31 May 2024

Europe’s boot is a destination rich in history, culture and delicious food that has not yet ceased to amaze visitors from all corners of the world – and there is a good reason why! In Italy, every monument, every corner and cobblestoned lane unfolds another layer of the country’s unequalled identity defined by an undeniable Mediterranean charm and countless landmarks to admire.

Because we believe embracing the Italian soul and lifestyle is the way to explore this country, a 15-day adventure is just the right way to do it. Over two weeks, a balanced itinerary will take you across the key monuments and sites in one of Europe’s most historically rich destinations, which you will be able to explore at your own pace. 

Are you ready to uncover the World Heritage of Rome, Florence and Venice?

Days 1 to 3 - Explore the historic ambiance of Rome

Days 1 to 3 - Explore the historic ambience of Rome

There is no better place to kick off your 15-day odyssey than Rome – the town where all roads lead to, and World Heritage sites are bountiful! The country’s capital breathes with the echoes of its past that, to this day, help preserve Italian identity and culture by immersing you in a magnetic ambience.

With three days on your hands to explore, Piazza di Santa Maria Maggiore might just be the place to start. This energetic square is the home to one of Italy’s most famous religious monuments, the Basilica di Santa Maggiore. Lose yourself in this site’s mesmerising architecture marked by a distinctively Baroque façade and interior golden details that stun the senses.

Days 1 to 3 - Explore the historic ambience of Rome 2

Continue your outing at the legendary Colosseum – a materialisation of the Roman Empire’s might and culture. As you stand before such a remarkable construction, close your eyes and let your mind wander into the roaring crowds watching the gory gladiatorial combats. To this day, each of the ancient stones still vibrate with the vivid energy of the past.

As your days in the city reach an end, pay a visit to the emblematic pantheon. Here, take a deep breath and let the scent of ancient stone fill your senses, while your eyes catch the sunlight beams stream through the oculus. The Trevi Fountain, is an equally obvious stop. Throw a coin over your shoulder and allow yourself to immerse in the magic of this timeless city!


Day 4 - Head north to the city of the Canals

Day 4 – Head north to the city of the Canals

The winding canals and floating gondolas are your invitation card to Venice, the “City of the Canals”. As you head north, this is your most important stop in the romantic Veneto region. Since this will be your first day in this enchanting destination, set aside some time to take in the first impressions on a leisurely stroll along the canals. With each step on the storied ground, your gaze will be directed to the surrounding pastel-coloured buildings, even more architecturally exquisite with the sunset’s golden glow cast upon them.

At the end of your day, dare to indulge in your first dinner at a local restaurant – the perfect place to taste traditional Venetian delicacies that will leave your mouth watering. Be sure to try the infamous Sarde in Saor, marinated sardines in a sweet and sour sauce served with onions, pine nuts and raisins – a true feast of flavours! 


Days 5 and 6 - Marvel at the mysticism of Venice

Days 5 and 6 – Marvel at the mysticism of Venice

Venice, otherwise known as the “City of Love”, exudes an unparalleled romantic charm, which stems from its outstanding scape made of countless bridges and labyrinthine streets. On days 5 and 6, your senses will surely be tested as you marvel at the destination’s shimmering canals and top landmarks. Here, history, culture and identity live together in perfect harmony.

Start your adventure at the historic Venetian Ghetto, which some say is the oldest ghetto in the world. Between narrow alleyways and ancient synagogues, you are taken through the defining places that marked the life of the Italian Jewish community in Venice. 

Days 5 and 6 – Marvel at the mysticism of Venice 2

For art enthusiasts, Venice is a treasure trove of Renaissance and modern art, which have defined generations of artists and creative minds. With this, the Peggy Guggenheim collection houses and the Galleria dell’ Accademia are two obligatory stops. Imagine seeing in real life Tintoretto’s spellbinding “Creation of the Animals” or Bellini’s “Holy Conversation”!

Marvel at the mysticism of Venice from the city’s charming streets and crossing bridges that offer views of the serene canals. This romantic ambience will come alive even more strongly on an end-of-day gondola ride. Drift along the shimmering waters as you listen to the humming of traditional Venetian songs.


Days 7 and 8 - Indulge in the gracious Bologna


On day 7, it is time to head over to the Emilia-Romagna region and the lovely town of Bologna. As you step on this destination, prepare to be enveloped by the scentful aroma of savoury ragù, aged Parmigiano-Reggiano, and freshly made pasta that will wow your senses! Bologna will reveal to you to be a true culinary paradise.

Begin by discovering the historic Piazza Nettuno and Piazza Maggiore – two bustling squares surrounded by alluring medieval palaces. Observe the buzz and hum of the local people passing by the grand Basilica of San Petronio, one of the largest churches in the world. Head over to the University of Bologna, one of the town’s most prominent landmarks renowned for being one of Europe's oldest, dating back to 1088.


Days 7 and 8 – Indulge in the gracious Bologna 2


On your last day, if you have the time, set your mind on exploring this destination’s religious heritage at the Sanctuary of the Madonna di San Luca. This sacred space, overlooking the city, not only displays stunning architecture but also offers jaw-dropping vistas of Bologna and the surrounding landscape.

Your visit will only be complete when you indulge in its world-recognized cuisine. As the home of the traditional Bolognese, you must try the tagliatelle al ragù and the mortadella paired with a glass of locally produced Sangiovese wine.


Days 9 and 10 - Immerse into the artistic spirit of Florence

Days 9 and 10 – Immerse into the artistic spirit of Florence

Welcome to Florence, the artistic hub of Italy where Renaissance perseveres through time and age! Here, every street shares glimpses of the artistic brilliance that once lived there. To this day, the spirits of Michelangelo, Dante, and Leonardo da Vinci are still very much alive and celebrated.

The first step is to immerse yourself in the sublime beauty of the city’s religious architecture. For that, use the Ghiberti Pass, which will unveil to you the treasure of the Duomo, the Baptistery and the Santa Reparata – Florence’s holy trinity of architectural might. Inside Santa Reparata, allow yourself to travel to the early days of the Christian era, when European history took its first steps toward an era of change.


Florence (endireitei)


On your second day, venture into an artistic odyssey that will immerse you in Florence’s undeniable artistic legacy. Swayed by the fresh breeze of the morning, walk up to the Uffizi Gallery, owner of one of the world’s most extensive collections of Renaissance art. Inside, you will find Botticelli’s iconic “The Birth of Venus” and Leonardo da Vinci’s “Annunciation”.

With the day nearing its end, it is then time to reach the emblematic Ponte Vecchio. As you cross this construction, take a moment to pause and admire the streets and pastel-coloured buildings running parallel to this landmark. It is no wonder such landscape inspired the world’s most revered artists!


Days 11, 12 and 13 - Delve into dreamy Tuscany


As you embark on the last days of your Italian adventure, it is time to explore the Tuscany region and its natural beauty. First stopping in San Gimignano, you will enter an idyllic rural realm of narrow medieval streets, lush green surroundings and quaint stone houses.

This destination will capture your heart with its punctuating towers that have earned it the nickname “Manhattan of the Middle Ages”.  Out on the streets, as your eyes wander upwards to observe such peculiar constructions, the lanes will guide you to the local shops and markets, where traditional delicacies and the world-famous Chianti wine await you.




Continue your adventure in the lovely town of Siena. History buffs and wine lovers find solace in its stunning architecture, rich history, and vibrant culture defined by the winegrowing Chianti estates. Jumping from the fabled streets to the spiritually enlarging cathedral, you will find the ornate dome will transport you to a pretend blue sky symbolising heaven and proximity to God.

With wineries scattered throughout the surrounding lands, Siena will present to you some of the finest wines Italy has to offer. Pay a visit to one of Tuscany’s wine estates and raise a glass to the beauty of a sun-drenched region. With each sip, your mind and eyes will take you to the encircling rolling hill and draping vineyards!


Days 14 and 15 - Discover Orvieto on your way back to Rome

Orvieto 1

As you wind your way back to Rome from the dreamy lands of the Tuscany region, make sure to stop at the captivating town of Orvieto. Burrowed amidst the rolling hills of Umbria, this Italian gem is a cultural and architectural delight.

Orvieto Cathedral, also known as the Cathedral of Santa Maria Assunta, is an Italian Gothic masterpiece with dazzling frescoes and stunningly intricate mosaics. Inside, the architectural wonders continue in the frescoed chapels and golden masterpieces, that bring spirituality to a visual plane.


Orvieto 2


Your historical rendezvous, across winding alleys and cobblestoned lanes, will guide you to Orvieto Underground, a descent into material history. Here, in well-preserved ruins, you are taken to the very site of ancient Etruscan tombs and medieval wells that whisper the tales of the city’s past.

Soak in the magical atmosphere of Orvieto immersed in the end-of-day golden haze. Out on the bustling piazzas, the chatter of visitors and locals meet the resounding church bells singing in all their splendour. Orvieto is not just a stop along the way, it is an experience to be savoured!


How about making it custom?

The way to explore Italy is to do it your own way! With our fully customisable approach, we guarantee that each stop of your trip is aligned with your preferences and interests. Whether you are already acquainted with Rome’s World Heritage sites or it is your first time ever in Europe’s boot, the process is simple: let us know which cities you would like to visit, and we will include them in your 15-day personalised Italian adventure. Want to shorten or lengthen your tour? We can take care of that too. Ultimately, our goal is to make your time in Italy as unforgettable as possible!

Get in touch with us to schedule a meeting with our local travel consultants to tailor your trip. You can also call us directly or request a quote, here. Sit back and see your dream vacation come to life right before you!


Topics: self-drive, travel agency, self-guided, history, gastronomy, culture, art, tourtailors, Italy, VisitItaly, Rome, Chianti, Chianti wine, Tuscany, Italian food, Venice, tourism travel, Orvieto, world heritage

We are a local tour operator specialized in custom Self-Guided Tours in Portugal, Spain & Italy

Our local team will craft a tailor-made trip plan with an itinerary and a selection of hotels, activities and transportation based on your interests and budget. We offer a turnkey package and take care of all the logistics. While you are travelling, our local team is available by phone 24/7, so that we make sure you have a hassle-free vacation.


We also want to guarantee you have all you need when you are on tour. You will get a personalized roadbook with your day-to-day planning designed especially for you and an exclusive guidebook with additional information written by our team. This information will also be featured on our exclusive mobile app, which also have maps connecting to your phone’s navigation apps. To ease the driving, you will receive a pre-programmed GPS with preloaded coordinates for all of the above.


We know sometimes life gets in the way, so all our tours are fully-refundable until 5 working days prior to your arrival – money back guarantee, no questions asked.


After we receive your enquiry, we will send you a free proposal, that can be changed as many times as necessary until meeting your expectations. Start planning your trip today!


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