Ultimate 28 Day Tour of Italy

After arriving in Rome, your private guide will meet you and transfer you into the city to begin your journey through Italy. Once checked into your accommodation, head out into the historic center for an easy first afternoon exploring Rome on foot.

Walk through Piazza Navona, the Pantheon district, and the surrounding streets while your guide introduces the city and helps you settle into the pace of the trip. Along the way, stop at cafés, churches, fountains, and local restaurants spread throughout the center.

The first evening is kept fairly relaxed after your arrival, giving you time to enjoy dinner and your first night in Italy.

Today, your private guide will take you into the center of Ancient Rome for a guided tour of the Colosseum. Visiting with a guide helps bring the site to life, explaining gladiator battles, Roman emperors, and how the amphitheater once operated.

After the Colosseum, continue around the Roman Forum and Palatine Hill area before heading back through the city center on foot.

The afternoon stays flexible depending on your interests, with time for additional churches, neighborhoods, cafés, or shorter walking routes.

This morning, your private guide will take you into Vatican City to visit St Peter’s Basilica before continuing through the Vatican Museums and into the Sistine Chapel. Along the route, you’ll walk through long gallery halls filled with paintings, sculptures, tapestries, and historic artwork collected by the Vatican over hundreds of years. 

After time inside the Vatican, continue across the city into Trastevere, one of Rome’s best-known neighborhoods for walking and local restaurants. Spend the afternoon exploring the smaller streets, churches, cafés, and piazzas spread throughout the area before stopping for dinner later in the evening.

Today, your private guide will drive you north from Rome into Tuscany in your Mercedes V-Class. Along the way, the scenery changes from the busy streets of Rome to vineyards, olive groves, countryside roads, and smaller hill towns before arriving in Siena later in the morning.

After arriving, spend time exploring Siena’s historic center on foot with your guide, including Piazza del Campo and the surrounding streets lined with cafés, bakeries, and local shops. You’ll also visit Siena Cathedral before stopping for lunch in the center of town.

Later in the afternoon, continue onward toward Florence, where you’ll check into your accommodation before spending the evening around the historic center.

Spend the day exploring Florence with your private guide, beginning in the area around the Duomo, where you’ll see Florence Cathedral, the Baptistery, and the streets surrounding the center of the city.

From here, continue walking with your private guide through the center of Florence toward Piazza della Signoria and Palazzo Vecchio before later crossing the Ponte Vecchio. Along the route, there will be time to stop at local cafés, bakeries, wine bars, and smaller food shops around the city center. 

The rest of the afternoon is left flexible, allowing time for museums, shopping, or more walking, depending on your interests, before dinner later.

Today, your private guide will take you west through Tuscany for a day exploring Pisa and Lucca. Begin in Pisa, where you’ll spend time around Piazza dei Miracoli seeing the Leaning Tower, cathedral, and baptistery before exploring some of the surrounding streets on foot.

Later, continue onward to Lucca, where your private guide will take you through the old town inside the historic city walls. Spend time walking through the center, passing churches, cafés, bakeries, local shops, and smaller streets away from the busier piazzas before stopping for lunch or coffee. 

After lunch and more time in Lucca, return to Florence later in the afternoon through the Tuscan countryside.

Leave Florence behind for the day and head deeper into the Tuscan countryside with your private guide. The drive takes you through vineyard areas, olive groves, wineries, and smaller hill towns spread across central Tuscany.

Throughout the day, stop at smaller villages and scenic countryside areas before visiting a local winery for wine tasting and lunch. Your guide can adjust the pace of the day depending on how much time you’d like to spend in the villages, wineries, or the countryside itself.

Return to Florence later in the evening after a full day exploring Tuscany beyond the larger cities.

This morning, travel north to Venice by high-speed train before meeting your private guide on arrival. From the station, continue by boat through the canals toward the center of Venice and your accommodation.

After checking in, head out on foot to begin exploring Venice. Walk through narrow streets and over small canal bridges before reaching the Rialto Bridge and the surrounding canal areas filled with restaurants, cafés, and local shops.

The evening is left fairly relaxed, giving you time to enjoy dinner beside the canals and your first full evening in Venice.

This morning, head into the center of Venice with your private guide to explore the area around St Mark’s Square. Spend time seeing St Mark’s Basilica and Doge’s Palace before continuing away from the busier parts of the city into Venice’s smaller streets and canals.

As you walk, your guide will take you through quieter neighborhoods with small bridges, local cafés, wine bars, and residential canals that most visitors never properly see. Venice changes quickly once you move away from the main landmarks, and much of the day is spent simply exploring the city on foot at a relaxed pace.

Later in the afternoon, return toward your accommodation with time to stop for coffee, drinks, or more walking along the canals before the evening.

Leave Venice by boat this morning to explore two of the best-known islands in the Venetian Lagoon. Start in Murano, where you’ll visit a working glass workshop to see Venetian glassmakers shaping and blowing glass by hand using traditional methods.

Continue by boat to Burano, where you’ll spend time walking through the island’s small streets, canals, bridges, cafés, and local shops. The island is known for its brightly painted houses and fishing history.

After exploring Burano for some time, return across the lagoon to Venice later in the afternoon by boat.

Leave Venice this morning and travel north with your private driver into the Dolomites. The journey takes you away from the Venetian plain and into the mountains before arriving in Cortina d’Ampezzo, your base for the next three nights.

After arriving, have lunch and spend some time in the center of Cortina. Walk along Corso Italia and around the streets near Piazza Angelo Dibona before meeting your driver again for the afternoon.

Continue to Passo Giau, one of the major mountain passes near Cortina. At more than 2,200 meters above sea level, the pass provides open views across the surrounding Dolomite peaks. Stop at the main viewpoints and take a short walk if you wish before returning to Cortina in the late afternoon.

Set out from Cortina with your private driver and guide for a day centered on Tre Cime di Lavaredo. The three distinctive rock towers are among the most recognizable sights in the Dolomites, and today gives you enough time to experience the area without rushing through a full list of mountain stops.

Choose a walk that suits your preferred activity level, from shorter routes and viewpoints to a longer section of the trails around Tre Cime. Stop regularly for photographs and take in the mountain scenery before having lunch at a refuge or in the surrounding area.

Later, continue to nearby Lake Misurina. Walk beside the lake and enjoy views toward the surrounding peaks before returning to Cortina during the afternoon.

Day 13 – Lago di Braies, Passo Falzarego & Lagazuoi

• Lago di Braies
• Passo Falzarego
• Lagazuoi Cable Car
• High-altitude viewpoints
• Dolomites scenery

Leave Cortina in the morning for Lago di Braies. Spend time beside this well-known alpine lake, walking along part of the shoreline and stopping at viewpoints across the water toward the surrounding mountains.

After your visit, return toward Cortina and stop for lunch before continuing west to Passo Falzarego. The pass sits high in the Dolomites and was an important location during World War I, with traces of the conflict still visible throughout the surrounding mountains.

Weather and seasonal operations permitting, take the Lagazuoi Cable Car from the pass to almost 2,800 meters above sea level. Spend time at the upper station enjoying the mountain views before descending. Your driver will then take you back to Cortina for your final evening in the Dolomites.

Leave Cortina d’Ampezzo this morning and travel south from the Dolomites towards Lake Garda. Break up the journey in Sirmione, a beautiful historic town set on a narrow peninsula extending into the lake.

Enter the old town beside Scaligero Castle, the striking medieval fortress that guards the entrance to Sirmione. Continue through the pedestrianized historic center, following its narrow streets towards the waterfront and stopping at viewpoints across Lake Garda.

Enjoy lunch in Sirmione and some free time to walk along the lakefront before meeting your private driver for the onward journey to Verona.

Arrive in Verona during the late afternoon and check into your hotel. Keep the evening free for dinner and a relaxed first look around the city, with your full private tour of Verona scheduled for the following day.

Meet your private guide this morning for a full day discovering Verona, beginning in Piazza Bra and the impressive Verona Arena. Step inside the ancient Roman amphitheater and learn how it has remained at the heart of the city for almost 2,000 years.

Continue into the historic center to Piazza delle Erbe, surrounded by colorful buildings, historic palaces and lively cafés. From here, walk through the medieval streets to Juliet’s House and its famous courtyard.

After lunch, continue your tour with Castelvecchio, the imposing medieval castle on the banks of the Adige, before following the river through another part of the historic center. Cross the ancient Ponte Pietra and enjoy views back towards Verona and the surrounding hills.

Finish the afternoon with your guide before enjoying your final evening in Verona at leisure.

Leave Verona after breakfast and travel west with your private driver towards Lake Como. As you approach the lake, the scenery changes to steep green hills, waterfront towns and mountains rising behind the water.

After checking into your accommodation, meet your guide for a relaxed introduction to Como. Walk through the historic center to Piazza del Duomo and see the impressive Como Cathedral, before continuing through the surrounding pedestrian streets and squares.

Head down towards the waterfront and follow part of the lakeside promenade, taking in your first views across Lake Como and the mountains beyond. Spend the evening beside the lake before exploring more of the area tomorrow.

Today is spent exploring Lake Como and some of the smaller towns surrounding the lake. Begin with a boat trip across the water before arriving in Bellagio, one of the best-known towns on the lake.

Spend time walking through Bellagio’s streets with your private guide, passing cafés, small shops, lakefront restaurants, and villa gardens overlooking the water. Throughout the day, continue between different parts of the lake by boat and road.

The afternoon stays fairly relaxed, allowing time for lunch by the water or more exploring, depending on your interests.

Today explores another part of Lake Como, with Varenna as one of the main stops. This attractive lakeside town is smaller than Bellagio and is well suited to a relaxed morning of walking through its narrow streets and along the waterfront.

Spend time in Varenna before visiting one of Lake Como’s historic villas and gardens. Depending on your accommodation, seasonal opening times and your interests, your guide can select the villa that fits most naturally into the day.

Stop for lunch beside the lake and keep the afternoon flexible. There is no need to visit several villages simply to cover more ground, allowing you to enjoy your final full day on Lake Como at a comfortable pace.

Leave Lake Como and make the relatively short journey to Milan. After checking into your accommodation, meet your private guide and begin around Piazza del Duomo.

Visit Milan Cathedral, taking time to see the enormous Gothic church before continuing into the neighboring Galleria Vittorio Emanuele II. Walk through the covered shopping arcade and continue into the surrounding streets of central Milan.

Back at street level, continue into the elegant Galleria Vittorio Emanuele II, with its glass-domed roof, mosaic floors and historic cafés. Walk through the gallery towards Piazza della Scala to see the famous La Scala opera house and the surrounding historic buildings.

Enjoy some free time around central Milan in the late afternoon before returning to your hotel. The evening is at leisure, with plenty of excellent restaurants nearby for your first night in the city.

Continue exploring Milan with your private guide, beginning with some of the city’s most important art and historic sites. Subject to ticket availability, visit Leonardo da Vinci’s The Last Supper at Santa Maria delle Grazie.

Continue to Sforza Castle, once home to Milan’s ruling families and now one of the city’s major cultural landmarks. Walk through the castle grounds before heading toward Brera for the second half of the day.

Spend time walking through Brera’s smaller streets, with galleries, shops, cafés and restaurants throughout the neighborhood. Stop for a Milanese lunch and enjoy the afternoon at a comfortable pace before returning to your hotel.

Leave Milan this morning for a private day trip into Piedmont and the Langhe countryside. Today provides a complete change from Milan, replacing city sightseeing with a hands-on food experience in one of Italy’s best-known gastronomic regions.

Join an experienced local truffle hunter and trained dog for a walk through the countryside in search of seasonal truffles. Learn how truffles are found, why they grow in particular areas, and how trained dogs work with their handlers during the hunt.

Afterward, sit down for a traditional Piedmontese lunch featuring regional dishes and local truffles. Your private driver will then take you back to Milan for your final night in northern Italy.

Meet your private driver at your Milan hotel this morning and transfer to the airport for your flight south to Naples.

On arrival, another private driver will be waiting to take you to Sorrento. Travel around the Bay of Naples and continue towards the Sorrentine Peninsula before arriving at your hotel and checking in.

Spend a relaxed afternoon getting to know Sorrento. Walk through Piazza Tasso and the narrow streets of the historic center, browse the small shops and make your way towards the clifftop viewpoints for beautiful views across the Bay of Naples.

The evening is at leisure. Enjoy an aperitivo overlooking the water before choosing one of Sorrento’s restaurants for dinner.

Enjoy a full day at leisure in Sorrento, with no scheduled touring and plenty of time to experience the town at your own pace. You could browse the shops, relax at your hotel, stop for a drink overlooking the sea or simply enjoy wandering through the Sorrentine Peninsula.

Return to the Amalfi Coast for a full day focused on its three best-known towns. Your private driver will handle the narrow coastal roads, allowing you to spend your time walking and sightseeing at each stop.

Begin in Positano, walking through the streets that descend toward the beach. Continue along the coast to Amalfi, where you can explore the historic center and visit the Cathedral of St. Andrew overlooking the main square.

Later, travel uphill to Ravello. Walk through the town and visit one of its historic villa gardens, where terraces look out across the coastline. After enjoying the afternoon in Ravello, meet your driver for the return journey to Sorrento.

This morning, travel by boat to Capri with your private guide before spending the day exploring the island. Visit the marina area, walk through the main town, stop at cafés and local shops, and visit viewpoints looking back across the coastline and surrounding sea. 

Depending on the weather and timing, there may also be opportunities for additional boat trips around parts of the island to see the coastline and smaller coves from the water.

Return to the mainland later in the afternoon for another evening along the Amalfi Coast.

Today, your private guide will take you to Pompeii for a guided visit through one of the world’s best-preserved ancient Roman cities. Walk through streets, houses, baths, theaters, and marketplaces while learning how the eruption of Mount Vesuvius buried the city nearly 2,000 years ago.

Later in the day, continue toward Mount Vesuvius itself, where you’ll have views across the Bay of Naples and the surrounding coastline.

Return to your accommodation later in the evening after a full day exploring southern Italy’s history.

Leave Sorrento after breakfast and travel back to Rome for the final night of your tour. After almost four weeks of sightseeing, there is no fixed touring program scheduled for today.

Check into your hotel and spend the afternoon however you prefer. Return to a favorite part of Rome from the beginning of the tour, do some final shopping, stop at a café, or simply relax at the hotel.

In the evening, enjoy a final dinner in Rome and look back over the journey from Tuscany and Venice to the Dolomites, Lake Como, Milan and the Amalfi Coast.

Depending on your flight time, enjoy a final morning in Rome before your private guide transfers you to the airport for departure.

If time allows, there may be opportunities for breakfast, coffee, or a short final walk near your accommodation before bringing your full journey through Italy to a close.