Florida: A Sun-Kissed Miami Road Trip




From $4,880pp excl. flights
(based on 2 ppl sharing)

How long

10 nights ideal length

Road trips are quite the favorite here at Black Tomato, and our travel experts know exactly how to create the perfect one. You’ll start things off in glam Miami before cruising up the coast to the natural beauty of Florida. From sipping champagne up in the air watching the sunrise to flying off to a private island for lunch, this 10-night luxury stay could be the dreamiest road trip ever.

After touching down at Miami International Airport, you’ll pick up your hire car and head off down to the electrifying Miami Beach. Kick back and relax at The Setai, your luxurious hotel for the first three nights, where you’ll enjoy a peaceful ocean view that will leave you forever in awe.


If Cuba has been on your bucket list, you’re in luck. Without even having to get your passport out, you can immerse yourself in real Cuban culture. Nestled within the glitz of Miami, lies the Little Havana Food Tour where you’ll be sure to get a true taste of Havana, quite literally. Expand your knowledge of the culture and history of Cuba as you take a stroll through Miami’s oldest and most vibrant neighborhood. With five restaurants to choose from, push your palette to the extreme by indulging in the finest Cuban foods. Whether you want to have breakfast, lunch or dinner, or even all three (don’t worry, we don’t judge), this is Miami’s finest Cuban cuisine. Admire the art of the ‘Cubano’ hand-rolled cigar, and sip on Cuba’s most famous cocktails whilst dancing the day away listening to traditional Cuban music.

Later, drive your way to Downtown Miami and find yourself in the heart of the Wynwood Art District. Rent a bike or take a stroll down the graffiti-filled streets for an eye full of the most vibrant street art. Flooded with color and life, the Wynwood walls have welcomed some of the greatest artists from all over the world. Take your creativity to the next level and work alongside some of these artists to create your very own masterpiece. Who knows, you may unearth a hidden skill in the art of graffiti.

Your next stop will be the Everglades National Park, a place that is home to some rare and endangered species. Filled with thick forests and grasslands, experience marine life in a whole new way and catch a glimpse of the enormous alligators – or, if you’re lucky, you may even see the elusive Florida panther. Your tour ends by speed riding through the swamps with a serene view of the wetland.

Make this itinerary yours

Each and every Black Tomato trip is tailored exactly to who you are and what you want to do So tell us about yourself and we’ll create something that’s entirely you.

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Return to the hotel for a restful sleep as you’ll be up early tomorrow – trust us though, it will be totally worth it. Here at Black Tomato, we love to go above and beyond, so just a few hours before sunrise, awaken those sleepy eyes and head down to the launch site of your next adventure. The roaring of the burners and explosion of colors will no doubt have you fully awake and bursting with excitement for your hot air balloon ride. As you float up into the air and watch the gorgeous sunrise in total tranquillity, take a moment to yourself and soak in the beautiful surroundings. You’ll want to bring your camera to snap this unforgettable moment – and obviously to make your family and friends back at home totally jealous.

After your early start, we figured a jungle trek may be too tiring – but don’t worry, we’ll still be sure to squeeze this into your trip. Instead, we thought there could be no better way to spend the rest of your day than by relaxing on a beautiful Italian yacht. Step onboard and sink into ultimate relaxation mode. Walk on down to the deck and recline on the leather sofas, as you sail away into the distance feeling the ocean breeze against you.


Prepare to ditch the phones as you’re whisked off to a secret island escape. Discreetly hidden just off the Florida Keys coastline, start your journey in ultimate style by arriving either by sea-plane or boat. For the next three nights, indulge in an exclusive slice of paradise at Little Palm Island, a best-kept secret amongst celebrities.

With the island as your home, it’s entirely up to you how to spend your days. Why not have champagne flowing by mid-morning and spend the day lounging around the island, gazing out at the glistening sea? If you fancy something a bit more exciting though, you will find yourself spoilt for choice by the range of activities. Conveniently close to Little Palm Island, dive down amongst the colorful reef in Looe Key, renowned as one of the best places in the US to scuba dive. Or if you prefer being up in the air, hop in a helicopter and sight-see your way around the island from above – or even go skydiving for the most spectacular views of Florida Keys.

Hold back the tears as you wave goodbye to the heavenly Palm Island; we have another resort waiting for you that simply defines luxury. Just seven minutes from Key West lies Sunset Key Cottages, a secluded 27-acre island full of gorgeous cottages surrounded by pure white sand. Over the next few days you’ll be waking up to the calming sound of the waves with a gorgeous view of the never-ending ocean. Bliss.

Your adventure at Key West starts on board a seaplane for the Dry Tortugas Tour where your pilot and personal tour guide will fly you over the Gulf of Mexico, the ending point of the Keys. As you soar over the incredible views, you’ll be flying at a close distance to the blue and green waters where you’ll have front row seats to the sharks, dolphins and turtles below. After circling the air, you’ll hit the waters at the Dolphin Research Center. Made up of a large series of saltwater lagoons, this is home to a family of dolphins and Californian Sea Lions. Later, you’ll get the chance to enjoy the water, and these intelligent creatures, as you swim with the dolphins.


As your last few days come to an end, you may think that you’ve experienced it all. Well, we thought we’d throw in a little something extra for you as the cherry on top of this fab trip. If you’ve always wanted to make a grand entrance in pure style, you can finally tick that off your list. Board a Havilland plane and fly to lunch on a private island and dine in ultimate luxury. How’s that for experiencing it all?

Where to rest your head

The Setai, Miami Beach

Discover The Setai, an intimate oceanfront luxury resort, perfectly positioned in the heart of Miami’s chic South Beach. The Setai’s design artfully combines the architectural…
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Sunset Key Cottages, Florida

Sunset Key Cottages sits on a 27 acre island of tropical greenery, sandy bays, and spacious private homes and cottages. The bougainvillea draped cottages are…
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Little Palm Island, Florida

On its own private island, Little Palm Resort offers travellers and holidaymakers alike the chance to sequester themselves away on a picture-perfect, tropical island. Often,…
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