Experience off-the-beaten path Rome, Umbria, a castle in the Tuscan countryside, and Cinque Terre in our Jewels of Italy tour.
All itineraries are sample itineraries and can be customized to suit your preferences.
- Rome
- Assisi
- Tuscan countryside
- San Gimignano
- Florence
- Cinque Terre
Please inquire for a custom trip quote based on your travel preferences and travel dates!
Your custom trip package will include accommodations, transportation within the country, guided tours and activities, unique experiences, trip planning, a downloadable, printable, and online itinerary, and personal support during your trip.
DAY 1: FLIGHT TO ROME, ITALY
Board your overnight flight to Rome’s Fiumicino airport.
DAY 2: WELCOME TO ROME!
Arrival in Rome, Italy. Transfer to your hotel and settle in. In the evening, explore Rome by foot! Have dinner along the way, enjoy an ice cream, and rest up.
DAY 3: ROME
After breakfast, head to the Vatican Museum where you will visit with a local guide. Here, you will see the Sistine Chapel and St. Peter's Basilica. You will also see one of Michelangelo's early works, the Pieta, and the dome completed after his death. After your visit, make your way back to the hotel to rest and freshen up. Explore Trastevere and dine in one of the many restaurants along the way.
DAY 4: ROME
After enjoying breakfast in your hotel, meet your experienced local guide for a walking tour of the historic center of Rome. Visit the famed Piazza Navona, Pantheon, Trevi Fountain, and other highlights along the way. After lunch in a typical Roman trattoria, visit the Colosseum and Roman Forum. Head back to the hotel for a rest, and eat dinner with a view of the artists in Piazza Navona.
DAY 5: ASSISI
After breakfast, check out of your hotel and make your way to the hillside town of Assisi. Upon your arrival, check into your hotel and rest/ freshen up. Enjoy a relaxing dinner with a view at your hotel this evening.
DAY 6: ASSISI
In the morning, meet your local guide in the lobby of your hotel for an expert guided tour of Assisi, the birthplace of St. Francis. Begin at Santa Chiara and work your way down through the village, ending up at the famous Basilica of St. Francis. After lunch, make your way to Florence, the city of the Renaissance. Upon your arrival, check into your hotel and then explore Florence this evening by foot.
DAY 7: FLORENCE
In the morning (dependent on the day) enjoy a Mass in the Florence Duomo. Afterward, meet your local guide in the hotel lobby and begin your tour of the Accademia and Santa Croce. Learn the history of the Duomo, Piazza della Signoria, and see Michelangelo's David. After lunch, explore Palazzo Pitti, Uffizi Gallery, Ponte Vecchio, the beautiful Florentine flea markets, and don't forget to rub the snout of the wild boar for good luck! Return to your hotel for a quick rest and dine at a Michelin star restaurant for an experience that you won't forget!
DAY 8: COUNTRYSIDE OF TUSCANY
Check out of your hotel after breakfast and head to the town of San Gimignano. Stroll through town and enjoy the scenery and shops! San Gimignano is known for its towers and Vernaccia wine (a white grape wine). Don’t forget to have an ice cream at the world famous Gelateria Dondoli located in the main square and known for its unique flavors, made from fresh local herbs and fruits. Enjoy lunch in town and make your way to Greve in Chianti where you will check into your hotel, tucked away in the rolling hills of Tuscany.
DAY 9: GREVE IN CHIANTI
Explore the small town of Greve in Chianti, relax, visit local wineries, or head to our favorite enoteca for self-service wine-tasting of the most delicious wines of the area.
DAY 10: GREVE IN CHIANTI/ TUSCAN COUNTRYSIDE
Today, explore the countryside of Tuscany, relax by the pool at your hotel, or take a Vespa ride through local vineyards! Have an exquisite dinner at your hotel this evening.
DAY 11: MONTEROSSO AL MARE
After breakfast, check out of your hotel and make your way to Monterosso al Mare in the Cinque Terre. A note that itineraries in the Cinque Terre are weather dependent. Upon your arrival, enjoy a seafood lunch at one of our favorite local restaurants. Monterosso hosts a beautiful beach and there are hiking trails between the various towns of the Cinque Terre. Today, relax by the beach, hike the trails, or enjoy a train ride to each town. This evening, get your bearings and enjoy local seafood specialties with a fabulous view of the sea.
DAY 12: CINQUE TERRE
After breakfast, if the sea is calm, take a boat cruise to see the magnificent villages of the Cinque Terre from the sea. This afternoon, enjoy the beach and relax!
DAY 13: CINQUE TERRE
Enjoy the trails and the towns of the Cinque Terre, shop, take a boat cruise, or enjoy the beach and relax.
DAY 14: TRAVEL TO ROME
After breakfast, check out of your hotel and make your way toward Rome. Stop in Pisa for a picnic lunch in the Square of Miracles and see one of the 7 wonders of the world: the Leaning Tower of Pisa. Continue on to Rome after lunch and check into your hotel. This evening, visit the center of Rome for a stroll along the Tiber River to explore and dine.
DAY 15: ROME
Today, experience Rome at leisure. Visit the town of Frascati to do some wine tasting, or do a tour of the beautiful Villa d'Este with its magnificent Tivoli Gardens. This evening, dine in the hotel and prepare for your departure.
DAY 16: DEPARTURE
Say farewell to la bella Italia (until next time!). Transfers to Rome Fiumicino airport are available.
Most trips are customized for private travel and can be tailored to your preferences. Click below to give us an idea of what you're looking for!