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Party and nightlife
Relax
Nature and adventure
City and cultures
Monuments and history
Physical effort
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Itinerary

Sunshine, ocean views, and the ultimate road trip vibes: welcome to Florida. This express adventure takes you from vibrant Miami all the way down to the tropical paradise of Key West, cruising along one of the most scenic highways in the U.S. Think turquoise water, epic sunsets, and that laid-back island energy you’ve been craving.

We kick things off in Miami, where Latin rhythms, pastel Art Deco buildings, and endless beaches set the tone. From there, we hit the road heading south, driving the iconic Overseas Highway — a bucket-list route that feels like you’re floating on the ocean. Along the way, we’ll stop at hidden gems, snorkel in crystal-clear water, and soak up the easygoing vibe of the Keys.

Key West is the grand finale: colorful streets, live music, fresh seafood, and sunsets that hit different. Whether you’re biking around town, kayaking through mangroves, or just chilling with a drink by the water, this is where time slows down.

This isn’t just a trip — it’s a full-on Florida state of mind.

A map showing a travel itinerary with a start and end point in Miami.
Two burgers and a salad bowl with meat and vegetables are displayed on a stainless steel counter at a food stall.

Touchdown in the Magic City

Arrival in Miami and check-in at the hotel and we'll gather for our Welcome Meeting! Take some time to settle in, recharge, and get your first taste of the city’s tropical energy.

Then, as the sun goes down, we head out for our first night together — think ocean breeze, neon lights, and that unmistakable Miami vibe.

A city skyline along a wide waterway with a docked cruise ship, viewed under a purple and orange sunset.

Colors, Culture & City Life

Today we explore some of Miami’s most iconic neighborhoods, starting with Wynwood Art District, famous for its bold murals and creative vibe. We’ll then move toward Brickell and Downtown, where modern skyscrapers meet local culture. It’s a full immersion into the city’s contrasts, blending art, architecture, and everyday Miami life in one dynamic day.

Sailing into the Sunset

In the afternoon, we make our way to Bayside for a memorable sunset cruise. As we glide over the water, you’ll enjoy breathtaking views of the Miami skyline glowing in golden light. It’s a relaxed yet unforgettable experience, perfect for photos, good conversation, and fully embracing that laid-back Florida feeling.

A purple airboat speeds through a marshy wetland filled with tall reeds, kicking up a white spray of water.

Into the Wild: Everglades Airboat Tour

This morning we leave the city behind for an adventure into the Everglades, with transportation included from our hotel. Hop on an airboat and glide through this unique ecosystem, home to alligators and incredible wildlife. It’s a completely different side of Florida. We return around lunchtime, giving you some free time to relax or recharge.

Cuban Vibes in Little Havana

In the afternoon, we head to Little Havana to experience one of Miami’s most vibrant cultural neighborhoods. Stroll through colorful streets filled with music, local flavors, and authentic atmosphere. We’ll stop for a classic happy hour and then enjoy dinner together, soaking in the energy of a place that feels like a world of its own.

An aerial view of a long highway bridge stretching across the sparkling sea towards a distant, hilly coastline.

Hit the Road: Overseas Highway

Today the real road trip begins. We pick up our rental car and start driving toward Key West along the legendary Overseas Highway. This scenic route connects a series of islands with stunning ocean views on both sides, making the journey itself a highlight. Expect stops along the way, plenty of photos, and that true on-the-road freedom.

Island Time Begins

Enjoy your final morning at a slower pace, whether that means grabbing a coffee, taking a last stroll, or simply soaking up the atmosphere one more time. Before we say goodbye, we’ll gather for one last unforgettable moment together: watching the sunset in the Keys, with golden light, ocean views, and that feeling of wanting time to slow down just a little more.

A blue and green lifeguard tower on Miami Beach at sunset, with a cruise ship on the ocean and seagulls flying by.

See you soon dear friends!

Our trip comes to an end, and it’s time to say goodbye to your travel companions and this unforgettable experience. You’ll leave with new memories, great stories, and maybe even new friendships. Until the next adventure, Florida will always be waiting for you with its sunshine and endless good vibes.

What's included

What's not included

Roundtrip flight to/from destination
  • Food and beverages when not specified
  • Gas/petrol, parking, toll fees 

  • All the extras you'll be able to fit in your backpack
  • Anything not mentioned in the "What's included" section

Additional info

Learn more about accommodation, transport, and other useful travel information.
  • Accomodation

    Small hotels, hostels or apartments - all well connected by public transport. Rooms are made up of 2 bunk beds and shared by 4 people. These rooms can be mixed.The first hotel will be shared with you at least 2 days before your departure by your Group Leader!

  • ID

    Remember to bring your ID - it is required to enter pubs, bars and night clubs

  • Drive-yourself tour

    This is a Drive-yourself tour - it isn’t compulsory to drive, however if you are willing to, then please tick the box when booking your trip.

  • Info on private roomsShow all details

Why WeRoad

  • Small groups, on average 11 people

  • Move or change your trip for free up to 31 days before departure

  • Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed

The Group Leaders

Our Group Leaders are chosen because they’re people just like you: passionate travelers who share the experience authentically, while having the skills to take care of the organisation, and help you get the most out of every moment of the trip.

Find your flight

For this trip, we recommend arriving and departing from these airports.

ArrivalMiami (MIA)
ReturnMiami (MIA)
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WeRoadX

This is a WeRoadX

A trip designed and created entirely by an experienced WeRoad Travel Group Leader.

This is a trip designed and created entirely by an experienced WeRoad Travel Group Leader. They organise the whole trip: from defining the itinerary to selecting accommodation and on-site experiences. On the WeRoad website you can book the trip and manage it in MyWeRoad, just like any other WeRoad.

FAQs – Frequently Asked Questions

About this trip

About WeRoad

About United States of America

From
$ 1,512
Book with $ 0
Free trip change
Interest-free installments