Combine the historical splendor of Italy with its natural charm in this 14-day tour, highlighting the ancient cities of Venice, Pisa, Florence, and Rome with sunset gondola rides, regional dishes in local neighborhoods, and guided walking tours, plus visits to many museums, art galleries, and monuments. Enjoy tasting wine in the picturesque hills of Tuscany, plus guided tours of Siena, Vatican City, and the Roman Forum. Swap lively city centers for outdoor experiences in Lake Como and Cinque Terre, like boat tours, day hikes, and traversing the seaside in search of colorful villages.


  • Cruise the extravagant shores and walk the scenic hills of Lake Como
  • Hike from one colorful, seaside village to another in Cinque Terre
  • Enjoy a romantic gondola ride at sunset in bustling Venice
  • Taste Chianti wine in Tuscany and meander the medieval streets of Siena
  • Discover Roman history at the Vatican Museums and the ancient ruins of the Roman Forum

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Venice - Explore Venice
Day 2 Private Walking Tour of Venice - Sunset Gondola Ride Venice
Day 3 Guided Food Tour and Traditional "Barcari" Wine Bars Venice
Day 4 Travel to Como by Train - Explore Como
Day 5 Private Boat Tour of Lake Como - Explore Bellagio Como
Day 6 Hike Mount Piatto on Lake Como Como
Day 7 Transfer to Cinque Terre - Prosciutto Excursion in Parma Levanto
Day 8 Hike the Villages of Cinque Terre Levanto
Day 9 Transfer to Florence - Day Trip in Pisa Florence
Day 10 Visit Uffizi and Accademia Galleries - Tour of Florence Florence
Day 11 Tour of Medieval Siena and Chianti Wine Region Florence
Day 12 Travel to Rome by Train - Explore Rome
Day 13 Tour the Vatican City and Ancient Rome Rome
Day 14 Depart Rome  

Detailed Itinerary

Day 1: Arrive in Venice - Explore

Grand Canal, Venice
Grand Canal, Venice

Welcome to beautiful Venice! You'll arrive in style with your own personal concierge greeting you at the airport and transporting you to your hotel by private boat.  After settling into your accommodation, you'll receive your trip itinerary and materials from your concierge, who is available to you during your entire trip.

The rest of the day is yours to explore Venice, as there is so much to see and do! Start with a museum or art gallery, such as the world renowned Gallerie dell’Accademia. Then take a boat tour through the Grand Canal to get a better idea of the layout of the city. Then grab dinner in the bustling San Marco neighborhood, or the quieter and charming Castello neighborhood.

Day 2: Private Walking Tour of Venice - Sunset Gondola Ride

Sunset Gondola Ride in Venice, Italy
Sunset Gondola Ride in Venice, Italy

After breakfast at your hotel, you'll join a private guide for a walking tour of the city. You'll learn all about the historical background of Venice while stopping at picturesque sites and monuments. 

By lunchtime, you'll enter the famous St. Mark's Square with its Golden Basilica and Doge's Palace. Here you'll see some of the most admired and well-known monuments and buildings in Venice. The Doge’s Palace is a masterpiece of Gothic architecture with vast council chambers and delicately-decorated residential apartments. The interior is filled with works by artists such as Titian, Veronese, Tintoretto, Vittoria, and Tiepolo. The past splendors of the Serenissima can be seen through the palaces, churches, bell towers, and wells, all with their elegant renaissance and baroque facades.

Grab lunch at one of the cafes in the square, or sneak down one of the many side streets to find a quieter cafe or bistro. If you prefer a picnic lunch, the lively Rialto Market area is also worth is a visit. It's filled with stalls of fresh produce and local delights, connecting the famous Rialto Bridge with St. Mark’s Square via Mercerie Street.

Later in the afternoon, you'll enjoy a romantic gondola ride, a must-do as the symbol of Venice. The gondola is well-suited for any type of traveler, offering a unique and spectacular view of the city.

Day 3: Guided Food Tour and Traditional "Barcari" Wine Bars

Cafe Culture in Venice
Cafe Culture in Venice

The morning is yours to explore the beauty of Venice. Enjoy a leisurely breakfast at your hotel, then roam the streets, alleys, and canals of this bustling city. One of the best ways to see Venice is to simply get lost and discover its charms on your own. Relax by the canals or stop in a cafe for an espresso.

If you want to escape the city center, try to explore some of Venice's surrounding areas. Visit its popular Lido Beach or the colorful village of Burano, accessible by a 45-minute ferry. 

In the afternoon you'll meet your local guide for a fascinating food tour, where you'll discover hidden cafes with traditional regional cuisine and wine. You'll start in a typical bacaro, a traditional wine bar that serves as a meeting point for Venetians, usually after work or during lunch breaks. Bacari don't just serve wine; rather, they're home to true Venetian cuisine.

Start with an un’ombra (a small glass of wine) and cicheti (traditional snacks similar to Spanish tapas). Some local favorites include baccalà (cod), spicy meatballs, fish, fried vegetables, and more. The ritual visit to this wine bar is an important part of the rhythm of life in Venice, and a Venetian way of catching up with friends.

Day 4: Travel to Como by Train - Explore

Beautiful Lake Como in the Springtime
Beautiful Lake Como in the Springtime

Enjoy breakfast at your hotel and prepare for your scenic train ride to beautiful Lake Como in Northern Italy. Your personal assistant will meet you in the lobby and take you to Venice's train station via private boat. When you arrive at the station, your assistant will guide you to the appropriate platform and help you board your direct train to Milan, showing you to your reserved seats. 

Enjoy the sights of Italy's countryside as you travel south of the country's mountainous region. On a clear day, you can see the beauty of the Alps. Some routes also pass the southern end of Lake Garda.

Upon arrival in Milan, you'll meet a private driver at the train station and proceed to the city of Como where you will stay the night. Enjoy walking the charming streets of this lakeside city, stopping for dinner at one of the many restaurants and cafes. If you're looking for water views, you'll find many eateries on the lake's shoreline.

Day 5: Private Boat Tour of Lake Como - Explore Bellagio

Mansions of Lake Como
Mansions of Lake Como

Famous for its turquoise waters, there's no better way of seeing magical Lake Como than by boat. From the water, you'll get a much better view of some of the extravagant villas that border the lake (including one owned by George Clooney), as well as the lush gardens that surround them.

Between Torno and Blevio, your private guide will show you the pretty little villages that line the shore, many with beautiful bell towers reflected in the water. Pass by the island of Comacina, the only island in the lake. Largely abandoned now—apart from a handful of artists and a restaurant—Comacina is, in fact, one of the earliest inhabited parts of the lake. There was already an established settlement on the island when it was taken over by the Romans.

At the town of Bellagio, known as the pearl of the lake, you can stop and wander its quaint little lanes. Explore the many wonderful craft shops filled with local goods. Towering above the town is the impressive Villa Serbelloni, an extravagant hotel built in the late 19th century. Stop here for lunch or find a quiet cafe in the town's center.

After lunch, you'll return to Como for the night.

Plan your trip to Italy
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Day 6: Hike Mount Piatto on Lake Como

Views of Como, Italy
Views of Como, Italy

Today's private hiking excursion starts at Lake Como's funicular, which climbs up to Brunate for superb panoramic views of the city of Como. From here, your guide will take you through the picturesque hills to San Maurizio. You'll stop at the Volta lighthouse, where you can enjoy more breathtaking views of Lake Como. On a clear day, you can even see the spires of Milan’s cathedral.

The hike then continues to Mount Piatto before descending to the charming town of Torno, a rare example of a medieval village on the lake. Your guide will then drive you back to Como for the night.

Day 7: Transfer to Cinque Terre - Prosciutto Excursion in Parma

Famous Prosciutto Ham in Parma, Italy
Famous Prosciutto Ham in Parma, Italy

After breakfast at your hotel, enjoy a quick stroll along Lake Como's edge. Then, meet your private driver in the lobby for your transfer to the hilly region of Cinque Terre.

Along the way, your driver will stop in Parma, a city renowned for the Parma Ham farm. Here you'll discover the secrets of this world-famous prosciutto, starting with the cooling, salting and “resting” rooms, each emulating the traditional winter-to-spring curing seasons.

End your experience by visiting the company's “Naso” (or master nose). The Naso deciphers the scent of the products, ensuring the quality of the prosciutto and preparing it for top restaurants in Parma, Italy, and the world.

After lunch—which includes delicious prosciutto, of course—your driver will take you to Cinque Terre. You'll stay the night in the town of Levanto, one of the quieter villages on the coast. Enjoy a stroll along the town's large public beach and grab dinner at one of the many seaside restaurants.

Day 8: Hike the Villages of Cinque Terre

Colorful Villages in Cinque Terre
Colorful Villages in Cinque Terre

Today you'll explore the beauty of 'Cinque Terre' (the five lands), quickly discovering its appeal and popularity. The five villages that constitute Cinque Terre are the highlight of any trip to the Ligurian coastline. They include Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore, together creating a UNESCO World Heritage Site.

These unique villages can only be accessed by foot, boat, or train. Steep terraces plunge down to the tiny harbors with colorful little houses, huddled together until you reach the sea. You will feel that you have stepped into a painting with such picturesque scenery! 

In the morning, you'll meet your private hiking guide in the lobby of your hotel. After receiving your Cinque Terre National Park Cards, you'll start your hiking experience. Your guide will help you choose which path to follow, based on your interests, the weather conditions, and your training.

Your hiking options include:

  • Monterosso – Vernazza. Difficulty: medium. Time: about two hours.
    This walking tour starts in Monterosso and will take you along a scenic path with amazing views. After an initial climb up a steep cliffside stairway of one hundred steps, the trail winds up and down through scrubby Mediterranean vegetation bordered by dry-stone walls.

  • Corniglia – Vernazza. Difficulty: medium. Time: about 2 hours.
    This walk starts in Corniglia. After winding your way through vineyards, olive groves, and along terraces dotted with scrubby Mediterranean bushes, you will end in Vernazza, probably the most photogenic of all the Cinque Terre villages.

  • Riomaggiore – Madonna di Montenero. Difficulty: medium. Time: about 1.5 hours.
    This trail takes you along the cliffs of Cinque Terre and brings you to the Sanctuary of Montenero. For centuries, it housed the only religious center for the whole area; now it operates as a youth hostel.

After enjoying lunch at your destination, your guide will transfer you back to Levanto for the night.

Day 9: Transfer to Florence - Day Trip in Pisa

Pisa, Italy
Pisa, Italy

Enjoy your final morning on the coast of Cinque Terre with a leisurely breakfast. Then meet your driver for a private transfer to Florence. Along the way, you'll stop in Pisa for a 2-hour guided tour of the historic city.

Pisa isn't just a leaning tower; in fact, the tower is merely the belfry for a magnificent cathedral complex with a stunning baptistery and walled cemetery. Though the sea has now receded, in medieval times Pisa was a great maritime republic, rivaling Genoa and Venice. The cathedral has a beautiful pulpit sculpted by Giovanni Pisano, as well as a mosaic, Christ in Majesty, completed by Cimabue in 1302. After years of work to stop the tower from falling down, you can once again ascend to the top.

After lunch in Pisa, you'll proceed to Florence, one of Italy's most beautiful cities. Enjoy walking its narrow  streets and crossing the famous Ponte Vecchio bridge. Duck into a side street or wander into an inner piazza to find many choices for dinner.

Day 10: Visit Uffizi and Accademia Galleries - Tour of Florence

Exploring the Streets of Florence
Exploring the Streets of Florence

Although it's a large city, the best way to explore Florence is by foot so you can capture as much of its impressive museums, art galleries, architecture, and history as possible.

Start your morning will a stroll through the narrow streets of the city with your guide. Your main focus of the day is the legendary Uffizi Gallery where you can admire masterpieces like the Botticelli’s Birth of Venues and Leonardo da Vinci's Annunciation. The Uffizi Gallery is set in the Palazzo degli Uffizi, which was originally designed to hold the uffizi (administrative offices) of the Medici Grand Duke Cosimo. The Medici housed their art collections here and, in 1591, created what was then Europe’s first modern museum, opening it to the public.

Next you'll visit the Accademia Gallery to see Michelangelo’s famous masterpiece, The David. After the tour, you'll be free to grab lunch at your leisure. Enjoy the rest of your day exploring the city center at your own pace. There are many more museums and galleries to peruse, and don't forget to see the impressive duomo of the Cathedral of Santa Maria del Fiore . Grab an afternoon snack at Sant'Ambrogio Market or enjoy a gelato in the buzzy Piazza della Signoria.

Day 11: Tour of Medieval Siena and Chianti Wine Region

Medieval Siena at Sunset
Medieval Siena at Sunset

This morning, you'll meet your driver in the lobby of your hotel and head to the medieval city of Siena. Start with a 2-hour waking tour with a private, English-speaking guide, discovering the highlights of this charming city. At first glance, you'll notice the harmoniousness of the architecture with virtually the entire city built of red-hued brick.

The first stop on the tour will be the incredible Piazza del Campo, the magnificent square in the heart of the city famous for the Palio, a horse race that takes place twice a year in July and August. Next, you'll visit the stunning gothic cathedral with its magnificent marble flooring and countless works of art. Opposite the cathedral is the former hospital of Santa Maria della Scala, a medieval building which was used as a hospital up until the 1980’s and now serves as a museum. In particular, you'll enjoy its incredible Sala del Pellegrino filled with frescos.

After your tour of Siena, you'll proceed to the beautiful countryside of Tuscany where you'll visit a locally renowned vineyard in the Chianti Wine Region. While touring the cellars, you'll learn all about the vineyards and the production of this world-famous wine. Then enjoy a wine tasting with the vineyard's wine sommelier.

Chianti takes its name from its picturesque region of production in Central Tuscany. As your driver returns to Florence, take the scenic route that reveals the unique beauty of the Chianti Wine Region. You'll pass through forests and rolling hills interspersed with acres of vines and gorgeous villages.

Spend your final evening in Florence strolling the streets, crossing the Ponte Vecchio bridge, and walking up to Piazzale Michelangelo for incredible panoramic views of the city and the Arno River.

Day 12: Travel to Rome by Train - Explore

Rome at Dusk
Rome at Dusk

After a relaxing breakfast, it's time to say goodbye to beautiful Florence. Your personal concierge will take you to the train station and help you find your reserved seats on a high-speed train to Rome. The scenic ride passes through the heart of Italy, as well as the rolling hills of Tuscany. Upon arriving in Rome, your concierge will transfer you to your hotel by luxury car.

According to legend, Rome was founded by brothers Romulus and Remus in 753 B.C. atop Rome's Palatine Hill. The long-time center of the powerful Roman Empire, Rome boasts nearly 3,000 years of architecture, history, and culture. These days, Italy's capital is considered one of Europe's top cities thanks to its ancient monuments, incredible art masterpieces, and cosmopolitan vibe. It's a center for fashion with a buzzing food culture and growing nightlife scene.

Although you'll see the big sites tomorrow, get your footing by strolling through the city in the evening. Rome is just as beautiful at night as it is during the day. Start with the evening glow of the Trevi Fountain and Piazza Navarro, then check out the nighttime lights of the Roman Forum and the Colosseum. If you're in search of some traditional dishes for dinner, cross the Tiber River and head into the hip neighborhood of Trastevere. Although this area of Rome has been discovered by tourists, it still maintains a truly authentic Roman culture.

Day 13: Tour the Vatican City and Ancient Rome

Ancient Roman Forum
Ancient Roman Forum

Fuel up for breakfast, as today will be busy with incredible and historic sightseeing. Today you'll visit some of the best-known highlights of Rome, including the Vatican City (Vatican Museums, Sistine Chapel, and St Peter's Basilica) and the relics of Ancient Rome (Colosseum, the Roman Forum, and Palatine Hill).

Start the day at the Vatican Museums, some of the largest, richest, and most splendid museums in the world. Throughout the centuries, the Popes created an immense collection of renowned classical sculptures and masterpieces of Renaissance art. Founded by Pope Julius II in the early 16th century, the museums contain roughly 70,000 works, of which 20,000 are on display.

You'll pass through 45 galleries before arriving at The Sistine Chapel. The chapel is set in the Apostolic Palace, which is both the official residence of the Pope and where the Papal conclave elects new Popes. The chapel is famous for its frescoed ceiling with Michelangelo’s Last Judgement.

The tour ends with the extraordinary St. Peter’s Basilica, which was designed by Donato Bramante, Michelangelo, Carlo Maderno, and Gian Lorenzo Bernini. It's one of the most renowned works of Renaissance architecture and remains one of the largest churches in the world. Once inside, you'll have the chance to admire Michelangelo’s extraordinary statue Pietà, Bernini’s bronze Baldacchino canopy, and the Throne of Saint Peter.

Enjoy lunch at your leisure. Avoid the tourist crowds by walking a few blocks north of Vatican City and into the Prati neighborhood of Rome. Here you'll find many excellent restaurants and cafes filled with locals.

Next, you'll explore the splendors of ancient Rome. Every city throughout the Roman Empire had a forum at its heart, and it goes without saying that the Roman Forum was the mightiest. It was the center of public life and the culmination point for triumphal processions, where courts would sit and senators debate. You will see the Rostra from which Mark Anthony most likely made the famous speech on the death of Julius Caesar. You'll walk along the Via Sacra (Sacred Way), the main street of ancient Rome, and see the beautiful gardens of the House of the Vestal Virgins. Then, make your way up Palatine Hill, the most central of Rome’s seven hills.

From Palatine Hill, you'll get an incredible view of the Circus Maximus, where spectacular chariot races took place. The tour culminates at the Colosseum, perhaps Rome’s most awe-inspiring ancient monument. Built by the Emperor Vespasian in 72AD, the Colosseum seated about 50,000 spectators and staged all the blood-thirsty games known to ancient Romans: gladiatorial combat, man against beast, beast against beast, land battles, sea battles, and executions, all designed to inspire the citizens at the heart  of a mighty Empire.

Day 14: Depart Rome

Charming Streets of Rome
Charming Streets of Rome

After one last Roman breakfast, you'll transfer to the airport or train station for your flight home or to continue on your journey.


Map of History and Nature in Italy: Venice to Rome - 14 Days
Map of History and Nature in Italy: Venice to Rome - 14 Days