Custom Trip Plan
Destinations

Trip Ideas
Itineraries
Themes

About Us

1 800 344 5785

Under the Radar Italy

11 Days / 10 Nights

Naples, Bologna, Lucca, Milan

from$3,825 per person

Travel and LeisureFodorsUSA TodayNew York TimesNational GeographicWashington PostVogue

There's no 'right' way to tour Italy and it's a country you can visit again and again. Your first visit might prioritize the 'Holy Trinity' of Rome, Florence, and Venice, but there's so much more to see in this magnificent land. With our extensive knowledge of the country, handpicked hotels, and trusted local tour guide and transport partners, you'll be in great hands as you explore several of Italy's less-visited delights. You'll get all the familiar ingredients: a rich and fascinating history, beautiful architecture, delicious food and wine, but you'll also get to enjoy places that aren't so crowded.

Start your tour in gritty Naples, the ideal base to see Herculaneum, Pompeii's less famous sister site, day trip to islands like Procida or Ischia, and enjoy the best pizza in the world. Head north to the heartland of Italian cuisine: Bologna in Emilia Romagna. A move sideways to Lucca gives you a taste of Tuscany but without the hordes of Florence. Finish up in Milan, the country's financial capital and discover how this city is misunderstood and isn't all business - there's great art and food to enjoy here too. Plentiful direct flights from Milan make the return home easy too.

All of our tours are custom, and this is just a sample meant to give an idea for what our trips are like, and the opportunities our destinations provide. You could take this tour in reverse, or swap out destinations.

One of our team members in the region will be available to you leading up to and during your trip to answer any questions and arrange local services. You will receive access to your Guest Page, with its information on the best these destinations have to offer, including things to see and do, and other inside tips from restaurant recommendations to tipping advice. Upon arrival, we will provide you with a local SIM that you can use to reach your local JayWay contact throughout your trip. In all of our destinations, we offer a variety of memorable 3-5 star accommodation options, including boutique hotels and charming B&Bs. With our firsthand experience, we can ensure they are all clean, comfortable, and centrally located, with local ambience.

Route for Naples, Bologna, Lucca, Milan tour

3 Nights in Naples

3 Nights in Naples

4 days in Naples
4 days in Naples

3 Nights in Naples

To call Naples rough around the edges would be quite the understatement. Yet amidst the chaos and beneath the grime is one of Italy's true gems. It's the third-largest city in the country, home to over three million people. An important port city for all the civilizations that have existed there, Naples is the original melting pot. Founded as Neapolis (literally "new city") by the Greeks in the 7th century B.C., Naples has many layers of history for you to discover.

To call Naples rough around the edges would be quite the understatement. Yet amidst the chaos and beneath the grime is one of Italy's true gems. It's the third-largest city in the country, home to over three million people. An important port city for all the civilizations that have existed there, Naples is the original melting pot. Founded as Neapolis (literally "new city") by the Greeks in the 7th century B.C., Naples has many layers of history for you to discover.

Day 1

Day 1 - Arrival in Naples

Upon arrival to Naples International Airport, our driver will be waiting for your at the arrivals and will take you to your accommodation in Naples.

First Night in Napoli!

Suggestion to explore on your own

So you've just arrived in Naples! This is a city that demands you throw yourself into it headfirst. The very best way to do that is to head to Centro Storico and get in line for one of the city's legendary pizzas. For a slightly less frantic first night, Quartieri Spagnoli next to the historical center is an alternative. Every local has their favorite place and won't be convinced otherwise. We've tried our fair share, and you'll find recommendations in your customized Guest Page. The first rule of pizza in Naples is that it's nothing like pizza in the US. It's not even like Neapolitan style pizza in the US. Sure some places get close, especially those with the Associazione Verace Pizza Napoletana designation but somehow pizza in Naples is just 'more'.

First Night in Napoli!

Day 2

Day 2 - Your First Full Day in Naples

Naples Private Walking Tour

Naples Private Walking Tour

Included in your vacation package price.

On this private walking tour you'll be seeing the best of Naples in just three hours. Your guide will give you a local's point of view on all the different sides of the city. You'll see breathtaking views above the rooftops, and stroll through the streets and alleys. Your guide will pick you up from your accommodation and take you back there at the end of the tour. This will be one of the highlights of your holiday.


Activity Level : Moderate
Duration : 3 hours

Pizza Lesson Small Group Experience

Pizza Lesson Small Group Experience

Included in your vacation package price.

Naples is famous as the birthplace of the modern day pizza and it is said that nowhere else does it taste quite as good. It could be the water, or the San Marzano tomatoes that are used to make the tomato sauce, or perhaps the magnificent buffalo mozzarella that is often used in preference to the run-of-the-mill cow's milk version. Today you'll be having a pizza lesson with an experienced pizzaiolo so you can find out for yourself. You'll start by mixing and kneading your own dough, and then top it with the finest local ingredients. When your work is done you'll sit down and finish your experience with a soft drink and a 3 course meal: starter, dessert and, of course, pizza you have prepared with your own hands.


Activity Level : Easy
Duration : 1.5-2 hours

Day 3

Day 3 - Your Second Full Day in Naples

Pompeii and Mount Vesuvius Private Excursion from Naples

Pompeii, Herculaneum, and Mount Vesuvius

Included in your vacation package price.

No visit to this part of Italy is complete without a stop at Vesuvius National Park. On this excursion you'll be picked up and driven there. To visit the crater there's an entrance fee of 10 euros, and the ticket includes guide service. Although the duration of the hike in Vesuvius National Park can vary widely according to the age and health of visitors, the whole hike should take about 90 minutes. You'll be truly impressed by this historic site, and in Pompeii you'll have a walking tour.


Activity Level : Moderate
Duration : 8 hours

Day 4

Day 4 - Traveling to Bologna by Train

Today you're leaving the pizza paradise that is Naples and heading for the heartland of Italian cuisine, Emilia-Romagna and more specifically, Bologna. We'll arrange for a driver to pick you up from your accommodation and take you to Napoli Centrale station in plenty of time for your direct train to Bologna. The journey takes a little under four hours. We've included standard class tickets but upgrades are available for an additional fee.

We also offer the following excursions in Naples

Amalfi Coast Small Group Tour
Moderate9 hours
Authentic Pizza Making Group Class with Aperitif
Easy2 hours
Half Day Small Group Tour of Pompeii
Light4 hours
Half-day Private Excursion to Caserta from Naples
Light5 hours

3 Nights in Bologna

3 Nights in Bologna

4 days in Bologna
4 days in Bologna

3 Nights in Bologna

Bologna is the capital of Emilia Romagna and makes a fantastic base for exploring the legendary 'food valley'. The city's history stretches back a few hundred years before Christ and it is home to the oldest university in Europe. These facts are responsible for two of the nicknames Bologna owns with pride. La Dotta – 'the learned one' and La Grassa – 'the fat one'. Truly you're never far from a spectacular meal in Bologna, as long as you're not vegan. Emilia Romagna might not be a name that's as well known as neighboring Tuscany but its food specialties are renowned the world over. The king of Italian cheeses: Parmigiano Reggiano, Prosciutto di Parma and traditional Aceto Balsamico are all from around here and a visit to see how they're produced is a must. Petrolheads will also find much to love in Emilia Romagna. Ferrari, Lamborghini, Ducati and Maserati are all produced close by and have museums or factory tours available. If 'slow food' and fast cars aren't your thing then Bologna still doesn't disappoint. A thriving arts scene means you'll easily find a more cultured diversion, from art galleries to operas. And if you want to work up an appetite, the gently leaning Asinelli Tower's almost 500 steps will help you burn some calories. From the top you'll see why Bologna has another nickname 'La Rossa' – the red one, as you gaze out over the red tiled roofs of the old city, which escaped WWII largely undamaged by Allied bombing raids.

Bologna is the capital of Emilia Romagna and makes a fantastic base for exploring the legendary 'food valley'. The city's history stretches back a few hundred years before Christ and it is home to the oldest university in Europe. These facts are responsible for two of the nicknames Bologna owns with pride. La Dotta – 'the learned one' and La Grassa – 'the fat one'. Truly you're never far from a spectacular meal in Bologna, as long as you're not vegan. Emilia Romagna might not be a name that's as well known as neighboring Tuscany but its food specialties are renowned the world over. The king of Italian cheeses: Parmigiano Reggiano, Prosciutto di Parma and traditional Aceto Balsamico are all from around here and a visit to see how they're produced is a must. Petrolheads will also find much to love in Emilia Romagna. Ferrari, Lamborghini, Ducati and Maserati are all produced close by and have museums or factory tours available. If 'slow food' and fast cars aren't your thing then Bologna still doesn't disappoint. A thriving arts scene means you'll easily find a more cultured diversion, from art galleries to operas. And if you want to work up an appetite, the gently leaning Asinelli Tower's almost 500 steps will help you burn some calories. From the top you'll see why Bologna has another nickname 'La Rossa' – the red one, as you gaze out over the red tiled roofs of the old city, which escaped WWII largely undamaged by Allied bombing raids.

Day 4

Day 4 - Arrival in Bologna

Bologna's train station is on the edge of the historic center of the city where your hotel is located. We'll arrange for our driver to pick you up from the platform and take you to your centrally located accommodation.

Climb the Asinelli Tower

Suggestion to explore on your own

For Bologna's best view, climb one of its landmarks: the Asinelli Tower. The taller of the Two Towers, its 498 steps will take you to more than 300 feet above the old town's center. This 900 year old tower was built with the same combination of wealth, hubris, and technological innovation that drive today's skyscrapers, it was the One World Trade Center or Burj Khalifa of its day. Unlike those giants however this tower is a serious workout and best attempted only if you're in good shape!

Climb the Asinelli Tower

Day 5

Day 5 - Your First Full Day in Bologna

Private Food Walking Tour

Private Food Walking Tour

Included in your vacation package price.

Explore one of Bologna oldest food markets with an insider and visit the most traditional food shops. Learn about the history, culture, architecture, that make Bologna's medieval market so unique. During this tour you will enjoy a variety of food specialties that has secured Bologna’s reputation as the foodie capital of Italy. Discover the secrets to having the ultimate food and cultural experience off the beaten path with an expert local guide.


Activity Level : Light
Duration : 2.5 hours

Day 6

Day 6 - Your Second Full Day in Bologna

A Day for Motorsports Fanatics

Suggestion to explore on your own

The region of Emilia-Romagna is often referred to as Motor Valley. Ferrari, Ducati, Lamborghini, Maserati, and Pagani are all found close to Bologna. UNESCO-listed Modena is home to the Enzo Ferrari Museum and an easy train journey from Bologna. In Modena, you might even fit in a visit to the Municipal Balsamic Vinegar Factory. Other factories are dotted around the area in smaller towns, but public transport links are quite good. Check out your favorite marque's museum or factory tour websites for opening hours and tour times.

A Day for Motorsports Fanatics

Day 7

Day 7 - Traveling to Lucca by Train

We hope you've had your fill of Emilia-Romagna's specialties because today you're headed to one of Tuscany's under-the-radar delights, Lucca! A private driver will take you from your accommodation to Bologna's main train station in plenty of time for your departing train and we will provide standard class tickets for the two regional trains you'll need to take to get there. Unfortunately the regional trains do not offer a first class option. The journey takes just under two and a half hours. If you would prefer a door-to-door service and maximum comfort we can arrange a private transfer for an additional fee.

You can upgrade your transfer

Upgrade to Lucca by Private Transfer

Lucca by Private Transfer

Upgrade for an additional cost
We also offer the following excursions in Bologna

Bologna Group Walking Food Tour
Light2 hours
Bologna Group Walking Tour
Light2 hours
Bologna Private Bike Tour
Light2 hours
Bologna Private Cooking Class
Easy3 hours

2 Nights in Lucca

2 Nights in Lucca

3 days in Lucca
3 days in Lucca

2 Nights in Lucca

One of Tuscany's most attractive and best-preserved towns, Lucca is a must-see for those exploring the region. While Lucca works as a day trip, it's best experienced as a base from which to explore the surrounding area, by foot, bike, or private transfer. Predating the Roman empire, Lucca's long history is visible in its Roman ruins (including a plaza shaped like the amphitheater it was built on), as well as its medieval and gothic towers, villas, and churches. The town's four kilometers of preserved city walls, which still encompass the historic center, are one of its chief attractions. Walking along the top of the walls, you can experience history while getting your bearings and figuring out where to go next. The hometown of Giacomo Puccini, Lucca draws many opera lovers, who come to visit his villa and see regular performances of his works. In July and August, the neighboring town of Torre del Lago hosts a festival devoted to Puccini. For those with more modern tastes, Lucca's center hosts a series of concerts by major international rock groups, held from the end of June into July.

One of Tuscany's most attractive and best-preserved towns, Lucca is a must-see for those exploring the region. While Lucca works as a day trip, it's best experienced as a base from which to explore the surrounding area, by foot, bike, or private transfer. Predating the Roman empire, Lucca's long history is visible in its Roman ruins (including a plaza shaped like the amphitheater it was built on), as well as its medieval and gothic towers, villas, and churches. The town's four kilometers of preserved city walls, which still encompass the historic center, are one of its chief attractions. Walking along the top of the walls, you can experience history while getting your bearings and figuring out where to go next. The hometown of Giacomo Puccini, Lucca draws many opera lovers, who come to visit his villa and see regular performances of his works. In July and August, the neighboring town of Torre del Lago hosts a festival devoted to Puccini. For those with more modern tastes, Lucca's center hosts a series of concerts by major international rock groups, held from the end of June into July.

Day 7

Day 7 - Arrival in Lucca

Upon arrival we will arrange for a private driver to welcome you at the train station and take you to your accommodation in Lucca.

Hiking or Biking from Lucca to Pisa along Renaissance Aqueducts

Suggestion to explore on your own

“Via degli Acquedotti” (the Aqueduct Trail) is a photogenic 25-km hiking route from Lucca Cathedral to Pisa Cathedral through the Monte Pisano, following the Nottolini and Medici aqueducts across a scenic, hilly swath of countryside. Well marked, it can be done in a long day by hikers in good shape, or with a mountain bike.

Hiking or Biking from Lucca to Pisa Along Renaissance Aqueducts

Day 8

Day 8 - Your First Full Day in Lucca

Lucca Private Walking Tour

One Roman Ampitheater, One Hundred Churches

Included in your vacation package price.

Lucca is commonly referred to as "The City of One Hundred Churches." Since you’ll hardly be able to visit them all in just one day, we suggest focusing on the cathedral, commonly referred to as "Il Duomo," and its beautiful art. St. Michael's Church, located in the square of the same name in the heart of the historic center, is set on the most famous street of Lucca, Il Fillungo, where you’ll find the city's most important and prestigious shops. From Fillungo, a nice walk will lead you to Piazza dell’Anfiteatro or Amphitheater Square, a true jewel from Roman times. As you stand inside the oval square, you can clearly see its buildings were built around the original elliptical structure typical of Roman amphitheaters.


Activity Level : Moderate
Duration : 3 hours

A Garden Atop a Medieval Tower

Suggestion to explore on your own

The famous Torre Guinigi is the most easily visible landmark in the city, thanks to the trees at the very top. Although it stands out over other city center buildings, you can't use it as a point of reference since all the narrow streets here are surrounded by historic buildings (which are home to antique shops) that often limit your general view. The roof garden is a splendid view point and a popular attraction, built when the Guinigi family sought to create a garden as a symbol of the town's rebirth while under their control.

A Garden Atop a Medieval Tower

Day 9

Day 9 - Traveling to Milan by Train

Your time in Lucca has drawn to a close and it is time to explore Milan, Italy's fashion and finance capital. We have included standard class train tickets but an upgrade to higher class is possible at an extra cost. The journey takes around five hours and you will most likely need to change trains at least once. We will arrange for a driver to pick you up from your accommodations in Lucca and take you to the train station for your departing train.

We also offer the following excursions in Lucca

Flavors of Lucca Group Food Tour
Light2 hours 30 minutes
Lucca Private Bike Tour
Moderate3 hours
Lucca Private Walking Tour With Food And Wine Tasting
Light3 hours

2 Nights in Milan

2 Nights in Milan

3 days in Milan
3 days in Milan

2 Nights in Milan

Italy’s fashion and business hub, Milan fizzes with energy. But don't let the city's professional side fool you: this is a place that prides itself on history and culture, and the locals always seems to be having a good time. Milan's signature building is the Duomo, an imposing Gothic cathedral that sits in the heart of this former Roman capital. The combination of its size and beauty make it a must-see sight. You can also look forward to elegant evenings at the legendary La Scala opera, charming cafes and restaurants, great shopping opportunities, and breathtaking art and architecture. Home to Da Vinci's Last Supper, Milan is also rich in art galleries, from the old masters to contemporary art. This being Italy, you'll find delicious cuisine here too, and the "aperitivo" is one of the most interesting traditions of Milan gastronomy. At many of the city's cafes and bars in the early evening you can pay a slightly higher price for a drink and get your pick from a free buffet. It's one of the best ways to experience the different flavors of Milanese cooking. The compact city center means that one or two days should be enough to satisfy your curiosity.

Italy’s fashion and business hub, Milan fizzes with energy. But don't let the city's professional side fool you: this is a place that prides itself on history and culture, and the locals always seems to be having a good time. Milan's signature building is the Duomo, an imposing Gothic cathedral that sits in the heart of this former Roman capital. The combination of its size and beauty make it a must-see sight. You can also look forward to elegant evenings at the legendary La Scala opera, charming cafes and restaurants, great shopping opportunities, and breathtaking art and architecture. Home to Da Vinci's Last Supper, Milan is also rich in art galleries, from the old masters to contemporary art. This being Italy, you'll find delicious cuisine here too, and the "aperitivo" is one of the most interesting traditions of Milan gastronomy. At many of the city's cafes and bars in the early evening you can pay a slightly higher price for a drink and get your pick from a free buffet. It's one of the best ways to experience the different flavors of Milanese cooking. The compact city center means that one or two days should be enough to satisfy your curiosity.

Day 9

Day 9 - Arrival in Milan

Upon arriving to Milan's main station, Milano Centrale, we'll arrange for our driver to pick you up from the platform and take you to your centrally located accommodation.

Milan By Night - Private Tour in a Fiat 500

Find Trendy Aperitifs with a Vintage Fiat 500

Please ask your travel advisor for the cost to add this to your package

Milan is where the modern Italian obsession with "aperitivo" was born. That's when most of the local bars prepare a rich buffet with finger food to go with their drinks. The out-of-center area of Navigli is a local favorite but your hotel reception can point you in the direction of places closer by too. We recommend venturing around and exploring, or using a local guide for a tasty tour. You could even ride in a cute Fiat 500 to attract the envious eyes of passers-by. Navigli is also an artsy neighborhood with many art studios and little galleries hidden down side streets well worth exploring by day too.


Activity Level : Light
Duration : 3 hours

Day 10

Day 10 - Your First Full Day in Milan

Milan Private Half-Day Tour

Milan Private Half-Day Tour

Included in your vacation package price.

This three-hour walking tour will give you a better idea of the layout of Milan and will also show you the city's most important monuments. An expert local guide will tell you all about the history that has made the city special. You'll come away with more knowledge of Milan and an appreciation of the past that has made it what it is today.


Activity Level : Light
Duration : 3 hours

Leonardo da Vinci and his Milanese Masterpieces

Suggestion to explore on your own

Leonardo da Vinci spent many years in Milan, where some of his works are still kept. Start at the Pinacoteca Ambrosiana, a treasure chest that displays "The Portrait of a Musician" and "The Atlantic Codex." You can see "The Last Supper" in the Convent of Santa Maria delle Grazie. Tickets are very hard to get, and the official website is sold out a year in advance. We recommend booking a tour with our expert local guide, which includes the entrance ticket.

Day 11

Day 11 - Departure Day

We will arrange for a driver to transfer you to Milan's main international airport, Malpensa, in plenty of time for your flight.

We also offer the following excursions in Milan

Best of Como Lakeside Private Tour from Milan
Light9 hours
Best of Milan: The Last Supper, Duomo & City Small Group Tour
Light3 hours
Historical Tour of Milan and the Last Supper Group Tour
Light3 hours
Milan City Center Private Tour with Fiat 500
Light2 hours

What's Included

Here are all the services provided as part of your complete vacation package. See what every JayWay trip includes.
Please let us know if you'd like to upgrade any transfers or add any additional tours or excursions to your itinerary.

Naples

3 Nights Accommodation
Breakfast (hotels only)
Naples Airport Transfer
Naples Private Walking Tour
Pizza Lesson Small Group Experience
Pompeii and Mount Vesuvius Private Excursion
Naples Train Station Transfer
Naples - Bologna Standard Class Train Ticket

Bologna

3 Nights Accommodation
Breakfast (hotels only)
Bologna Train Station Transfer
Private Food Walking Tour
Bologna Train Station Transfer
Bologna - Lucca Standard Class Train Tickets

Lucca

2 Nights Accommodation
Breakfast (hotels only)
Lucca Train Station Transfer
Lucca Private Walking Tour
Lucca Train Station Transfer
Lucca - Milan Standard Class Train Tickets

Milan

2 Nights Accommodation
Breakfast (hotels only)
Milan Train Station Transfer
Milan Private Half-Day Tour
Milan Malpensa Airport Transfer

package excludes:


  • Flights to and from Europe.
  • Tips for Tour Guides, Drivers and Local Reps.
  • Meals (other than breakfast if included in room rate and meals listed as included in food tours and excursions, unless explicitly stated otherwise).
  • Parking fees for your Rental Car (if you are booking one with us) unless otherwise indicated. Some hotels provide free parking facilities.
  • Travel Insurance. See the insurance link on our website
Benefits of Traveling with JayWay

A JayWay vacation is more than the sum of its parts. Our team work tirelessly to ensure your experience is memorable for all the right reasons. Your trip is personalized to maximize your enjoyment. You're taken care of every step of the way.

A Travel Advisor who speaks your language

We will make sure that all your requirements and interests are taken into account in preparing your itinerary.

A totally tailored itinerary for your vacation

Your trip is customized for you by  an experienced trip planner and an expert on the region.

A choice of hand-picked hotels and excursions

We've personally inspected and tested all the hotels and local tour providers we work with to ensure quality.

Detailed pre-trip preparation to make the most of every day

Your Europe-based Tour Manager will be in touch by email and phone a month before you arrive to finalize timings.

On-trip Concierge Service to smooth out any bumps in the road

Your tour manager is at your service throughout your journey. We'll provide a local SIM so you can stay connected.

Personalized Guest Page to make sure you're not missing out

Packed with detailed information and recommendations curated by locals on the best things to do, see and eat.
Get an Instant Price Estimate

Choose the month of travel, how many travelers and what star level accommodation you'd like to stay in, then get an instant price estimate.

Once you’ve done that you can request a tailor-made itinerary based on this by entering just a few more details.






Per Person Package Price from*
Get your personalized itinerary based on this trip.


Sending ...
Thank you!

Thank you for your interest in taking a trip based on this itinerary. One of our expert travel advisors will be in touch soon to start tailoring it precisely to your preferences.

Ooops!?

Something went wrong at our end, please try again in a moment.

Go To Top