The ultimate Italian (road)trip
Last update: February 7th, 2026
1st DAY - VENICE
Start off your road trip by exploring Venice, one of the must-dos in the country. Do not let the crowds scare you. If you are an art lover start with some cultural hidden gems in the city, such as the Gallerie dell’Accademia (the biggest collection of Venetian art in the world and one of the biggest collection of Leonardo's drawings including the Vitruvian Man) and the Peggy Guggenheim Collection.
Food-wise you should have an aperitivo, a must when in Venice. Our top picks are the Harry’s Bar, where you should order their iconic Bellini, or one of the typical bacari where you could have the Venitian-style aperitivo with tapas-like food called chicchetti. Our fav spot to have a typical Venetian aperitivo is at Ae Forcoe.
For dinner you should try one of our favourites for Italian food: Ristorante Wistèria, El Magazen or Trattoria Antiche Carampane. If you want something more fancy choose Amo Alajmo or Ristorante Quadri.
Sleep at Aman Venice, the Gritti Palace or at Palazzina Grassi - all magical spots to have - we are sure - one of the best nights of your life.
2nd DAY - VENICE —> FLORENCE
Your first day in the car will start from Venice and end up in Florence. Your first recommended stop is Padua, a town not far from Venice. It’s known for the frescoes by Giotto in its Scrovegni Chapel and the vast 13th-century Basilica of St. Anthony. You should have a walk in its charming city center and have a stop at the Pedrocchi cafe, a city institution.
Your second stop will be Bologna, where you are going to be in food-paradise. Have a typical piadina or many tigelle with local hams and cheese accompanied with a glass of wine: one of the best spots there is 051, located in the heart of the city and in one of the most picturesque streets.
Once arrived in Florence, sleep at St. Regis Florence for a fancy stay or at the Relais Piazza Signoria, which has an amazing location in Piazza della Signoria.
3rd DAY - FLORENCE
Explore Florence with a stroll at the Giardino dei Boboli. For fashion lovers, we recommend a visit to the Gucci Museum and to the Fondazione Palazzo Strozzi - watch out for temporary exhibitions there.
For lunch you should eat a focaccia and try local ham and cheese. Our fav spots to eat dinner are Gurdulù, Gucci Osteria da Massimo Bottura or Regina Bistecca.
For sunset lovers, a walk in Piazzale Michelangelo during sunset hour is a must - it is crowded but worth it.
4th DAY - TUSCAN COUNTRYSIDE
After having visited Florence, exploring the Tuscan countryside will be your next stop. Wander around the most picturesque and postcard-perfect towns of San Gimignano, Volterra and Montepulciano. Get inspired by the moment and stop for a picture (or two!) in these amazing locations, but do not miss a visit to Siena, which is distinguished by its medieval brick buildings. Visit its fan-shaped central square, Piazza del Campo, and stroll around the city’s 17 historic contrade (districts).
Spend the night in one of the countryside relais in the area (our fav is Rosewood Castiglion del Bosco) or if you prefer to sleep in the city choose a cozy and small hotel in Siena city center.
5th DAY - TUSCANY —> ROME
Your next day on-the-road will end up in Rome. We advise to stop in Orvieto and visit its picture-perfect Duomo, have a stroll and a bite to eat.
Once you arrive in Rome we advise to stay in one of our favs: Palazzo Manfredi with its beautiful Colosseum view, G-Rough with its decadent yet classy vibes, or Fendi Private Suites, located in a Roman Palazzo in the Fendi maison.
6th DAY - ROME
It's Rome day! Rome is a unique city and so much is to explore and see. If it is your first time there, do not miss the must-dos like a visit to the Colosseum and the Fori. Also, a visit to the Domus Aurea will amaze you - it is a very unique gem, often under-discovered.
Talking of unique gems, you must have an aperitivo (or drinks) with a unique Colosseum view at The Court in Palazzo Manfredi. Food-wise, in Rome you cannot go wrong: our favourites for the best Roman food in the city are Trattoria Sora Lella, Virginiae or Tonnarello.
For a fancy decadent dinner, choose Enoteca La Torre which is a Michelin-starred restaurant located in a Roman Palazzo - enjoy their 5-course menu to explore unique Italian flavours with a modern touch.
Conclude your nights at Sacripante Gallery, where you can enjoy some drinks in a artistic and exclusive location - check out for events and exhibitions! Also Club Derrière is a good spot to have unique cocktails and creations.
7th DAY - ROME —> POSITANO
From Rome your next stop will be one of the most famous hill-top villages in the world - Positano. Before arriving to your destination, we have some things planned for you!
A must-do is definitely Pompeii where you can have a walk and a visit. Pompeii is a city overlooked and buried by the still active volcano Vesuvius in a 79 A.D. eruption
After your visit, a 40-minutes drive will take you to Positano where you are going to spend the night. You should stay in one of these gems: Le Sirenuse (our top pick), Hotel Poseidon, Hotel Eden Suites or Hotel Marincanto. All of them are in the center of Positano and have unique views of the sea and of the hill-top village. They are all immersed in the magical and colorful vibe of the city and offer a very traditional yet classy experience.
8th DAY - POSITANO
Today will be dedicated to explore Positano and its surroundings, the area called Amalfi coast.
Known as the most chic and trendy village in area, Positano is a cliffside fishermen village in the South of Naples. It is a well-known holiday destination with a pebble beachfront and steep, narrow streets lined with boutiques and cafes. Nowadays, it is definitely a place to see in your Italian holiday: it will be crowded but this will not make it less charming. Colorful, lively and traditional, Positano has an incredible vibe characterized by the Mediterranean vegetation and majolica houses.
You should have a walk in the colorful town and experience a limoncello tasting. If you are in the mood for some brunch/lunch the place for you is Casa e Bottega. For aperitivo you should go for Aldo’s Bar and for a fancy dinner choose La Sponda.
If you decide to stay a few more days in the area - which we totally recommend - you can visit the surrounding towns in the coast such as Amalfi and Sorrento. All of them reachable by car and very near to Positano. You can also goto Capri for the day by ferry or boat. If you rent your own boat make sure to have a private tour of the coast and visit the Faraglioni and the caves all around.
We hope you will love our itinerary and that you will try some (or all) of our favourite gems around Italy! We can't wait to know your thoughts, and if missed any unique gems do let us know - buon viaggio e a presto!
For more tips on Venice go to our full guide