Itinerary
Let us take care of every detail, so you can simply live Amore Italy.
Discover Italy the way it was meant to be experienced — with friends, freedom, and a private driver leading you through the heart of the country. Amore Italy is designed exclusively for American travelers who want the best of Italy without the crowds, confusion, or hidden costs of traditional tours. For about the same price as a 50-person bus tour, guests enjoy a private, all-inclusive VIP journey where every detail — from your driver to your dining — is handled with care. No stress. No surprises. Just pure Italian joy.
This 10-day escape is a celebration of discovery—crafted with signature experiences, regional flavors, and the intimacy only small-village life can offer.
Day 1
Depart the U.S. tonight and dream of Italy—your overnight flight is the overture to an unforgettable 10-day escape.
Your Italian adventure begins today with an overnight international flight from your selected U.S. gateway city to Rome Fiumicino Airport (FCO).
Whether you’re flying from Chicago, New York, or another major hub, we recommend arriving at the airport at least 3 hours before departure to allow ample time for check-in, security, and some pre-flight relaxation.
Day 2
Touch down in Rome, sip your first espresso, and set out to explore the city’s iconic landmarks before settling in for an overnight stay.
Rome, Italy
Morning
Arrive in Rome Italy
Benvenuti in Italia! Upon arrival at Rome’s Fiumicino Airport, you will be greeted by your private driver and escorted to your luxury Mercedes Van.
Afternoon
Lunch at Domiziano Piazza Navona
Your driver will drop you off in Piazza Navona, one of Rome’s most vibrant and storied squares. Enjoy lunch at Domiziano Piazza Navona, perfectly positioned at Piazza Navona 88, just across from the iconic Fountain of the Four Rivers. Settle in, relax, and watch the lively rhythm of the piazza unfold around you—we highly recommend the pizza.
After lunch, meet your driver at the same spot where you were dropped off and begin your journey to the Ancient Wonders of Rome golf cart tour.
Late-Afternoon
Highlights of Rome Tour: A Grand Introduction
Today’s immersive golf cart tour showcases the Eternal City’s most iconic landmarks, guided by a knowledgeable local expert. Highlights include: The Colosseum, Roman Forum, Trevi Fountain, Pantheon, Piazza Navona, and Spanish Steps.
Evening
Check-In (Hotel in Rome)
Arrive at your 4-star boutique hotel and take a moment to unwind.
Orazio Palace, Rose Garden Palace, Aria Palace, Hotel St. Martin *or similar*
Late Evening
Dinner in Rome
After a day spent exploring the lively beauty of Piazza Navona, ease into the evening with a peaceful dinner tucked along one of its charming side streets.
Day 3
Wake to breakfast in Rome, uncover the city’s iconic landmarks, then journey north to Montone where you’ll settle in and enjoy a warm welcome dinner as you ease away the last of the jet lag.
Rome, Italy
Morning
Begin your day with breakfast at the hotel before checking out, as your luggage is seamlessly transferred ahead. Set off on a guided exploration of Vatican City, taking in the Vatican Museums, Sistine Chapel, and the grandeur of St. Peter’s Basilica.
Afternoon
Enjoy a relaxed lunch in Rome before continuing your discovery with a guided visit inside the Colosseum, uncovering its rich history and enduring legacy. Later, depart the city by private transfer, soaking in the scenic countryside as you make your way to Umbria.
Montone, Italy
Evening
Arrive in the hilltop village of Montone and check in to Fortebraccio Hotel & SPA, your home for the week. Settle in before gathering for a welcome dinner at L’Antica Osteria, where regional flavors and local wines offer a warm introduction to Umbria.
Day 4
Soar above the Umbrian countryside at sunrise, then explore the sacred beauty of Assisi before returning for a relaxing afternoon at your leisure. End the day with a festive barbecue dinner under the stars.
Morning
Start the day with a sunrise hot air balloon ride over the Umbrian countryside, followed by a celebratory winery breakfast and wine tasting. This unforgettable morning pairs sweeping aerial views with local flavors.
Assisi, Italy
Afternoon
Travel to Assisi for a guided tour of the Basilica of St. Francis and its renowned frescoes, then enjoy lunch overlooking the Umbrian valley. Continue with a visit to the Basilica of Santa Maria degli Angeli before returning to the hotel for free time or optional activities like e-biking, Vespa rides, or a relaxing spa treatment.
Evening
Unwind and gather for a festive barbecue dinner under the stars, the perfect ending to a day rich in scenery, culture, and relaxation.
Montone, Italy
Day 5
Begin the day with breakfast before visiting a traditional ceramics studio in Deruta, then continue to Perugia for a relaxed lunch and time to explore its historic streets. Return to Montone in the evening for a regional dinner at L’Antica Osteria.
Depart Deruta
Head to Deruta for a morning immersed in the art of traditional ceramics.
Deruta, Italy
Ceramics Studio Experience
Visit a traditional ceramics studio where you will watch artisans create hand-painted pottery and explore the showroom.
Perugia, Italy
Lunch & Free Time in Perugia
Enjoy a casual lunch featuring local Umbrian specialties, followed by time to explore Perugia at your own pace.
Return to Hotel Fortebraccio
Return to Montone for an evening to unwind at the hotel after dinner.
Montone, Italy
Enjoy Dinner at L’Antica Osteria
End the evening with a fun and casual dinner.
Day 6
Start the day with a guided truffle hunt through the countryside, followed by a vineyard picnic featuring local Umbrian flavors. Enjoy a leisurely afternoon before a hands-on cooking class, ending the evening with dinner.
Montone, Italy
Truffle Hunt
Join expert hunters and their trained dogs as you search for prized truffles in the Umbrian countryside.
Picnic in the Vines
Celebrate your truffle adventure with a beautiful picnic among the vineyards.
Leisure Time
Spend the afternoon enjoying free time with options such as spa treatments, countryside walks, or Vespa and e-bike rides.
Signature Experience: Italian Cooking Class
Learn the secrets of Italian cooking as a local chef guides you through preparing traditional regional dishes.
Amore Moments
Another memorable moment celebrating food, culture, and friendship.
Dinner
Enjoy the delicious dinner you prepared in the hands-on cooking class.
Day 7
Travel into Tuscany to explore the medieval city of Siena with a guided tour of its historic streets and landmarks. After lunch, continue to the charming hilltown of Cortona for a scenic walk and gelato before returning to Montone for a lively evening in the piazza.
Montone, Italy
Morning
Depart for Siena
Travel into Tuscany to visit the stunning medieval city of Siena.
Florence, Italy
Siena, Italy
Tour Guide
Explore Siena’s winding streets, historic architecture, and the famous Piazza del Campo with a local expert.
Florence, Italy
Lunch at La Speranza
Enjoy a traditional Tuscan lunch at this beloved local restaurant.
Florence, Italy
Depart for Cortona for a Tour Under the Tuscan Sun
Continue to the charming hilltown of Cortona, made famous by the film Under the Tuscan Sun.
Florence, Italy
Cortona, Italy
Walk the Cobblestones of Cortona and Gelato
Stroll through Cortona’s picturesque streets and enjoy a refreshing gelato.
Florence, Italy
Depart for Hotel Fortebraccio
Relax on the return journey to Montone.
Florence, Italy
Montone, Italy
Traditional Italian Dinner & Drinks
Enjoy a lively evening with drinks and light bites to end the day.
Florence, Italy
Day 8
Begin the day with a relaxed morning at leisure, followed by a visit to Cantina Blasi for a guided wine cellar tour and a wine-paired lunch showcasing regional flavors. Spend the afternoon unwinding before ending the day with a casual dinner in Montone’s piazza.
Montone, Italy
Morning
Relax & Unwind During the Morning
Enjoy a relaxed morning with free time to explore, unwind at the spa, or take part in optional activities such as Vespa or e-bike rides.
Florence, Italy
Guided Wine Cellar Tour
Visit Cantina Blasi for a guided wine cellar tour and learn about the region’s winemaking traditions.
Lunch & Wine Tasting
Enjoy a wine-paired lunch featuring local dishes and multiple tastings.
Free Time
Spend the afternoon at leisure, continuing to enjoy the Umbrian countryside.
Dinner
End the day with a casual dinner in Montone’s piazza.
Day 9
Depart for Florence after breakfast, stopping for panoramic views and a guided tour of the city’s iconic landmarks. After time to relax and explore, end the day with a farewell dinner.
Florence, Italy
Florence, Italy
Piazzale Michelangelo Visit
Your driver will take you to Rome’s Fiumicino Airport for your journey home, bringing unforgettable memories of Italy with you.
Florence, Italy
Florence, Italy
Guided Walking Tour
Explore Florence on a guided walking tour, including the Duomo, Ponte Vecchio, Piazza della Signoria, and the Accademia Gallery to see Michelangelo’s David.
Florence, Italy
Florence, Italy
Hotel Check-In
Check in to your boutique hotel and take time to relax before departing for an afternoon of exploring Florence at your own pace.
Florence, Italy
Florence, Italy
Farewell Dinner
Celebrate your final evening with a farewell dinner at Caffè Gilli.
Florence, Italy
Day 10
Rise early for transfer to the airport.
Florence, Italy
Florence, Italy
Early Morning Pick Up From Hotel & Transfer to FLR
Your driver will take you to the Florence Airport for your journey home, bringing unforgettable memories of Italy with you.