Florida 360°: Orlando, Miami and Key West




Florida 360°: Orlando, Miami and Key West
The trip in a nutshell
Self-driven tour
This is a self-driven tour - it isn’t compulsory to drive, however if you are willing to, then please tick the box when booking your trip.
Get ready for an amazing tour of Florida! Our road trip starts in Orlando, where you'll relive your childhood at Disneyland, meeting beloved cartoon characters and Marvel superheroes. Next, we'll head south on the scenic Overseas Highway to Key West, the southernmost point of the United States. Explore the vibrant streets, indulge in fresh seafood, and relax on beautiful beaches. Heading back north, we'll visit the incredible Everglades National Park. Take an exciting airboat ride through the swamps and spot alligators and crocodiles in their natural habitat. Our last stop is the famous Kennedy Space Center in Cape Canaveral. Discover the history of space exploration and marvel at NASA's achievements. Throughout our trip, you'll experience Florida's unique mix of cultures and bask in the warm sunshine. Get ready for an unforgettable adventure in the Sunshine State!
Trip type
360º - it's our great classic that allows you to discover the destination in all its aspects. We recommend packing a backpack rather than a suitcase as there will be lots of moving around.
Physical rating
LOW - this itinerary is easy-going and any extra sports or activities are entirely optional.
Entry requirements
Please visit your country's official government website to find out the necessary requirements for entering the country of destination.
Arrival and departure
This trip will begin and end in Miami. Aim to arrive on the first day by 6pm - on the last day you are free to leave whenever!
What's included
9 nights accommodation in shared bedrooms
Car rental from day 2 to day 8
Road tolls
An exciting airboat ride, the best way to experience the unique subtropical ecosystem of the Everglades
Speedboat excursion in Miami
Spend the evening learning Salsa (mojito included)
Travel coordinator services
Free cancellation with 100% refund up to 31 days before departure
Itinerary
Welcome to Florida!
Check-in
Round trip flights are not included in the package, so you can choose from where and when you want to fly. This is to give you maximum freedom of choice!
Check-in at the hotel in Miami, and meet the rest of your group! Let's head out together to explore the city and find somewhere nice to grab some food. Here, let's cheers to the beginning of our adventure!
Included: overnight stay
On the road to Key West
On the road!
We won't be in Miami for long (but don’t worry, we'll be back very soon!). We'll grab our rental cars and hit the road. Let's make sure we have the perfect playlist for our 4-hour drive to our destination today: the beautiful Key West! This drive will be anything but boring; we'll be traveling on the Overseas Highway, a stunning route that stretches over the sea with a series of bridges connecting the Keys and leading us to the southernmost point of the United States!
Exploring Key West
We'll arrive just in time for lunch, where we can eat whatever we want, but for dessert, we can't miss out on Key Lime Pie, the signature treat of Key West. With our bellies full, we'll head to the beach for an afternoon of our choice: water sports, relaxation, or starting early with some cocktails! In the evening, we'll enjoy a nice dinner and toast to our adventure. After dinner... how about we kick off the night with some dancing?
Included: overnight stay, car rental
Money Pot: fuel, entrance fees, other transportation
Not included: meals and drinks
The southernmost point of the States!
We are close to Cuba!
We'll take a stroll through the centre of Key West to soak in the spirit of this charming island, located just 170 km from Cuba - it already feels like the Caribbean! We'll visit Hemingway's house, where he lived for ten years, and explore the museum to discover what inspired the famous author to write his works. After our visit, we'll head to the Southernmost Point for the customary photo at the buoy marking the southernmost point in the United States.
Roads on the Sea
Before lunch, we’ll carve out an hour to rent kayaks and paddle through the waves, exploring Key West from the sea. After returning to the mainland, we'll grab a bite to eat and then set off. Our first stop is Honda Bay for a quick dip, and then we continue to Marathon via the Seven Mile Bridge, a spectacular stretch spanning the sea. This evening, we'll unwind in some of Marathon's bars: beer in hand and good music will be the perfect accompaniment!
Included: overnight stay, car rental
Money Pot: fuel, entrance fees, other transportation
Not included: meals and drinks
Everglades National Park
In the swamps
Rise and shine! We have many kilometers ahead of us. We'll reluctantly say goodbye to the Keys and head into Everglades National Park, a vast region of swamps, mangroves, subtropical flora, and wildlife. Keep an eye out for alligators, crocodiles, herons, ibis, storks, and the inevitable mosquitoes (don't forget the insect repellent!). We'll arrive by lunchtime and board an airboat for an excursion through the park, aiming to spot at least one crocodile.
Still on the road
In this part of Florida, some places serve fried alligator meat, so it's up to us to decide if we're brave enough to try it! After lunch, we'll hit the road again, and in a couple of hours, we'll arrive in Naples, our final stop for the day. We'll unwind for a bit and then pick a restaurant for dinner. Maybe tonight we'll go for a hamburger, a favourite here in the States!
Included: overnight stay, car rental, airboat excursion
Money Pot: fuel, entrance fees, other transportation
Not included: meals and drinks
Clearwater: Let's enjoy the sea!
The ocean, finally
This morning, we'll set off again, reaching Tampa by mid-morning, but we won't stop in the city. Instead, we'll head straight to Clearwater Beach, where we'll spend a couple of hours enjoying the sun and sea, just enough to recharge our batteries. We'll grab something to eat on the way and then get back on the road. Today's final destination is the capital of Florida!
Heading to Orlando
Orlando is famous for its amusement parks. Tomorrow, we'll have plenty of time to explore them (choosing between Universal Studios and Disneyland will definitely test the group's unity!). This evening, we'll take a stroll around the city, enjoying its relaxed atmosphere and the palm trees that remind us of the beaches we've seen in the past few days. We'll find a restaurant that catches our eye and enjoy a lovely evening in Orlando!
Included: overnight stay, car rental
Money Pot: fuel, entrance fees, other transportation
Not included: meals and drinks
Orlando: Disneyland or Universal Studios?
Where shall we go today?
As we planned yesterday, today is all about having fun! We'll pick our favourite park to spend the day: Disneyland will transport us back to childhood, with princesses wandering through castles and beloved cartoon characters greeting us along the way. At Universal Studios, we'll dive into the iconic sets of Marvel's blockbuster films and step into the enchanting realm of Harry Potter—fans will be thrilled by the sight of Hogwarts and the adventure of boarding the Hogwarts Express!
A night in Orlando
Included: overnight stay, car rental
Money Pot: fuel, extra transportation
Not included: meals and drinks, parks entrance fees
Kennedy Space Center
1:1 with NASA
Sunset in Miami
After coming back to Earth, we’ll set off again and return to base camp: the compass this afternoon is pointed towards Miami! We’ll arrive in the late afternoon, put down our backpacks and go straight to the beach: we’ll enjoy the last hours of the day, when the sun is gentler and the tan turns golden! We’ll wait here for the sunset: the sun is not swallowed by the sea but by the city skyline and the view is really impressive!
Included: overnight stay, car rental
Money Pot: fuel, Kennedy Space Center entrance fee
Not included: meals and drinks
Miami
South Beach baby!
Today we finally enjoy the sea of Miami : the beach of Miami Beach is infinite and we can decide where to lie down in the sun - let's not forget the sun cream, the rays are unforgiving here! This morning we'll take it easy: we can take a long walk along the seafront , rent a bike and cycle or dive into the waves - the water here is inviting so saying no will be almost impossible! For lunch we find a stall where we can try street food - here the fish tacos are amazing!
Party... on a boat!
The fun doesn't end here, this afternoon we're taking a one-hour tour to see the city from another point of view... from the sea aboard a speedboat: the most exciting way to combine the thrill of speed with beach life vibes.
Included: overnight stay, speedboat excursion
Not included: meals and drinks
Miami
Cuba or Graffiti?
After last night's party, this morning we'll take it easy: we'll get up at an easy pace and then head for the centre of Miami. Once here we'll decide how to spend the morning: there are many districts worth visiting but two are a must-do! The first one is Little Havana, where you can already breathe the Cuban air and the Latin rhythm, the second one is Wynwood, the heart of Miami street art, where we can walk through the streets and see graffiti by some of the best artists in the world.
Last hours at the beach
After lunch we are free for the afternoon : we can continue exploring the city, perhaps doing a pre-departure shopping session, or we can return to Miami Beach to enjoy the last hours at the beach .
In the evening we can have an aperitif in the heart of Miami Beach in a chic place, but let's not relax too much, tonight we have a salsa lesson to recall the Cuban vibes of this morning. To let us go to the rhythm a bit, there will be an excellent mojito waiting for us and, after having learned the first steps, we can throw ourselves on the dance floor all evening long! What better way to say goodbye than by getting involved on the last evening too?!
Included: overnight stay, salsa lesson, mojito drink
Money Pot: local transport
Not included: other meals and drinks
Goodbye Florida!
Check-out and goodbye
Time to go back home: see you again on your next WeRoad adventure!
End of services. The itinerary may undergo some variations that differ from what stated above. These variations may not be predictable nor depend on WeRoad’s will, i.e. climate conditions, national holidays, strikes, etc.

The travel coordinators
Our travel coordinators are chosen because they are people like you. Not only are they the best travel buddy you could hope for, but they're trained professionals guaranteed to show you a travel experience like never before
Info to know
Staff
You'll travel with a WeRoad Coordinator, which is more or less the best travel buddy you could wish for.
Visas and Vaccinations
Before booking, please ensure you check what documents, visas, and vaccinations are required to enter the country you are visiting. If you have any questions, please contact us.
Available dates
Group
2 WeRoaders
Group
2 WeRoaders
1 person interested
1 person interested
FAQs – Frequently Asked Questions
Round-trip flights are not included in any of our trips because we like to give you autonomy and flexibility: you can choose the airline you want to fly with, the departure airport that suits you best, and how many and which stops you want to make.
Since flights are not included, you also have more flexibility with your travel dates: if possible, you can arrive at your destination a few days earlier or return home a bit later – or even continue independently to a nearby destination!
This is the question of all questions, and here’s the answer, broken down into points!
The Money Pot is a common fund collected in local currency from all tour participants and managed by your Travel Coordinator.
It is used to streamline paymentsfor extra activities, goods and services that the whole group decides to do and to guarantee flexibility in choosing activities and excursions at the destination in line with the mood of the group.
It is typically collected on the first day of the trip in local currency, although at times, the Travel Coordinator may ask for it to be paid before departure.
You’ll find the amount of the money pot on the website under the section ‘What’s included in the money pot’ – how do you get there? Look for ‘What’s included’, scroll down to ‘Money pot? Click here’, and you’ll find the details.
The amount varies depending on the destination chosen.
It is used exclusively for group expenses that ALL participants decide to take part in.
It is estimated based on the experiences of other groups but can vary depending on the needs of the group itself. As such, the Travel Coordinator may need to increase the amount during the trip.
If not all of the money pot is used, the difference will be returned to all participants at the end of the trip in equal amounts.
The Money Pot also covers the Travel Coordinator’s share of the activities included in the money pot, except for those activities that are free for the Travel Coordinator.
If you pay in advance part of the money pot before the trip for certain non-refundable optional activities, unfortunately, the amount cannot be refunded in case of trip cancellation.
We offer several payment methods to meet all needs:
1. Credit or debit card from Visa, Mastercard, or American Express.
2. Installment payments for certain countries only
If you choose the deposit and balance option, you can pay the balance from your MyWeRoad Personal Area via bank transfer.
Anyone who books a WeRoad trip has the option to cancel or modify the trip – including both the dates and the destination – free of charge up to 31 days before departure. In case of cancellation, you will receive a 100% refund of the WeRoad trip price. If you make a change, a price adjustment will be applied to the new trip chosen – meaning, if the new trip is cheaper, we will refund the difference; if it’s more expensive, you will need to pay the difference.
If you’ve purchased the Flexible Cancellation Option (which you can add in the first step of the booking process), you can request a cancellation or trip change until 8 days before departure. In case of cancellation, you’ll receive a 100% refund of the WeRoad trip price, minus the cost of the Flexible Cancellation option.
How to request a cancellation or change to your trip? Send us an email at [email protected] or a WhatsApp on +447716573700. Please share the booking reference for the trip you want to cancel or change, and, in case of a change, the new trip you would like to join.
In general, we always choose local accommodations, avoiding large hotel chains, because we love to experience the culture of the place and, whenever possible, contribute to the local economy. Typically, our accommodations are hotels, apartments, guesthouses, and hostels run by local entrepreneurs, with the same standard maintained across all trips in the same destination.
For our Collection trips, which are our premium category, the accommodations are always 4 or 5-star or carefully selected boutique hotels.
The list of accommodations for your trip will be shared with you by your Travel Coordinator between 5 and 3 days before departure, along with other useful details for your adventure!
If you're wondering why WeRoad trips have a money pot, we’re assuming you already know what it is. If not, or if you have any doubts, we invite you to read all the information here!
Let’s quickly recap: The Money Pot is a common fund collected in local currency from all tour participants and managed by your Travel Coordinator. It’s used to speed up payments for extra activities, goods and services that the whole group decides to do and to guarantee flexibility in choosing activities and excursions at the destination in line with the mood of the group.
But let’s get to the point: why the money pot? First of all: it gives us a lot of flexibility. In all WeRoad trips you will have a bunch of Must See/Must Do activities already included - these are experiences, places or activities that simply cannot be missed! Any extra activities is decided by the group, why? Because each group is unique and may have particular wants or desires and the Money Pot allows each group to customise their trip to make it perfect for their requirements!
It also helps us speed up payments – imagine being in the subway in New York City, one by one purchasing the ticket...a nightmare right? Thanks to the Money Pot, the Travel Coordinator can simply purchase the tickets for everyone making the entire processes smoother! Any leftover money will be returned at the end of the trip and split equally amongst all participants.
In some destinations, buying goods or services on site is more economical as you are able to negotiate the price - places like Morocco, or South East Asia, bargaining is part of the culture. As such, our Travel Coordinators will be able to secure the best deal for all participants.
The amount of the money pot is specified in each trip – look for this button
which will take you to a detailed breakdown for each trip, like this:
WeRoad is not authorised to provide this information due to privacy reasons.
However, there is a solution - you can connect with your travel buddies by joining our Facebook group. Look for a post related to your trip, or ask the group admins for help in connecting with your future travel companions!
If a Travel Coordinator has already been assigned to the trip you're interested in, you can easily find their introduction post in the group via the website: in the tour list, click on 'Ask the coordinator', or in the trip details page, in the coordinator section, click on 'Ask [coordinator's name] for information on this trip in our Facebook group'. For both cases, see the screenshots below!
Tour List
Trip details page
In all our groups, the Travel Coordinator and participants speak English – knowing how to speak and understand English is therefore a fundamental requirement to participate in our trips.
On average the groups are made up of 6-15 people, with a minimum of 3/4 participants and a maximum of 15.
All our travellers are in theirs 20s, 30s and 40s. If you're very curios to know the age range of the group for a tour you're interested in, you can contact us by WhatsApp at +447716573700
Regarding the male-female ratio, this is not guaranteed and varies trip by trip.
The WeRoad Travel Coordinator is an experienced and skilled traveller and will be the perfect companion for your trip. They will be available for any eventuality and will manage all the logistical aspects of the itinerary (transports, timings, accommodations, meeting points, etc.), so you can enjoy the trip without any worries!
You will have the chance to get to know them when the WhatsApp group is created approximately 2 weeks before departure - this will be the moment to ask any pre-departure questions and get to know the rest of the group! If the trip you are interested in already has a Travel Coordinator assigned, you can contact them before booking – their details will be specified in the schedule or on the trip page, or you can search for their name here. After booking, you will find their contact details in your Personal Area, under ‘Bookings and Trips’ > ‘Your Upcoming Trips’ > ‘Trip Details’.
Yes, in all our trips you will share a room with other same-sex travellers, and the bathroom will either be private or shared only with fellow participants of the trip. The rooms we select can be doubles, triples, quadruples, or multi-bed (up to 8 people in exceptional cases), depending on the destination and availability.
There are never dorms with people outside the WeRoad group, except in certain cases for local experiences, which are specifically mentioned in the itinerary or communicated before booking. These typically involve specific nights in unique accommodations like tents, homestays, or camping, offering a more adventurous travel experience in exchange for some comfort.
During the booking process, you can also choose to opt for a mixed room: in this case, if needed, only those who have agreed to this option may share a room with travellers of a different sex. If you are booking for multiple people together and select this option, the room will not be exclusive to your group but may be shared with other travellers in the group.
When you set off on a WeRoad trip, you’re officially a WeRoader – and as we often say, 'Once a WeRoader, always a WeRoader'. This means that once you’re part of the community, a little piece of WeRoad will always stay with you, even if you no longer travel with us.
But you’re not just a WeRoader during your trips, far from it! The community is alive and active all year round: you can stay in touch by following and interacting on our social media channels, like the Facebook group or the Instagram profile. We can also meet up for a dinner or a trek together at one of the events organised by our coordinators around the world!