Italy Express: Tuscany Cities and Landscapes
The trip in a nutshell
Embark on an unforgettable journey through Tuscany, the crown jewel of Italy's regions, boasting a rich tapestry of culture, history, gastronomy, and wine. From the enchanting streets of Florence, steeped in the legacy of the Medici family, we venture into the picturesque Chianti hills, where historic villages and panoramic vistas await, accompanied by the finest wines.
Our next stop is Siena, another exquisite gem of Tuscany, where we indulge in the flavours of Pici alla Senese and marvel at the renowned Piazza del Campo. Returning to Florence, we delve into the grandeur of palaces, verdant gardens, and iconic landmarks before making a captivating detour to Pisa, a coastal city steeped in centuries of heritage and culture.
Join us on this immersive journey, where every moment promises to be a feast for the senses. Your Tuscan adventure awaits!
Trip type
Express: jam-packed itinerary to make the most of the few days of holiday allowance you have.
Physical rating
MODERATE - this itinerary may involve hiking or other activities that require a moderate amount of physical effort. Be prepared for some potential long transfers and early wake up calls!
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 Florence. Aim to arrive on the first day by 6pm - on the last day you are free to leave whenever!
What's included
4 nights accommodation in shared rooms
Car rental for days 2 and 3
Local wine tasting experience in the Chianti region
Entrance to the Duomo Cathedral in Florence
Entrance to Torre Grossa in San Gimignano
Travel coordinator services
Free cancellation with 100% refund up to 31 days before departure
Itinerary
Welcome to Italy
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 Florence and meet the rest of your group! Let's kickstart our adventure in Tuscany by taking a nice walk to find a fantastic local restaurant where we can toast and grab some dinner.
Included: overnight stay
Not included: meals and drinks
Chianti hills, Pienza and Siena
Chianti Landscapes
Today we head towards the stunning Chianti region. The landscapes are postcard-like and, after stopping ever-so-often to take pictures, we will reach a local winery and enjoy a special local wine tasting experience. We will also discover some of the secrets to the winemaking processes. Afterwards, we will set off again to visit some of the unique and historic villages such as Greve and Castellina in Chianti. We then head to Pienza, famous for its pecorino cheese. - ready to taste another Italian masterpiece? In the evening we reach Siena where we will spend the night.
Included: overnight stay, car rental, local wine tasting experience
Money pot: fuel, tolls, and local entrance tickets
Not included: meals and drinks
Siena, San Giminiano and Pisa
Siena and San Giminiano
Good morning Siena, a city where we will explore it's medieval streets, Torre del Mangia, the Cathedral and the famous Piazza del Campo. After dedicating a good part of the morning to wandering around the city, we head to San Giminiano and Monteriggioni, two well-preserved medieval villages in which we lose ourselves among food tastings and unique landscapes. From Piazza della Cisterna we will climb to the top of Torre Grossa to witness a unique viewpoint.
Road to Florence via Pisa
After a typical Italian lunch and some sing along in the car, we will finally reach the sea for a short stop in the city of Pisa; famously known for the Leaning Tower and the Campo dei Miracoli, a square rich in history and monuments such as the Pisa Cathedral, the Baptistery and the Camposanto cemetery. This will be a short but intense stop before returning to Florence, ready to make the most of our last full day!
Included: overnight stay, car rental and entrance to Torre Grossa in San Gimignano
Money pot: fuel, tolls, and local entrance tickets
Not included: meals and drinks
Exploring Florence
Duomo Cathedral and Uffizi Gallery
We dedicate our last full day in this beautiful country to Florence, a city of Renaissance full of timeless charm and beauty. We will explore the Piazza del Duomo and its Cathedral built by Brunelleschi, to then reach Piazza della Signoria, the historic seat of the city municipality and gateway to entrance of the Uffizi Gallery. Are you ready to indulge in some art and culture?
Pitti, Ponte Vecchio and Boboli Gardens
After an amazing few days, it is now our last afternoon together in Italy. Let's walk through the historic streets of Florence and discover iconic spots such as Palazzo Vecchio and Palazzo Pitti, and the infamous Ponte Vecchio. The love and romance that Ponte Vecchio if unique, as is the walk along the Arno river which takes us directly to the last stop of the day, the Boboli Gardens. It will be here that we say goodbye to Florence, admiring a breathtaking sunset from the Boboli terrace and sharing one last drink with our new friends.
Included: overnight stay, entrance fee to the Duomo Cathedral
Money pot: Boboli Garden, Uffizi Gallery and other ticket admissions
Not included: meals and drinks
Goodbye Italy
Check out and goodbye
Time to say goodbye: see you all at the next WeRoad adventure!
End of services. The itinerary may undergo some variations that differ from what is 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
Available dates
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!