (If Sunset Key sounds familiar to you, it could be because Oprah rented out every cottage on the island one time for her friends and family).

Latitudes offers an exceptional menu for breakfast, lunch, and dinner. If you go for breakfast, treat yourself to the lobster benedict, you will not regret it.

After breakfast, we puttered around Sunset Key before hopping back on the ferry to Key West.

We spent most of the day exploring the streets of Key West. We walked the boardwalks, biked up and down Duval Street, checked out the quaint architecture, and then relaxed on the beach at The Southermost Beach Resort.

Following afternoon refreshments at the Resort, we made our way back to the piers to board our second sunset sail, this time with Sebago. Aboard Sebago’s large catamaran you’ll find friendly staff, lots of deck space, bottomless beer, margaritas and sangria, plus a cash bar. We made a bunch of new friends while out on the water and although we prefer the Danger Charters experience, Sebago definitely provides a good economical option.

Upon arriving back at the dock we headed down the boardwalk and popped in for dinner at Turtle Kraals, another Key West classic. We sat outside up top with a great view of the marina and enjoyed a couple of key lime margaritas with delicious conch fritters, ribs, and ceviche.


Key West, it’s been great! Time to work our way back.

After a superb breakfast at La Mer House, we said goodbye to our gracious hosts and headed north. We headed up to Lazy Dog where we had rebooked our kayak excursion from earlier in the week.

Kayaking through the mangroves is without a doubt the best way to see them. We were able to see all kinds of marine life (PLUS super cool iguanas!) and paddle through channels where mangroves were literally growing above our heads. The pace of the tour was relaxing and our guide, Lindsay, was friendly, knowledgeable, and ecologically responsible.

We came off the water, bid adieu to the fantastic Lazy Dog staff and made our way up the highway to our destination for the night, The Tranquility Bay Beach House Resort in Marathon.

We had worked up an appetite kayaking and so it was the perfect time to check out their on-site restaurant, The Butterfly Cafe. Remember how I mentioned above about the Yellowtail Snapper? Well, this is where we discovered its magic.

Yellowtail Snapper is a Florida Keys speciality, so as per the chef’s recommendation, we both had it at The Butterfly Cafe, and it was game-changingly delicious.

We spent the rest of the day exploring the incredible grounds of the Resort. We hung out on the beach, grabbed a drink at the Tiki Bar, and putted on the putting greens (Lauren won). They also have kayaks and jet skis to take out, but we had already had our day out on the water. Tranquillity Bay is a fantastic place to stay for families and couples alike as their beautiful multi-bedroom units provide full kitchens, balconies, and plenty of amenities.

For our last dinner in The Keys, we went to The Lighthouse Grill at Faro Blanco Resort. They offer a flight of local craft beers and amazing seafood – the scallops with Boursin risotto was absolutely fantastic. Although we went for dinner this would be a great place for happy hour to catch the sunset and enjoy the goings on of the marina.

The next morning, we woke up and made our way back to Miami airport, from where we flew home. On your way back, make sure to take the highway 1 route, as our GPS suggested the backroads, which was a lot of stops and starts on one-way roads.

Overall, our trip to The Florida Keys exceeded our expectations. It’s hard to find a place with so much beauty, history, and great things to see and do. You can do as little or as much as you want, and have an incredible time. When we go back – which we surely will! – here are some of the things on our list that we didn’t have time for this time around: hire a fishing charter for the day, visit the Turtle Hospital in Marathon, check out the craft breweries, visit the Mel Fisher Maritime Museum, and so much more! If you’re looking for a full list, check out our other blog of 9 epic things to do in the Florida Keys.

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