Road Trip to an Island Paradise

Most island escapes require a lot of logistics, booking flights, chartering a boat, or at minimum boarding a ferry, but visiting Key West only requires that you plan a road trip and jump in the car. Heading out across the Overseas Highway had always been one of my bucket-list road trips, so when Acura gave me the ok to go on a nearly 3,000-mile road trip in the new RDX, I packed my bags, picked up my girlfriend, and we headed towards one of America's best vacation destinations.

Along the way we stopped at a lot of great places, to see my story from the whole road trip CLICK HERE.

From Miami, it's about 160 miles, and once you are in Key West, you are actually closer to Havana than Miami. Driving out on the Overseas Highway is surreal, at times you are surrounded by the green-blue waters where the Gulf of Mexico meets the Straits of Florida, and at others keeping a sharp eye out for Key Deer that have been known to dart out in front of cars. The trip takes about 3 hours, as the average speed on the highway is around 45mph. We stopped in Marathon, which is about halfway, for lunch at Herbie's Bar & Chowder House, which has been popular with locals and tourists alike since the 1940s. But if you pack a lunch there are several public parks and beaches where you can stop for a picnic.

The highway follows the original route of the Overseas Railway, which was mostly wiped out in the Labor Day Hurricane of 1935. The loss of the railway meant that the keys were once again only reachable by boat, devastating tourism, and hindering rebuilding efforts. But by 1938, thanks to the Works Projects Administration, the new Overseas Highway was open and tourists began flocking back to the Keys. 

Once you get to Key West it is best to stay in Old Town if you can and since you are road tripping make sure that the hotel you have booked includes parking, because street parking is not only hard to come by, but it's expensive too. If you are a fan of history Old Town has a lot to offer, from Fort Zachary Talyor to the home of Ernest Hemingway (above), and even President Harry S. Truman's Little White House. It is easy to spend a day walking Old Town, just find Mallory Square, Bahama Village, or any stretch of Duval Street and you'll find something to do. From museums and art galleries to shopping and dining, Key West has something for everyone.

You can't just fill up on Key Lime pie, but you have to at least have a slice, and the best we found on the island is Kermit's. For more than pie, the island offers a wide range of culinary choices that includes everything from amazing food trucks to top tier fine dining. For dinner check out Café Marquesa, one of the island's highest rated restaurants, the Yellowfin Tuna Tartare is excellent and the Seared Duck Breast will be committed to your memory forever. For breakfast head over to the Banana Café for crêpes or eggs benedict, they have limited patio dining, but depending on when you are there, it can make for excellent people watching on Duval Street.

Hotels can be costly on the island, but there are a lot of options, during high season and holidays expect to pay upwards of $400-$500 a night for a 3-star hotel. Even the local hostels charge $125-$140 a night for a bed in a dormitory, so if you are hoping for a $129 Holiday Inn Express, your out of luck.

If you are adventurous there are several Airbnb options including live aboard boats and historic condos that are generally around $200-$250 a night during the busy season. Some are moored offshore and require you paddle out by rowboat, so double check the listing before booking a stay on a boat. Offseason is the best time to go if you are looking for a deal, between the summer vacationers and the annual return of the snowbirds, just remember that May-October is the rainy season, so plan accordingly.

Key West is a very unique place, it's an island paradise, with a rich cultural heritage that blends U.S., Cuban, and Europan traditions, food, and art. We can't wait to go back and spend more time there, hopefully during the off season so we can really experience the locals and community. Visiting during a major holiday meant it was very crowded, loud, and parking (my pet peeve) was a nightmare. The island plays host to a number of major events including one of the largest LGBTQ pride festivals in the Americas, which completely takes over the island for a week each summer during Pride Month. If you are planning a quiet getaway, you might want to double check the official calendar before booking, it lists everything from Fishing Tournaments and the Cuban American Heritage Festival to the annual Mermaid Festival and Hemingway Look-Alike Contest.

If you are looking for a relaxing retreat or a vibrate street festival, Key West can offer you a variety of experiences. For more info or to help plan your own trip, check out

This trip wouldn't have been possible without the support of Acura who let us drive the all-new Acura RDX. For my full review on the RDX click here. Check out Jennifer's take on the RDX and road trip on