STARTING AT $2695 per person

2026 price $2995

Fully planned & booked 10-day self-guided Italy itinerary

Blend of train travel & self-drive

Minimum of 2 people

International airfare

Additional in-country transportation (only as indicated)

Additional meals not listed, or optional excursions and activities

Required travel insurance

Note on driving: For this itinerary we’ve chosen to start you out by train, with your car rental starting on Day 6 from Florence. The trains in Italy are superb and a relaxing way to see the landscape without the stress of small, windy roads and limited parking in the towns and cities. Some trains in Italy only have 2nd class cabins, but whenever possible we’ll get you 1st class train tickets. Either way, we have found this combo of train + car rental to be a very enjoyable experience!

Arrive to the Linate (LIN) or Malpensa (MXP) airport outside of Milan and take an easy bus or train ride to your hotel. Feel free to rest and recoup or begin to explore the area near your centrally located hotel. We’ll provide you with tips for navigating Milan’s metro system, and a suggested walking route around Milan’s city center bringing you to the jaw-dropping Milan cathedral in addition to more central sights.

Be sure to experience the early evening Italian custom of aperitivo, featuring traditional refreshments complemented by an array of light snacks. End your evening with a nice meal at one of our recommended restaurants.

Meals: N/A

Following breakfast, you’ll hop a train toward beautiful Liguria while enjoying beautiful Italian landscapes along the way. Your 3-ish hour ride will bring you to one of the villages of Cinque Terre (a UNESCO World Heritage sight). The name Cinque Terre translates to "five lands," comprising five traditional fishing villages scattered along the dramatic coastline. Each village - Riomaggiore, Manarola, Corniglia and Vernazza - has a distinct feel to it. A world-renowned location, these postcard-perfect towns with a uniqueness truly unmatched anywhere in the world have attracted artists and visitors for decades.

On your first afternoon here, take some time to enjoy a seasonal lunch and explore the town and beachfront where you’ll be staying. Ease into your travels by relaxing at the beach or slowly wandering the streets of this seaside town, or for those eager to explore there are miles of trails that start from Monterosso and connect to the other villages of Cinque Terre. We will provide dinner recommendations for this evening that highlight the delicious seafood and other local specialties for your first night in Cinque Terre.

Meals: B

After enjoying breakfast at your hotel, today is the perfect day to visit any of the other villages in Cinque Terre. Each exquisite village offers its own special flavor from picturesque harbors to stunning views from cliff tops looking out at vineyards and blue waters. Exploring the romantic colorful buildings, narrow cobble-stoned alleyways, delicious gelato shops, and relaxed pace of life will no doubt leave you entranced. A train will connect you between each village, and a quick bus journey or small uphill hike will take you to Corniglia, perched atop a hill.

Be sure to take your time as you go, perhaps stopping for a swim on Vernazza’s beach or a long lunch on a flower-filled patio. We’ll provide you with the best tips to get the most of your time in each village, including advice on how to avoid the thickest crowds so you can fully enjoy the day and restaurant tips for another special dinner along the coast!

If you’re up for hiking, you can also use today to hike the trails that link each village to the other. Maps can be found in the tourist office in each town, and you can also book a guide for the day if you’d like a customized hiking route.

Meals: B

Optional add-on: Hiking guide for the day

After breakfast you'll head out by train for Florence, arriving at your hotel by midday. Florence, the capital of Italy’s Tuscany region, is the incomparable home to prolific masterpieces from Renaissance art and architecture. This is where the famous Galleria dell’Accademia houses sculptures from Michelangelo. There is also the iconic Duomo, Florence’s main cathedral. One of the most breathtaking sights in a city teeming with beauty, this imposing cathedral has a terra cotta-tiled dome engineered by Brunelleschi and a bell tower by Giotto. Enjoy your time visiting the site, including the Cupola del Brunelleschi and the Baptistery. Your ticket entry will also include the option to walk up to the top of the Duomo and/or the tower for impressive views of the city, as well the possibility to visit the fascinating Duomo museum.

You can explore on your own using your Duomo and Accademia entry tickets. Or, choose to book an expert guide to accompany your explorations and provide further insights into the history and stories that make Florence so unique.

In the evening you will have free time to relax and enjoy dinner at any number of delicious restaurants in the center.

Meals: B

Add-ons: 3-hour guided visit in Florence

Today is flexible to further explore Florence or beyond. In the morning, you may want to take a short walk over to Florence's incredible Central Market where there are options for a leisurely lunch or a quick lunch with a *bit* of shopping. There is also the Uffizi Gallery which exhibits Botticelli’s “The Birth of Venus” and da Vinci’s “The Annunciation” and is considered Italy's most prominent museum of renaissance art.

You can also visit nearby Lucca, a city known for its well-preserved Renaissance walls encircling the historic city center and cobble-stoned streets. Explore the city center and its beautiful churches, with tips for independent wanderings and shopping as well as options for lunch. We will also offer suggestions for you to enjoy the most traditional artisan shops in the city, learning from amazing local wood carvers and textile makers.

Another option is to visit Pisa. Its uniquely beautiful Piazza dei Miracoli is a UNESCO World Heritage site and an iconic Tuscan site.

In the evening we recommend a jaunt up to Piazzale Michelangelo -- the only site offering a breathtaking panoramic view of Florence. You can also head back to the Central Market for dinner options — especially for Bistecca Fiorentina!

Meals: B

Add-ons: Round trip train tickets to Lucca or Pisa (about 1.5 hours each way); Uffizi Gallery Tickets (if staying in Florence)

Tuscany is known worldwide for its art, picture-perfect rolling hills, breathtaking landscapes, unique architecture, and of course: all the delicious, delectable food!

Today you’ll pick up your rental vehicle in Florence to explore the Chianti region. You'll set off to visit our Community Partner at one of their nearby olive orchards set in the Tuscan countryside. Get ready for a fascinating insight into the cultivation and production of Italy’s staple ingredient: olive oil. World-class olive oil is much more than a condiment, and today you’ll become experts on the history, variety, and craft involved in creating this ‘liquid gold,’ including a full olive oil tasting and outdoor lunch amid the rural vista.

You’ll continue with a lovely drive through the Via del Chianti (the Chianti way) in the afternoon, through charming villages and rolling hills and finish the day at another beautiful farmhouse hotel. Shortly after your arrival, enjoy an informative vineyard tour and exemplary wine tasting with light appetizers provided. As day turns to evening, be sure to wander the expansive grounds of your rural paradise. This evening, gather up for a farmhouse dinner with delicious local dishes prepared fresh for you.

Meals: B, L, D

Inclusions: Olive oil tasting, wine tasting

Your journey continues after breakfast as you set off to the postcard-perfect Tuscan town of Siena. Distinguished by its uniquely medieval brick buildings and its hilltop setting providing expansive views of the region, Siena is a true gem. The fan-shaped central square, Piazza del Campo, is the site of the Palazzo Pubblico, the Gothic town hall, and Torre del Mangia, a slender 14th-century tower with sweeping views from its distinctive white crown. The city’s 17 historic “contrade” (districts) extend outward from the piazza.

After arriving in Siena you’ll have plenty of time to explore the town, visit the stunning main cathedral and several key sights. You may also choose from a plethora of activities like climbing the tower, exploring the ruins of an ancient Roman amphitheater, shopping til you drop or simply wandering through the picturesque lanes and cobbled streets. History buffs can opt for a guided walking tour in the afternoon, given by a local expert. Choose to stay in Siena for dinner with plenty of charming trattorias or have a delicious dinner at your charming farmhouse hotel.

Meals: B

Wake up to the Tuscan sun once more as your journey draws to a close. Before arriving to Italy’s mecca, how about stopping to visit an iconic ancient town along the way? Sitting majestically high above the valley floor atop a big slab of tufo volcanic stone, Orvieto overlooks cypress-dotted Umbrian plains. Its monumental Duomo also boasts a very intricate Gothic facade.

On arrival in Rome, you’ll drive to the Rome airport to return your vehicle, and from there you can take an easy public transit hop into Rome city center to your hotel. After setting in to your hotel in the Testaccio neighborhood take an orientation walk around the neighborhood of Testaccio and nearby Trastevere. The rest of the afternoon and evening are free for you to explore at your leisure, and it's a great city to wander by foot.

Meals: B

Throughout your time in Rome you may explore independently although we recommend booking a local Roman-native guide who knows all the ins and outs of this overwhelmingly impressive city, as only a local could! It’s a great day for an in-depth day of Rome’s main sites such as the Colosseum, the Roman Forum and Pantheon, Piazza di Spagna, Navona Square, Vatican CIty and Trevi Fountain.

Meals: B

Depart any time today from the Rome airport (FCO) or add additional days if you’d like to explore further!

Meals: B

Prices are based on double occupancy. For groups of odd numbers (3, 5, etc.) please add a “my own room” option for one guest. A minimum of 2 people are required to book this trip.

STARTING AT $2695 per person, double occupancy

2026 price $2995

+$695 'My own room' option: private room with en suite bathroom

Vehicle Rental: For days 6–9 you’ll need a vehicle, picking up in Florence and dropping off at the Rome airport. You can book this on your own, or we can book for you for cost + a service fee. You can indicate your preference on the booking form.

High Season Surcharge: June-July-August starting at +$200 per person

Holiday Surcharge: If your dates fall +/- 5 days around US Thanksgiving, December 25th, or January 1st there will be a holiday surcharge of $200 per person.

We can offer numerous add-ons for this itinerary. The pricing is dynamic, so just let us know in your booking form what you’d like and we’ll be able to provide pricing!

Cinque Terre: Guided day hike tailored to your experience level

3-hour guided visit in Florence

Uffizi Gallery Tickets

Round trip train tickets to Lucca or Pisa

Rome walking tour, full or half day

Extra nights in Rome

It depends! Driving in big cities in Italy can be quite chaotic, and finding parking can prove extremely challenging. That is why for this itinerary we’ve chosen to use train transit for the first part of the journey. It’s a much more relaxing experience, and you get to enjoy incredible countryside scenery en route. Then once you get into Tuscany, the countryside driving route is much more enjoyable and easy.

Yes, you could…but it would be quite expensive as you’d be paying a day rate for the driver plus the cost of the vehicle hire. That said, if this option appeals to you don’t hesitate to ask!

Shoulder season in spring (March-May) and fall (Sept/Oct) is our favorite time to visit for fewer crowds and less heat. That said, you can book this itinerary any time of year.

The trails that connect the 5 villages of the Cinque Terre region spans a little under 9 miles (14 km). It can be done in one day, though many choose to do portions of the trail each day. There are also additional trails in the region that can be explored.