A Southern Florida Peninsula Roadtrip

Arrive at Miami Airport, where your rental car waits for a swift journey to Coconut Grove, one of Miami's charming oceanfront neighborhoods boasting historical landmarks and emerging restaurants. Check in at the Mayfair House Hotel & Garden and relax after your flight by indulging in the hotel's rooftop pool and bar, Sipsip Calyspo Rum Bar, known for their signature cocktails. Dive into dinner here (I highly recommend the lobster roll) or explore the diverse culinary offerings in the vicinity. Coconut Grove is incredibly walkable, allowing you to easily explore its vibrant streets and captivating atmosphere.

After a restful night at the Mayfair House, kick off your day with brunch at the Green Street Cafe, a neighborhood classic. Alternatively, if you're in the mood for a quick on-the-go bite, grab a bagel from El Bagel, conveniently located across the street from your hotel. Be prepared for a local hotspot experience, especially on weekends.

Explore the cultural gems of Miami by taking a tour of the Vizcaya Museum & Gardens or immersing yourself in the vibrant city scene. Miami offers a plethora of options, from strolling through the captivating street art of Wynwood Walls to admiring the architecture in the historic Art Deco district. Delight your taste buds with authentic Cuban cuisine in Little Havana or unwind by the iconic, colorful lifeguard towers on Miami Beach.

As the day winds down, the city offers an array of dining choices. My personal recommendation is Kiki on the River, followed by a refreshing cocktail at one of the rooftop bars in Brickell. Miami's culinary scene is diverse and vibrant, ensuring a memorable experience for every palate.

Begin your morning by checking out from the Mayfair House and embarking on a scenic drive to Key West. The journey, spanning three to five hours depending on traffic along the two-lane highway, offers breathtaking views, which makes the time fly by. Break up the drive by stopping at Robbie’s to hand-feed fish, then navigate through the chain of islands to the southern tip of Florida and check into the Oceans Edge Resort & Marina, a picturesque marina-front hotel tucked away from the hustle of town.

While the hotel provides a complimentary shuttle to the town center, I recommend unwinding after the drive by taking advantage of the hotel's amenities, such as its six pools or complimentary use of stand-up paddleboards, kayaks or bikes. Indulge in a delightful dinner at the hotel's Yellowfin Bar & Kitchen, offering a stunning sunset view and a nightly lobster special. Alternatively, venture to the HogFish Bar & Grill, a laid-back local spot known for the freshest seafood (straight from the boat to your plate) accompanied by live music and panoramic waterfront views.

Today, immerse yourself in the charm and tranquility of Key West. Start with a complimentary breakfast at your hotel, a delightful perk of booking with us, before taking a quick shuttle to downtown Key West. Delight your taste buds with the Guy Fieri-approved lobster roll at Garbo's Grill, savor the island's best doughnuts at Glazed Donuts (available until noon) or sip cocktails at Four Flamingos or the iconic dive-bar, Sloppy Joe's (a fantastic spot for watching a game if you're a sports enthusiast). Duval Street offers excellent opportunities for bar-hopping and for those with a sweet tooth, embark on a "key lime pie crawl" to uncover the island's best pies; locals may recommend Blue Heaven as a top contender.

If you're drawn to the water, consider booking a dolphin tour, riding a floating tiki bar, exploring the mangroves with the hotel's kayaks or opting for an all-day excursion to Fort Jefferson in Dry Tortugas National Park, 70 miles west. This adventure includes lunch, a tour and snorkel equipment.

Key West's town is highly walkable—explore the Southernmost point buoy, the 0-mile markers, visit Harry S. Truman's Little White House or take a stroll through Hemingway's Home & Museum where you'll learn about Hemingway's time in Key West and may even spot some six-toed cats!

As the day unfolds, embark on a boat journey to Sunset Key for a dinner experience at Latitudes, a beachfront restaurant on an island just off Key West. The picturesque views make it a highlight of this road trip, creating memories against the backdrop of a breathtaking sunset. Revel in the unique island charm of Key West to the fullest.

Following breakfast at the hotel, relish the scenic drive up the keys and through Everglades National Park. I recommend opting for the two-lane Tamiami Trail (US 41) instead of the faster four-lane Alligator Alley (I-75) for better views and potential wildlife sightings. Along the way, make stops at the Big Cypress Visitor Center or consider a swamp tour for a unique experience throughout your drive.

To add a refreshing pause to your journey, think about spending a night in Naples or Fort Myers. Alternatively, continue your route up to Sarasota and check into the Hyatt Regency Sarasota. St. Armands Circle, just a bridge away, is a haven of delightful dining options. While I personally favor Tommy Bahama restaurants, the circle also boasts numerous non-chain dining spots and shops for a diverse and enjoyable experience.

Begin your day with a refreshing walk over the bridge to St. Armands Circle for breakfast, coffee and a leisurely stroll along the wonderful white sand beach. Afterward, check out and make your way to the Disney World Resort. If you prefer not to spend a half day at the park, explore the fantastic dining, shopping and experiences at Disney Springs, or indulge in a shopping spree at the Orlando outlets. For the remaining day(s), fully immerse yourself in the magic of Disney. With four theme parks and two water parks, a week could easily be spent here, though I find that three days is the perfect amount of time to savor all the attractions each park has to offer.

Staying at one of the Disney World hotels comes with added perks, such as early park entry or extended evening hours, and my personal favorite is the Contemporary Hotel. This hotel offers quick access to Magic Kingdom, a monorail inside the hotel connecting to other parks, or busses to Animal Kingdom. The Contemporary Hotel features the California Grill on the 15th floor, providing a perfect spot to dine and watch the fireworks over Magic Kingdom - a magical conclusion to a great trip. At night, you might even be surprised by a charming boat light parade from your water-view room - just an added touch of the magic Walt Disney World hotels offer. As your journey comes to an end, Orlando Airport is just a short drive away, providing a convenient location to drop off your rental car and bid farewell to the enchanting experiences of your Southern Florida road trip… until your next trip!