Wine, food, beach days, culture, this itinerary has it all.
Italy is on most peoples’ bucket list. But where do you even begin. There are so many cities that you could visit and plenty of options of things to do in each of those cities.
That was where my head was when my boyfriend gifted me vouchers for flights to any city I wanted to visit Italy. I’d never been to Italy before and had practically everywhere on my bucket list. I wanted food, beaches, wine, history, hiking, mountains and sun, which is quite a big ask from a single holiday - and way more than my boyfriend originally signed up for. But through many months of researching and planning I figured out a rough itinerary that included all the activities I wanted to do and even some that my boyfriend would be interested in. Several tweaks later, we had a fully formed travel plan that satisfied the both of us and suited our (slightly inflated) budget.
There were many discussions had around what our priorities would be and whether we wanted to do a few places in depth or take whistle stop tour of lots of places, sampling everything but not getting really stuck into the essence of each place. In the end, we settled on the best of both worlds, with a few days in a number of places. We were lucky enough to be able to take a 2 and a half week break from work and explore the central and southern parts of the west coast of Italy. This, we felt, would allow us to experience the feel of each town and see most of what we wanted whilst allowing us travel around and make the most of our time in Italy. We still have plans to go back and explore the remaining 70% of the country though!
In summary we spent 18 days visiting, please use the links to navigate to specific sections):
Pisa - easily see the main sites (the tower) in an afternoon
Cinque Terre - 1 day (would recommend 2 though if you have the time)
Florence - 3 days
Radda in Chianti - 1 day
Siena - 1 day
Rome - 3 days
Aiolian islands - 4 days
Catania - 1 day
Salerno - 3 days
As we had packed so many places into our final plan, we didn’t want to splash out on fancy accommodation so we managed to keep a lid on our budget (somewhat) and where possible we chose to take public transport to give us flexibility and for the convenience of travelling from city to city.
In total the trip cost us £2400 each including flights, accommodation, transport, meals and spending money. You could reduce this by not including the sicilian portion of the trip (Catania and Aolian islands) and the toal would have been £2000 each and the trip would take 2 weeks.
A note on public transport in Italy (as with many European countries) you NEED to purchase your ticket ahead of time and then validate it upon use when you board the bus or metro or are on the train platform. We just happened to overhear someone mention this is English as we were waiting for our first train and probably would have got a hefty fine to start the holiday if we hadn’t so I just wanted to pay that tip forward!
Pisa
How to get there?
We got a direct flight from the UK to Pisa and jumped on the PisaMover shuttle directly from the airport to the central train station. This service runs every 5-10 mins is a super convenient option for getting to Pisa. At the station we were able to store our 2 large suitcases at the Left Luggage baggage drop also within the station to collect when we returned that same day to catch our train.
The station is in a fairly convenient location for exploring the city and it was a 25 minute walk to the cathedral, or "Duomo" in Italian, and the leaning tower, although you can get a 12 minute bus (the number 1+) for €2 if that seems like a bit much.
How much time to spend there?
You probably only need to spend 3 or 4 hours in Pisa if you want to have a meal and visit the leaning tower. You could spend longer exploring the city but we didn’t spot an awful lot else to do whilst we were there.
What is there to do?
Culture - The leaning tower of Pisa - duh
How much do the main attractions cost?
You can buy a pass to enter the cathedral, the tower and the exhibition for €20 or the full package of entry fees for €27 but we decided against it as the outside of the buildings are spectacular enough and the setting is beautiful. If you are interested however, ticket prices can be found here https://www.opapisa.it/en/tickets/prices/
Itinerary and costs
Landed at Pisa airport at 8.15am
Shuttle from the airport | €5 per person (one way) | 20 mins.
Bag storage at the station | €5 per bag
Brunch | €15 per person | 1 hour
Walk to Piazza del Duomo (Optional bus) | Free (€2 per person bus fare) | 30 mins (15 on the bus)
Explore the Piazza del Duomo (Optional entry to the Leaning Tower of Pisa) | Free (€20 per person entrance fee) | 1.5 hours
Walk to Pisa Centrale station (Optional bus) | Free (€2 per person bus fare) | 30 mins (15 on the bus)
Train to La Spezia at 1.30pm 23rd September | €12 per person | 1 hour
Total time spent in Pisa - 5 hours
We ate a delicious breakfast at a cafe a short way en-route to the tower before we continued wandering through the city. We were struck by how busy it was with locals and tourists shopping on the high street and found it extremely pleasant navigating our way across the city.
As you approach to the square with the cathedral and leaning tower the sheet density of tourists and hubbub of all the tour guides trying to keep an eye on their pack of patrons tells you that you’re getting close.
It is magnificent. As an introduction to Italy it really doesn’t get better than the iconic white stone edifice of the tower, precariously tilting towards the cathedral. We opted not to go inside because it was quite busy, we didn't want to spend too long there and seeing it from the outside was enough for us.
Cinque Terre
How to get there?
The train between Pisa and La Spezia is only 45 minutes and from there you can pick up a connecting local service to take you to the villages of Cinque Terre.
How much time to spend there?
We were able to see and do everything we wanted in 1 full day. It was nice to have an evening beforehand to relax and experience the beauty of the place so I would recommend between 1 and 2 full days to really see the place. As with anywhere though, if you fall in love with it and have the flexibility, you can always find more to do.
What is there to do?
Hiking - There are a number of hiking routes between the villages
Culture - You can explore the different villages, meandering through the shops and picking up souvenirs
How much do the main attractions cost?
The hiking route takes you through the National Park and so there is an entrance fee of €18. This price also includes tickets for the local train line so you can get back.
Itinerary and costs
Day 1 - 23rd September
Arrive at La Spezia at 2.30pm
Local train from La Spezia to Riomaggiore €5 per person | 25 mins
Arrive at Riomaggiore 3.30pm
Check into hotel €90 per night - we stayed at a no frills hotel, that was fine for what we needed.
Exploring Riomaggiore, getting snacks and drinks (including ice cream) | €15 per person
We stopped for a glass of wine and some olives here |
We ate dinner at a small local restaurant in the harbour - they dont ,have a website unfortunately. It was ok food but had a great view | €25 per person
Day 2 - 24th September
We woke up early to get a breakfast from a cafe on the high street
Blue Trail hike | €18 per person | 7 hours
Start in Riomaggiore 9.30am | Arrive in Manarola at 11am | 1.6km
Snacks and drinks €5 per person
Leave Manarola 11.30am | Arrive in Corniglia 1.30pm | 6km
Lunch in Corniglia
Leave Corniglia 2.30pm | Arrive in Vernazza 3.30pm | 3km
Drinks in Vernazza
We were pretty tired by this point so we got the train back to Riomaggiore, showered and changed and got the train to Monterosso al Mare for dinner
We arrived in Monterosso al Mare around 7pm and walked along the promenade before having dinner in a very quaint italian restaurant | €35 per person
Day 3 - 25th September
Early start to check out of hotel
We ate breakfast here and bought snacks for our train to Florence
Departed 9.30am
Total time in Cinque Terre -1.5 days
Total spend
Nestled along the rugged coastline of the Italian Riviera, Cinque Terre is a destination that seems to have leaped out of a postcard. This UNESCO World Heritage site is a collection of five picturesque villages, each offering its own unique charm, breathtaking landscapes, and a glimpse into a simpler, more tranquil way of life. Whether you’re a lover of the sea, a hiking enthusiast, or a foodie with a penchant for fresh seafood and regional wines, Cinque Terre is a dream come true. Let’s take a journey through the five towns that make this region so special.
Riomaggiore: The Gateway to Cinque Terre
Riomaggiore, the southernmost town, is often the starting point for visitors arriving by train from La Spezia. This vibrant village is characterized by its steep, narrow streets and houses painted in shades of red, orange, and yellow. The main street, Via Colombo, is lined with shops, restaurants, and gelaterias, making it a lively place to explore.
The tiny harbor is a great spot to watch the fishing boats come and go, and if you’re up for a hike, the trail leading to the nearby hill offers panoramic views of the village and the sea. Riomaggiore is also known for its excellent diving spots, thanks to the clear, deep waters of the Marine Protected Area of Cinque Terre.
Manarola: The Colorful Cliffside Gem
Manarola is perhaps the most iconic of the Cinque Terre villages, thanks to its colorful houses perched precariously on a rocky outcrop above the sea. The town is a photographer’s dream, especially at sunset when the colors of the buildings seem to glow in the evening light.
Manarola is also one of the oldest villages in Cinque Terre, with a rich history tied to wine production. You can still see the terraced vineyards that surround the town, where the famous Sciacchetrà wine is made. A walk along the Via dell’Amore, a romantic path that once connected Manarola to Riomaggiore, offers stunning views of the coastline and is a must-do for couples.
Corniglia: The Quiet Hilltop Retreat
Perched high above the sea, Corniglia is the only town in Cinque Terre without direct access to the water. This gives it a more secluded, tranquil atmosphere, perfect for those looking to escape the crowds. To reach Corniglia, you’ll need to climb the Lardarina, a steep staircase with 382 steps, but the effort is well worth it.
Corniglia’s charm lies in its quiet, winding streets, lined with colorful houses and fragrant gardens. The village is surrounded by vineyards, and you can sample the local white wine, Vernaccia, in one of the cozy wine bars. Don’t miss the panoramic views from the terraces at the edge of the town, where you can see the other four villages in the distance.
Vernazza: The Picture-Perfect Harbor
Vernazza is often considered the jewel of Cinque Terre, and it’s not hard to see why. This small village is built around a natural harbor, with pastel-colored houses clustered around the water’s edge. Vernazza’s beauty is best appreciated from above; the hike to the Sanctuary of Madonna di Reggio offers stunning views of the village and the surrounding coastline.
Wander through the cobblestone streets, visit the Church of Santa Margherita d’Antiochia, and relax in the small piazza overlooking the harbor. Vernazza is also home to some of the best seafood in Cinque Terre, so be sure to indulge in a plate of fresh anchovies, a local delicacy.
Monterosso al Mare: The Beach Lover’s Paradise
Monterosso al Mare, the largest of the five towns, is often the first stop for visitors. It’s the only village with an extensive sandy beach, making it a popular choice for sun-seekers. The town is divided into two parts: the old town, with its charming narrow streets, and the new town, where you’ll find the beach and the bustling promenade.
Take a stroll through the old town to discover historical landmarks like the 14th-century Church of San Giovanni Battista and the Aurora Tower. Don’t miss the opportunity to taste some local specialties at one of the many seafood restaurants lining the shore. Monterosso is also famous for its lemon trees, so be sure to try some limoncino, the local lemon liqueur.
Cinque Terre is more than just a collection of beautiful towns; it’s a place where time seems to stand still, where the simple pleasures of life are celebrated in every corner. Whether you’re exploring ancient streets, savouring delicous food or simply watching the sun dip below the horizon, Cinque Terre is sure to leave a lasting impression on your heart.
Florence
How to get there?
Florence is fairly well connected by train, we took the train from Riomaggiore to Florence (with a connection in Pisa) but it was fairly straightforward.
How much time to spend there?
What is there to do?
Culture: view famous masterpieces and take in the birthplace of the Renaissance.
Food: there are local dishes that you can try (like tripe sandwiches) or homely trattorias where you can order delicious pasta.
Shopping: Florence is the home of Italian leather and you can buy any leather good you can think of, usually handmade in front of your eyes.
How much do the main attractions cost?
Itinerary and costs
Arrive in Florence at 1pm 25th September
Train tickets from Riomaggiore to Florence €18 per person
Train from Florence central to Florence Rovezzano €1.50 per person per trip
Meals in Florence €55 per person
Snacks and drinks in Florence €60 per person
Florence tour €15 per person
Firenze card €85 per person
Accommodation €80
Return bus from accommodation to Florence €3 per person. Total cost for duration of stay €10 per person.
Bike hire from Rovezzano to acommodation €15
. Departed 11am 28th September. Total time 3 days.
Florence, or Firenze as it is known in Italian, is a city that resonates with art, history, and culture at every corner. As the birthplace of the Renaissance, Florence is a treasure trove of masterpieces, where you can take in the legacies of artists like Michelangelo, Leonardo da Vinci, and Botticelli at the galleries and in the architecture of the city. The city is a maze of narrow cobblestone streets, and we joined a free walking tour of the city (note they ask for a donation at the end, which we more than happily paid for), which transported us to a time when creativity and innovation flourished, and you can feel the influence on our world today. Whether you’re an art lover, history buff, or simply in search of beauty, Florence is a must! I've described some of the key attractions below, but there are is so much you could do.
The Magnificent Duomo: Florence’s Iconic Cathedral
No visit to Florence is complete without visiting the Cattedrale di Santa Maria del Fiore, commonly known as the Duomo. The cathedral’s façade is an intricate design of pink, white, and green marble. We didn't make it inside, however, as we kept missing the opening times, but even from the outside, the cathedral is magnificent and a great place to stop for a glass of wine.
The Uffizi Gallery: A Treasure Trove of Renaissance Art
The Uffizi Gallery is one of the most famous art museums in the world. Home to an unparalleled collection of Renaissance art, the Uffizi is a place where you can immerse yourself in the works of masters like Botticelli, Leonardo da Vinci, and Michelangelo. Highlights include Botticelli’s The Birth of Venus and Primavera, and Leonardo’s Annunciation.
There is more than enough artwork for you to spend all day here and the gallery itself is a work of art, with its long corridors lined with classical statues and rooms filled with stunning frescoes. Take your time to explore, as there are countless masterpieces to discover. However, the gallery is an extremely busy attraction and we were only able to tolerate it for a couple of hours before needing some personal space.
Palazzo Vecchio and Piazza della Signoria: The Heart of Florence
The Palazzo Vecchio, Florence’s town hall, is a fortress-like structure that dominates Piazza della Signoria, the city’s main square. The building’s towering Arnolfo Tower is a symbol of the city’s power and influence during the Renaissance. Inside, the palazzo is adorned with magnificent frescoes, sculptures, and intricate ceilings, offering a glimpse into the grandeur of Florence’s past.
Piazza della Signoria itself is an open-air museum, home to impressive statues such as a replica of Michelangelo’s David, Cellini’s Perseus with the Head of Medusa, and the Fountain of Neptune. The square has been the political heart of Florence for centuries, and today it remains a vibrant hub where locals and tourists alike gather to soak in the city’s atmosphere.
Michelangelo’s David: The Masterpiece of Human Perfection
One of Florence’s most famous residents is undoubtedly Michelangelo’s David, a symbol of strength, beauty, and human perfection. Most guide books will tell you that this iconic statue, housed in the Galleria dell’Accademia, is a must-see for any visitor to Florence. And I am inclined to agree. There isn't a huge amount of artwork in the gallery, however David makes the ticket absolutely worthwhile. Carved from a single block of marble, David is huge. The statue stands at 17 feet tall (5m) and is so detailed it's hard to believe that someone carved it, what I would name, the most accurate depiction of the human form.
While the original David resides in the Accademia, if you really can't find the time, or justify the cost of the ticket, replicas can be found in Piazza della Signoria and Piazzale Michelangelo. With any version, viewing the statue up close is a humbling experience, as even I could appreciate Michelangelo’s genius and his ability to bring marble to life.
Boboli Gardens and Pitti Palace: A Royal Escape
For a taste of royal life in Florence, head to the Pitti Palace, the former residence of the powerful Medici family. The palace now houses several museums, including the Palatine Gallery, which features works by Raphael, Titian, and Rubens. The rooms themselves are richly decorated, offering a glimpse into the opulent lifestyle of Florence’s ruling families.
Behind the palace lie the Boboli Gardens, an expansive green space filled with statues, fountains, and grottoes. The gardens are a perfect place to relax and take in the beauty of Florence from a different perspective. Wander through the landscaped terraces, enjoy a picnic, or simply find a quiet spot to soak in the tranquility.
Chapel de Medici
You'd be forgiven if you weren't familiar with this attraction before now. We had a spare hour and wanted to make the most of our Firenze card so dipped inside the personal chapel (and tomb) of the Medici family. The entrance is tucked away behind the Basilica di San Lorenzo and we wandered in without really knowing what to expect. But once we made our way down and through the chapel, we were struck by the sheer opulence of the place. So much marble and granite that so ostentatiously advertised the sheer wealth of this powerful family. It's definitly worth a visit if you have some time.
Radda in Chianti
How to get there?
We got a taxi from Florence directly to our accommodation in Chianti. We haggled a little bit down to €110, which was expensive but this is an expensive leg.
How much time to spend there?
We were quite happy with our 1 day in Chianti. The hotels are set up to entice you to syat longer - offering cooking courses and day trips out to the countryside but to really enjoy Chianti, you can take it all in in a day.
What is there to do?
Wine, wine, wine and wine... and views.
How much do the main attractions cost?
Wine tasting at Tenuta di Carleone cost €30 per person.
Itinerary and costs
Arrived 11.30am 28th September. Departed 4pm 29th September. Total time 1 day.
Taxi from Florence to Radda €110
Lunch €15 per person
Wine tasting €30 per person
Dinner €25 per person
Accommodation €250
The day we spent in Chianti holds the title of the best day of my entire life! It was such a perfect combination of romance, serendipity and luxury. We made an active decision to ignore our budget for this leg of our trip and I don't regret it one jot.
We chose to stay in Relais Vignale & Spa which was in the centre of the small village of Radda in Chianti, which is a classic tuscan village with rolling landscapes filled with cypress trees and vineyards as far as the eye can see. We arrived a bit before check-in so we left our luggage at reception before exploring the village and finding a charming trattoria called Bar Dante where we ordered a glass of red wine and some lunch.
When we returned to the hotel we quickly showered and changed and decided to walk to a local winery nearby. They didn't look particularly open but I poked my nose around the door and found the owner who was more than happy to set up a wine, gin and olive oil tasting for us. I can't overstate how overwhelming beautiful the setting was and the six wines we tried were delicious. If you stop by Radda, you have to try this winery out.
A little bit tipsy, we giggled our way back to the hotel and changed for dinner, which turned out to be an extremely romantic, lucky mistake. Based on a quick google of the local restaurants, we chose a restaurant that had great reviews and decent vegetarian options but when we arrived it appeared that they were hosting a ticketed event. The host checked and discovered there were two tickets available for us if we wanted and that they permitted entry to a "Sensorial wine tasting experience" which included a glass of wine and a small plate of food. Well of course we accepted.
The building is an old monastry and they had set up interactive rooms where you had to try and identify the characteristics of your unknown wine. It was really good fun but I couldn't hand on heart say we were any good. One we had made it through all of the rooms we were led into a candle lit courtyard with a live jazz band playing and were served a huge - and I mean absolutely massive - plate of cheese, breads and antipasti - more than enough food for dinner - as well as a beautiful dessert. Honestly, as far as accidents go, this has to be the best.
Siena
How to get there?
We managed to get a bus directly from Radda in Chianti to Siena and, as both are within Tuscany, the prices fall within the regional bus fares - which was €2 each, which is crazy cheap for an hour long bus journey. The bus station in Siena is a little ways out of the town, so we could have caught another bus but we weren’t super sure which one we needed to take so we we ended up walking 1km to the hotel, which wasn't particularly fun with back packs. However, if you were to plan this properly, you could probably find more convenient accommodation.
How much time to spend there?
As this stop was a complete accident, I didn't have time to fully research the best attractions but the city is fairly compact and we were able to visit the most obvious sights within easily within a day
What is there to do?
Culture: the city really feels like Tuscany's answer to York so even walking around you can takein the history of the place.
How much do the main attractions cost?
Entry to the Torre del Mangia and Palazzo Publico €15 per person and you have to buy the tickets to the Duomo separately, they cost €10 per person.
Itinerary and costs
Arrived at 5.30pm 29th September.
Bus to Siena €2 per person
Dinner in Siena €25 per person
Drinks in Siena €5 per person
Coffee and breakfast €5 per person
Snacks and lunch in Siena €15 per person
Bus to train station in Siena €2 per person
Accommodation €65
Entry to the Torre del Mangia and Palazzo Publico €15 per person
Entry to the Duomo €10 per person
Departed 5.30pm 30th September. Total time 1 day.
Another happy accident on our trip was Siena. We didn't originally plan a stop here but due to public transport limitations from Radda in Chianti this is where we ended up stopping next. We managed to book a last minute room in a central location for fairly cheap and it turned out to be a really charming city.
Whilst we did a bit of reading about what to expect from Siena, most of the blogs and travel guides gave quite a different impression to our experience. We found Siena to be a lively city, with plenty of historical sights to see, an immersive medieval architecture and a buzzing nightlife.
We explored the main Piazza del Campo, which has plenty of restaurants and bars around the outside, although these tended to be a bit more expensive and we weren’t overly impressed by the quality of the food. From the square, you can also access the Torre del Mangia, which, after climbing a narrow staircase, has some amazing views of Siena from the top., as well as the Palazzo Publico, which has some interesting frescoes and is worth poking your nose into.
Finally, you should definitely pay a visit to the Duomo. We never made it inside the Florence Duomo so I can’t compare, but this was gorgeous - and extremely intricately designed. The highlight of the Duomo is that the mosaic floor is designed in sections, and each depicts a different biblical scene or is dedicated to a different saint, it in itself is a storytelling masterpiece, but underneath the exquisitely painted ceiling and walls, it really is something special. The ticket we bought included a free audio guide so we were able to learn a bit about what we were looking at.
Our stay also happened to overlap with an annual vintage bike race that meanders through tuscany and made for a very entertaining morning of people (and bike) watching over fresh coffee and pastries.
Rome
How to get there?
We got a direct train from Siena to Rome, it took about 2 hours and was a very easy journey.
How much time to spend there?
You could spend a whole week here exploring all the churches and sampling restaurants to your hearts content but, given the extent of this itinerary, we opted to spend 2 and a half days here, which was enough time to see the most notable sights.
What is there to do?
Good for: Culture, food, leather shops.
How much do the main attractions cost?
Itinerary and costs
Arrived 9pm on the 30th September. Departed at 6.30am on the 3rd of October. Total time 2.5 days.
Train from Siena to Rome €15 per person
Metro €2 per person per journey
Breakfast in Rome €7 per person
Entry for
Ice-cream €5 per person
Dinner in Rome €15 per person
Cocktails €15 per person
Breakfast €7 per person
Collosseum entry €17 per person
Lunch €15 per person
Villa Adriane €16 per person
Dinner €30 per person
Accommodation in Rome
Good for: Everything - it’s Rome.
Roman Forum
Colosseum
Vatican - Sistine Chapel
Villa Adriene
Walking around Rome
If you're going to be organised and book tickets ahead of time for any part of this trip, do it in Rome! I cannot stress to you how busy some of these attractions get. The colosseum was booked up for pre-bookable tickets from a week ahead of our arrival but we managed to get in and see it by queuing in line from 7am (that meant waking up and leaving the hotel room at 6.30). We didn't make it into the Sistene chapel becasue it was completely sold out and they didn't offer at the door ticket sales.
Rome, like a lot of Italian cities, offers free entry to a lot of the main attractions on the first Sunday of the month, and if that doesn’t overlap with your trip you can often get city tickets that seem expensive initially, but actually work out more affordable in the long run. You can check for up to date information about this here.
Exploring Rome is like stepping into a living museum where every corner reveals a story from the past. As you wander through its ancient streets, you encounter iconic landmarks like the Colosseum, the Roman Forum, and the Pantheon, each a testament to the city’s rich history. The Vatican City, with St. Peter’s Basilica and the Sistine Chapel, offers a glimpse into the world of Renaissance art and spirituality. Beyond the monuments, Rome’s vibrant neighborhoods, bustling piazzas, and charming trattorias invite you to savor the timeless atmosphere of the Eternal City.
Aiolian islands
How to get there?
You can fly directly from Rome to Catania or Palermo, but by the time you go through security and check in and get out the airport at the other end, we decided it would be more time effective and more relaxing to get the train. There was a direct train from Rome to Milazzo (the port town nearest the islands) that took 7 hours and cost €70. We were then able to hop on a ferry whcih took us to Lipari, where we were staying.
How much time to spend there?
We allocated 3 days to exploring the islands. We could have easily spent longer, travelling to and through all
What is there to do?
Good for: Culture, food, leather shops.
How much do the main attractions cost?
Itinerary and costs
Lipari
Vulcano
Boat trip
Good for: Hiking, swimming, souvenir shopping, exploring the islands.
Catania
How to get there?
How much time to spend there?
What is there to do?
Good for: Culture, food, leather shops.
How much do the main attractions cost?
Itinerary and costs
Good for: Food, cocktails, hiking.
Mount Etna
Salerno
How to get there?
How much time to spend there?
What is there to do?
Good for: Culture, food, leather shops.
How much do the main attractions cost?
Itinerary and costs
Good for: Beaches, history, culture, food, hiking.
Amalfi coast
Amalfi
Maoiri grande
Pompeii
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