Though I’ve been traveling to Florida annually since birth, it wasn’t until my 30s that I actually made it to the Florida Keys. And what fun SVV and I had! We flew into Miami the day after Thanksgiving, drove to Key Largo to start our week-long road trip through the Keys, ended in Key West and flew home from there.

This time around, we did things in reverse. We hopped a flight to Key West from Nashville that connected in Charlotte, landed a few hours later, then hit the ground running. Either way you want to do it totally works. Here’s how we laid out our trip.

Day 1

Upon touching down at Key West airport, it’s just a 10-minute drive to the heart of town. In fact, one of Key West’s biggest selling points is that it’s compact and very walkable. You can easily stay downtown without needing your own car.

We hailed a cab and headed straight for Marquesa Hotel, the most charming inn in Key West and conveniently located just a block off of Duval Street.

This historic home was built in 1884 and lands itself on every “best of” hotels list around. And with good reason: The rooms are stunning in their sophistication and the service top-notch. For those on the hunt for a bed and breakfast type of stay in Key West, look no further than Marquesa Hotel. Several locals we met throughout our stay also named the Marquesa restaurant as one of the best in town; I regret that we didn’t have time to try it, but as I always say—next trip!

After getting our bearings, we set out on foot in search of food; we were famished after a half-day of flying and wanted lunch as quickly as we could get it into our stomachs. Thanks to using the Yelp app, we found Frita’s Cuban Burgers, which is a legit hole-in-the-wall Cuban joint just a few blocks from our hotel that serves phenomenal street food (and plenty of that Key West beer!).

On our last visit, we’d done several of the big Key West attractions like the Butterfly and Nature Conservatory, the Maritime Museum and Tucker’s Provisions, so we explored the area with our cameras before returning to the hotel for a bit of much-needed pool time.

That night after cleaning up, we headed out on a boat for Wind & Wine Sunset Sail with Danger Charters. This isn’t your average booze cruise; it’s run by a handful of men who could easily double as stand-up comics. They make sure your glass is never empty and that there’s never a moment devoid of jokes.

And for those of you who are wine-adverse, there’s free-flowing craft beer. Hands down, this was my favorite sunset cruise to date in all of my travels. Oh, and the views aren’t bad either!

Our sailing adventure departed from Mallory Square, and once we were back, it was just five minutes by foot to our destination for the evening: Bagatelle.

It was a humid night, but we opted for an upstairs patio spot so we could do a little people-watching over Duval Street as we ordered a starter of lamb lollipops to share. I also tried my first ever hogfish, the specialty dish of the Keys, and now I can never go back. That might be my new favorite fish, period (sorry, walu!).

We each sipped a couple of Manhattans as we gulped down dinner at this must-eat spot in Key West. And what else to end the day but a slice of key lime pie, my first of seven for the trip and arguably the best key lime pie in the Keys?

Day 2

The next morning, we were up and at ’em early. Now, I’m not normally one to rise with the sun while on vacation, but we had a special reason to get out of bed: We were going diving!

We were booked for a two-tank excursion with Dive Key West, the first (and largest) full-service dive facility in the Keys. Bob and Cece, the owners, got us all decked out in our rental equipment, then drove us to the marina where Victoria, our dive master, and Jesus, the boat captain, took us to the outer reef for a morning of fun.

After we got back, it was well past lunchtime so we went into town and had our second day of Cuban fare at El Siboney, a local institution, then took a little photo walk as we meandered back to our hotel. The houses in Key West are so dreamy that I might just have to dedicate a future post all to them!

That evening, we ventured east once more to Ibis Bay Resort for dinner at the Stoned Crab, where I ordered … hogfish. Again. This time, it came encrusted with pistachios and macadamia nuts. Yum! The restaurant also makes some pretty delicious drinks, served up in tiki-style barware.

We didn’t have to wander far for our nighttime activity as we booked to go night paddleboarding with Ibis Bay Paddle Sports, but in the end decided on kayaks instead. What an interesting spin on traditional kayaking and one of the coolest experiences of my time in the Keys (stay tuned for the next post where I’ll go more in depth on each of our water sports).

When we got back to the Marquesa that night, the hotel was also lit up and I contemplated diving right in for a second time that day. But alas, time for a little shut eye before a busy day to follow.

Day 3

In the morning, we picked up our rental car and drove out to Smathers Beach for some photos in the early morning light. Key West isn’t super beachy—the sand is actually imported from the Bahamas—but there are a few stretches of coastline you can hit up if you need your fix.

Fun fact: Did you know the Keys are made of limestone and not volcanic, hence why they aren’t actually islands?

We had to be at Stock Island at 10am for a SUP Yoga class with Lazy Dog Adventures, and I’d been looking forward to this all week long. I own a paddleboard and frequently play around with yoga poses on it at home in Tennessee, but my 90-minute class with Kyla was next-level awesome. A bonus that the water was perfectly placid.

After paddleboarding, Kyla pointed us toward Salute! on the Beach for lunch, which was exactly what we wanted after expending so much energy out on the water. Healthy salads with a view of the ocean to boot.

On our way out of town en route to the Middle Keys, we hit up the Hemingway Home for another visit. We took a more extensive tour of the house on our last trip to Key West, but the home is just so lovely I couldn’t help but swing on through again. And it happened to be ol’ Ernest’s birthday, too!

Plus, you really can’t leave Key West without a visit with the famed six-toed cats. That’s just crazy talk.

Next, it was on to Islamorada—with a few stops en route. Adventurous Kate also happened to be traveling the Keys the same week, so we met halfway in Big Pine Key and had a pint (for me) and an iced tea (for her) at the iconic No Name Pub, which we figured is wallpapered with more than $20,000 in one-dollar bills.

Henry Flagler took a great interest in the Keys and during the heyday of the railroad, the Overseas Railroad extended all the way to Key West. It was destroyed more than 80 years ago by a hurricane, but you can still see remnants at Bahia Honda State Park, which doubles as a refreshing swimming hole and snorkeling spot.

We only stopped on Bahia Honda Key briefly before continuing to Islamorada, arriving while still light. We got situated at our hotel, Amara Cay Resort, before heading out again.

As opposed to our city stay in Key West, our Islamorada hotel was right on the ocean and has an on-site water sports outfitter. I still can’t get over how glassy the water is here!

If you’re thinking right about now that it seems odd we’ve been in the Keys for three whole days and not found a brewery, I feel ya. Luckily, we changed that in Islamorada.

Florida Keys Brewing Co. had come highly recommended to us by several fellow beer lovers, so this was a priority on Islamorada. The brewery is just two years old and run by a husband-wife team, Craig and Cheryl. He tends to the brewing while she spearheads the marketing artwork—taps and beer cans included—and boy is it fun and colorful! Straight-up mermaid vibes going on at Florida Keys Brewing.

But aesthetic aside, the beer was damn good, too. I love how Craig weaves in so many local flavors, including—you guessed it—key lime. SVV’s favorite brew was the Iguana Bait, a honey hibiscus kolsch, while I gravitated toward the Smuggler’s Moon, an oatmeal stout.

Dinner that night was at Marker 88, a 50-year-old seafood establishment where we were slated to dine alfresco but a looming storm changed that plan.

Instead, we nabbed a table inside and indulged gluttonously before rolling ourselves back to the resort for the night.

Day 4

We started our fourth day by backtracking a bit to Marathon to do the cutest activity in all of the Keys: visit the Turtle Hospital!

This amazing facility rescues and rehabs turtles, many of them having suffered human-inflicted injuries from boats, fishing hooks and pollution, while others having been victims of shark bites.

You can’t just show up and visit the premises without a guided tour—and tours usually sell out, too—so be sure and call in advance to secure your spot. It’s an hour and $22 well spent to get to see these peaceful creatures—with names such as Bonnie, Clyde, Spartacus and Donatello—up close and personal.

Fun fact: Any idea how they ship turtles who can’t return to the ocean to their aquarium or zoo forever homes? Fed-Ex! I’m not even kidding you.

The renowned Robbie’s and its on-site restaurant, the Hungry Tarpon, are on the way back to Islamorada, and we couldn’t resist a lunch of coconut shrimp fish tacos by the pier while we watched the other tourists feed the fish.

That evening, we headed over to the Postcard Inn for cocktails at the Tiki Bar, which created the original rumrunner back in 1972. There were key lime mojitos and coladas on the menu, so I had one of each while SVV tested the rumrunner (neither of us regret our decision).

Then, we went to the Third Thursday art walk, which overtakes the “downtown” one night a month, before settling in for a meal at Chef Michael’s, the cherry on top of an already excellent vacation. More tuna, more hogfish and, yes, more key lime pie. Chef Michael’s was the best meal we had during our entire five days in the Keys.

As we left the restaurant, we ran into a local and asked her where the best sunset in Islamorada is. She first told us we were standing in front of the house on Bloodlines—seriously, I must watch that show already! the filming locations are all over the Keys—and then followed it up by pointing across the street to Pierre’s at Morada Bay.

She wasn’t wrong. And it took all of five minutes for us to see why Islamorada is said to have the best sunsets in all of the Florida Keys.

Day 5

On our final morning in the Florida Keys, we kicked it at the pool at Amara Cay until checkout time. The South was under a pretty stifling heat wave, and it was hard to motivate ourselves to do anything besides being fully submerged in water.

Then, begrudgingly, we packed our things in our rental car and tried to prolong our trip with a second visit to Morada Bay. This time, we had lunch at the Beach Cafe—and one last key lime pie—to hold us over until we got to Miami for our flight.

For divers and water sports enthusiasts, this trip didn’t include time in Key Largo and at John Pennekamp Coral Reef State Park, known for its snorkeling, fishing and diving. If that interests you, I’d suggest swapping out the time in Islamorada and focusing on Key Largo instead. Or better yet? Stay a full week, then you can allot a couple days to each!

For those of you looking for more information on planning a trip to the Upper and Middle Keys, here are past posts I’ve written, jam-packed with travel tips:

• A Road Trip Through the Florida Keys
• The USS Vandenberg: The World’s Coolest Shipwreck
• Conservation in the Florida Keys
• Big Pine Key Adventures: Kayaking in the Florida Keys
• Don’t Miss Bahia Honda Key in the Florida Keys
• Florida Fun: Feeding the Fish on Islamorada
• Key West: A Multicolored Dream Island
• Florida Keys Dining: A Lavish Dinner Out at Sunset Key
• Key West’s Gardens Hotel: Hemingway Would Have Stayed Here

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