14-Day Ultimate Italy Highlights Tour

A 14 day trip to Italy 
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Discover for yourself the quintessence of Italy as you enjoy pizza in Naples, pasta in Bologna while taking in the cliffside colors and lively cities. Journey through the Venetian canals, the Tuscan vineyards, the Roman plazas, and the Florentine domes, and at no point will you have seen enough. In a country of beautiful regional contrasts, each destination will bring its own authenticity and intimate local appeal. From Amalfi to Venice, it is all so different, and that is the greatest highlight of this customized tour. 

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General Information

Detailed Itinerary

Places Visited 

Amalfi Coast, Sorrento, Capri, Pompeii, Naples, Rome, Vatican City, Vatican Museums, Colosseum, Trevi Fountain, Spanish Steps, Roman Forum, Pantheon, Castelli Romani, Frascati, Piazza D’Allessandria, Piazza Navona, Trastevere, Tuscany, Chianti, Florence,  Florence Cathedral, Uffizi Gallery, Ponte Vecchio, Palazzo Vecchio, Chianti, Siena,  Bologna, Colorno, Parma, Maranello, Reggio-Emilia, Modena, Verona, Venice, Grand Canal, St Mark’s Square, Murano

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Naples to Amalfi Coast – Stop, Rest, Relax

Colors shimmer along the Amalfi Coast with reds and greens and yellows against the blue of the Mediterranean. Villages are tucked into cliffs with plazas and cafes perched high above the water. You must descend to reach them, down some steep steps and into places where vehicles cannot reach. In these villages, it will be restful and relaxing, an intimate Italian home away from home where your guesthouse terrace catches the soft sea breeze. You will land in Naples today and transfer straight to the coast, a 90-minute journey that leads to three days of Amalfi tranquility. This is a great place to unwind, especially after your flight, ensuring you have the energy for the culture and wonder that comes during the next two weeks.

What’s Included: airport transfer, accommodation

Day 2: Amalfi Coast – Colors on the Cliffs and Another Relaxed Day

Nothing is planned for today as you settle into the Italian experience. While the Amalfi Coast has become very popular with tourists, it has maintained a local feel, as have most of the country’s destinations. You do not come here to see the sights, but you will feel the country nonetheless as you enjoy a morning cappuccino overlooking the sea at a quiet cafe on the plaza. Church bells ring through the day, and you can descend to the waterside and dip your toes in the blue. Villages are slung along the coast, some directly on the water and others tucked into cliffs. You can set off on a coastal hike between some of them, or you can ascend from your base in Positano towards a monastery above it all. But most of all, today is another chance to kick back and settle into Italy.

What’s Included: accommodation, tour, breakfast

Day 3: Amalfi Coast – Discovering Sorrento and Capri

Visitors have been wowed by the Isle of Capri since the time of the Roman Republic. What was once a getaway for emperors is now a getaway for afternoon indulgence. Sail across on the wind, stop at a couple of small caves and even swim in the beautiful turquoise waters. Check out the island’s ruins and wander through its mystical charm with not a building out of place on one of Europe’s most beautiful spots. An afternoon here is complemented by an evening in Sorrento, a town of lemon smells, plunging cliffs and vintage, old-world architecture. Like Amalfi, it is a famous coastal resort, with the atmosphere being entirely Italian.

What’s Included: accommodation, tour, breakfast

Day 4: Naples to Pompeii to Rome – Contrasts of Historic Italy in One Day

It will be a celebration of contrast as you explore three majestic destinations. Begin with Pompeii, an archaeological site to showcase the wealth of Roman history with incredible scale and detail to the town for you to explore. Then move to Naples, a lively and misunderstood city on the coast with the faded charm of its exterior hiding rich artistic treasures and a famous search for pizza. The classic Italian dish originates here, and your guide will know where to seek out the locals’ choice. Spend a languid afternoon in Naples before taking the train to Rome, where you will disembark into a city of icons. On this first evening, you can walk the squares, pass the fountains, descend the Spanish Steps and enjoy one of the world’s great people watching cities.

What’s Included: accommodation, tour, breakfast

Day 5: Rome – From the Republic to Modern Rome

Columns rise like the flumes of history they are. The Colosseum stands majestic, far more impressive than the photos suggest. You can wander beneath the eyes of sphinx and goddesses, but Rome is more than just the past, so after the Forum and Colosseum you will be led on a journey through its subsequent eras. This was the second Renaissance city, Palazzo Venezia and other open-sided galleries a clear change from Romanesque times. Baroque evolved in Rome as well, Piazza Navona and Piazza di Spagna just two of the dazzling city squares constructed in this style. 

And then there is the neoclassical with Piazza delle Niaadi the best place to understand the style. And it would not be the complete Roman tour without a look at the incongruent Fascist style designed by Marcello Piacentini. With architecture as a lens, you can also spend the day exploring the neighborhoods of Rome, getting beneath the city’s skin and enjoying plenty of stops for espresso and delicacies. As the saying goes, Rome wasn’t built in a day. By the end of today, you will appreciate how the city has evolved over two millennia.

What’s Included: accommodation, tour, breakfast

Day 6: Rome – Intimate Trastevere and Exclusive Nighttime Vatican Museums Access

Small churches hide artistic treasures in the district of Trastevere. They can be reached in a horse and carriage, a timeless mode of travel to the most intimate place in Rome. You find cobbled streets and small cafes here, everything a clear change from the more eye-catching grandeur of yesterday. The afternoon is free before a visit to the Vatican after it has closed for the day. With after-hours access, you can explore the world’s greatest art collection without any of the crowds. Early Christian sculpture, Greek and Roman remains, Raphael’s Rooms and other glorious odes to Italian artists. And then finish with Michelangelo, his Sistine Chapel ceiling all the more impressive when it is so silent and serene.

What’s Included: accommodation, tour, breakfast

Day 7: Chianti – Impressions of the Tuscany Countryside

To Tuscany you will go with a short drive into vineyards and villages. You will be staying amid the vines in your guesthouse located on a working wine farm. Enjoy a tasting with the cellar master and get to know Chianti wines. Young, subtle, and fresh on the palette, these are some of Italy’s most loved wines, all cultivated from the Sangiovese grape. These are wines best paired with food, so you can get to know Tuscan delicacies as well with cheeses, hams, and herbs that make everything so aromatic. The afternoon is relaxed as you take a tour of the farm and take in the Tuscan scenery, the countryside so different from the Roman cityscape.

What’s Included: accommodation, tour, breakfast

Day 8: Chianti – Wine Tasting and Indulgence Across Chianti

With a Chianti base, you can easily get to know more of Tuscany. Head off with your guide and today’s itinerary is flexible, based on what you want to see and how much you would like to wine taste. Visit local producers for some old-world wine tasting, or check out one of the larger, world-famous wineries. Explore the old city square in Siena or travel as far afield as Pisa. Take in small Tuscan villages, where the food is sublime and the atmosphere so laid-back you can easily fall asleep after lunch. And then return to the vineyard and watch how the landscape changes color, such depth to the landscape when the sun makes its wondrously slow descent. 

What’s Included: accommodation, tour, breakfast

Day 9: Chianti – Getting to Know the Heart of Florence

With Chianti as your home base, you can also get to spend a full day in Florence. The Uffizi Gallery, stuffed full of the great Renaissance works is a great place to start, and you will be even more delighted as you find even greater wonder in Galleria dell’Accademia, including Michelangelo’s David. Take a break from galleries on Piazza della Signoria before a journey across the best of Renaissance architecture. Like Rome, you might use the grand buildings as a focal point to exploring neighborhoods, except this time you barely cover two centuries. It is well worth staying in Florence into the evening, as the domes turn a lovely color at dusk. But you can return to Chianti at your leisure, whenever you feel ready to do so.

What’s Included: accommodation, tour, breakfast

Day 10: Bologna – Food, Food, Food

Arrive in Bologna, and it will be easy to be won over by its easy-going style. Wander beneath the arched colonnades and savor the aromas of coffee and cacao. Alongside an enormous Gothic church, you can begin to understand Bologna’s lively history. But you are not necessarily here for the sights, as impressive as they may be. Instead, you will be here for the food. Bologna is Italy’s culinary capital, and in a country so famous for its food, that is quite a distinction. Just think about the origins of Bolognese, and you can imagine the pasta on offer. 

This afternoon you can delve mouth-first into Bologna pasta, a local chef guiding you around Italy’s most revered food market. Sample local produce and learn to inspect through sight and smell, before taking your finds back to the kitchen. Many pasta varieties originate here, and you will learn how to craft a couple of stuffed pastas. It will be a great time spent in the kitchen, and there will be a serious attention to detail, a tortellini bolognesicreated alongside a tagliatelleand perhaps also a passatelli.You will dine on this pasta of course, before joining the chef in a post-dinner paseo, or walk, across the main piazzas.

What’s Included: accommodation, tour, breakfast

Day 11: Bologna – And Even More Food (Plus Glorious Medieval History)

From warm pasta dishes to the best cold cuts in the world, your tasting journey continues. Today you will explore wider Emilia-Romagna, the region Bologna is the capital of. Parma is where you go for cured ham, the pungent smell of a local producer as memorable as the tasting. Modena is your next stop for balsamic, an evergreen addition to every Italian dinner table. Move next to Parmesan cheese, found in Parmigiano, another quaint old village that has influenced the culinary world. These three treats are combined with all manner of medieval glories, the towns and villages as inspiring as the food. Back in Bologna, you will appreciate why the locals are so fussy about what they eat. With such glorious raw produce on their doorstep, nothing but perfection is expected.

What’s Included: accommodation, tour, breakfast

Day 12: Verona to Venice – Two Contrasting Cities to Explore

Whizz to Verona on the train and meet your local guide. With bags stored at the station you can take a walk through scenes from Shakespeare’s Romeo and Juliet, pausing to picture the balcony where the star-crossed lovers famously met. Verona feels very much like a fiction, everything from the Roman amphitheater to the quiet cafes expressing a city that revels in fictitious tales. You can get around the best of Verona in two hours, then follow a private tour with lunch on the main piazza. By evening, it will be onwards by train to Venice, the final stop on your Italian journey.

From the train you travel on the canals, a gondola transfer to your hotel in the heart of the city. The rest of the day is left free with some time for you to pick up all your own Venetian impressions. Wander across famous bridges and go searching for gelato.Dine on a piazza as church spires rise high above. Walk between islands and admire how the townhouses still stand so proudly. Settle into the city’s evening atmosphere as a large proportion of visitors to Venice stay outside the old city, where the hotels are much cheaper.  Your accommodations will be in the city center, and along with that will be the delight of a quiet city as dusk falls. 

What’s Included: accommodation, tour, breakfast

Day 13: Venice – The Best of the Canals and Islands

Spend your day on the water as you sail out to Murano and Burano, outlying islands famous for glass production and their waterside charm. Here you can go into the workshops and take lunch on the water for a quiet way to bring your 14 days in Italy to a close. Take your time to explore central Venice with another journey down the Grand Canal before an intimate look at Doge’s Palace, where artistic grandeur meets with a peculiar history. You will have traveled from southwest to northeast, and the Italian rhythm will be firmly coursing through you. So head out late into the evening, enjoying the cafes and terraces, toasting to the highlights of Italy.

What’s Included: accommodation, tour, breakfast

Day 14: Venice – Departure 

After a relaxed morning and one last Italian breakfast, you will depart from the Venice airport to connect to your international departure.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.