How to Take a Killer Florida Road Trip

Begin your Florida journey with an overnight at Naples’ Edgewater Beach Hotel and fuel up with breakfast by the hotel’s pool the next morning before hitting the road.

A drive through Florida might be just the ticket for a fun getaway. So tell your clients to load up the rental car, put on their sunglasses and hit the road. We’re going from Naples to Miami to Key West, with a few hotel suggestions along the way. (Note for cat and dog lovers: Except for the Conrad, the hotels cited below are all pet-friendly.)

One way to start off a road trip is to celebrate a friendship or romance — and Colleen Sugden, chief concierge at Naples’ all-suite, boutique Edgewater Beach Hotel, knows how to make it happen. She once cleared traffic from a busy downtown street so her guest, who was celebrating his birthday at a local restaurant, could receive his surprise gift in style: a brand new Bentley driven up to the front of the restaurant. The hotel’s own Coast restaurant can set you up for some seaside dining, custom menu and butler included.

Need to pick up a few items you forgot to pack? Take the hotel’s electric trolley to Naples’ Fifth Avenue South where there’s plenty of shopping. Also be sure to take time to visit Norman Love Confections’ Naples Chocolate and Dessert Salon at 3747 Tamiami Trail North.

You can drive the 195 miles from Naples to Miami in a number of ways, but if you want to take it slow and see old Florida, the Tamiami Trail (U.S. 41) provides all of that, with stops at Ochopee (home to the smallest Post Office in the U.S.); Big Cypress National Preserve (check out the alligators) and Everglades National Park. Biscayne National Park is a must for boating, fishing and snorkeling before heading deep into Miami for some good food and pampering.

At the brand new SLS Brickell, close to downtown Miami and the Design district, you can unwind from driving in one of the three pools on a deck where there are eight cabanas and al fresco dining. The hotel also has two restaurants and the Ciel Spa. If you need to stock up on things to wear and such, give the rental a rest and ask for a ride in the BMW house car to the nearby Mary Brickell Village or Brickell City Centre, which just opened with 125 shops and restaurants.

Want to get into the Miami culture? Conrad Miami just launched a “1 / 3 / 5” program that immerses travelers in local settings for one, three or five hours. Activities include stand-up paddleboarding, diving, museum tours, boating and more. This hotel is also close to the new Brickell City Centre.

Time now to head down to Key West and the Casa Marina, A Waldorf Astoria Resort. The 150-mile route from Miami to Key West is an iconic drive; it’s always scenic and sometimes slow since you’re traveling on a two-lane highway. But there are plenty of places to stop to imbibe, shop or dine, and if you catch it in time you might get some amazing sunset views.

Opened in 1920, Casa Marina has that classic Florida feel, as well as its own large, private beach, made all the better with new cabanas that have daybeds, TVs and fridges. Since you’ve arrived at your final Florida destination and parked your car, we can safely advise you to head to RUMba, a new rum bar serving up some fine rums, classic cocktails (Key Lime Mojitos!), rum flights and cigars. The resort also has a casual restaurant, but if you want to take it up a notch go next door to its sister hotel, The Reach, for Spencer’s by the Sea, where you can book private beach dining.