Highlights of Italy - 9 Days



Who is this trip for
Genders
- Female50%
- Male50%
Average age
Start / End
- Rome
- Venice
Physical rating
Group size
1 - 16Meals included
9Highlights
- Sample the famous Italian gastronomy and local wine scene
- Stand in the shadow of some of the most famous landmarks in the world
- Witness the impressive art and architecture of Florence
- Enjoy the winding canals and grand squares in Venice.
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Summary
Check off every bucket list dream on this highlight-packed adventure through the heart of Italy. Stand in awe of Rome’s ancient history as you explore landmarks that have shaped the world, then lose yourself in Florence’s Renaissance art and architecture that redefined creativity. Walk along Venice’s iconic canals, where every turn feels like a scene from a romantic postcard. And just when you think it can’t get better, indulge in Montepulciano’s rich culinary traditions and savor its world-renowned wines. From timeless history to indulgent flavors, this life-changing journey will leave you longing for just one more taste of Italy’s magic.
Itinerary
Day 1
Rome
Arrive at any time. There are no planned activities until tonight's welcome meeting.
Day 2
Rome
Enjoy a the tour operator supported migrant led walk of Rome before enjoying a free day to explore a myriad of options. Opt to tour Vatican City, cross the river to charming Trastevere, eat some gelato in Piazza Navona, or swing by the Colosseum and Forum. While you're here, why not opt to rent a Vespa for the day? Live "la dolce vita" and opt to pre-book the Rome Vintage Vespa Tour on the checkout page ahead of time, to include this optional on your tour.
Day 3
Rome/Montepulciano
Depart Rome by train then transfer to the town of Pienza for a visit and for some free time to explore. Continue on to Montepulciano in the heart of the Tuscan countryside and enjoy the medieval and renaissance hill town with an orientation walk and a local wine tasting. Montepulciano is famous for producing delectable local pork, cheese, "Pici" pasta, and honey. It is also major wine producing area. Take in the stunning vistas, wander cobbled lanes, or opt to sample the local delicacies in small, family-run establishments.
Day 4
Montepulciano
Spend the day in the Italian countryside. The famous wine-producing region is the perfect place for an optional vineyard tour and wine tasting, or a bike ride in the rolling hills. Opt to travel further afield to the thermal springs of Bagni San Filippo.
Day 5
Montepulciano/Florence
Travel to picturesque Siena. After an orientation walk around this medieval city, opt to visit Torre del Mangia, Battistero, il Campo, or the Duomo or to take a "passeggiata" and meet the Sienese locals. Continue on to Florence and enjoy an evening walk to Piazzale Michelangelo for a fantastic panoramic view of the city. Arrive to the inimitable Firenze. Walk through the city catching a glimpse of the Duomo, Piazza Indipendenza, Piazza della Signoria, and the Ponte Vecchio. Head to Piazzale Michelangelo with your CEO for the most famous and photographed vista of the city.
Day 6
Florence
Immerse yourself in the splendor of Florence on a guided walking tour this morning. Catch a glimpse of the intricate buildings that make Florence a favourite to travellers the world over, and better understand the rich history and local way of living, then enjoy lunch at the local market. With a free afternoon, the choices are endless. Opt to visit the Duomo, David at the Galleria dell’Accademia, Uffizi Gallery, medieval Ponte Vecchio, or the Medici Chapels, just to name a handful. The afternoon is yours to explore. Check out the Mercato Centrale or any number of cafés and trattorias. If you came to shop, start at one end of the city and just keep going. There's beautiful architecture, famous museums, Renaissance art pieces, and charming cobblestone streets everywhere. If you wish to go further afield, take a wine tasting bike tour up to Fiesole and the vineyards of Chianti.
Day 7
Florence/Venice
Settle in for the journey to Venice by train this morning and soak in the beautiful scenery along the way. Once at the hotel, take time to relax before heading out on foot for a guided walking tour and immerse yourself in this incredible city's beauty and history. Enjoy a free evening or join the group for an optional dinner at one of your CEO's favourite local spots. Known as the “City of Canals” or “The Floating City,” Venice is one of Italy’s most famous and picturesque destinations. Between the winding canals connecting San Marco with the Santa Chiara church, the bridge of sighs, and the Doge’s Palace, there are no shortage of photo ops and iconic moments.
Day 8
Venice
Take advantage of a full free day to experience everything that Venice has to offer. Explore Venice’s diverse culinary scene with a food tour, take a gondola ride, or wander along canals and through the maze-like streets; pass world-class museums and incredible architecture in all directions. Regroup in the evening for an optional final dinner out with the group.
Day 9
Venice
Depart at any time.
What's Included
Accommodation
Hotel (8 nts).
Meals
Breakfasts: 8, Lunches: 1, Dinners: 0
Vegetarian options are available on all meals throughout the adventure.
Vegetarian options availableLocal Guide
GuidedThis adventure is led by a local guide throughout. The main language of this adventure is English. Please contact us for other languages available.
Wifi
Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.
Dates & Prices
Mar 2026
from £1,262Apr 2026
from £1,781May 2026
from £1,930Jul 2026
from £1,781Aug 2026
from £1,781Sep 2026
from £1,930Nov 2026
from £1,534Jan 2027
from £1,534Feb 2027
from £1,682Mar 2027
from £1,682Apr 2027
from £1,781May 2027
from £1,781Jun 2027
from £1,930Jul 2027
from £1,781Aug 2027
from £1,781Oct 2027
from £1,534Nov 2027
from £1,534
- Save 26%Sun 1 Mar 2026 > Mon 9 Mar 2026Guaranteed Departure6+ spaces of 16 left£1,699Best offer£1,262
- Save 21%Sun 15 Mar 2026 > Mon 23 Mar 2026Guaranteed Departure6+ spaces of 16 left£1,699£1,346
Essential trip information
Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.
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