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.

This morning, leave Venice behind and travel north into the Dolomites with your private guide in your Mercedes V-Class. The scenery changes quickly as the route moves away from canals and historic cities into mountain roads, forests, lakes, and alpine villages.

Along the drive, your private guide will stop at scenic viewpoints and smaller mountain villages along the route, including some of the best places to properly take in the Dolomite scenery and get photos across the peaks and valleys. There may also be time for short walks, lake stops, or coffee breaks in local alpine towns before arriving at your accommodation later in the afternoon. 

Spend the evening settling into the mountains and enjoying dinner surrounded by the alpine scenery of northern Italy.

Today, you will spend time exploring the Dolomites with your private guide. The route follows mountain roads through valleys, forests, lakes, and smaller alpine villages spread across the region.

Depending on the weather and season, the day may include cable car rides, lakeside stops, walking routes, or time in local mountain towns. Your guide can adjust the pace and route depending on your interests and preferred level of activity.

The Dolomites feel completely different from the cities and coastline visited earlier in the trip, giving you a chance to experience another side of Italy before continuing onward.

Leave the mountains behind this morning and continue south toward Lake Garda with your private guide. Spend time around the lakefront towns before continuing onward to Verona later in the day.

After arriving in Verona, spend time exploring the center of the city with your private guide, including Juliet’s Balcony, Piazza delle Erbe, and the surrounding streets filled with cafés, wine bars, and local shops. The compact layout of Verona makes it easy to explore on foot, with most of the main sights located within the historic center. 

The evening is left open for dinner and more time exploring the city before continuing the journey the following day.

Today, your private guide will take you west toward Milan, where you’ll stop to explore the area around the Duomo and the city center before continuing north to Lake Como.

After arriving at the lake, spend time walking along the waterfront areas and smaller streets surrounding the lakefront towns. The scenery changes again here, with mountains, villas, ferries, and lakeside promenades replacing the larger cities visited earlier in the trip.

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.

Travel south this morning toward the Ligurian coast to explore parts of Cinque Terre with your private guide. Begin in Monterosso before continuing onward to Vernazza and Manarola later in the day.

Throughout the visit, spend time walking through the villages, seeing the harbors, cafés, restaurants, and narrow streets built directly into the coastline. Your guide will help manage transportation and timings between the villages throughout the day.

After time along the coast, continue onward toward your next destination later in the afternoon.

Your private guide will drive you along the Italian Riviera coastline toward Portofino, following the coastal roads past marinas, beach towns, waterfront cafés, and smaller villages built along the Mediterranean shoreline. 

Stop first in Santa Margherita Ligure before continuing onward to Portofino, where you’ll spend time around the harbor and surrounding streets. There will be time for lunch by the water before continuing along the coast later in the day.

Spend the evening enjoying the coastline before continuing inland tomorrow.

Leave the coastline behind and travel inland toward Bologna with your private guide. After arriving, explore the city’s historic center on foot, including Piazza Maggiore and the streets surrounding the old markets.

Spend time walking beneath Bologna’s famous covered porticoes while visiting bakeries, delicatessens, cafés, and local food shops spread across the city center. Bologna is one of Italy’s best-known food cities, making it an excellent stop for lunch and local specialties.

The afternoon is left flexible before continuing south toward your next destination.

Today, travel south toward Naples and the Amalfi Coast. After arriving in Naples, spend time around parts of the historic center and waterfront before continuing onward toward Sorrento.

As the drive approaches the coast, the scenery changes to cliffside roads, marinas, beaches, and sea views overlooking the Bay of Naples. After arriving in Sorrento, spend the evening walking through the town center or having dinner beside the water.

The slower pace here gives you time to enjoy southern Italy before the next stage of the trip.

Next, your private guide will take you along the Amalfi Coast, following one of Italy’s most famous coastal roads. The drive passes cliffside villages, beaches, viewpoints, lemon groves, and smaller seaside towns overlooking the Mediterranean.

Stop first in Positano before continuing onward to Amalfi later in the afternoon. Spend time exploring the towns on foot, including harbors, cafés, shopping streets, and waterfront areas.

There will also be time for lunch beside the sea before returning to your accommodation later in the day.

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.

Today, fly south to Sicily to begin the final section of your Italy journey. After arriving, your private guide will transfer you to Taormina, one of Sicily’s best-known coastal towns.

Spend the afternoon walking through the town center, passing cafés, restaurants, churches, and smaller streets overlooking the coastline below. The atmosphere here feels very different from mainland Italy, with strong Sicilian influences in both the food and architecture.

The evening is left relaxed, allowing time to enjoy dinner and your first night in Sicily.

Today, your private guide will take you inland toward Mount Etna, Europe’s largest active volcano. The route passes lava fields, volcanic landscapes, vineyards, and smaller mountain villages on the slopes surrounding the volcano.

Later, return to Taormina to explore more of the town, including the Greek Theater and the surrounding streets filled with cafés, restaurants, and local shops.

Spend the evening back along the Sicilian coastline before continuing further across the island tomorrow.

Today, your private guide will take you south through Sicily toward Syracuse and Ortigia. After arriving, explore Ortigia on foot, walking through the old streets around the waterfront, local markets, churches, small piazzas, and seaside areas that make this part of Sicily so well known. 

Continue through the center of Syracuse later in the afternoon before stopping for lunch or coffee beside the sea.

The rest of the day is left fairly relaxed, allowing more time to experience the slower pace of Sicily before continuing onward.

Today, your private guide takes you west through Sicily toward Palermo. Along the way, pass smaller coastal towns and countryside areas before arriving in the Sicilian capital.

Spend the afternoon exploring Palermo’s busy streets, churches, markets, and food stalls with your guide. The city feels very different from northern Italy, with strong Arab, Norman, and Mediterranean influences throughout the architecture and food culture.

The evening is ideal for trying Sicilian street food and exploring more of the city center.

Take a short flight to return to Rome for your final full day in Italy. After arriving, spend time revisiting favorite parts of the historic center or exploring areas you may not have seen earlier in the trip.

There will also be time for shopping, cafés, churches, or a final long Italian lunch before your farewell dinner later in the evening.

The final night gives you one last chance to enjoy Rome before departing tomorrow.

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.