Road tripping is in my blood– I love the idea of cruising down back roads, windows down, music turned up. And since I traded my stilettos for flip flops when i moved from NYC to Florida almost 5 years ago, I’ve been more than content to explore all our neighboring sandy destinations, one summer road trip at a time.

One of the best trips of this kind, is the 230 mile, 4 hour drive (give or take) from West Palm Beach to the Keys–taking us to the charming and historic destination located at the southernmost point of Florida: Key West.

DAY 1

Once we made it to Key West, we checked into the Cuban inspired, Havana CabanaWaterfront Resort. Between the mid century cars, bright and colorful décor, lush pool oasis and tropical outdoor bar, this vibrant hotel brought on the charm and character.

Fair warning, Havana Cabana is located in New Key West, a 10 minute drive from the downtown area, but since parking downtown can be an issue, the hotel’s convenient shuttle service was actually perfect.

We dropped off our bags, grabbed a snack and headed down to the pool area. Fun fact: Havana Cabana actually boasts the largest pool in Key West–and it didn’t disappoint. A nice afternoon dip was the best antidote to the long drive.

With our bags packed, we began our journey bright and early and were well into the Keys by noon. Here, we were delighted to pass local shops and restaurants, popular travel stops and incredible views, as far as our gaze could reach.

Islamorada is a great place to have a leisurely lunch or keep driving over the seven-mile bridge, that spans– you guessed it, seven miles– and connects the middle and lower Keys. It’s a spectacular view, with the ocean embracing you from both sides. Here you’ll also catch the remains of Flagler’s Overseas Railroad.

We began our first evening with an unforgettable Wind and Wine Sunset Cruise with fabulous hosts, Nate & Briana of Danger Charters. This sunset sail aboard a Historic 65ft Schooner serves an impressive eight different fine wines, as well as a selection of quality beers, and hors d’oeuvres, while you watch the fiery sun melt into the ocean. This might have been my favorite experience of the entire trip. I highly recommend it!

All that fresh ocean breeze and seemingly endless amounts of wine, definitely stirred up our appetites. We headed for a stroll down the famous Duval Street and stumbled onto Bagatelle Island Restaurant, a charming historic 1800s home that was converted into a restaurant in 1979. Right on Duval, close to Mallory Square, Bagatelle was the ideal spot to have some light seafood fare while enjoying some people watching, to cap off our night.

DAY 2

We started the next morning in the hotel pool before heading out to take in a little Key West culture. On the agenda, visiting Key West’s most famous former resident, in spirit that is, at Earnest Hemingway’s Home and Museum.  On the way, we stopped off at the distillery inspired by the famous author’s life. The Hemingway Rum Company Distilleryand Experience Center, located in a historic building just yards from where Hemingway used to dock his boat, the Pilar, serves as home to a working distillery, experience center, innovation lab, trading post and tasting room. A definitive must to celebrate the bold and complex nature of the Key West local.

Although hot and humid in the summer months, the walk was beautiful, allowing us to take in all of the pastel colored cottages and charming historic properties.

If it’s your first time in Key West, you can also take the Conch Tour Train or the Old Town Trolley that provides insight on the historical sights during your ride and also allows you hop on and off. Make sure to keep an eye out for Key West’s most colorful characters, the free roaming chickens and roosters.

When it was time for lunch, we headed over to the beach side of the island to The Reach Resort’sFour Marlins restaurant. Overlooking the only natural sand beach, it was the perfect place to savor more fresh local seafood while taking in some of the best views on the island.

After the tour, we head over to Hemingway’s Home on foot, where you can enjoy enjoyed a guided tour of the bon vivant’s home and work studio, as well as make friends with all the famous “six-toed” cats that roam the gardens lining the property.

Speaking of colorful residents, the Key West Butterfly and Nature Conservatory is home to the most beautiful winged creatures. With over 60 butterfly species and over 20 bird varieties, It was a magical hidden gem that I highly recommend!

That evening, we hopped over to Key’s West famous Mallory Square for their nightly sunset celebration, where you can enjoy conch fritters and street performers or just watch the boats disappear under the ring of a golden sundown.

DAY 3

For our last day on the island, we booked the BugeyeBackcountry Adventure Tour that combined three great adventures into one day:

  • A Key West schooner day sail.
  • A guided kayak tour of mangrove islands
  • And a snorkel tour of sponge gardens

There is certainly no shortage of things to do in this small island town and I look forward to coming back soon. In the meantime, I hope this itinerary inspires your own exciting Key West adventure. I’ll be posting a list of other suggestions soon. If you have a favorite bar or restaurant to share, I would love to hear your recommendations in the comment below!

A big thank you to keywestattractions.org and fla-keys.com/

#keywest #travelguide #travelblog #floridastaycations #floridadestinations #keywestvacation

It was an intimate nature tour limited to only 16 passengers– in fact, we were exactly 4 couples on board for this fun and relaxing day on the water. After departing from the picturesque Key West’s Historic Seaport, our day was spent exploring uninhabited mangrove islands in the Key West National Wildlife Refuge. After some fun snorkeling, we were back on the beautiful tallmast wooden ship for lunch and unlimited drinks. Not a bad way to end this fun-filled 3 day/2night stay on the island.