16 Day Highlights of Italy Tour Package – Milan, Como, Venice, Dolomites, Bologna, Tuscany & Rome

Visits Milan, Venice, Como, Bellagio, Florence, Tuscany, Rome, Bologna, Dolomites, CortinaStarts in MilanAvailable Every day - varies seasonallyClick on 'check availability' to view the calendar
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Explore the heart of Italy with our 16 Day Highlights of Italy Tour Package, from Milan to Rome. Begin your adventure with a delicious food tour through Milan, followed by a trip to the shores of Lake Como and Bellagio. Arrive in Venice and explore the Doge’s Palace and St. Mark’s Basilica with skip-the-line access. Escape to the Dolomites to admire the alpine peaks of Cortina and the blue waters of Lake Misurina. In Bologna, delight your taste buds with iconic dishes, like ragu alla Bolognese. Make your way to Florence to explore Renaissance marvels before discovering Siena, San Gimignano, and Pisa in the Tuscan countryside. End your journey in Rome, where you’ll explore the Colosseum and Roman Forum before eating your way through the Eternal City on a tasting tour. Lastly, let the legendary art of Michelangelo amaze you with a visit to the Vatican’s Sistine Chapel and St. Peter’s Basilica.

Looking for the perfect mix of mountains, food, art, and history? Our 16 Day Highlights of Italy Tour Package lets you travel from Milan to Rome, with curated tours, devoted guides, hotel accommodations, food tastings, train transfers, and more. Book now and make your dream Italian escape a reality!

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16 Day Highlights of Italy Tour Package – Milan, Como, Venice, Dolomites, Bologna, Tuscany & Rome Highlights

  1. Taste your way through Milan on a local food tour
  2. Explore Lake Como and the charming village of Bellagio
  3. Visit Doge’s Palace and St. Mark’s Basilica with skip-the-line tickets
  4. Journey into the Dolomites to see Cortina and Lake Misurina
  5. Savor Bologna’s best bites on a traditional food tour
  6. Discover the historic landmarks of Florence, Rome, and Vatican City
  7. See the rolling hills of Tuscany with stops in Siena, San Gimignano, and Pisa
  8. Enjoy a tasting tour in the Eternal City of Rome
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16 Day Highlights of Italy Tour Package – Milan, Como, Venice, Dolomites, Bologna, Tuscany & Rome Itinerary

Day 1 - Arrival in Milan
  • Optional airport transfer
  • Overnight in Milan
Day 2 - Milan Food Tour
  • Start your food tour with panzerotti stuffed with mozzarella, tomato, or seasonal fillings
  • Sip local craft or classic Italian beer
  • Enjoy pizza topped with classic or creative ingredients, and arancini
  • For dessert, indulge in chocolates, traditional sweets, or creamy gelato
  • Finish off with a bold Italian espresso
  • Overnight in Milan
Day 3 - Lake Como & Bellagio
  • Travel by bus from Milan to Lake Como
  • Stop in Tremezzina, known for its villas and scenic views
  • Enjoy a 1-hour boat cruise on the lake
  • Dock at Bellagio to explore its alleys and relax with a coffee or gelato
  • Continue by boat to Cadenabbia
  • Visit Como’s historic center
  • Free time for shopping and exploring
  • Return to Milan by bus
  • Overnight in Milan
Day 4 - Transfer to Venice
  • Train to Venice
  • Overnight in Venice
Day 5 - Venice
  • Skip the lines and step inside the Doge’s Palace to explore its grand halls and rich political past
  • Admire the stunning interiors and hidden stories of Venetian power
  • Enjoy fast-track entry to St. Mark’s Basilica, a masterpiece of mosaics and history
  • Overnight in Venice
Day 6 - Dolomites
  • Travel to the Dolomites among the Italian Alps
  • Visit the posh town of Cortina
  • See the Tre Cime di Lavaredo mountain range from multiple viewpoints
  • Free time at Lake Misurina to walk, dine at the local restaurant or take photos
  • Return to Venice
  • Overnight in Venice
Day 7 - Transfer to Bologna
  • Train to Bologna
  • Overnight in Bologna
Day 8 - Bologna Food Tour
  • On your Bologna food tour, try tigelle with cured meats
  • Taste tortellini in broth or other local styles
  • Enjoy tagliatelle al ragu and traditional Bolognese cotoletta
  • To finish, sip espresso with local gelato
  • Overnight in Bologna
Day 9 - Transfer to Florence
  • Train to Florence
  • Overnight in Florence
Day 10 - Florence
  • Start at Piazza della Repubblica and learn about Florence’s medieval history
  • Walk through historic streets with tower houses, Renaissance palaces, and artists’ workshops
  • See the exterior sites of Dante’s house, the Duomo, and the Baptistery
  • Stroll Via Tornabuoni and Via Maggio for designer boutiques and antique shops
  • Cross Santa Trinita and Ponte Vecchio into the artisan-filled Oltrarno district
  • From the outside, marvel at Orsanmichele, Santa Maria Novella, Ruccellai, and Strozzi Palaces
  • Visit the interior of Santa Trinita Church to spot amazing art and frescoes
  • Discover the Pitti Palace, Santa Felicita, and the Vasari Corridor
  • Overnight in Florence
Day 11 - Pisa, Siena & San Gimignano
  • Explore Siena’s medieval streets, Piazza del Campo, and the Duomo
  • Free time for shopping, wandering, or grabbing some coffee
  • Visit a family-run Chianti vineyard for a wine tasting
  • Pair cantucci with Vino Santo, in classic Tuscan tradition
  • Enjoy a Tuscan lunch with homemade pasta, cured meats, local cheeses, and more
  • Visit the hilltop town of San Gimignano
  • Take a scenic drive through Tuscany to Pisa
  • Marvel at the Leaning Tower of Pisa (outside), a worldly icon
  • Overnight in Florence
Day 12 - Transfer to Rome
  • Train to Rome
  • Overnight in Rome
Day 13 - Colosseum & Rome Afternoon Food Tour
  • Tour the Colosseum Arena in-depth
  • Enjoy some free time
  • Visit Palatine Hill and the Roman Forum
  • In the afternoon see the icons of Rome and walk through the main squares, like Piazza Navona
  • Stop at local food vendors sampling a range of local bites, like supplì, Roman pizza, cured meats, and more
  • Enjoy delicious complimentary beer
  • For dessert, indulge in classic tiramisu or gelato, paired with espresso
  • Overnight in Rome
Day 14 - Free Day in Rome
  • Free day to discover the cobblestone streets or Vatican City on your own
  • Overnight in Rome
Day 15 - Vatican, Sistine Chapel & St. Peter’s Basilica
  • Visit the Vatican Museums and Sistine Chapel with skip-the-line tickets
  • Explore St. Peter's Basilica
  • Overnight in Rome
Day 16 - Departure
  • Optional airport transfer
NB - all timings on 16 Day Highlights of Italy Tour Package – Milan, Como, Venice, Dolomites, Bologna, Tuscany & Rome are approximate

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Availability

Available dates are shown in green along with the starting price for that date based on recent searches for 2 adults. Click on a date to move to the next step and customize your trip such as adding airport transfers, choosing your hotel, and adding extra nights.

Important Details

Includes
All touring and accommodation
Trains: Milan-Venice, Venice-Bologna, Bologna-Florence, Florence-Rome
Entrance fees: Skip-the-line entrance to the Doge's Palace & St. Mark's Basilica, Colosseum, Roman Forum, Palatine and Imperial Forum, Skip-the-line tickets to the Vatican Museums, Boat tour on Lake Como
Meals & tastings: Food tastings during the Milan, Bologna & Rome Food Tours, Lunch & Wine tasting on the Tuscany day tour
Excludes
Anything not mentioned above
Personal travel insurance
Gratuities
Essential Information
Each day will be led by an expert local guide to provide an enhanced experience along Tourist Journey's values
Choose your own hotel from our hand-picked selection during the booking process
The order of the days is subject to change so that we can optimize your itinerary to provide the best experience
During the booking process, it's possible to add extra nights of accommodation before or after the tour package
During the booking process, it's possible to add a private airport transfer
Transfers between hotels and train stations are not included in the package that day
Please note that while we aim to follow the outlined Florence itinerary on day 10, there is always a chance of slight itinerary changes
Vatican: Shoulders and knees must be covered for both men, women, and children
Vatican: At times, certain sites may be inaccessible to the public; in such cases, the itinerary will be adjusted accordingly while still guaranteeing an in-depth experience
Colosseum: Please note: Depending on ticket availability, we will start either at the Colosseum or the Roman Forum/Palatine Hill
Tastings on food tours may slightly vary based on availability and/or season
Participants are responsible for making their own way between the hotels and meeting points. Unless otherwise requested, included hotels are chosen for their close proximity to the meeting points
Cancellation Policy
Please note: It is mandatory to provide a first and last name during the Colosseum ticket booking process. Upon issuing, the ticket becomes non-refundable. Guest must ensure they have their passport with them on the day of the tour to guarantee entry. In case of incorrect personal data, access to the Colosseum will be denied
As a result of the above policy, the Colosseum part of the tour is non-refundable
The train tickets are non-refundable
The remaining tours are subject to the general cancellation policy and can be canceled up to 4 weeks before the start of the package with a 95% refund (5% handling fee)