Itinerary Snapshot
Day 1 – September 23
Arrive at Pisa International Airport (PSA) and travel by private transfer to La Spezia, settling into your coastal accommodations for the next two nights. This evening, gather for a welcome dinner featuring fresh Ligurian seafood and local pesto, the region’s culinary pride.
Meals: Dinner
Day 2 – September 24
Spend the day exploring the five villages of Cinque Terre by foot, boat, and train. Hike sections of the famous coastal trail offering breathtaking views of terraced vineyards and turquoise waters. Wander the narrow lanes of Vernazza and Manarola, stopping at family-run trattorias for focaccia and gelato. This afternoon, take a private boat back to La Spezia and photograph the colorful harbors from the water.
Meals: Breakfast, Lunch
Day 3 – September 25
This morning, board the train to Pisa. After checking into your hotel, visit the iconic Piazza dei Miracoli to see the Leaning Tower, Baptistery, and Cathedral. You’ll have the option to climb the tower for panoramic views or simply admire these architectural marvels from the ground. This evening, stroll along the Arno River and dine at a local osteria.
Meals: Breakfast, Lunch, Dinner
Day 4 – September 26
Depart Pisa by private coach, stopping in the ancient hilltop town of Volterra. Walk through Etruscan gates and medieval streets, visiting artisan workshops where craftsmen shape alabaster using centuries-old techniques. After lunch, continue to Siena, arriving in time to explore the shell-shaped Piazza del Campo and settle into your Tuscan accommodations.
Meals: Breakfast, Lunch, Dinner
Day 5 – September 27
Enjoy a free day in Siena. Visit the stunning Siena Cathedral with its black and white marble facade and explore the winding streets of the contrade (historic neighborhoods) and wander the ancient alleyways for shopping. Or, choose to do a day trip to the Chianti countryside for a wine tasting at a local vineyard, savoring Tuscan reds paired with regional cheeses and cured meats. Gather as a group this evening for dinner to share stories.
Meals: Breakfast, Dinner
Day 6 – September 28
Travel by bus to Rome, checking into your hotel near the historic center. This afternoon, begin exploring the Eternal City with a guided walking tour through the cobblestone streets, visiting the Trevi Fountain, Spanish Steps, Pantheon, and Colosseum. This evening, dine in the charming Trastevere neighborhood.
Meals: Breakfast, Lunch, Dinner
Day 7 – September 29
Today is yours to explore Rome at your own pace. Perhaps visit Vatican City to marvel at the Sistine Chapel and St. Peter’s Basilica, or wander through the Borghese Gardens for a peaceful escape from the city bustle. Browse boutiques along Via del Corso, hunt for treasures at the Porta Portese flea market, or discover hidden churches adorned with Caravaggio masterpieces. Linger over cappuccino in Piazza Navona, take a cooking class to learn the secrets of Roman cuisine, or simply embrace the art of doing nothing at a sidewalk café. Rome reveals herself differently to every traveler, so follow your curiosity wherever it leads.
Meals: Breakfast, Dinner
Day 8 – September 30
Board the train to Naples, gateway to the Amalfi Coast. After settling into your hotel, explore Naples’ vibrant historic center, visiting Spaccanapoli street and sampling authentic Neapolitan pizza at its birthplace. This evening, stroll along the waterfront promenade with views of Mount Vesuvius and the Bay of Naples.
Meals: Breakfast, Lunch, Dinner
Day 9 – October 1
This morning, journey to Pompeii for a guided tour of the ancient city preserved by volcanic ash in 79 AD. Walk the original Roman streets, viewing homes, temples, and frescoes frozen in time. After lunch, travel along the stunning Amalfi Coast to Maiori, a charming seaside town with the coast’s longest beach and a more relaxed pace than its famous neighbors.
Meals: Breakfast, Lunch
Day 10 – October 2
Set sail this morning on a private boat tour along the legendary Amalfi Coast, experiencing the dramatic cliffs and pastel villages from the sparkling Mediterranean. Cruise past Minori’s hidden coves and arrive in postcard-perfect Positano, where you can disembark to wander steep lanes lined with lemon trees and boutiques. Continue to the town of Amalfi to explore its grand cathedral and charming piazzas, then glide back to Maiori. Wrap up the trip with a farewell dinner overlooking the sea, toasting to an unforgettable Italian adventure.
Meals: Breakfast, Lunch, Dinner
Day 11 – October 3
After breakfast, private transportation will take you to Naples International Airport (NAP) for your departure flight home, carrying memories of Italy’s diverse treasures from north to south.
Note: Your arrival and departure airports are different. You must arrive to Pisa (PSA) Airport and depart from Naples (NAP) Airport.
Highlights
Iconic Landmarks
History and Culture
Incredible Landscapes
Pricing & Inclusions
WHAT’S INCLUDED:
10 nights accommodations in boutique hotels
Single occupancy rooms
Daily breakfast, 7 lunches, 8 dinners
Airport transfers on arrival from Pisa and on departure to Naples
Train tickets between Cinque Terre, Pisa, and Naples
Private coach transportation from Pisa to Siena via Volterra
Bus transportation from Siena to Rome
Guided tours of Cinque Terre, Pisa, Volterra, Rome, and Naples
Guided tour of Pompeii archaeological site
All entrance fees for listed activities
Gratuities for guides and group activities
WHAT’S NOT INCLUDED:
International airfare to Pisa and from Naples
Travel insurance (strongly recommended)
Electronic Travel Authorization if required
Items of a personal nature
Meals not listed above
Alcoholic beverages
Tours and activities during free time
Gratuities and tips for personal services
Is This Tour For Me?

Travel Style: History/Culture
Physical Rating: 3
Age requirement: 18+

Alice West



















