Tuscany 360°: a journey through art, wine, and culture
Tuscany 360°: a journey through art, wine, and culture
The trip in a nutshell
Welcome to an unforgettable adventure through Tuscany! In eight days, we’ll dive into the region’s rich culture, stunning landscapes, and incredible food.
We start in Rome, where we’ll soak in the city’s vibrant energy before heading north to Montecatini with a stop in Orvieto—a charming hilltop town perfect for exploring. Next, we hop on a train to Florence, the birthplace of the Renaissance, where art and history surround us. From Pisa’s iconic Leaning Tower to a hands-on cooking class in Lucca’s countryside, we’ll experience the best of Tuscany. Then, we switch gears with an e-bike ride through Chianti’s vineyards, complete with a wine tasting, before heading to Chianciano.
The rolling hills of Val D’Orcia and Montalcino offer us postcard-worthy views and world-class wines before we return to Rome for one last adventure. Here, we indulge in la dolce vita—savoring a perfect plate of carbonara, strolling through lively piazzas, and soaking up the city’s irresistible charm before we say arrivederci! Italy is calling—are you in?
Trip type
360°: our great classic that allows you to discover the destination in every aspect. The pace will be fast to be able to see as much as possible, but we will also have moments of relaxation and fun - the right mix!
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!
2 people interested
What's included
7 nights accommodation 4* hotels in twin rooms
All breakfasts
All main transportations
Roundtrip 2nd class train Montecatini – Florence SMN
Florence walking tour with a local guide (3 hrs)
Local Experience: authentic Italian cooking class followed by light lunch
Wine tasting and visit to a local farmhouse (taste of 3 local wines with snacks)
Travel coordinator services
Cancellation up to 31 days before departure - 100% refund (deposit refunded as a gift card) or option to change trips.
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
Road to Tuscany: a stop in enchanting Orvieto
Orvieto, a stunning hilltop town
Our Tuscan adventure begins as we leave Rome behind and journey north towards Montecatini. But first, we make a stop in Orvieto, a stunning hilltop town perched on a dramatic cliff of volcanic rock. With two hours to explore, we can wander its medieval streets, admire the breathtaking Duomo, and maybe sip a glass of local Orvieto Classico. A quick funicular ride whisks us up to the historic center, where time seems to slow down.
After soaking in the charm of this hidden gem, we continue our scenic drive to Montecatini, ready for the next chapter of our Italian escape.
Included: breakfast, transportation and overnight stay
Money pot: funicular ride (Orvieto), entry fees and optional excursions
Not included: food and drinks not mentioned above
Florence: art, vibes and the perfect panino
Florence is pure magic
Florence is a city that needs no introduction—home to Michelangelo’s David, breathtaking architecture, and a buzzing atmosphere that blends history with a modern, youthful energy. We’ll hop on a train from Montecatini and, in no time, here we are, wandering through the heart of the Renaissance.
Included in our adventure is a three-hour walking tour with a local guide who will bring Florence to life with stories of Medici power, artistic genius, and hidden gems you’d never find on your own. We’ll stand in awe of the Duomo, stroll across the iconic Ponte Vecchio, and soak up the vibrant energy of Piazza della Signoria.
After the tour, it’s time to indulge—think creamy gelato, a classic panino from an old-school bottega, or a Florentine steak if we’re feeling bold. Florence is a feast for the senses, and today, we’re savoring every bit of it!
Included: breakfast, roundtrip train to Florence, 3 hrs walking tour with a private local guide and overnight stay
Money pot: mandatory headsets for the walking tour, entry fees and optional excursions
Not included: food and drinks not mentioned above
Pisa, Lucca and the secrets of Italian cuisine
A day of discovery and deliciousness!
Get ready for a day packed with iconic sights and mouth-watering flavors! We start our adventure in Pisa, home to the world-famous Leaning Tower. But did you know Pisa is also a medieval gem, with quirky streets and cool spots beyond the tower?
After snapping some pics, we’ll make our way to the stunning Lucca area. Here, we’ll dive into an Italian cooking class, where we’ll learn to whip up some local delicacies. Ever tried making fresh pasta from scratch? Or perfecting a classic Tuscan ragù? Now’s your chance! Once we’re all masters of the kitchen, we’ll enjoy a light lunch with fresh, local ingredients that’ll make our taste buds dance. This day is all about discovering new flavors, new places, and new memories!
Included: breakfast, transportation, 2 hrs cooking class with light lunch and overnight stay
Money pot: tips, entry fees and optional excursions
Not included: food and drinks not mentioned above
Chianti: bike adventure and wine tasting
Wine tasting and a scenic transfer
Get ready for a day filled with adventure, nature, and of course, amazing wine! We start with an exciting tour in the breathtaking Chianti hills—an area renowned for its rolling vineyards, charming medieval villages, and cypress-lined roads. We can also decide on a bike tour: whether we’re seasoned cyclists or just here for the views, the electric assistance will make sure we enjoy the journey without breaking a sweat!
Along the way, we’ll visit a beautiful local farmhouse, where the air is filled with the scent of fresh Tuscan earth and vine. Here, we’ll have the chance to taste three exquisite wines, each carefully selected to represent the flavors of Chianti. As we sip it, let’s enjoy a selection of local snacks, including pecorino cheese, salami, and freshly baked bread. It's the perfect way to get a taste of the region's rich culinary tradition.
After soaking in the flavors of Chianti, we’ll move to Chianciano, a charming spa town nestled in the heart of Tuscany. It's the perfect spot to relax and unwind after an unforgettable day of exploration, cycling, and indulging in Italy’s finest wine. Fun fact: Did you know that Chianti wine is made from a grape variety called Sangiovese, and the region itself has been producing wine for over 2,000 years? The E-Bike tour makes it all the more special, combining history, nature, and the best local flavors!
Included: breakfast, transportation, e-bike tour, wine tasting and overnight stay
Money pot: tips and optional excursions
Not included: food and drinks not mentioned above
Val d'Orcia and Montalcino
A journey through Tuscany's timeless beauty
Get ready to explore the stunning landscape of Tuscany as we move through the enchanting Val d'Orcia and the historic hilltop town of Montalcino. This half-day adventure takes us through picturesque rolling hills, vineyards, and charming medieval villages that seem to have leaped out of a painting. Val d'Orcia is not just about breathtaking views; it’s a UNESCO World Heritage site known for its perfect harmony between nature and human activity.
As we visit Montalcino, we’ll find ourselves walking in the footsteps of history. This town is famed for its Brunello wine, one of the most prestigious in the world. And did you know? The area has roots that stretch back to ancient Roman times! In fact, the Romans had a heavy presence here, and it’s said that the ancient roads passing through the region were some of the main routes for transporting their wine.
Some of the land around Val d'Orcia was even used in the making of the famous movie Gladiator, where the breathtaking landscapes provided the perfect backdrop for the epic film! So, get ready for a mix of natural beauty, history, and a touch of Hollywood magic as we wander through this Tuscan paradise.
Included: breakfast, transportation and overnight stay
Money pot: entry fees and optional excursions
Not included: food and drinks not mentioned above
La dolce vita in Rome awaits
Transfer to Rome and free time to explore
Get ready for an unforgettable Roman adventure! After a smooth transfer to the Eternal City, the rest of the afternoon is for us to explore at our own pace. Stroll through the charming cobblestone streets of Trastevere, where vibrant houses and hidden trattorias invite us to experience authentic Roman life. Then, let’s get to the iconic Fontana di Trevi—and let’s not forget to toss a coin and make a wish! From there, head to Piazza di Spagna and climb the famous Spanish Steps, where we can enjoy breathtaking views of the city below.
Whether you're sipping a coffee at a piazza, browsing boutique shops, or simply soaking up the lively atmosphere, this is your chance to indulge in the true essence of la dolce vita. Let the city’s timeless beauty charm you!
Included: breakfast, transfer to Rome and overnight stay
Money pot: public transport within Rome, entry fees and optional excursions
Not included: food and drinks not mentioned above
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
FAQs – Frequently Asked Questions
About Italy
About WeRoad
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 fit every need:
1. Credit or prepaid card (Visa, Mastercard, American Express);
2. Instalment payment with Scalapay up to €4,999 (only available with the “Full trip payment” option – not available with the “Deposit and balance” option; pay in 3 instalments up to €1,200 or in 4 instalments over €1,200);
3. PayPal (for selected destinations);
4. Revolut Pay to pay even faster straight from your Revolut account;
5. Welfare credit – BEFORE BOOKING, reach out to us at [email protected].
If you choose the deposit and balance option, you’ll also be able to pay the balance via bank transfer from your Personal Area.
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. (Deposits will be refunded in the form of a gift card valid for 365 days from issue date.) 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. Deposits will be refunded in the form of a gift card valid for 365 days from issue date.
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:
Even if we don't know the flights of all WeRoaders, there are several ways to find out which flights your travel companions have purchased.
1. Each WeRoader has the ability to communicate their flight details after booking within their personal area so that other travel companions can see the details anonymously. Enter your booking and you will find this section:
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2. If you want to find out before booking, instead, you can contact us and we will support you in your search or you can ask your travel companions for direct information by joining our Facebook group 'WeRoad... let's get to know each other before leaving! (official)' – (here is the extended link: https://www.facebook.com/groups/weroadit) look for a post associated with your trip, or ask the group administrators for help in getting in touch with your future adventure companions!
If the coordinator has already been assigned to the trip you are interested in, you can easily find his/her presentation post in the group through the site: in the shift list click on 'Ask the coordinator', or in the trip tab, in the coordinator section, click on 'Ask [coordinator name] about this shift in our Facebook group'. For both cases, see the screenshots below!
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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 curious to know the age range of the group for a tour you're interested in, you can see this by finding the trip on our website, and clicking the down arrow to see the ages & genders of participants. You'll need to have created a WeRoad account with us to do this.
Any issues finding this info just give our team in the office a call, we're always happy to help!
Regarding the male-female ratio, this is not guaranteed and varies trip by trip.
Yes! If you're curious, you can take a sneak peek at the group before booking – although, in our opinion, that kind of spoils the surprise! You’ll find the info in the ‘Group’ section for each trip on the departures page, showing how many WeRoaders have already booked. Click the little arrow and you’ll even see their gender and ages – but hey, that’s exclusive info, so we’ll ask you to log in or sign up to see that!
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.
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’.
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!