If you’ve never visited Key West. I strongly recommend driving rather than flying in because the views make it an incredible road trip and there is so much to do along the way that driving through the Keys should be part of the itinerary. It’s about a 3.5-hour drive from Miami to Key West, and it’s a classic American road trip.
We first stayed in Key Largo, which is laid-back while offering every water activity imaginable – snorkeling, diving, fishing, kayaking, you name it.
Islamorada, which encompasses six of the Florida Keys, was only a short drive away. According to legend, Spanish explorers witnessed a purple sunset and designated it the Purple Island ever since. If you’re looking to explore shipwrecks, this is the place for you! And of course, Robbies Marina is here. You cannot miss this stop in Islamorada.
Robbie’s provides snorkeling, boat rentals, SNUBA diving, sunset cruises, parasailing, and the chance to hand feed massive tarpon.
Or you could grab some conch fritters and a drink at the Hungry Tarpon Restaurant and watch other people enjoy the feeding frenzy (like me). Don’t leave without trying Charli’s Shaved Ice.
Marathon is the perfect halfway point between Miami and Florida. So, if you’re short on time and want to break up the drive, I recommend staying in Marathon. If you’re looking for aquatic activities, Marathon has you covered with deep-sea fishing, jet skiing, and paddleboarding.
To avoid a rushed road trip, I recommend stopping in these beautiful keys to rest and refuel on your way to Key West. I can assist you in planning your trip to the keys and deciding where to call home. When it comes to the keys, the journey is just as important as the destination.
Our stay at Baker’s Cay was the perfect start to our Florida Keys adventure.
With two waterfall pools (separate adults-only area), beach hammocks, and water activities offered like diving, parasailing, or a catamaran sail – you can stay plenty entertained or just relax and enjoy the waves on the private beach.
Each morning, fishing rods are set out by the dock with bait so you can wake up with a cup of coffee and fish right off the dock. Personally, I prefer kayaking, and the first hour is included in your stay.
At sunset the place fills up with guests as complimentary bubbly is served for a sunset toast, because a sunset in the keys deserves to be celebrated. I didn’t see a green flash, but it was still gorgeous. I felt so relaxed and at ease wandering around the property because the atmosphere was so comfortable and casual.
We stayed in the coconut wing, in a lovely full-waterfront room. Baker’s Cay just opened in 2019, it provides a modern and fresh option for your Key Largo stay. Click HERE for a room tour!
Isla Bella, with its 24 oceanfront acres of white sand and vibrant blue sea, is setting a new standard for modern luxury in the Keys. I love that every room here has an ocean view and outdoor terrace, so you don’t miss an ounce of that Florida weather indoors. Add world-class dining, a beautiful beach bar shaded by palm trees, five fantastic pools to choose from, and access to world-class fishing and adventure, and you’ve got yourself a paradise home. We spent the day swimming, biking, and playing bocce ball with a signature pina colada in hand.
The activities schedule is packed with fun things to do, from beachfront yoga, sandcastle building, and gelato happy hours to paint & sip events for the 21-and-up crowd. When you’re ready for some relaxation, the serene hammocks set up at Pelican Point felt like the essence of vacation.
Did you know that one of the best private island resorts in the world is right here?! Driving past Marathon and before arriving in Key West, you’ll notice a welcome hut and dock ready to transport some very lucky guests to their private, adults-only island oasis. Consider thatched-roof bungalows, chic pool cabanas, and five-star dining at all times. After a 20-minute boat ride from Little Torch Key, you’ll arrive at this British West Indies-style resort with posh beachfront loungers. A well-known destination for celebrities and the jet-set to get away in style.
Paddle boards, fishing equipment, snorkel gear, kayaks, Hobie Cat sailboats, and four 13-foot Boston Whalers are available for guests to use at their leisure to visit nearby sandbars and reefs. A stay a Little Palm Island comes at a premium, but consider the value of paying for the convenience of a Maldives experience without flying half way around the world.
Then there’s Key West, the last stop on your itinerary. You’ve arrived at the United States’ southernmost point. For nightlife, go to Duvall Street, and for sunset, go to Mallory Square. A jet ski tour is a unique way to experience Key West. The Hemingway House, where the author lived until the 1930s, is the most popular museum. Because so much of a destination’s culture is found in the food, don’t leave without key lime pie on a stick from Kermit’s or an iced coffee from Cuban Coffee Queen.
This is a must-see Key West attraction as well as a fantastic restaurant! The restaurant and bar are charming, but I was most taken with the fact that this is the birthplace of PanAm!
Pan American was the world’s largest airline for many decades until it went bankrupt in 1991. PanAm Flight #1, which took off from Key West for Havana on October 28, 1927, was the first commercial international flight. The food exceeded my expectations for a brewery.
Get on my custom travel planning calendar for assistance with hotel bookings, restaurant recommendations, and a list of top spots to check out along your drive through the Keys so we can design the perfect getaway for you!