Next trip Previous trip
Prices from
International flights excluded
$ 9,402
Price based on 4 pax
$ 9,402 p.P.
Price based on 6 pax
$ 9,402 p.P.

20 days


Request your free quote now! Receive a free quote from your local travel agency within 48 hours by e-mail.
No obligation to purchase.

Filippo is our Destination Expert in Italy.


  • Roman & Italian Cuisine
  • Immersive Experiences
  • Exclusive Activities
(avg rating 5.0/5)
Show latest reviews  

Rouan Du Rand
"Italy is amazing. Venice, Rome, Florence...we have to go back!! This was an absolutely incredible v...".

Go to complete review. Payment Plus

  • Credit card or bank transfer payment option
  • Protection against agency insolvency
  • Ease of mind
  • All this for only 2.5% more
See more

Activities & Transport

  • Hiking
  • Meet the Locals
  • Rafting
  • Trekking
  • Wellness
  • Car with driver
  • Train

Main travel focus

Cultural visits
Nature & landscapes




Countryside Italian Explorer

Boat Day in Lake Como - Wine Day in the Chianti Hills - Town Hopping in Cinque Terre - Pompeii and Mount Vesuvius
Unique about this tour:
  • Private Boat Trip in Lake Como
  • Brunello di Montalcino Wine Day in Tuscany
  • Tour of Pompeii and Mount Vesuvius Climb
  • Day Trip to Montecassino

If you are planning a trip to Italy and love the great outdoors, this trip is for you! Nature, adventure, and culture encompass this 20 day trek through the north of the country, through Tuscany, and eventually to the Eternal City of Rome. This trip is not for the faint of heart, but we promise the experience of a lifetime for those who want to become a true Countryside Italian Explorer!

  Show more


  • Concierge service
  • 19 nights accommodation in double room in 4-star hotels with breakfast
  • Private, English-speaking guides for each tour
  • All admissions
  • Private transfers in air-conditioned car to and from the airport/train station
  • High-speed train tickets
  • City tax for hotels
  • Flights
  • Any special events not included in the itinerary
Optional (Available upon request)
  • Private transfer to the meeting point of your tour or back to your hotel after the tour

Example Trip to customize

Lake Como  

Welcome to Italy!

Welcome to Italy!

It's time to start your luxury vacation. We have some great activities planned for you and your family - first stop is Venice!

Once you arrive in Venice, an English-speaking attendant will be there to greet you right after baggage claim to take you to your Venice hotel.

An exciting and fascinating setting awaits you in Venice with spaces and rooms evoking an enchanting atmosphere at Palazzo Barbarigo.

Head to Da Fiore for a superb meal. 35 years ago, this old tavern was first transformed into one of the most prestigious and exclusive places in the city for high quality food in and elegant environment.

Day 1
Hotels Hotels

Comfort Accommodation

Palace Hotel

Lake Como  

Discover Enchanting Venice

Venice, the most romantic city in the world, never ceases to dazzle newcomers and seasoned veterans alike.

Although it is a small island, there is so much to see!

It’s best to see it with an expert, local guide who will show you the city by walking and by boat!

You'll benefit from the skip-the-line tour of St. Mark’s Basilica, the church of gold.

Take a private cruise on the Grand Canal and see the wonders of Venice in style!

Visit the Peggy Guggenheim Museum, where you'll find the biggest and the most beautiful collection of art dedicated to the Italian European and American art from the 1900s. You will find masterpieces by artists like Pollock, de Chirico, Picasso, Kandinsky, Brancusi, and Duchamp.

Have a meal at Taverna Scalinetto, located within walking distance of San Marco Square, just outside of the tourist-filled area.

Day 2
Hotels Hotels

Comfort Accommodation

Palace Hotel


Explore the Impressive Doge's Palace

Venice is an amazing city full of artwork, culture, beauty and romance. Amidst the canals, gondolas, cafe’s and grand piazzas you have the Doge’s Palace with its breathtaking facade, the epicenter of this city and a cornucopia of its splendor.

Continue discovering this majestic city with your personal English-speaking local tour guide and skip the line at the Doge's Palace with a special ticket. Take the comprehensive tour including the Palace Courtyard, The Giant Staircase, Doge’s Apartments, Bridge of Sighs, and more.

In the magnificent rooms of the Doge's apartment in Palazzo Ducale, Tintoretto returns to the forefront of a major exhibition project.

Dine at Osteria Enoteca San Marco, a popular spot on the main island in Venice with over 300 types of wine and a delicious menu.

Day 3
Hotels Hotels

Comfort Accommodation

Palace Hotel

Lake Como  

Travel to Romantic Florence and Visit the Santa Maria Novella Pharmacy

The next stop in your journey is Florence, the cradle of the Renaissance.

Here, artistic treasures and architectural masterpieces of the past blend with ancient streets lined with elegant boutiques, peaceful parks, and cafes. This city is a definite must see while you are in Italy.

You will find your personal English-speaking assistant ready to accompany your from the hotel to the train station to catch your train south.

Once you arrive you will find your personal English-speaking driver waiting for you at the train station to drive you to your hotel in Florence.

Visit the Santa Maria Novella Pharmacy, which has been operating since the 13th century. Pay attention to the address marked on a small sign. You'd walk right by unless you knew there was something there.

Head to Ristorante Malborghetto, a restaurant with great views of Ponte Vecchio.

Day 4
Hotels Hotels

Comfort Accommodation

Palace Hotel


See Michelangelo's David and Admire Ponte Vecchio

We have the perfect tour for you to experience and see a majority of Florence. Learn how the power of the Medici family shaped the Renaissance capital of the world and discover Dante’s district! No rush, just highlights and an expert, local English-speaking guide.

Benefit from skip-the-line tickets to see Michelangelo’s David at the Galleria dell'Accdemia and visit the leather market, Dante’s district, and Ponte Vecchio.

Also, explore Via de' Neri, named after a famous old family. It’s a lovely street with many cafes, gelaterias, restaurants, and other shops. It's worth taking a walk along this street and just enjoy the day.

At tonight’s restaurant, ‎Cinghiale Bianco, consider being adventurous and trying wild boar as your main dish.

Day 5
Hotels Hotels

Comfort Accommodation

Hotel Giglio

Tuscan Hills  

Take a Private Tour of the Uffizi Galley

Calling all art lovers!

The Uffizi Gallery is filled with artwork from renowned Italian Renaissance masters like Michelangelo, Leonardo, Caravaggio & Botticelli.

Skip the long lines with one of the best private guided Uffizi tours in Florence, a tailored tour of the most important masterpieces and hidden gems in the museum!

Also, tour the Central Market, an open-air market that has a cast iron structure dating back to 1874, offering a variety of food shops catering to local residents and restaurants.

Enjoy dinner at the Trattoria Sostanza. This beautiful place is a great restaurant for families with kids and it has a huge vegetarian-friendly menu.

Day 6
Hotels Hotels

Comfort Accommodation

Hotel Giglio


Admire the Piazza IV Novembre in Perugia

Ah Tuscany!

Great wines, fantastic food, rolling hills, breathtaking there more to add about this region?

Today is your turn to visit this beautiful part of Italy rich in history and culture.

You will have a private car and English-speaking driver to cruise in style and comfort to your hotel in Tuscany, the Castello delle Serre, a perfect environment for wine lovers, romantics, and adventurers!

Admire the Piazza IV Novembre, the most important and beautiful square of the city of Perugia.

In the center of this square you'll have the chance to see the Fontana Maggiore, the symbol of this city.

Today's special restaurant will be Agriturismo Ischieto, an elegant and romantic restaurant that offers traditional Italian, and especially, Tuscan food.


Day 7
Hotels Hotels

Comfort Accommodation

Hotel Giglio


Be Mesmerized By the Rolling Hills of Montalcino and Taste Some of the Best Wine in the World

Today you will discover the heart and soul of Tuscany! Our English-speaking driver will pick you up at your hotel and guide you through the rolling hills of Montalcino.

Taste some of the best wine in the world, Brunello! Make sure to bring a camera to take pictures of the spectacular scenery and vineyards.

Since you’ll be drinking wine, then definitely fill up on some of the local Tuscan traditional foods you’ll find at the restaurants around the countryside, including wild boar which is quite delicious!

Tonight, have dinner at Enoteca Bacchus - I Sapori Di Montalcino, a place with great reviews from us and clients! Surrounded by a classic Italian atmosphere and some wine, you are sure to enjoy this evening.

Day 8
Hotels Hotels

Comfort Accommodation

Hotel Giglio

Tuscan Hills  

Tour Pretty Siena and the Impressive Hilltop Town of San Gimigiano

Get ready for a day of medieval cities!

See alluring Siena and the amazing hilltop town of San Gimignano. For this trip, you’ll have a private car and English-speaking driver to bring you to each location in comfort.

First, use your skip-the-line tickets to stroll right into Siena’s stunning cathedral.

Then, hit the Piazza Tolomei. In this small square in Siena you will find the Palazzo Tolomei, the oldest private residence in Siena. It is an imposing, Gothic style urban palace erected between 1270 and 1275 by the Tolomei family.

Next, discover hidden gems in charming San Gimignano

The seasonal variations and the richness of the farming products are expressed in the cooking at Ristorante il Celliere a Castagnoli and have come to create some notable dishes typical of Tuscany cuisine. Enjoy your top notch dinner here!

Day 9
Hotels Hotels

Comfort Accommodation

Hotel Giglio

Sieve River  

Travel to Eternal Rome and Stop in Orvieto and Civita di Bagnoregio En Route

Today you will be traveling from Tuscany to the eternal city... Rome!

Enjoy your journey and welcome to Roma, the home of gladiatorial tales and artistic masterpieces by the likes of Michelangelo and Bernini!

Along the way you will stop in two beautiful places for time to stretch out, grab lunch and do some exploring outside of the car. Enjoy your journey and welcome to Roma!

Stop in Orvieto and take some time for lunch and exploration. You may also stop in Civita di Bagnoregio, which used to be a thriving medieval town, but now it's home to just 14 full-time residents!

The view of Civita di Bagnoregio from the Belvedere is one of the most out-of-this-world panoramics in Italy.

Once in eternal Rome, go to the Osteria Del Pegno - This restaurant is located near Piazza Navona, offering amazing authentic Italian food and atmosphere.


Day 10
Hotels Hotels

Comfort Accommodation

Hotel Giglio

Cinque Terre  

Experience the Sistine Chapel Without the Crowds

What makes this tour the best Vatican tour in Rome? When you reserve these Vatican tour tickets, you'll skip the line and enter a full hour before the general public.

Experience the Sistine Chapel when it is practically empty with a guide dedicated just for you.

Afterwards, head to Pincio Square. This square on the edge of Villa Borghese Park and near the Piazza del Popolo has an amazing panoramic view of the Roman skyline.

Have lunch at Il Peperoncino D’Oro, an excellent bistro style restaurant tucked away on Via del Boschetto. 

In the afternoon, stop at the Pantheon, Trevi Fountain, Piazza Navona, Aventine Hill, and more to enjoy the many wonders of Rome.

We recommend the Sant'Eustachio Il Caffè coffee shop near the Pantheon, famed for its home-roasted beans, blended with water from an ancient aqueduct.

Have dinner at I Monticiani, a cozy local restaurant.

Day 11
Hotels Hotels

Comfort Accommodation

Hotel La Toretta

Cinque Terre  

Take a Wonderful Skip-The-Line Colosseum Tour

Used for gladiator fights, mock sea battles, animal hunts and fights, mythology drama shows and even public executions, the Roman Colosseum is a must-see attraction in Rome. 

Witness the incredible history of this 2,000 year old building up close and personal on our exclusive skip the line Colosseum Tour.

Take a private skip-the-line Colosseum tour with exclusive Arena Floor access and a guided tour of the Roman Forum and Palatine Hill.

Discover Monti Area, with winding cobbled streets that will mesmerize you as you stroll through and observe the Italian families on their evening strolls and the atmosphere of the cafes, restaurants, and shops in the area.

Situated down a little cobbled street in Trastevere, Le Mani in Pasta is a must visit while you are in Rome!

In our opinion, it has some of the best fish dishes in all Rome!

Day 12
Hotels Hotels

Comfort Accommodation

Hotel La Toretta

Cinque Terre  

Arrivederci, Roma!

You have eaten and drunk your way through Italy like the royalty you are.

You have seen many amazing sights and are ready to go home and show off your pictures to friends and family. This is definitely not a goodbye.

We will see you again next year to explore some more!

An English-speaking driver will wait for you outside your hotel to take you in luxury to the Rome Fiumicino Airport.

Day 13
Hotels Hotels

Comfort Accommodation

Hotel La Toretta