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Miami to the Florida Keys

Animated cities, vast wilderness and tropical islands come together in Florida for a varied five-day adventure. Take a deep dive into the Art Deco wonders and Cuban culture of thriving Miami, zip through the mangroves and marshes of the Florida Everglades from atop an airboat, venture to the tropical Florida Keys to kayak over the shimmering waters of Key Largo and uncover the layered history of Key West. Driving on the Overseas Highway is an adventure in itself and undoubtedly one of America’s greatest road trips. Colourful, lively and soaked in sunshine, Florida is a joy to explore.

5 days, from


per person


12 people max


Trip code: SSEF
Style: Original
Theme: Explorer
Print itinerary


Countries Visited:  United States Of America
Accommodation: Hotel (4 nights)
Transportation: Private vehicle
Meals: dinners, 4 breakfasts
Group size: Minimum 1, Max 12

  • Get a behind the scenes look at Miami’s Little Havana neighbourhood during an in-depth tour, uncovering the area’s rich Cuban history, art, architecture and cuisine.

  • Discover Miami’s fantastic collection of colourful and glamourous Art Deco buildings and visit the trendy Wynwood neighbourhood to admire its display of street art murals.

  • Zip through the wildlife rich landscapes of the Florida Everglades on an exhilarating airboat tour, looking out for alligators and unique flora and fauna.

  • Take a trip to paradise and travel to the Florida Keys on the iconic Overseas Highway, stopping off at the tropical Key Largo for a kayaking adventure over its crystal-clear waters.

  • Walk through years of history during guided explorations of Key West, from its successful industrial endeavours to its reputation as a getaway for many of the USA’s important figures.


Show Full Itinerary

Day 1: Miami

Welcome to Florida! Your adventure begins in Miami – this colourful city delights with Art Deco architecture, dazzling beaches and a vibrant Cuban influence. A welcome meeting will take place at 9am this morning where you’ll meet your local leader and fellow travellers, then it’s time to get out and explore the city. First, learn about Cuban life in Miami during a behind the scenes tour of the Little Havana neighbourhood with your leader. Head to some favourite hang outs and chat with the locals, tour a cigar factory, sample Cuban coffee and pay a visit to Cuban-owned art galleries. Stop off and get to know your new travel companions over a tasty lunch at a local café (at own expense). This evening, your leader will be able to recommend some great spots to sample the best of Miami’s food scene.

Day 2: Miami

Detour from the bright lights of the city and travel to the Florida Everglades , the country’s largest sub-tropical wilderness. This World Heritage site is home to a fascinating array of wildlife, including alligators, birds, mangroves and cypress domes. The best and most iconic way to explore this wilderness is on an airboat, so jump aboard and whizz through the Everglades while learning about the unique and diverse life it sustains. Return to Miami and grab some lunch in the trendy Wynwood neighbourhood, famed for its street art murals. Take some time to peruse these colourful works by contemporary artists and learn about their backstories. Enjoy an evening at leisure in Miami.

Day 3: Key West

Say goodbye to Miami and drive on to the Florida Keys, a charming archipelago of tropical islands found off the southern coast of mainland Florida. Connecting the mainland and the keys is one of the world’s most remarkable roads – the Overseas Highway. This island spanning stretch of road serves up some seriously impressive scenery and the drive is widely considered one of America’s great road trips. First make a stop on Key Largo, the longest island in the Keys. You’d be forgiven for thinking you’d left the USA and arrived in the Bahamas – this place truly is a tropical paradise! Set out on a kayaking adventure to discover the abundance of marine life beneath Key Largo’s waters. Continue your journey south and travel to Marathon Key, where you’ll have time to wander around and have some lunch (own expense). Finally, venture on to Key West, Florida’s southernmost point and perhaps the most famous spot in the Keys. This beautiful island is home to an intriguing mix of Caribbean style buildings, lively bars and inviting coastline. Settle into your hotel then join your leader on a walk to get to know Key West, which you may like to follow with dinner in one of the island’s many wonderful establishments.

Day 4: Key West

Set out this morning to get to know the Key West of the past during a historical walking tour with your leader. With a history stretching back to the Age of Exploration, there’s so much to uncover here. Learn about the industrious endeavours that made Key West the USA’s richest city per capita in the mid-19th century, the industrial revolution and the introduction of tourism to the island. Once you’re well-versed in Key West’s history, enjoy an afternoon for your own discoveries of the island. You may like to explore the former residence of American writer Ernest Hemingway or tour the Truman Little White House, where former President Harry Truman spent his winters. You can also visit the lighthouse, hire a bike, chill out on the beach or take part in a sunset sailing tour.

Day 5: Key West

Enjoy a final morning to relax or explore more of Key West, then travel back up through the Florida Keys in the late morning. We will stop for lunch along the way and you can expect to arrive in Miami around 4pm, at which point your Florida adventure will come to an end.

5 days, from $1,955

to book call 1-844-205-6226

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