Italy Bellissimo
If toasting epic Tuscan sunsets, soaking up the sun-kissed sophistication of Italy’s most popular cities and olive oil tasting in a real Italian Borgo with new friends sounds like your idea of perfection, this is one of those bellissimo Italy trips that would seduce even the sirens of Capri.
- 29 May 2026 – 08 Jun 2026
from $5,962.50 pp twin share * - 31 May 2026 – 10 Jun 2026
from $6,450 pp twin share * - 05 Jun 2026 – 15 Jun 2026
from $5,917.50 pp twin share * - 07 Jun 2026 – 17 Jun 2026
from $5,782.50 pp twin share * - 12 Jun 2026 – 22 Jun 2026
from $6,295 pp twin share * - 14 Jun 2026 – 24 Jun 2026
from $6,495 pp twin share * - 19 Jun 2026 – 29 Jun 2026
from $6,425 pp twin share * - 21 Jun 2026 – 01 Jul 2026
from $6,250 pp twin share * - 26 Jun 2026 – 06 Jul 2026
from $5,175 pp twin share * - 28 Jun 2026 – 08 Jul 2026
from $6,375 pp twin share * - 05 Jul 2026 – 15 Jul 2026
from $5,995 pp twin share * - 12 Jul 2026 – 22 Jul 2026
from $6,175 pp twin share * - 26 Jul 2026 – 05 Aug 2026
from $6,150 pp twin share * - 16 Aug 2026 – 26 Aug 2026
from $5,395.50 pp twin share * - 23 Aug 2026 – 02 Sep 2026
from $5,512.50 pp twin share * - 28 Aug 2026 – 07 Sep 2026
from $6,795 pp twin share * - 30 Aug 2026 – 09 Sep 2026
from $6,025.50 pp twin share * - 04 Sep 2026 – 14 Sep 2026
from $6,345 pp twin share * - 06 Sep 2026 – 16 Sep 2026
from $7,050 pp twin share * - 11 Sep 2026 – 21 Sep 2026
from $7,050 pp twin share * - 13 Sep 2026 – 23 Sep 2026
from $6,457.50 pp twin share * - 18 Sep 2026 – 28 Sep 2026
from $7,175 pp twin share * - 20 Sep 2026 – 30 Sep 2026
from $7,175 pp twin share * - 25 Sep 2026 – 05 Oct 2026
from $7,175 pp twin share * - 27 Sep 2026 – 07 Oct 2026
from $7,175 pp twin share * - 02 Oct 2026 – 12 Oct 2026
from $7,150 pp twin share * - 04 Oct 2026 – 14 Oct 2026
from $6,435 pp twin share * - 09 Oct 2026 – 19 Oct 2026
from $7,225 pp twin share * - 11 Oct 2026 – 21 Oct 2026
from $6,925 pp twin share * - 16 Oct 2026 – 26 Oct 2026
from $6,412.50 pp twin share *
* Prices and category availability are subject to change without notice.
Itinerary
- Day 1 – Welcome to Rome:
Take time to embrace the Italian passion for life on this grand adventure that starts and ends in the ‘Eternal City’ of Rome. Spend the day exploring on your own before meeting your Travel Director and fellow travellers this evening for a light meal. - Day 2 – Explore Ancient Rome and the Vatican City:
Begin your journey through Rome at the Vatican Museums, where you’ll join a Local Specialist to see Michelangelo’s frescoed ceiling in the Sistine Chapel and his Pietà inside St. Peter’s Basilica. Explore the landmarks of Ancient Rome, viewing the Circus Maximus and visiting the Colosseum. This afternoon is yours to explore—relax in a lively piazza with a coffee or visit one of the city’s world-class museums. Please note: On some departures, access to St. Peter’s Basilica may be restricted due to the Papal Audience. You’ll still have time to take in the atmosphere of St. Peter’s Square during your visit to Vatican City. - Day 3 – Admire Pompeii and on to Capri:
Our Italy travel itinerary continues south towards the ancient city of Pompeii, which remains frozen in time since it was covered in ash during the eruption of Mount Vesuvius centuries ago. Here, you’ll join a Local Specialist who will share insights into the city’s tragic history. Cruising across the Bay of Naples next, arrive at the Isle of Capri, where you’ll spend the next two nights in picture-perfect surroundings. - Day 4 – A Day on the Isle of Capri:
Explore the glamour of Capri and see views of the marina and Augustus Gardens on a walking tour with a Local Specialist. Venture to the heart of the island and the legendary piazzetta, where the locals come to people-watch. Spend free time shopping at elegant boutiques or perhaps join an optional experience to explore the rugged coastline and hidden grottos by private motor launch. Tonight, we dine at our hotel. - Day 5 – Onwards to Assisi:
Sail back across the Mediterranean to Naples and venture north to the historic city of Perugia. Here, you’ll discover Italy’s weaving tradition during an impressive MAKE TRAVEL MATTER® Experience at our visit to Laboratorio Giuditta Brozzetti, a TreadRight and JoinTrafalgar Heritage Initiative project. Explore one of the last remaining traditional wooden frame hand-weaving workshops in the country, before continuing to the ancient hilltop town of Assisi where tonight we stay at one of our hotels that overlooks the old town. - Day 6 – Journey to Venice:
Join a Local Specialist and visit the Basilica of St. Francis, famous for Giotto’s exquisite frescoes and 13th century stained glass windows. Continue north past hilltop medieval villages and through picturesque farming plains towards Venice, the ‘Queen of the Adriatic’. Enjoy a free evening watching the sunset over the Venetian Lagoon or consider joining an optional experience before retiring at your Stays With Stories hotel, once a beloved home-away-from-home for Romantic poet, Robert Browning. - Day 7 – Cruise the Canals of Venice:
The Winged Lion of Venice is your constant companion as you cruise by private launch to your memorable MAKE TRAVEL MATTER® Experience bringing to life the 13th-century tradition of Venetian glassblowing. Watch the talented master craftsmen use the same techniques that have been passed down through the generations, perhaps inspired to buy a souvenir or two to remind you of your visit. Next, you’ll continue on to St. Mark’s Square where you’ll view the Basilica, the ornate Doge’s Palace and Bridge of Sighs, so named because of the sound prisoners made as they took one last look at their beloved city from the bridge before meeting their fate. The rest of the afternoon is yours to explore what was once the haunt of Casanova and Marco Polo, and you’ll want to relish every second experiencing life in this enchanting city. - Day 8 – Discover Pisa and the Tuscan Hills:
Wondering what’s next on our Italy trip itinerary? This morning, travel to Pisa and visit its Field of Miracles to view the famous Leaning Tower before arriving in the spa-resort of Montecatini Terme in Tuscany, your home for the next two nights. - Day 9 – Off to Renaissance Florence:
Explore one of the world’s most cultural cities today – the former home of great masters and a testament to the ambitious legacy of the Medici family. Your Local Specialist shares all the sights, including views of the magnificent marble Duomo and Baptistery. Visit Piazza della Signoria, the heart of this flourishing city with its statues and stunning palazzi, then view the Ponte Vecchio. Later, enjoy some free time to stroll around the city and embrace this Renaissance gem. This evening, you’ll enjoy a Be My Guest experience with the Callistri family at their borgo for a delicious Italian dinner, olive oil tasting and leisurely walk through their olive groves and lemon orchards. - Day 10 – Venture to San Gimignano and Rome:
Admire the medieval beauty of San Gimignano today, walking to the triangular Piazza della Cisterna, the hub of this historic town. See the extraordinary architecture of this hilltop ‘medieval Manhattan’, shop for local products or relax with a gelato at a pavement cafe. This evening, celebrate a magnificent Italian adventure with newfound friends at dinner. - Day 11 – Arrivederci Rome:
After breakfast, say a fond farewell to Italy and prepare to return home after a memorable Italian journey of discovery.
Highlights
- Soak up the sun-kissed sophistication of Italy’s most popular cities.
- Indulge in olive oil tasting in a real Italian Borgo.
- Toast epic Tuscan sunsets with new friends.
If toasting epic Tuscan sunsets, soaking up the sun-kissed sophistication of Italy’s most popular cities and olive oil tasting in a real Italian Borgo with new friends sounds like your idea of perfection, this is one of those bellissimo Italy trips that would seduce even the sirens of Capri.
Inclusions
- An expert Travel Director and professional Driver.
- Cherry-picked hotels, all tried and trusted.
- All porterage and restaurant gratuities.
- All hotel tips, charges and local taxes.
- Must-see sightseeing.
- Audio headsets for flexible sightseeing.
FAQs
- Albergo Quattro Fontane Lido
- Grand Tiberio
- Minerva Palace
- Regina Cristina
- Shangri-La Roma, Grand Tiberio
- Valle di Assisi
How long is this journey?
This itinerary runs for 11 days and 10 nights.
When can I travel?
Departures are currently scheduled between 29 May 2026 and 05 Apr 2028, subject to live availability.
Are there different departure options?
Yes, multiple departures may be available depending on your preferred travel period.
Are discounts available?
Seasonal or loyalty discounts may be available on selected departures at the time of enquiry.
What is generally included?
Inclusions typically cover guided touring and selected experiences, with exact details listed in the itinerary.
Provided by: Trafalgar ToursFine Print
Terms and conditions apply. Click here for more details.