Classic Italy Vacation

.Classic Italy Vacation

From small-group & private tours to cooking classes, private transfers, the best hotels, and accommodations – we curate the most incredible authentic experiences through Italy for the entire family.  No matter if your travelers’ ages range from 5 to 75, we will make sure that everyone is comfortable and enjoying the journey while creating life-long lasting memories.

Here are some of the experiences our clients have enjoyed during this trip. All activities can be customized to match our clients’ preferences.

Grab a FREE CONSULTATION here to start planning your trip.

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Day 1 

Depart from your home airport

Classic Italy Vacation

Day 2

Arrive at Venice Marco Polo Airport (VCE)

Our transfer will be waiting for you at the airport to take you to your hotel.

Check in at Hotel.

Venice Afternoon at Leisure After Arrival.

Day 3

Absolute Venice: Walking Tour, The Doge’s Palaces & Golden Basilica

Combine three exciting tours of Venice for a fun and also comprehensive experience of the Serenissima Repubblica, the best way of learning all there is to learn about this most beautiful of European cities. On the first tour, you will be taken on a delightful stroll to all of the city’s most important landmarks. After beginning at the magnificent Piazza San Marco, where you see the Basilica, the Bell and Clock Tower and more, head off towards Santa Maria Formosa, another magnificent square. Along the way you will discover very interesting buildings such as Marco Polo’s home and even the Pantheon of Venice. Finish with a walk through the Mercerie.

The second tour is that of the Doge’s Palace, where you will explore the magnificence and also opulence that decorate the ample interior of the Palazzo Ducale. Admire the wealthy ornaments and also decor, cross the famous Bridge of Sighs like prisoners in ages past and even delve into the Venetian prisons. Feel transported to the privileged side of the Mediaeval Ages.

Classic Italy Vacation

The final tour of this triple decker is The Golden Basilica, by far the most majestic cathedral in Venice. Roam around the interior of this masterpiece of byzantine art and also gorge your eyes on the splendid gold mosaics and marble inlays. After learning all about the biblical scenes represented in the cathedral, this tours offers an optional private boat trip to Murano to visit the glass factory that blows life into Venice’s famous glass.

Duration: Approx. 4 hours.

Start/opening time: At 8.45am.

Classic Italy Vacation

Romantic gondola serenade in Venice

Lose track of your senses and also give up to the beauty of Venice on this romantic promenade by gondola. One cannot simply visit the Queen of the Adriatic and not enjoy a ride on the long black gondolas that glide through the city’s many labyrinthine canals; and what better way to do it than with live music on board, so as to further enhance the overall artistic essence of this wonderful city.

So book a Gondola Serenade Group Tour and take pleasure in this delightful soothing journey along the quiet canals. This is by far the best way to soak up the atmosphere of the city. With the elegant ride, the music and the magnificent architecture, some might be tempted to lie prone, enraptured with Stendhal’s Syndrome due to the overwhelming beauty of it all.

Classic Italy Vacation

As you softly glide along the dark waters of the canals, you will soon come to realize why Venice was destined to become a large seaside power during the Mediaeval Ages, paving the way for the splendorous Renaissance age that then bloomed throughout the many Italian cities during the fourteenth and fifteenth century. The legacy of these wonderful times for science and art is made obvious on the facades of the many incredible buildings you’ll glide by.

Come along for the ultimate romantic tour of Venice.

The moment you step onto the gondola, you will feel like you are stepping onto a dream; a dream that will recur in your thoughts for a very long time afterwards.

Duration: Approx. 35 minutes.

Start/opening time: April to October at 6.30pm and 7.30pm.

Classic Italy Vacation

Day 4

Check out at Hotel.

Transfers to Venice Train Station from Hotel Private Boat.

Train from Venice to Florence About 2 hrs train ride.

Transfer to Hotel in Florence From the Train Station Private Luxury High Class Sedan.

Check in at Hotel – 4 nights in Florence.

Classic Italy Vacation

Day 5

GRAND TUSCAN DRIVING – FULL DAY TOUR

We like to run our tours as if we were welcoming a friend who has come to visit! We’ll take you to all our most favorite places that we know in our beloved Tuscany, such as a friend’s villa in the countryside, and over the roads to see the best sights while making the most of your day in Tuscany.

You and our expert tour escort will start from our meeting point in the center of Florence, exit out through the walls of the city and drive towards the panoramic Piazzale Michelangelo to admire a unique view of Florence and the picturesque church of San Miniato.

Classic Italy Vacation

Then a scenic ride up will lead us to the picturesque town of Fiesole, located to the northeast of Florence. Once in Fiesole you get to see one of the best views of Florence. The ride then continues further into the hills where you will eat at one of our favorite restaurants in the area – which is claimed by many of our guests to be one of the best meals of their trip!

On the return trip back to Florence, we will stop at a local family run Chianti vineyard to see where their wine is made and stored, and a look at their personal stash of olive oil. Tasting of both is encouraged!

We drive back to Florence arriving no later than 3.30-4 p.m. The tour includes a Tuscan lunch and wine tasting, a fully equipped Fiat 500 and an expert guide to show you the way.

Classic Italy Vacation

Day 6

CHIANTI AUTHENTIC EXPERIENCE

A comprehensive experience in one of the most fascinating areas of Tuscany, known all over the world for its wine and its countryside of unrivaled charm, where woods alternate with vineyards and olive groves, in a landscape dotted with Romanesque parish churches, farmhouses, villas and castles of rare beauty.

The first stop of the tour is in the heart of the Florentine area of Chianti Classico, in a historic Winery with Castle producing also one of the most appreciated Chianti extra virgin olive oil. Here we experience an original itinerant tasting tour with four different wines and local products, guided by an expert winemaker, while visiting the ancient wine cellars under the Castle, admiring the vineyards and enjoying the delightful garden.

Classic Italy Vacation

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We continue then to the picturesque medieval village of Greve, birthplace of the famous navigator Giovanni da Verrazzano, where every year takes place the most important wine fair of the Chianti region. Here we will have free time to admire the famous main square of the ancient “market” with its characteristic arcades and to browse through the local artisan shops. Moving along the ancient “Via Chiantigiana”, we cross the heart of the Chianti Classico, admiring the breathtaking views of the rolling hills that made so famous this part of Tuscany. We reach then a family-run Winery located in the Sienese area of the Chianti Classico, which stands out for the excellent quality of its wines.

Classic Italy Vacation

Here we will be warmly welcomed by its passionate winemaker and after the guided tour of the cellars and also the lovely aromatic garden, a delicious tasting of four different wines and local products will be waiting for us. The last stop of the tour is Castellina, a fortified hilltop village of Etruscan origin, among the most lively and picturesque of Chianti, characterized by an imposing fortress: here, walking through the picturesque medieval covered street “Via delle Volte”, the tour leader will guide us to discover the charming historical centre and its picturesque houses, squares and shops.

Duration: Five hours approx.

Start/opening time: At 2 pm.

Classic Italy Vacation

Classic Italy Vacation

Day 7

Tuscany in a Day – Pisa, San Gimignano and Sienna

Day Trip from Florence.

See the best and also the most beautiful spots that Tuscany has to offer with this one day tour to Pisa, San Gimignano and Sienna.

We kick-start our day of discovery from Florence with a tour of Pisa, home of the legendary Leaning Tower. Stand in the centre of the stunning Piazza dei Miracoli, and also take in the magnificence of the Baptistery, Cathedral and Leaning Tower surrounding you. We enjoy a traditional Tuscan lunch in a wine bar or restaurant complemented by a tasting of renowned local wines.

Classic Italy Vacation

After lunch, our discovery continues on to the splendid medieval town of San Gimignano. A Unesco World Heritage Site, the town is set in a charming location, perched atop one of the rolling Tuscan hills, with its golden buildings contrasting beautifully with the verdant green landscape.

Classic Italy Vacation

We continue along the panoramic roads of the Chianti region on to the city of the Palio, Sienna. Here, our official guides will take you on a whirling tour of the city; pointing out important monuments, palazzos and also piazzas, including the famous Piazza del Campo (where the Palio di Siena horse race is run). We also have time to admire the Piazza del Duomo, as well as inside and outside the cathedral. Enjoy some free time in Sienna to stroll along its historic streets before we return back to Florence.

Meeting/pick-up point: Inside Santa Maria novella train station, in front of the pharmacy. Please be at the meeting point 15 minutes before the start time.

Duration: 12.5 hours.

Start/opening time: At 7:45 am.

Day 8

Check out at Hotel.

Transfers to Florence Train Station From the Hotel Private Luxury High Class Sedan

TRAIN FLORENCE TO ROME 1.5 hrs train ride

Transfers from Rome Train Station to Hotel

Check in at Hotel – 3 Nights In Rome.

Day 9

Vatican Museums, Sistine Chapel and St. Peter’s Basilica Tour

Skip the line.

The Vatican Museums attract millions of tourists every year and it’s also clear to see why. Come and also see for yourself the beautiful artwork and artefacts which inhabit the museums from Vincent Van Gogh’s Pietà, after Delacroix, which is housed in the Collection of Modern Religious Art, to the Augustus of Prima Porta in the Braccio Nuovo. The various sculptures and paintings are a sight to behold and at night they’re even more so.

After the visit to the Museums you will be taken to the renowned Sistine Chapel, the official residence of the Pope in Vatican City. Get a taste of the architecture and also the art which has gone into making the Sistine Chapel what it is today, with work from some of Italy’s most famous Renaissance artists, including Michelangelo and Pinturicchio. See the gorgeous Sistine Chapel Ceiling, covered in art including The Creation of Adam and also many more pieces by Michelangelo.

Visit the renowned St Peter’s Basilica. Venture inside the Basilica and find yourself lost in the amazing architecture and also the artworks which have gone into bringing this magnificent building to life. Created during the Renaissance period, the building is filled with art from famous Italian artists of the time and was even designed by the famous Michelangelo himself. See the beautiful altar which sits above the resting place of the tomb of St Peter himself, taking pride of place as the centrepiece of this wonderful example of Renaissance architecture. Take this fascinating tour through the Vatican City!

Duration: Approximately 3.5 hours.

Start or opening time: At 8.30am

Day 10

Ancient Rome and Colosseum Tour– Skip the Line

Roam through Rome in a three hour introductory tour of the Eternal City. See the Colosseum, Palatine Hill, Roman Forum and also many more!

Discover the main attractions of Ancient Rome in this comprehensive tour and also beat the queues at the Colosseum and the Palatine Hill. Admire the spectacular Arch of Constantine and climb the Palatine Hill following the steps of Julius Caesar along the Via Sacra. This guided tour is ideal for anyone visiting Rome for the first time and is also a perfect introduction to Ancient Rome.

In three hours you will have plenty of time to discover several of the main attractions and also will have the opportunity to learn all about the fascinating history of the eternal city. First you will enjoy panoramic views over the Colosseum from the top of the Oppian Hill before getting skip the line entry to the Colosseum itself, beating the queues. Once inside, your official guide will tell you all about the bloody history of this ancient amphitheatre with tales of gladiators, simulated battles and executions.

After a brief stop at the Arch of Constantine we will move on to the Palatine Hill, the most famous of Rome’s Seven Hills. From there you will be able to enjoy splendid views over the Roman Forum and also the Nero’s Circus Maximus. Then we walk down the Via Sacra, or Sacred Way, the ceremonial way that crosses the Forum. The excursion ends at the temple that houses the altar where the remains of Julius Caesar were cremated.

Duration: Approximately 3 hours.

Start or opening time: At 1:30pm.

Day 11

Check out at Hotel.

Transfer to the airport for your flight back home, having the best impression from your trip!

Depart from Leonardo da Vinci-Fiumicino Airport (FCO)

Arrive at your home airport.

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For an idea on where to go in 2023, check out one of our sample itineraries here

Here are some “extras” I can help you with to make your travel experience seamless.
Want to arrange for a special anniversary dinner, bespoke champagne tasting, catamaran day trip, or a private, pre-opening museum tour for your family? You got it.
Private, luxury transfers: relax and enjoy your vacation without worrying about driving in a foreign destination after a long transatlantic flight. We can arrange for a luxury car with drivers that have knowledge of each destination.
Unmatched culinary experiences: Looking for a reservation at a specific Michelin-star restaurant or a private walking food tour, wine tasting, or whiskey experience? We can help.
A digital itinerary on an app that’s available even when your phone is offline. The app includes all activities, vouchers, and confirmations. You never have to worry about losing your printed travel documents again.

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Ready to take your family to Italy?

Customize your trip and start creating memories!

Grab a time on Anna’s calendar for a free consultation here

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