From Hidden Gems to Beloved Highlights – 14 Day Italy Tour Package

From Hidden Gems to Beloved Highlights – 14 Day Italy Tour Package

Visits: Venice, Rome, Tuscany, Florence, Milan, Naples, Pompeii, Siena, San Gimignano and Pisa Starts in: Venice Available: Every Monday and Wednesday (varies seasonally)
Semi Private Guided Tour
Air Conditioned Transport
Accommodation Included
14 days package
$2,639per person
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From Hidden Gems to Beloved Highlights – 14 Day Italy Tour Package Highlights


Join us for an immersive journey through Italy, from the top north to the toe (south)!


Meet and be led by Italian local experts - from chefs and wine experts, to historians and passionate locals


Delve deep into the flavors Italy's food and wine culture with tasting experiences, from bars and restaurants to local wineries


Visit some of the most important cities including Venice, Milan, Florence, Rome, Naples and more


Learn all there is to know about Roman history, from the ruins in Rome to Pompeii


Choose your hotel from our hand-picked selection of exceptional options


This is truly a once in a lifetime Italian experience

Why we chose this tour

Our From Hidden Gems to Beloved Highlights is a 14 Day Italy Tour Package with a difference. A once-in-a-lifetime Italian experience full of flavors, smells, sights, and sounds. This is an Italy tour package like no other. You'll not only visit the major cities (Venice, Verona, Milan, Florence, Siena, Rome, Naples, and Pompeii) and their famous sights but do so as a real insider. You'll meet and be guided by passionate local experts in each location - chefs, wine specialists, historians, and artisans along the way. And whether it's the eccentric gondolier in Venice, a historian in Florence, or a Milanese wine expert, the people you'll meet will be an important part of the memories created by this journey. You'll select your hotels from our curated selection which includes some of Italy's most renowned properties, lying on the banks of Venice's canals, Florence's historic streets, of Milan's bustling city center. And best of all, our From Hidden Gems to Beloved Highlights tour package is available with guaranteed departures throughout the year.

Start in Venice, enjoying treats like a gondola ride and a walking tour of the fabled town. Eat and drink your way through the city with a food and market tour, hopping between delightful bacaros (small bars). Spend some time in glorious Milan, covering the ground with an e-bike tour and tasting your way through the city’s most delicious food and wine hotspots. Spend some time in Florence, learning about its artistic history and heading out towards Siena, Pisa, and San Gimignano. Head to the capital city of Rome with a comprehensive tour of all the best sights, from the Colosseum to the Vatican. Get down with Naples and its gritty past, including a trip to Pompeii. There will be wine tastings, food tastings, walking tours, and everything else you can possibly think of to make this holiday the most memorable one you’ve ever had.

You can pack a lot into 14 days as our From Hidden Gems to Beloved Highlights Italy Tour Package shows! This is one of our most comprehensive tours of Italy, showcasing the best the North, Tuscany, Rome, and Campania has to offer. There is a nice mix of city and countryside-based experiences to ensure you get as much out of this package as you possibly can. Each experience will be led by a passionate local guide, handpicked by us for their enthusiasm and knowledge of the city they call home. We always keep experiences small and personal so you know you’ll have the best time. And even better, you get to choose your hotel at the time of booking, to ensure they all suit your wants and needs. Italy, here you come!

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Book With Tourist Journey
  • We hand-craft each tour package which we offer
  • Each tour and experience is led by a true local expert full of passion
  • Hassle-free experience promise. We take care of everything so you just have to enjoy
  • Choose the hotels you stay at from our curated selection
  • Great memories and the best stories guaranteed
  • Easy booking, easy cancelation and best price guaranteed

From Hidden Gems to Beloved Highlights – 14 Day Italy Tour Package Itinerary

Day 1 - Arrival in Venice
  • Day one will be reserved for your arrival in Venice. Check into your handpicked hotel and explore the delights of the city for yourself for the evening.
Day 2 - Venice Walking Tour, Gondola Ride & St Mark Cathedral and Doge’s Palace
  • Get to know the ins and outs of Venice on an intimate walking tour. You and a small group of like-minded travelers will meet your friendly guide who will show you the very best Venice has to offer.
  • Learn the secrets of Venice's past, starting at the Rialto Bridge and Grand Canal. Wind your way through canals and small streets until you hit Piazza San Marco, exploring the Basilica on a guided tour.
  • Hop on a gondola, gliding through the canals, experience an old mode of Venetian transport for yourself.
  • Enjoy some free time in Venice for an hour, perhaps grabbing a bite to eat.
  • Reconvene at the Doge's Palace and skip the queues for a tour of the building and grounds. Climb to the terrace for spectacular views across Piazza San Marco, before finishing your tour with the old prisons below the palace.
  • Return to your hotel for some well-deserved rest and relaxation.
Day 3 - Venice Food & Market Tour & Transfer to Milan
  • Lose yourself in the flavors and sights of Venice's famous Rialto market, where the whole city goes shopping.
  • Learn all about the local produce and recipes as you hop from stall to stall with a knowledgeable guide.
  • Take a tour around small hole-in-the-wall bars called 'bacaros', famous for their cicchetti - small slices of bread with mouthwatering toppings.
  • For the adventurous among you, there will be the chance to try some more unique toppings on your cicchetti!
  • Chase down your cicchetti with the best of Italian drinks: wine, prosecco, and ever grappa!
  • Your guide will be on hand with fascinating insights about Venice, from the food and wine to how to navigate the city and its cultural life.
  • After collecting your belongings from your hotel, head out on a scenic drive to Milan.
  • Overnight in Milan.
Day 4 - Milan Food Tasting Tour
  • Embark on a delightful progressive gourmet meal walking tour in Milan's beautiful city center, experiencing the transformation of haute cuisine into pop culture.
  • Taste a variety of exquisite dishes, from local wines and Italian appetizers to fresh handmade pasta or gourmet pizza, and gourmet stuffed potatoes with a mix of tradition and creativity.
  • Indulge in sweet treats, including freshly filled Cannoncini, paired with a fine espresso coffee, and unique cake design mignons that are both Instagram-worthy and a joy for your palate.
  • Overnight in Milan
Day 5 - Free Day in Milan
  • Free day to explore Milan solo.
  • Walk around to take in the stunning architecture, amazing shopping opportunities, incredible cuisine, iconic art museums and historical monuments.
  • Overnight in Milan.
Day 6 - Milan E-Bike Tour & Transfer to Florence
  • Milan's terrain makes it perfect for a bike tour - why not make it an e-bike one for extra comfort!
  • Meet your guide and a small group and head around the city, pedaling away to some off-the-beaten sights.
  • Admire the glamor of the Old Town brimming with ancient architecture and contemporary city life.
  • Pass by elegant squares, in the Navigli neighborhood, as well as newer districts like Gae Aulenti. See skyscrapers like the Vertical Wood Building, and the famous CityLife that houses a number of VIPs and international stars.
  • Experience some of the best sights in the city including the iconic Milan Stock Exchange and the exquisite Sforzesco Palace, the lush Sempione Park.
  • Learn about the history of Milan and its modern rebirth from your knowledgeable guide before your tour ends in the center of the city.
  • Today you will self-transfer to Florence and check into your handpicked hotel there.
Day 7 - Florence Walking Tour
  • Today is all about Florence, art, and walking. Meet one of our expert guides who will take you and a group of like-minded travelers around this iconic city.
  • Visit some of the most famous Renaissance monuments and landmarks, learning all about the two thousand years of Florentine history.
  • See where locals used to live in areas such as the Piazza Duomo, Piazza Della Signoria, and Ponte Vecchio.
  • Visit the famous Uffizi courtyard and the spectacular architecture of Brunelleschi Dome which overlooks the Baptistery golden ‘Gates of Paradise.
  • You'll see what Florence is really famous for - art and vibrant culture.
  • Return to your hotel for an afternoon of free time.
Day 8 - Tuscany
  • You can't visit Florence without visiting the famous Tuscan countryside that surrounds it and that's exactly what you'll do today on our Best of Tuscany Tour.
  • Head towards Siena, a gorgeous, ancient city with its yellow buildings and terracotta rooftops.
  • Enjoy a tour of the city before heading to a local organic family-run winery for a feast full of pasta, cured meats, local cheeses, and of course, wine from their own estate.
  • Head onto San Gimignano, famous for its towers that dominate the landscape.
  • Travel onto Pisa where you'll have the chance to eat, shop and have your picture taken with the famous leaning tower.
  • Return to Florence filled with Tuscan memories that are sure to last forever.
Day 9 - Transfer to Rome
  • The morning of day 9 is reserved for your self-transfer to Rome.
  • Once you have checked into your Rome hotel, you can explore the city on your own
Day 10 - Highlights of Rome
  • Meet your local guide at a centralized location in Rome. Please be there 15 minutes before the tour starts.
  • Explore the Colosseum with skip-the-line access, delving into its rich history and archaeological wonders.
  • Gain insights into the architecture and captivating past of this colossal amphitheater, which once hosted ancient Romans, emperors, senators, gladiators, and exotic animals.
  • Next, enjoy a seamless transfer to the Vatican Museums, where you'll encounter a treasure trove of artistry. These museums comprise 54 diverse galleries, including the Museo Pio-Clementino, Museo Chiaramonti, Museo Gregoriano Etrusco, and Museo Gregoriano Egiziano. Here, you'll encounter masterpieces by renowned artists like Leonardo Da Vinci, Michelangelo, Caravaggio, Raphael, and Giotto.
  • The Vatican Museums culminate in the illustrious Sistine Chapel, adorned with Michelangelo's iconic frescoes. Completed around 1483, this chapel is globally celebrated for its artistic heritage. Witness some of the world's most renowned frescoes, including the iconic ceiling and The Last Judgement.
  • The Sistine Chapel, not only a repository of precious art, also serves religious purposes, notably hosting the Papal conclave for the selection of new Popes
  • Concluding your journey, visit the awe-inspiring St. Peter's Basilica, a colossal Renaissance masterpiece and one of the world's largest basilicas.
  • Overnight in Rome
Day 11 - Free Day in Rome & Transfer to Naples
  • Day 11 is reserved for your transfer to Naples. As Naples is only an hour or so from Rome, you may want to spend some free time beforehand, soaking up the last of what Rome has to offer. Or, head early to Naples and explore the streets of this atmospheric town.
  • Check into your Naples hotel for some rest and relaxation - or perhaps some famous pizza - before tomorrow's adventure.
Day 12 - Naples
  • Naples is an outstanding city but to get the very most out of it, you need a guide. We will have one picked out for you who will take you on a private tour around this fascinating city.
  • This is a flexible and customizable tour that will show off the very best Naples has to offer. Discover the Piazza del Plebiscito, a square covered with ornate churches.
  • Refresh yourself at Gambrinus, the oldest bar in the city before strolling through the historic center to admire its many churches, pizza trattorias, and shopping opportunities.
  • Head into the Spanish Quarter, a busy and colorful neighborhood where the entrances to underground catacombs lie.
  • Learn more about daily life in Naples with a visit to Pignasecca Market, the city's oldest street market that sells everything you can wish for.
  • Visit churches, palaces, and bell towers that make Naples the fascinating historical city that it is, before returning to your hotel.
Day 13- Ancient Pompeii & 2 Vesuvian Wineries
  • Head out of Naples towards Pompeii. Meet your archaeologist guide at the entrance to this famed site before heading in.
  • Be treated to a comprehensive tour of Pompeii, learning about what everyday life in this city would have been like.
  • Marvel at the eateries, brothels, and residences and how perfectly preserved they were under the layer of ash from Mount Vesuvius.
  • After your tour, head towards two local wineries located in Mount Vesuvius National Park.
  • Walk around the vineyards before being treated to a wine tasting and lunch, before heading back to your Naples hotel.
Day 14 - Departure
  • Day 14 is reserved for your departure from this extraordinary 14-day tour of Italy.
NB - all timings on From Hidden Gems to Beloved Highlights – 14 Day Italy Tour Package are approximate
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Important Details

All touring and accomodation
Meals as mentioned above
St. Mark and Doge's Palace fast-track ticket & Gondola Ride
Food & Market Tour Venice: Street food samples & seasonal desserts 4 Drinks
Food Tasting in Milan
All equipment for the Milan E Bike Tour
Skip the line entrance: Colosseum & Vatican Museum
Entrance fees to Pompeii
Anything not mentioned above
Transfers: Venice-Milan; Milan-Florence; Florence-Rome; Rome-Naples, Naples-Pompeii-Naples
Personal travel insurance
Essential Information
Each day will be led by an expert guide to provide an enhanced experience along Tourist Journey's values.
You can choose your hotel from our hand-picked selection during the booking process.
The order of the days might change because we optimize the itinerary to provide the best experience.
Vatican: Everyone must pass through security to enter the Vatican, which can take up to 30 minutes on busy days. Please dress modestly, covering your shoulders and knees. Around religious holidays at the Vatican, areas may be closed and certain stops will not be possible. Accessible areas will have longer visits instead.
The minimum age required for the package is 14 years old due to the Milan E Bike Tour.
Cancellation Policy
Please note: From October 18, 2023, 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 Rome tour component of this package (DAY 10) is also 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)
Customize this tour

Book From Hidden Gems to Beloved Highlights – 14 Day Italy Tour Package as a private tour, and customize the itinerary and locations for yourself, your family or a small group.

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