Remarkable Journey: Italy

Let this trip inspire you, so together we can design your own Remarkable Journey.

Welcome to Italy, a country with no end of ruins, UNESCO World Heritage Sites, or natural beauty. It’s impossible to see it all, try as you might. But even if you could, the true flavor of Italy isn’t found in tourist hotspots so much as it is found in the spontaneity and moments that make every trip unique. Take time to linger over a glass of Chianti wine in the Tuscan countryside. Visit Rome’s fountains in the moonlight. Sail Lake Como beneath the descending Alps. These experiences are as much a part of the country as the Roman Forum.

  • Explore the canals and alleyways of Venice by Gondola.
  • Witness the Italian masterpieces, history, and architecture.
  • Cycle your way through the backstreets of Siena.
  • Marvel at the beauty of the Amalfi Coast and roam through the hilly coastal towns of Sorrento, Positano, and Ravello.

Trip Itinerary

Day 1

Rome, Italy

Your journey begins in the eternal city of Rome, where you will experience the place where much of western history began, the ruins and monuments of Ancient Rome and the city of the Caesars.

We recommend you start at the Colosseum, where you will meet your guide to experience a tour of the finest antiquities and ancient ruins of Rome. Continue on to the Roman Forum, the nucleus of Roman government and society, and the Capitoline and Palatine Hills where the palaces of the Caesars commanded majestic views of the city. Take some time at the end of the tour to walk among the hilltop gardens and fragments of ancient villas located on the tree-shaded Palatine Hills.

Day 2

Rome, Italy

Today, you will explore the other pivotal power of Roman history, one which still exerts its influence today; the seat of Christendom of the Vatican. Begin with the Vatican Museums housing one of the greatest concentrations of masterpieces in the world.

Highlights of the tour include the Raphael Rooms—entirely frescoed by the artist, the sculpture hall, and of course the Sistine Chapel, where Popes are elected and where you will see Michelangelo’s famous painted ceiling. End your tour in St. Peter’s Basilica, the largest church in the world.

Day 3

Florence, Italy

Departing Rome, you will enjoy a two-hour scenic train ride north to Florence, the birthplace of the Renaissance.

As this city is an ideal size for walking, so spend the day wandering through the narrow and cobbled streets and explore Piazza dei Ciompi, one of Florence’s historic markets or the secluded Piazza d’Azeglio.

Day 4

Florence, Italy

This morning, enjoy a walking tour of Florence. Included in your tour will be the famous Ponte Vecchio Bridge, the Piazza della Repubblica (the center of Medici power in Florence), the imposing Duomo cathedral, the elegant Uffizi Square, and the renowned leather market of Santa Croce. Cap it off with a visit to see the symbol of Florence itself, Michelangelo’s David.

UNESCO estimates that 60% of the world’s most important artworks are in Italy, with over half of them located in Florence. For art lovers, we recommend continuing today’s tour with a reserved entrance into the Ufizzi Gallery, home to the finest Renaissance art collection in the world.

Day 5

Tuscany, Italy

Leaving Florence, the next destination is Tuscany with its romantic hilltop villages, ancient walled cities, and scenic countryside of vineyards, olive groves, and fields of sunflowers. With either a rental car or private driver, we recommend visiting San Gimignano, known as the ‘city of beautiful towers’, or the walled city of Siena, with its labyrinth of narrow cobbled streets and Palazzo Pubblico, possibly the most complete Medieval piazza in Italy.

This evening perhaps add a private cooking lesson, learning the intricacies of Tuscan cooking first hand, or if you prefer, just enjoy a meal at one of Florence’s excellent restaurants.

Day 6

Tuscany, Italy

No visit to Tuscany would be complete without a visit to its famous wine country. Immediately south of Florence beckons the town of Chianti, with its numerous vineyards and small towns. The ideal way to experience this wine country is with a private guide, and Remarkable Journeys has some of the best in the region.

For an alternate wine experience, we recommend a full-day private tour of Brunello & Vino Nobile wine country in spectacular southern Tuscany’s Val d’Orcia. This area combines a renowned wine growing region with stunning beauty and scenery in an area less crowded than the Chianti region.

Day 7

Cinque Terre

Head back to Florence today where you will catch a train north to the region known as the ‘Cinque Terre.’ Named for the five fishing villages along a stretch of the rugged coast on the Italian Riviera, the area is most popular for hiking, however, you can also see the area by boat, or train. While in the villages you can find an outdoor table for lunch, perhaps swim, drink red wine, or watch blazing Mediterranean sunsets.

Day 8

Cinque Terre

Today is a full day open for experiencing the Cinque Terre in your own way. There is a passenger ferry service running between the five villages, providing an ideal vantage point of the rugged coastline at each village, but the ideal way to see the beauty of the landscape is the well-laid out walking trails that link the villages, hug seaside cliffs, and wind through vineyards and olive groves. If you have a little extra time, there are a number of lovely small medieval churches on the hillsides overlooking the villages.

Day 9

Cinque Terre

While it can take two full days to fully hike the five villages at a leisurely pace, you may also want to venture along the coast to some other equally interesting locations. Just to the north is Santa Margherita Ligure, a charming seaside resort with lovely shops, fine restaurants, and exceptional views. From there you can either walk, or take a taxi or boat to the picture-perfect resort of Portofino, one of the highlights of the Italian Riviera known for its yacht-filled port, fine-dining, upscale shopping, and beautiful hiking.

Day 10

Lake Como

Back on the train today for a ride north, past Milan to Lake Como, part of the Italian Lake District. The lakes are among northern Italy’s greatest treasures. Stretching from the Piedmont border across northern Lombardy to the Veneto border, backed by the Alps and ringed by lush gardens and verdant forests, each has its own charms and, accordingly, its own enthusiasts.

Spend the day settling into your lakeside villa and exploring the nearby town of Bellagio, filled with arcaded streets and little shops, considered one of the prettiest towns in Europe.

Day 11

Lake Como

Explore beautiful Lake Como today. An ideal way to get around is the public Ferry. North of Como is some of the loveliest areas on the lake, in the section known as “Centro Lago”. The highlight is the town of Bellagio. Sitting on a promontory at the point where Lake Como forks, Bellagio is one of the prettiest towns in Europe.

If you prefer, Remarkable Journeys can include a private guide to show you around for the day, either using the public boats for your transportation, or perhaps hiring a private boat for the day to add a more exclusive experience to your visit.

Day 12

Lake Como

Enjoy your final day in Italy at your own pace. Some options are to explore the town of Como for some final sightseeing and a little shopping. Como is the largest and southernmost town on the lake and a center of silk making, offering many shops to purchase the local specialty. You may also want to venture to nearby Lake Maggiore to explore the Borromean islands, and the town of Stresa.

Day 13

Departure

You will be picked up at your hotel today for a private transfer to the Milan Airport and your return flight home. Ciao!

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