13-Nights Country Roads of Southern Italy & Sicily - Classic Group from $4,995

Insight Vacations

OFFER ID 1663417

Country Roads Of Southern Italy & Sicily
Indulge in Italy’s finest food and views during this 2-week guided tour. In Rome, explore the city on foot with a Local Expert, uncovering its layers of history and architecture. On Capri, settle into Anacapri and enjoy views across the Bay of Naples towards Mount Vesuvius. In Puglia, explore Alberobello, a UNESCO World Heritage Site known for its whitewashed trulli houses and distinctive conical stone roofs. Savor traditional Apulian cuisine, including seasonal dishes such as orecchiette, a pasta closely associated with the region’s culinary heritage. In Palermo, a historian will guide you through the old city, including its cathedral and the Palatine Chapel in the Palace of the Normans, where 12th-century mosaics reveal the city’s rich cultural legacy.

Dining Summary

7 Dinner (D)
13 Breakfast (B)

Authentic Dining

Rome: Savor dinner at a uniquely Roman restaurant, offering a perfect exploration of Lazio's typical flavors.
Alberobello: Enjoy a freshly prepared Farm-to-Table meal featuring recipes and flavors typical of the region.
Palermo: Experience local customs as you delve into tantalizing flavors and rustic dishes served with Sicilian wine.

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.
Anacapri NA, Italy: Perched atop the cliffs, look out across the Bay of Naples to the mighty Mount Vesuvius.
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.
Taormina: Visit Taormina’s ancient amphitheater with your Local Expert. Carved from honey-colored stone and set high on the cliff, the theater frames wide views of the Ionian Sea and the distant rise of Mount Etna through its weathered arches.
Agrigento: Explore the Valley of the Temples and its impressive Hellenistic ruins like the well-preserved Temple of Concordia and the clifftop Temple of Juno, overlooking the vast Sicilian landscape.

Insight Experiences

Rome: Follow in the footsteps of gladiators for a deeper insight into life in ancient Rome when you enter the Colosseum.

Insight Choice

Capri: Explore the island's natural beauty on a visit to the Gardens of Augustus with views of the Faraglioni Rocks.
Capri: Savor the flavors of the island with a tasting of its renowned limoncello.

Make Travel Matter

Grottole: Participate in the fascinating Wonder Grottole Project. This regeneration initiative works to rehabilitate the abandoned historic center and preserve village life. Your visit directly supports United Nations Sustainable Development Goal 11: Sustainable Cities and Communities.

Choice Highlights

Choose between two carefully selected activities
Capri: Explore the island's natural beauty on a visit to the Gardens of Augustus with views of the Faraglioni Rocks.
Capri: Savor the flavors of the island with a tasting of its renowned limoncello.

13 nights from $4,995 per person

Valid for new bookings deposited Now – September 30, 2026 for travel January 1, 2027 – December 31, 2027.

*Promotion may not be combinable with other promotions and is subject to availability. Other restrictions may apply. Ask your Travel Advisor for more information.

Itinerary

Insight Vacations: Country Roads of Southern Italy & Sicily

Day 1 - Welcome to the Eternal City of Rome
Welcome to Rome, a glorious city filled with classic antiquities, medieval buildings, Renaissance palaces and baroque churches. Settle in, before meeting your Travel Director. Later today, get to know your fellow travelers over Roman-specialties 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. Cross the Tiber river to enjoy ancient Rome. Enter the Colosseum and imagine the roar of the spectators as you hear stories of how ancient Romans liked to be entertained.
Accommodations: Radisson Blu GHR, Rome
Meals: Breakfast

Day 3 - Rome to Capri
The journey south brings you to Pompeii Archaeological Park, where your Local Expert reveals a Roman city preserved beneath the ash of Mount Vesuvius since A.D. 79. Walk streets once lined with homes, shops and public buildings, gaining a vivid picture of everyday life almost 2,000 years ago. Continue to the Bay of Naples and cross to Capri, approaching the island by sea as its limestone cliffs rise from the water. From here, make your way to Anacapri, set high above the coastline, where you’ll settle in for the evening and enjoy dinner.
Accommodations: San Michele, Anacapri
Meals: Breakfast, Dinner

Day 4 - Capri, the Isle of Dreams
Begin the day discovering Capri Town with your Local Expert before exploring further with Insight Choice. Visit the Gardens of Augustus, where terraces overlook the Faraglioni, Capri’s three limestone sea stacks, and see Via Krupp, the remarkable switchback path carved into the cliffs in the early 20th century. Alternatively, enjoy a limoncello tasting in the Piazzetta and learn why the island’s intensely fragrant lemons are so prized. Later, you may choose to join an Optional Experience cruising the Amalfi Coast and visiting Positano.
Accommodations: San Michele, Anacapri
Meals: Breakfast

Day 5 - Pompeii and Alberobello
Capri gives way to the landscapes of southern Italy as you travel towards Puglia, where olive groves, whitewashed towns and dry-stone walls define the countryside. Your destination is Alberobello, known for its extraordinary trulli: traditional limestone houses with conical roofs unique to this part of the region. Wander through the town’s narrow streets to see these distinctive homes up close and learn why Alberobello has been recognized as a UNESCO World Heritage Site.
Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello
Meals: Breakfast, Dinner

Day 6 - The Trulli of Alberobello
Join a Local Expert to explore one of Italy’s many UNESCO World Heritage Sites — the unique trulli of Alberobello, circular limestone dwellings with domed interiors and distinctive conical roofs, ingeniously built without mortar. You may also opt to join a Local Expert for an exploration of Ostuni, a whitewashed town that echoes the charm of a North African Arab Medina. Stroll through its winding cobbled streets and admire its striking architecture. In the evening, enjoy a Farm-to-Table dinner, showcasing traditional Apulian dishes made with seasonal produce.
Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello
Meals: Breakfast, Dinner

Day 7 - Alberobello at Leisure
Today is yours to enjoy at leisure or unwind and make the most of the exceptional amenities at your remarkable hotel. You can also choose to discover cliffside Polignano a Mare with a Local Expert, enjoying Adriatic views and a stroll through the historic hometown of Volare singer Domenico Modugno.
Accommodations: Grand Hotel La Chiusa di Chietri, Alberobello
Meals: Breakfast

Day 8 - Journey West to Matera
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 recognize 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 the advocate behind a local initiative dedicated to revitalising the traditional ways of living in the area. 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: UNAHOTELS MH Matera
Meals: Breakfast, Dinner

Day 9 - To Sicily: Acireale
In the morning, travel 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.
Accommodations: Grande Albergo Maugeri, Acireale
Meals: Breakfast, Dinner

Day 10 - Taormina
Join a Local Expert for a visit to the Greek Theater of Taormina, graced with the most spectacular of backdrops. Don't miss the chance of an optional drive through the national park to Mount Etna.
Accommodations: Grande Albergo Maugeri, Acireale
Meals: Breakfast

Day 11 - A New Dawn in Sicily
Early risers may experience what D.H. Lawrence christened the ‘dawn coast of Europe'. The day is free to explore at your leisure, or to embark on an Optional Experience to Syracuse.
Accommodations: Grande Albergo Maugeri, Acireale
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

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

Featured Destinations

Palermo

Taormina

Matera

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.

Excursions

Rome Highlights and Vatican: 9 hours

Meet your private English-speaking driver at the pier side of Civitavecchia port.
Rome is a mix of architecture styles, of antiques and new, of sacred and profane. In this full day tour you can enjoy a sample of this capital city. With your guide reach the Vatican city where you can visit the Museums, admiring its priceless collection of art and architecture: highlights include Raphael's Transfiguration, The Raphael Rooms, the Sculpture Garden featuring the famous Laokoon. Finally, the restored Sistine Chapel, famous all over the world for the breathtaking Michelangelo’s ceiling and the Last Judgment. From here you walk to St. Peter's Basilica to marvel at Michelangelo's Dome, his statue Pietà, Bernini's magnificent Baldacchino and the Tombs of the Popes. The tour will continue with a look at the ancient part of the Eternal city and its symbol: the Coliseum, where, jumping the lines, you will be able to enter in the magnificent Flavian Amphitheatre and admire where the gladiatorial duels, wild beast fights were arranged for the entertainment of Roman people.
The second part of the day will be dedicated to the visit of the city center, starting from Navona Square, the most important of Baroque Rome, where today it is possible to admire the monumental Fountain of the Rivers by Bernini. Continue your tour visiting the Pantheon, the jewel of Roman architecture, then Trevi Fountain, the most famous and beautiful fountain in Rome. End the tour at the Spanish Steps, built entirely in travertine in the 18th century.
We will ensure your timely return transfer to the Civitavecchia Port

Access to the Vatican Museums and St. Peter's Basilica is allowed only to properly attired visitors.

Highlights:

Vatican Museums, Ancient Rome, main highlights

Tour Duration: 8 hours

Tour can Operate: Morning

Wheelchair Accessible: Yes

Physical Activity Level: low

Inclusions:
·         Luxury Mercedes minivan at disposal for the entire day
·         English-speaking driver at disposal for the entire day
·         6 hour private English-speaking guide
·         No Line entrance fees for the Vatican Museums and Colosseum

Exclusions:
·         All cruise travel, personal items, meals and associated costs
·         Gratuities

Tivoli: Villas in the Countryside - 8 Hours

Ostia Antica - 6 Hours

Roman Castles - 8 Hours

Lake Bracciano and the Monster Park - 8 Hours

Vacation Details

Valid Date Ranges

04/10/2027 - 04/23/2027

from $4,995 per person *

04/24/2027 - 05/07/2027

from $5,650 per person

05/08/2027 - 05/21/2027

from $5,486 per person *

05/15/2027 - 05/28/2027

from $6,095 per person

05/29/2027 - 06/11/2027

from $6,075 per person *

06/26/2027 - 07/09/2027

from $5,085 per person

07/10/2027 - 07/23/2027

from $5,650 per person

08/07/2027 - 08/20/2027

from $5,550 per person

08/21/2027 - 09/03/2027

from $5,595 per person

08/28/2027 - 09/10/2027

from $5,036 per person *

09/04/2027 - 09/17/2027

from $6,175 per person *

09/11/2027 - 09/24/2027

from $6,175 per person *

09/18/2027 - 10/01/2027

from $6,175 per person *

10/02/2027 - 10/15/2027

from $6,175 per person *

10/09/2027 - 10/22/2027

from $6,175 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 $4,995 per person

Length

13 Nights

Air City

Call for airfares from your city.

Vacation Rating

Deluxe
Fine dining, on-site bars or lounges and room service with extended hours are characteristic of deluxe establishments. Guest services usually include valet parking, concierge services, baggage assistance and laundry services. Other on-site facilities often include shops and boutiques, full service spas, full fitness facilities with pools and tennis courts. Business amenities may include available up-to-date technology and support staffs available for services. Attention to detail is apparent in the guestrooms which typically have stylish furnishings, quality bedding and bath products and often provide an evening turn down service.

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. 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

1663417

Reference this number when contacting our agency so we may better serve you. Also keeping this number handy will allow you to locate this document again quickly.

JB Cruises | JB Vacations

7460 West Boynton Beach Blvd., Suite 102
Boynton Beach, FL 33437
USA

(561) 880-2790
(800) 329-7447

13-Nights Country Roads of Southern Italy & Sicily - Classic Group from $4,995

Excursions

Palermo and Monreale - 8 hours

Excursions

Taormina and Mt Etna Day - 8 hours

Excursions

Sorrento: The Ancient City of Pompeii - 6 Hours

Sorrento: The Iconic Amalfi Coast - 6 Hours

Sorrento: Capri Exploration by Private Motorboat – 8 hours

Excursions

Rome Highlights and Vatican: 9 hours

Tivoli: Villas in the Countryside - 8 Hours

Ostia Antica - 6 Hours

Roman Castles - 8 Hours

Lake Bracciano and the Monster Park - 8 Hours

Vacation Details

JB Cruises | JB Vacations