13-Nights Country Roads of Southern Italy & Sicily - Classic Group from $4,455

Insight Vacations

OFFER ID 1556442

Country Roads Of Southern Italy & Sicily - Classic Group
Indulge in Italy’s finest food and views during this 2-week guided tour. When in Rome, you will toss a coin into the Trevi Fountain during a walking tour with a Local Expert. In Sorrento, settle into a luxurious resort and take in the views of Mount Vesuvius, which buried Pompeii in a pyroclastic cloud of ash and lava stones in 79 A.D. A restaurant’s founder will share why the family uses only organic ingredients that they grow themselves - and you will indulge in those freshly picked vegetables during a Farm-to-Table dinner featuring fresh orecchiette pasta. In Palermo, a historian will take you through the old city, showing you its cathedral and the Palatine Chapel in the Palace of the Normans, where glittering 12th century mosaics will surely take your breath away.

Dining Summary

2 Dinner (D)
13 Breakfast (B)
5 Dinner with Wine (DW)

Choice Highlights

Choose between two carefully selected activities
Capri: Discover the luxuriant Gardens of Augustus with a Local Expert and admire views of the Faraglioni rocks.
Capri: Enjoy a tasting of limoncello and learn the history behind this traditional lemon liqueur.

Authentic Dining

Rome: Savor dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavors.
Palermo: Experience local customs as you delve into tantalising flavors and rustic dishes served with local wine.

Insight Choice

Capri: Discover the luxuriant Gardens of Augustus with a Local Expert and admire views of the Faraglioni rocks.
Capri: Enjoy a tasting of limoncello and learn the history behind this traditional lemon liqueur.

Insight Experiences

Rome: Enjoy exclusive access to the Basilica of Saint Praxedes during an after-hours visit. This 9th-century basilica’s simple facade guards the world's best-preserved Byzantine mosaics. The history of the church springs to life as you admire the interior’s treasured collection, including Bernini's first sculpture and the renowned mosaics, illuminated for your visit. This once-in-a-lifetime experience is a rare and unforgettable insight into Rome and its religious history.
Rome: Follow in the footsteps of gladiators for a deeper insight into life in ancient Rome when you enter the Colosseum.

Make Travel Matter

Alberobello: Dine at Trattoria Terra Madre, where owner Alessandro and his nonna have built a restaurant that focuses on sustainability and creating jobs for locals. Everything is grown organically and harvested on site, and excess produce is donated to their community. The restaurant sources their produce locally, implements a strategy to reduce their food waste and promotes sustainable agricultural practices. Trattoria Terra Madre, advances UN Sustainable Development Goal 12: Responsible Consumption & Production.
Grottole: Participate in the fascinating Wonder Grottole Project. This regeneration initiative works to rehabilitate the abandoned historic center and preserve village life. Your visit advances United Nations Sustainable Development Goal 11: Sustainable Cities and Communities.

Top Rated Highlights

Rome: Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place, around ancient treasures like the Trevi Fountain, the Pantheon and Piazza Navona.
Sorrento: Perched upon the cliffs, lookout to see the mighty Mount Vesuvius across the Bay of Naples.
Capri: Cruise by jetfoil to this famous isle through beautiful blue Mediterranean waters.
Pompeii: Walk with a Local Expert through the cobbled streets of this ill-fated town, frozen in time since the first century.
Alberobello: Led by a Local Expert, explore this UNESCO World Heritage Site showcasing the Trulli of Alberobello. Circular structures with conical roofs that are domed within, built from local limestone and stacked without using mortar.
Matera: With your Local Expert, visit the famous Sassi or cave dwellings, which were home to approximately 20,000 people until 1950s and are now a UNESCO World Heritage Site.
Agrigento: Admire magnificent Hellenistic remains in the Valley of the Temples, such as the massive Temple of Concord and clifftop Temple of Juno.
Palermo: Discover the Sicilian capital with your Local Expert. See Pretoria Square and the 16th century fountain. View the composite architectural styles of the Palermo Cathedral and visit the Palatine Chapel.

13 nights from $4,455 per person

Itinerary

Click here for Full Itinerary Details

Itinerary Details

Insight Vacations: Country Roads of Southern Italy & Sicily - Classic Group

Day 1 - Welcome to the Eternal City of Rome
2025 marks a Jubilee Year, a momentous Roman Catholic event celebrated every 25 years, turning Rome into a center of celebration. As festivities unfold, itineraries may be adjusted to ensure you make the most of your time as you visit the Eternal City. Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in before joining your Travel Director for a private visit to the Basilica of Saint Praxedes, welcomed by the Rector of the basilica. End the day getting to know your fellow travelers over Roman specialties during dinner at a local restaurant.
Accommodations: Radisson Blu GHR, Rome
Meals: Dinner

Day 2 - Rome with the Locals
Rome is about art, antiquity, piazzas and palaces, and our guided walk with a Local Expert has it in abundance. Sightsee the local way, with a leisurely passeggiata through the backstreets, where a friend in Rome will explain how modern life takes place. Toss a coin into the spectacular Trevi Fountain, see the Pantheon, the best-preserved monument from the Roman period, and enjoy free time to do as the Romans do. Perhaps join a tour to discover the incredibly characteristic Roman quarter of Trastevere. Get off the beaten track and explore Rome’s most untouched and unique districts and most consistently unchanged medieval neighborhoods, Trastevere is dotted with ancient and dimly lit churches, crumbling buildings and streets barely wide enough for a Fiat. With your Local Expert, explore the medieval labyrinth of alleyways and pause from time to time to take in this very atmospheric area. A maze of food shops, art galleries, cafes, apartment buildings and pretty squares, this district was once rather run-down and working-class, but has now become one of the city's liveliest and most popular neighborhoods.
Accommodations: Radisson Blu GHR, Rome
Meals: Breakfast

Day 3 - Rome
Meet your Local Expert for a guided visit to one of the icons of the Roman era. Enter the Colosseum and imagine the roar of the spectators as you hear stories of how ancient Romans liked to be entertained. Later, depart for Sorrento.
Accommodations: Isabella, Sorrento
Meals: Breakfast, Dinner

Day 4 - Capri, the Isle of Dreams
The impossibly blue sea welcomes you to the sun-drenched island of Capri as you cruise by jetfoil. On arrival, meet your Local Expert for an orientation walk through the narrow alleyways. Explore Capri with Insight Choice. Choose to visit the immaculate Gardens of Augustus with a Local Expert and admire the views over the Faraglioni Rocks. Alternatively, enjoy a tasting of limoncello, Capri’s famous lemon liqueur.
Accommodations: Isabella, Sorrento
Meals: Breakfast

Day 5 - Pompeii and Alberobello
Start your day in Pompeii, buried in A.D. 79 by the historic eruption of Mount Vesuvius. Walk with your Local Expert through the cobbled streets to see a city frozen in time. Venture on to Alberobello.
Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello
Meals: Breakfast, Dinner with Wine

Day 6 - The Trulli of Alberobello Relaxed Start
Admire another of Italy's record number of UNESCO World Heritage Sites with a Local Expert. The trulli of Alberobello are circular structures with conical roofs that are domed within. They are built from local limestone and stacked without using mortar. In the evening, join a MAKE TRAVEL MATTER® Experience using home-grown organic and locally sourced, seasonal produce, you sit down to a delicious four-course, Farm-to-Table dinner.
Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello
Meals: Breakfast, Dinner with Wine

Day 7 - Alberobello at Leisure Relaxed Start
The day is free for you to enjoy. Perhaps choose to visit Lecce – often referred to as ‘the Florence of the south’ - with its dazzling architecture and beautiful Baroque buildings. Later, relax and indulge in the amenities of your remarkable hotel.
Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello
Meals: Breakfast

Day 8 - Journey South to Matera Relaxed Start
Visit Matera with a Local Expert for an in-depth exploration of the UNESCO World Heritage Site of Sassi - a labyrinth of cave dwellings, churches, staircases and arches, hewn out of the solid rock. You may recognise Matera as the biblical backdrop for the film ‘The Passion of the Christ.’ Continue to the small village of Grottole. Once a thriving community, it has lost most of its activity and population. Meet Andrea, a local striving to bring back the area's traditional way of living. On this MAKE TRAVEL MATTER® Experience explore the historic old town to learn about the fascinating history of the village and enjoy an aperitif with local snacks helping to preserve the culture.
Accommodations: MH Matera Hotel
Meals: Breakfast, Dinner with Wine

Day 9 - To Sicily and the Taormina Riviera
In the morning, travel along the Violet Coast to the very toe of Italy and board your ferry bound for Sicily, across the Strait of Messina. According to Grecian legend, this was home to the mythical sea monsters Scylla, a six-headed rock monster, and Charybdis, a whirlpool, based on either side of the strait. Together, they posed an inescapable threat to passing seafarers as avoiding one meant passing too close to the other. You will soon arrive at your hotel where you will spend three glorious nights on the Taormina Riviera. Join a Local Expert for a visit to the Greek Theater of Taormina, graced with the most spectacular of backdrops. Stroll along the elegant Corso Umberto to the Piazza IX Aprile and admire the panoramic views and hews of blue from the sky to the azure sea. Later, take your pick of specially selected restaurants for your Dine-Around evening.
Accommodations: Hellenia Yachting Hotel & SPA
Meals: Breakfast, Dinner with Wine

Day 10 - Free Time on the Taormina Riviera Relaxed Start
The day is at leisure to relax at your resort's private beach, or perhaps explore the medieval quarter? Don't miss the chance of an optional drive through the national park to Mount Etna, Europe's largest volcano.
Accommodations: Hellenia Yachting Hotel & SPA
Meals: Breakfast

Day 11 - A New Dawn in Sicily Relaxed Start
Early risers may experience what D.H. Lawrence christened the ‘dawn coast of Europe.' The day is free to explore Taormina at your leisure, or to embark on an Optional Experience to Syracuse.
Accommodations: Hellenia Yachting Hotel & SPA
Meals: Breakfast

Day 12 - Agrigento, the Valley of the Temples and on to Palermo
Drive to Agrigento and explore the Valley of the Temples with a Local Expert. See the massive Temple of Concord and clifftop Temple of Juno, overlooking the sea. In the afternoon, continue to the Sicilian capital of Palermo.
Accommodations: NH Palermo
Meals: Breakfast

Day 13 - Palermo and the Golden Age of the Normans
Join a historian on a guided walk to see the gems of the old city. Visit the amazing Palatine Chapel in the Palace of the Normans. Outside, there are few clues to its astonishing interior, completely covered in glittering 12th century mosaics. Continue to the Palermo Cathedral which has been altered over the years and observe its unique blend of architectural styles. In the afternoon, there is free time to explore or shop in Palermo or continue sightseeing. In the evening, join your fellow guests and Travel Director at a local restaurant for a dinner of delicious local cuisine and wine.
Accommodations: NH Palermo
Meals: Breakfast, Dinner with Wine

Day 14 - Depart Palermo
Your journey draws to an end. Departure transfers arrive at Palermo Falcone–Borsellino Airport.
Meals: Breakfast

Featured Destinations

Palermo

Matera

Taormina

Alberobello

Sorrento

Sorrento is a town of extraordinary beauty and is known as a popular gateway to Italy's most spectacular stretch of coastline - the Amalfi Drive lined with fishing villages and famous resorts. The seaside resort of Amalfi sits with weathered houses scrambling up steep cliffs. Visitors marvel at its location and its magnificent cathedral. The religious sanctuary of Cloister of St. Francis is worth a visit. The tiny, exclusive resort of Positano has its famous world-class hotel, San Pietro. Excavations of the ruined city of Pompeii, which was destroyed in 79 A.D. during the disastrous eruption of Mount Vesuvius, give visitors a vivid impression of life in a very wealthy ancient city and the tragic end of its population. The Isle of Capri ranks as one of the most beautiful islands and has captured visitors for centuries with excellent climate, spectacular landscape and fantastic sea caverns. Capri has lavish villas, elegant hotels, chic boutiques and quaint restaurants. Museo Correale contains a death mask of poet Torquato Tasso and some special editions of his works, pictures, furniture and porcelain.

Excursions

Sorrento: The Ancient City of Pompeii - 6 Hours

Sorrento: The Iconic Amalfi Coast - 6 Hours

Sorrento: Capri Exploration by Private Motorboat – 8 hours

Rome

Sprawled across seven legendary hills, romantic and beautiful Rome was one
of the great centers of the ancient world. Although its beginning is shrouded
in legend and its development is full of intrigue and struggle, Rome has always
been and remains the Eternal City.

Rome enjoyed its greatest splendor during the 1st and 2nd centuries when art
flourished, monumental works of architecture were erected, and the mighty Roman
legions swept outward, conquering all of Italy. These victorious armies then
swept across the Mediterranean and beyond to conquer most of the known world.
With Rome's establishment as capital of the western world, a new ascent to glory
began.

Today's Rome, with its splendid churches, ancient monuments and palaces, spacious
parks, tree-lined boulevards, fountains, outdoor cafes and elegant shops, is
one of the world’s most attractive and exciting cities. Among the most famous
monuments is the Colosseum. As you walk its cool, dark passageways, imagine
the voices that once filled the arena as 50,000 spectators watched combats between
muscled gladiators and ferocious animals.

Stop to see the remains of the Forum, once the city's political and commercial
center. In later times, Rome's squares were enhanced with such imposing structures
as the Vittorio Emanuele Monument and grandiose fountains like the Fontana di
Trevi. Join the millions who stand in awe of Christendom’s most magnificent
church and admire the timeless masterpieces of Michelangelo's frescoes in the
Sistine Chapel.

Rome jars the senses and captures the soul. Grasp all you can during the short,
precious time you have available in the Eternal City. With so much to see and
do, a day or two will only allow you a sampling of the city's marvelous treasures.

Caution: As in many big cities and tourist destinations purse snatching
and pickpocketing is common. Valuable jewelry and excess cash are best left
in a safety deposit box in your hotel.

Shopping For most visitors shopping for beautiful Italian leather articles,
designer shoes, fashions for men and women, linens, knitwear, silk scarves and
ties is a favorite pastime. Except for tourist-oriented shops, the majority
of stores are closed on Sundays. Some of the department stores, such as Rinascente,
open in the late afternoon on Sundays.

Cuisine Rome's choice of restaurants is mindboggling as is the variety
of cuisine. Whether your meal is at a top-rated restaurant or a rustic trattoria,
you can be sure that you will enjoy your food, especially when accompanied by
wines from the hill towns surrounding Rome.

Other Sights Rome's attractions are endless, and depending on how much
time you have at your disposal a careful selection has to be made about what
to see. Be aware of horrendous traffic conditions and major construction work
all around the city in preparation of Jubilee 2000, the Holy Year. Some of the
sights not to be missed:

Piazza Venezia - This busy square is easily recognized by its imposing Vittorio
Emanuele II Monument. The white marble structure was inaugurated in 1911 as
a symbol of Italy’s unification.

The Forum - Once the civic heart of ancient Rome, today the remains include
a series of ruins, marble fragments, isolated columns and some worn arches.

Colosseum - No visit to Rome is complete without a stop at this awe-inspiring
theater, which is among the world’s most celebrated buildings. Here ancient
Rome flocked to see gladiatorial contests and numerous other spectacles.

Trevi Fountain - Take a stroll to Rome's famous fountain. A spectacular fantasy
of mythical sea creatures and cascades of splashing water, the fountain is one
of the city's foremost attractions. Legend has it that visitors must toss a
coin into the fountain to ensure their return to Rome.

St. Peter's Square - Part of Vatican City, this square created by Bernini
is considered one of the loveliest squares in the world. Twin Doric colonnades
topped with statues of various saints and martyrs flank either side of the square.
In the center stands an 84-foot obelisk, brought from Egypt in 37 A.D.

St. Peter's Basilica - At the head of the square stands Christendom's most
magnificent church, which was begun in 1452 on the site where St. Peter was
buried. Throughout the following 200 years, such Renaissance masters as Bramante,
Michelangelo, Raphael and Bernini worked on its design and created an unparalleled
masterpiece. Of special note are Michelangelo's Pieta and the bronze canopy
over the high altar by Bernini. The immense dome was designed by Michelangelo.

Vatican Museum - To see this museum's immense collection would take days.
As you enter, there are special posters that plot a choice of four color-coded
itineraries. They are repeated throughout the museum and are easy to follow.
It is a good idea to pickup a leaflet at the main entrance and concentrate on
exhibits of major interest. Of course, the Sistine Chapel is a must. Most likely
you may have to wait in line to enter.

Vacation Details

Valid Date Ranges

04/12/2025 - 04/25/2025

from $4,478 per person

04/26/2025 - 05/09/2025

from $4,496 per person *

05/03/2025 - 05/16/2025

from $4,995 per person *

05/10/2025 - 05/23/2025

from $4,496 per person *

05/17/2025 - 05/30/2025

from $4,496 per person *

05/24/2025 - 06/06/2025

from $4,496 per person *

05/31/2025 - 06/13/2025

from $4,496 per person

06/28/2025 - 07/11/2025

from $4,545 per person

07/12/2025 - 07/25/2025

from $4,545 per person

08/09/2025 - 08/22/2025

from $4,478 per person

08/23/2025 - 09/05/2025

from $4,455 per person

08/30/2025 - 09/12/2025

from $4,478 per person

09/06/2025 - 09/19/2025

from $5,395 per person *

09/13/2025 - 09/26/2025

from $5,395 per person *

09/20/2025 - 10/03/2025

from $5,395 per person *

09/27/2025 - 10/10/2025

from $5,395 per person *

10/04/2025 - 10/17/2025

from $5,325 per person *

10/11/2025 - 10/24/2025

from $5,325 per person *

* This departure has been designated a guaranteed departure by the operator, meaning that the minimum number of guests has been met, although still subject to weather and other conditions.

Prices Start At

from $4,455 per person

Length

13 Nights

Air City

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Vacation Rating

Deluxe

Remarks

Trip prices are per person, land only, based on double occupancy and reflect applicable discounts. Trip prices and discounts are subject to change. Airfare is additional. Tour prices, dates and itineraries are correct at the time of the website going live, however are subject to confirmation at the time of booking. Other restrictions may apply.

All fares are quoted in US Dollars.

OFFER ID

1556442

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13-Nights Country Roads of Southern Italy & Sicily - Classic Group from $4,455

Itinerary Details

Excursions

Sorrento: The Ancient City of Pompeii - 6 Hours

Sorrento: The Iconic Amalfi Coast - 6 Hours

Sorrento: Capri Exploration by Private Motorboat – 8 hours

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