Italy Classics: Rome, Florence and the Tower of Pisa
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.
Italy, often dubbed the "beautiful country," boasts a rich cultural heritage, making it a must-visit destination. Our 8-day itinerary begins in Rome, the eternal city, where ancient marvels like the Colosseum and the Pantheon blend with modern delights in neighbourhoods like Testaccio and Trastevere.
Heading north to Tuscany, we'll traverse the picturesque landscapes of Val d'Orcia and Chianti before reaching Florence, the birthplace of the Renaissance. Nearby, we'll explore Lucca and Pisa, where the iconic leaning tower awaits our obligatory photo. En route back to Rome, a stop in Siena offers the chance to witness the famous Palio horse race. Our journey concludes in Rome, where we'll savour a traditional supplì with a smile, reflecting on the beauty and history we've encountered throughout our Italian adventure.
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 - minimum physical effort is required.
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 Rome. Aim to arrive on the first day by 5pm - on the last day you are free to leave whenever!
1 person interested
What's included
7 nights accommodation in shared rooms
All breakfasts
Car rental from day 4 to day 7
Local Experience: authentic Italian cooking class
Travel coordinator services
Free cancellation with 100% refund up to 31 days before departure
Itinerary
Welcome to Italy!
Check in: our adventure starts in Rome!
Roundtrip flights or transportation to reach the destination are not included in the package, so you can decide from where and when you want to leave! This gives you complete freedom of choice to adjust your travel itinerary to your needs.
Upon arrival at our Rome accommodation, we'll have a welcome meeting. Once settled, let's dive straight into the vibrant Roman nightlife. What shall we choose for our inaugural Capitoline aperitif: a refreshing Spritz or a timeless glass of wine?
Included: overnight stay, breakfast
Not included: airport transfer, food and drinks
Classic Rome: from the Colosseum to the Vatican
The Eternal City
Rome, with its blend of ancient marvels and modern delights, offers a diverse and stunning experience. Today, we'll embark on a 4-hour guided tour, delving into the city's rich history. We'll marvel at iconic landmarks like the Colosseum, the Imperial Forums, the Pantheon, the renowned Trevi Fountain, and the Spanish Steps, culminating in Piazza del Popolo.
The afternoon is yours to explore as you wish, but we highly recommend a visit to the Vatican City, the world's smallest state, for an unforgettable experience.
The smallest state in the world
How about a little excursion abroad? Vatican City, one of Italy's two independent states, offers a chance to step beyond Italian borders. A stroll in St. Peter's Square is a must, and for those interested, weather permitting, the Vatican Museums await (ranked in the top 10 most visited museums globally!). Should we decide to explore, prepare to crane our necks in awe at the stunning Sistine Chapel.
Afterward, a delightful reward awaits us: a refreshing dinner in a traditional Roman restaurant. Shall we indulge in the classic pasta carbonara or opt for the tantalizing cacio e pepe?
Included: overnight stay, breakfast
Money Pot: any extra activities or fees
Not included: food and drinks
*Anyone wishing to visit the Vatican Museums must independently purchase the ticket online in advance
Authentic Rome: from Trastevere to Garbatella
Exploring
Today, we'll uncover the authentic essence of Rome, away from the tourist hubs, delving into the local neighbourhoods. We'll begin our journey in Trastevere, meaning "beyond the Tiber" in Latin, a district pulsating with the true spirit of the city. Here, amidst its labyrinthine alleys, artisans, small traders, and traditional trattorias coexist with trendy venues and foreign artists' workshops.
Three iconic squares await our exploration: Piazza di Santa Maria in Trastevere, Piazza Trilussa, and Piazza Sant'Egidio. Nearby lies the historic Jewish Ghetto of Rome, one of the oldest in the world. We'll indulge in the flavors of Judeo-Roman and kosher cuisine, sampling delicacies like artichokes alla giudia, cherry jam tart with ricotta, and anchovy and endive pie. It's essential to savor these culinary delights before continuing our Roman adventure.
Garbatella
To shake off the lunchtime indulgence, let's embark on a leisurely stroll to Garbatella! Here, we'll momentarily escape the bustling city and immerse ourselves in a genuine, unfiltered Rome. We'll encounter the voices of elders in historic bars and the echoes of mothers and grandmothers calling out to their children. It's the Rome of the locals, captivating us with its authenticity and making us yearn to linger.
However, our journey continues tomorrow, so let's relish this evening to the fullest.
Included: overnight stay, breakfast
Money Pot: any extra activities or fees
Not included: food and drinks
From Lazio to Tuscany: Val D'Orcia and Chianti
Stunning scenery
Good morning, WeRoaders! As the first rays of sunlight beckon, it's time to rise, enjoy breakfast, and make our way to the car rental. Today, we bid farewell to Rome and set our course for Tuscany. Our journey along the motorway leads us to our initial destination: Val D'Orcia. Here, in the province of Siena, we're greeted by the quintessential Tuscan landscape—rolling hills, expansive vineyards, rows of cypress trees, and charming farmhouses. This picturesque region, a UNESCO World Heritage Site, epitomises the postcard-perfect image of Tuscany found in souvenir shops.
As we pass through San Quirico D'Orcia, let's seize the moment to capture the iconic cypress trees in more than one photograph, even if our time is brief. Continuing our journey, we make our way to the Chianti area, where a stop for a delectable meal paired with fine wine, or perhaps a wine and charcuterie tasting, is a must. Later in the afternoon, we head towards our final destination: Montecatini Terme.
Included: overnight stay, breakfast, rental car
Money Pot: any extra activities or fees
Not included: food and drinks
Florence: the cradle of the Renaissance
Exploring the city
Welcome to the city of Humanism! Florence, a place where the brilliance of Dante Alighieri, Leonardo Da Vinci, and Michelangelo Buonarroti shone, alongside countless other artists, writers, and scientists fostered by one of Italy's greatest patrons, Lorenzo de Medici, the Magnificent. A guided stroll through the historic center immerses us in an era where the clash of lords was intertwined with monumental artistic and engineering endeavors.
Our journey begins at Piazza del Duomo, dominated by the awe-inspiring Santa Maria del Fiore, Giotto's Bell Tower, and the intricately adorned Baptistery of San Giovanni. The murmur of the Arno River leads us to Ponte Vecchio, still home to jewelers and goldsmiths' shops. On the opposite bank, the grand Pitti Palace and enchanting Boboli Gardens await.
After the tour, as hunger beckons, let's savour the quintessential Tuscan lampredotto sandwich, a quick and delightful street food option. In the afternoon, enjoy the freedom to explore Florence at your leisure, with markets, shopping, and cultural delights aplenty!
Included: overnight stay, breakfast, rental car
Money Pot: any extra activities or fees
Not included: food and drinks
Pisa, Lucca and the secrets of Italian cuisine
Authentic Italy
Today, we venture beyond the noble Tuscan landscapes of Florence to explore the captivating cities of Pisa, famed for its leaning tower, and Lucca, embraced by medieval walls. Yet, no Italian journey is complete without indulging in the gastronomic wonders that define the nation's culinary legacy.
As we ponder the secrets behind perfect pasta, the nuances of exceptional pizza, and the revered "tricks" employed by Italian mothers for a flawless tiramisu, we'll immerse ourselves in a cooking class. Here, we'll unravel the mysteries of Italian cuisine, striving to master its artistry, knowing that our efforts will culminate in a delightful dinner featuring our own creations!
Included: overnight stay, breakfast, rental car, cooking class
Money Pot: any extra activities or fees
Not included: food and drinks
On the way to Rome: Siena and Piazza del Campo
The most beautiful square in Italy?
As we journey back to where it all began in Rome, our final stop awaits us in the enchanting city of Siena. Renowned worldwide for its iconic Piazza del Campo, with its distinctive shell shape and architectural splendour, Siena captivates visitors with its unique charm and hosts the traditional Palio di Siena twice a year.
A brief pause in Siena allows us to savour its delights, indulging in Sienese delicacies like ribollita, tomato soup, panforte, and ricciarelli—culinary treasures not to be missed. With hearts and bellies full, we bid farewell to Siena and make our way back to Rome, ready to conclude our journey through the Bel Paese with fond memories of our Italian adventure.
Included: overnight stay, breakfast, rental car
Money Pot: any extra activities or fees
Not included: food and drinks
Goodbye Italy
Check out and goodbye
Check-out and goodbye – until your next WeRoad adventure!
Not included: airport transfer, food and drinks
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
Info to know
Staff
Our trips are led by a Travel Coordinator who has been specifically trained by us to lead group travels to ensure you have the best time. A WhatsApp group with all travel participants will be created two weeks prior to departure by your Travel Coordinator.
Luggage
Backpacks are mandatory to allow easy transfers - we recommend a 45L backpack for our trips.
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!