country

Classic Highlights Of Italy

Explore magical Venice and its melancholic lagoons, then on to Renaissance Florence and the picturesque surrounding Tuscan countryside. And finally, Rome—La Città Eterna.

Destinations Explored

1

Venice

2

Florence

3

Tuscany

4

Rome

Optional Add-ons

Cinque Terre

Naples & Pompeii

Amalfi Coast

Welcome to Italy, a high-heeled boot of culinary wonders, Roman and Etruscan ruins, breathtaking mountains, beaches, and cities—not to mention the birthplace of the Renaissance. It's no wonder visitors fall in love with the country. Over the course of 10 days, you'll immerse yourself in Italian culture, history, cuisine, and la dolce vita.   

Key Highlights

Private after-hours tour of St. Mark’s Basilica and Doge’s Palace

Visit hidden bacari and cicchetti spots in Rialto Market

Complete Vatican tour with Sistine Chapel and St. Peter’s Basilica

Explore famous wineries in the Tuscan countryside

Best Times to Visit

April - June

September - Early November

Sample Trip Itinerary

Day 1-3

Venice

Arrival at Venice Marco Polo Airport.

Accommodation in Venice

Suggested options (actual bookings will vary based on pricing and availability)

Tour Rialto Market and Cannaregio for an introduction to the city's cuisine

This gastronomic adventure will introduce you to traditional, unique Venetian cuisine. Unlike other regions of Italy, Venice does not have access to farmable land, which means no local meat, dairy, or grains. And because the city was constructed of wood (and thus a fire hazard), wood-burning pizza ovens aren't common here. However, what you will find is a fish-forward, spice-heavy cuisine due to the city's strategic location along the trading port. On this tour, you'll visit the Rialto Fish Market, wander through the off-the-beaten-path neighborhood of Cannaregio, and taste signature cicchetti, wine, fritti, and pasta along both sides of the Grand Canal. 

Visit Doge's Palace and St. Mark's Basilica after hours

Situated in St. Mark's Square, Doge's Palace (Palazzo Ducale in Italian) and St. Mark's Basilica are two of Venice's most recognizable sights. As such, they're essential stops for any visitor, and often have the crowds to prove it. We'll set you up with a tour that visits the palace in the evening, when crowds are thinner, and includes an exclusive after-hours visit to the basilica. A custodian will even unlock the crypt, which is otherwise off-limits to day-time visitors. 

See Venice from a local's perspective on an off-the-beaten-path walking tour

Much of Venice's magic comes from its artisans and bakeries, beautiful churches, and pastel-colored architecture. With a Venice local by your side, find these lesser-visited corners of the city. Stops may include Ca’ Rezzonico, an 18th-century palace with works by Tiepolo and Tintoretto, the oft-overlooked Basilica di Santa Maria Gloriosa dei Frari, and shopping for real Venetian masks at Ca’ Macana. 

Take a gondola ride (it's worth it!)

A gondola ride in Venice is neither a rip-off nor a tourist cliché—think of it instead as a must-have experience. You can pick up a gondola almost anywhere, but if you really want to take a trip back in time, head away from the Grand Canal to the quiet backwater canals, like Fondamenta Vin Castello near the Rialto Mercato. Ask your gondolier to take you across to Cannaregio, a residential area where you’ll find Marco Polo’s house, among other impressive palazzi and churches.

Explore the colorful islands of Murano, Burano, and Torcello by private boat

The islands of Murano and Burano in the Venetian Lagoon are known for their vibrant-hued buildings and artisan workshops, particularly glassblowing and lacemaking. Skip the long ferry lines and explore the lagoon by private motorboat, including a visit to peaceful Torcello Island, the site of one of the first settlements in Venice. 

Enjoy a wine tasting at Venissa Wine Resort on Mazzorbo Island

Venissa winery represents a resurrection of the Venetian Lagoon's long-lost viticulture ways. While the region used to have an abundance of vineyards, widespread flooding in the 1960s wiped out many varietals, including the rare Dorona grape. Gianluca Bisol, whose family has a centuries-long history producing wine in Veneto, rediscovered the golden grapes on the neighboring island of Torcello in 2002, and after confirming the grapes' lineage through DNA testing, he replanted a crop within the walls of a former monastery on the island of Mazzorbo. Now, Venissa wine is highly sought-after by vinos. A visit to the winery, and its Michelin-starred restaurant, is the best way to experience it. 

Day 4-5

Florence

2 hours and 15 minutes by train from Venice to Florence.

Accommodation in Florence

Suggested options (actual bookings will vary based on pricing and availability)

Witness Michelangelo's David and the Duomo on a walking tour

Kick off your stay in Florence with some of the biggest hits. On this guided (small group or private) tour, you'll skip the lines to visit the Accademia and see Michelangelo’s David, followed by a tour of the Duomo. You’ll also learn the incredible story of Brunelleschi’s design of the dome, along with the beautiful baptistry and Gates of Paradise. Continue with a stroll through Piazza della Signoria and Piazza della Repubblica, ending with a walk across the famous Ponte Vecchio. 

Snack your way through Mercato Centrale

The 19th-century built Mercato Centrale is a gastronomic nirvana, a 95m-long neoclassical food market that is both culinarily and architecturally impressive. The market is essentially an enormous maze of food stalls, which are bursting with local produce, astonishingly fresh fish and seafood, artisan bread, cured meat, and extra creamy Buffalo mozzarella. All the shops are run by artisanal traders who are passionate about their craft, so feel to chat them up as you ogle, taste, and purchase. On the ground floor, you'll find the butchers, fishmongers, fruit and vegetable vendors, and small specialty shops selling local olive oils, meats, cheeses and much, much more. Recently re-opened to the public and renewed in 2014 is the second level to the market, a food hall open seven days a week. 

Shop for leather at San Lorenzo Market

The San Lorenzo Markets are actually made up of two separate markets. One is known as the Central Market (Mercato Centrale), which is a two-level indoor food market (you’ll find butchers, fishmongers, produce, and specialty shops with quality pantry items). The other is an outdoor market filled with stalls selling leather, clothes, and kitschy souvenirs. It’s a great place to search for bargains and little trinkets. 

Visit the 14th-century Ponte Vecchio and its gold shops

Dating back to 1345, Ponte Vecchio was the only Florentine bridge that survived destruction by the German forces. After several floods and consequent reconstructions, many jewelers set up shop. The original storefronts still remain at the twinkling Ponte Vecchio today, their trade passed down from generation to generation. By going in the early morning, you'll be able to observe the shop-owners as they raise the blinds with a special hoist construction. In the afternoon when the bridge gets crowded, it's difficult to catch a glimpse of its intricacies. 

See the work of Italy's most famous artist at the Uffizi Gallery

The Uffizi Gallery is located adjacent to the Piazza della Signoria and is home to the world’s greatest collection of Italian Renaissance art. The collection includes Piero della Francesca's portraits of the Duke and Duchess of Urbino and a room full of works by Sandro Botticelli. With the help of a private guide, you'll be transported back in time to when these famous figures wandered the streets of Florence. 

Day 6-7

Tuscan Countryside

Private transfer or car rental to your Tuscany accommodations.

Accommodation in Tuscan Countryside

Suggested options (actual bookings will vary based on pricing and availability)

Visit the charming town of Panzano in Chianti

Set off into the Tuscan countryside, a pastoral dream with rolling hills, wineries, and tiny towns. We'll arrange a private driver to whisk you to and from your accommodation in a traditional Tuscan estate. 

First up: the town of Panzano in Chianti. Originally a medieval castle and village, Panzano is a picturesque town located on a high ridge between Florence and Siena. Known for its wine bars, restaurants, and quaint stores, Panzano is an idyllic place to spend an afternoon strolling through its winding cobblestone streets and admiring the beautiful atmosphere. Don’t miss the Church of Santa Maria Assunta, a beautiful church built into the ruins of the old castle.

Visit the medieval and Renaissance town of Montepulciano

Just south of Siena sits Montepulciano, one of the gems of the Tuscan countryside. The medieval city overlooks the picturesque Val d’Orcia and Val di Chiana. Enjoy a stroll through the city center—no cars means you can meander in peace. Of course, one of the most important things about Montepulciano is the local wine; the Vino Nobile di Montepulciano is one of the best and most famous wines made in Tuscany.

Explore picturesque Siena

Discover the quintessential medieval Italian city of Siena. Within the fortified walls are winding streets lined with Gothic brick architecture and a wide open central piazza, Il Campo. This a perennially popular stop in Tuscany. 

Visit the gorgeous medieval town of San Gimignano

A UNESCO World Heritage Site, San Gimignano is a picturesque walled village composed of striking medieval architecture and incredible towers that look like ancient skyscrapers. It was once an important relay point for pilgrims traveling to Rome on Via Francigena, and today, you can still see the 14 remaining towers once constructed by patrician families to show off their wealth. Be sure to try the local white wine, Vernaccia di San Gimignano, in enotecas.

Day 8-10

Rome

1 hour and 30 minutes by train from Florence to Rome.

Accommodation in Rome

Suggested options (actual bookings will vary based on pricing and availability)

Visit the Trevi Fountain

The scene of Anita Ekberg's unforgettable dip in La Dolce Vita, the Trevi Fountain, or the Fontana di Trevi, is a lavish Baroque ensemble of mythical figures and sea creatures. A restoration (sponsored by Fendi) finished in 2015, and the fountain now gleams brighter than it has for years. If you want to ensure you’ll return to Rome, the tradition is to toss a coin into the water—about €3000 makes it in the water every day. Two coins are for those seeking love, and three for the wedding bells.

People-watch on the Spanish Steps

The Scalinata della Trinità dei Monti, or the Spanish Steps of Rome, are your go-to spot to perch and people-watch while in the city. Once a favorite haunt of artists, painters, and poets, the steps are a majestic meeting place between the Piazza di Spagna and the Trinità dei Monti church. 

And for the romantics, the steps are home to the Keats-Shelley Memorial House, where poet John Keats spent his final months—it’s now a museum dedicated to Romantic poetry.

Tour the Colosseum, Roman Forum, and Palatine Hill

Ancient Rome's most significant sites—the Colosseum, Roman Forum, and Palatine Hill—stand today in the midst of a modern-day city. Here, everyday life carried on, celebrations and battles took place, and Western civilization was shaped irrevocably. With a millennia-long history, you'll need some help taking in everything you're seeing. We'll pair you with an expert local guide to help navigate Rome then and now. 

Explore St. Peter's Basilica and the Vatican Museums

Vatican City is a city-state encircled by a two-mile border with Rome. As the official headquarters of the Roman Catholic Church, it's governed by and home to the Pope. Travelers from around the world flock to Vatican City for its historic art and architecture on display in the Vatican Museums, St. Peter's Basilica, Sistine Chapel, and Castel Sant'Angelo. Taking a guided tour is an absolute must when visiting the Vatican. You will experience the rich history and magic of the museum (and the Sistine Chapel) with a passionate tour guide who makes the visit informative, exciting, and less overwhelming. As an added bonus, you get to skip the long entrance line.

Wander the cobblestone streets of medieval Trastevere

Trastevere is a cobblestoned Medieval neighborhood in the heart of Rome. In recent years, it has become the stomping grounds for many US study abroad students, but don't let that deter you—Trastevere is still a picturesque setting.

With a bit of a discerning eye, you'll find local gems (think cool bars and hole-in-the-wall restaurants). Check out the Ponte Sisto and Piazza Trilussa (where young people meet and drink in the evening) before you enter the heart of the neighborhood, and allow yourself to get lost in the winding streets.

Learn to cook pasta like an Italian

Enjoy an authentic, homemade taste of Italy by learning to cook fresh pasta on a rooftop terrace in Rome. With just a few simple ingredients, a local chef will show you how to recreate the Italian classics you've tried at trattorias across the country. 

Explore Villa Borghese's gardens, villas, and museums

Covering over 200 acres of forests, gardens, and banks, the luxurious Villa Borghese has earned its place as Rome’s most celebrated park. 

Originally the estate of Cardinal Scipione Borghese during the 17th century (built by architects Flaminio Ponzio and Giovanni Vasanzio), it’s now home to several museums, landscaped gardens, and film events. If 200 acres sounds like too much to walk, rent a bike at one of several kiosks.

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Essential Italy

Venice, Florence, Tuscany, Rome

Prices start from $4393 per person.

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Testimonials

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Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

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Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

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Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”

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Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

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Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

Testimonial Profile Image

Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”

Testimonial Profile Image

Carol’s Family Trip to Japan

“The experience was out of this world! Anything that we requested or that we were interested in, Sarah was able to accommodate it for us.”

Testimonial Profile Image

Omar’s London & Paris Family Vacation with Kids

“We really enjoyed the mix of cultural, food and shopping experiences. Most of all, it was great to hit the ground with a plan for each day, but also improvise depending on how our kids were feeling.”

Testimonial Profile Image

Deborah & Lew’s 25th Wedding Anniversary in Italy

“Couldn’t be happier with how it turned out. I had some specific ideas about what to see—what art, what part of the countryside, etc. Elena (our trip designer) was very patient with me as we worked out just the right itinerary.”