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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 9-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 9-day escape.
Day 2
Touch down in Rome, sip your first espresso, then glide north to the hilltop village of Montone.
Rome, Italy
Morning
Arrive in Rome Italy & Roman Wonders
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. Settle in, relax, and enjoy the first glimpses of Italy as you head into the heart of Rome.
Mid-Morning
Highlights of Rome Tour: A Grand Introduction
Today’s immersive walking and driving tour showcases the Eternal City’s most iconic landmarks, guided by a knowledgeable local expert.
Highlights include:
The Colosseum – Step back in time at the world’s most legendary amphitheater.
Roman Forum – Wander the ruins where ancient Roman civilization once thrived.
Trevi Fountain – Toss a coin to ensure your return to Rome. Pantheon – Marvel at the architectural perfection of this 2,000-year-old masterpiece.
Piazza Navona – Soak in the baroque splendor of one of Rome’s most beautiful squares.
Spanish Steps – Snap a photo at this iconic Roman landmark before a gelato break. Stop for lunch at our favorite cafe in Piazza Navona. Watch the hustle and bustle go by as we enjoy the best pizza in Rome along with refreshing drinks.
Late-Afternoon
Depart for Umbria: Scenic Drive to Montone
After a full day soaking in Rome’s magic, your driver will take you on a relaxing and scenic 2.5-hour journey north into the rolling hills of Umbria. Along the way, enjoy glimpses of olive groves, hilltop villages, and vineyard-covered valleys.
Montone Umbria, Italy
Early-Evening
Check in at Hotel SPA Fortebraccio
Check in to your home for the week—Hotel SPA Fortebraccio is a charming 4-star boutique hotel nestled on a hillside just outside the medieval walls of Montone, a picturesque town in the Umbria region of Italy. The hotel offers breathtaking panoramic views of the surrounding countryside, characterized by rolling hills, olive groves, and vineyards. The hotel itself is a beautifully restored country house, featuring a blend of traditional Umbrian architecture and modern comforts. Guests can enjoy a variety of amenities, including a swimming pool, a spa, and a well-regarded restaurant serving delicious local cuisine. The rooms are spacious and elegantly furnished, providing a peaceful and relaxing atmosphere.
Evening
Signature Experience: Aperitif & Digestif Experience
Gather at the bar for a delightful evening ritual: the Italian aperitivo. You’ll sip your way through the beloved aperitifs and digestifs of Italy, from bitter-sweet Campari to velvety Amaro, accompanied by savory bites and spirited conversation. Complimentary wine, spirits and other favorite drinks and cocktails compliment the most amazing charcuterie display. Enjoy
cold cuts and the best cheeses Italy has to offer.
Evening
Cozy Evening in Montone
As the sky turns pink above the village, the evening is yours to enjoy. Stroll the quiet streets, or simply curl up and let the peace of Umbria settle in.
Day 3
Wake to an Umbrian breakfast, uncover Assisi’s sacred frescoes, picnic beneath olive groves, and melt away jet-lag with a signature spa massage & fortress-feast dinner.
Montone, Italy
Morning
Umbrian-Inspired Breakfast at Hotel SPA Fortebraccio
Begin your day with a nourishing breakfast served on the terrace overlooking the Umbrian hills. Enjoy fresh-baked pastries, farm eggs, prosciutto, pecorino, ripe fruit, and strong Italian coffee. It’s the perfect start to your day of inspiration and relaxation.
Assisi, Italy
Morning
Assisi Unveiled: Art, Faith & Timeless Beauty
Depart from the hotel for a scenic drive to Assisi, the birthplace of Saint Francis and one of Italy’s most spiritual destinations. A local guide will walk you through the Basilica of St. Francis, adorned with stunning frescoes, and share the
stories that made Assisi a beacon of peace. Take time to stroll the cobbled streets, visit artisan shops, or light a candle at one of the peaceful chapels.
Mid-Day
Picnic Among the Vines
Enjoy a casual picnic lunch as we learn how to slow down and enjoy a refreshing picnic lunch with a menu of seasonal Umbrian fare—fresh greens, local salumi, and artisanal cheeses served with crusty bread and a glass of chilled Orvieto.
Montone Umbria, Italy
Early-Evening
Signature Massage Suite: “The Art of Reawakening”
Let the tension melt away. This afternoon the Signature Massage Suite is reserved for each lady to receive a 50 minute customized treatment designed to soothe sore muscles and banish jetlag. Whether you choose deep tissue or
aromatherapy, you’ll emerge refreshed and rebalanced. Sessions available at 4:00PM, 5:00PM, and 6:00PM.
Evening
Dinner at L’Antica Osteria: A Fortress Feast
This evening Meik and Belinda Andriani welcome you to L’Antica Osteria—a local culinary treasure. Enjoy a multicourse meal crafted with seasonal ingredients, local wines, and the warmth of old-world charm.
Day 4
Start with terrace pastries, then journey through Tuscany’s patchwork hills to Montepulciano’s wine cellars and Cortona’s cobbled lanes—gelato in hand—before an Umbrian-style feast back in Montone.
Montone, Italy
Morning
Umbrian-Inspired Breakfast at Hotel SPA Fortebraccio
Start your day with a hearty breakfast on the terrace. Fresh baked cornetti, local yogurt, honey from the valley, and madeto-order cappuccinos await as the morning mist lifts from the hills of Montone.
Morning
Depart for Siena
The journey takes you through the heart of Umbria and into Tuscany, two of Italy’s most picturesque regions. Rolling hills, patchwork farmland, cypress-lined roads, sunflower fields (seasonal), olive groves, and vineyards dominate the landscape.
Montepulciano, Italy
Late Morning
Arrive and Walking Tour of Siena. A timeless Jewel of Tuscany
Our journey brings us to Siena, one of Tuscany’s most captivating medieval cities. Enclosed within ancient walls and crowned by its striking Piazza del Campo, Siena feels like stepping into a living Renaissance painting. As we wander through narrow cobblestone lanes, you’ll discover Gothic architecture, centuries-old traditions, and the warm, earthy colors that give the city its signature charm.
At the heart of Siena lies the fan-shaped Campo, famous as the stage for the thrilling Palio horse race. Nearby rises the magnificent Siena Cathedral, a masterpiece of black-and-white marble, intricate carvings, and soaring artistry. Whether you choose to explore artisan shops, enjoy a Tuscan espresso in the square, or simply soak in the skyline from a quiet viewpoint, Siena offers a perfect blend of history, beauty, and authentic Italian life.
A stop in Siena isn’t just sightseeing—it’s an experience of culture, craftsmanship, and timeless Tuscan spirit.
Mid-Day
Lunch in Siena
Wine Tasting and Lunch in Local Cantina
Spend a leisurely afternoon immersed in the flavors of Tuscany with a wine tasting and lunch at a local cantina in Montepulciano. Begin with a guided tasting led by passionate hosts, who will walk you through a selection of locally
produced wines. Following the tasting, enjoy a relaxed lunch featuring seasonal, regional cuisine made with fresh, locally sourced ingredients. The setting—whether inside a centuries-old stone cellar or on a terrace overlooking rolling hills. This is more than just a tasting—it’s a chance to slow down, savor, and connect with the soul of Montepulciano through its
food, wine, and warm hospitality.
Early-Afternoon
Depart for Cortona for a Tour Under thier Tuscan Sun
After a leisurely lunch in a cozy Montepulciano cantina, the drive to Cortona unfolds like a living postcard beneath the golden Tuscan sun. Rolling hills stretch endlessly, dotted with vineyards, olive groves, and cypress trees standing tall like sentinels along winding country roads. The light is soft and warm, casting long shadows that dance over fields of sunflowers and rustic farmhouses.
Cortona, Italy
Late-Afternoon
Arrive and walk the cobblestone streets of Cortona for Gelato
After arriving in Cortona, stepping out onto its sun-drenched cobblestone streets feels like walking into a scene from a Tuscan dream. The town’s medieval charm is everywhere—stone archways, flower-filled balconies, and centuries-old buildings that lean gently into one another. As you explore, quaint boutiques and artisan shops line the narrow lanes, offering everything from hand-stitched leather goods and linen clothing to ceramics, jewelry, and locally made olive oils. Each shop feels personal, often with the owner ready to share the story behind the craftsmanship. In the main piazza or tucked into a shaded corner, the irresistible scent of freshly made gelato beckons. Enjoy a creamy
scoop in a handmade cone as you sit on a worn stone bench, watching the rhythm of daily life pass by—locals chatting, church bells chiming, and the golden Tuscan light casting a warm glow over everything.
Early-Evening
Return to Montone
Relax on the way back to Montone after a busy day to freshen up for dinner.
Montone, Italy
Evening
Countryside Farm to Table Experience
This evening, you’ll visit a family-run Umbrian farm, alive with chickens, goats, and sheep grazing in the fields. After a warm welcome and a stroll among the animals, settle in at long farmhouse tables for a dinner made from the farm’s own harvest—seasonal vegetables, fresh cheeses, golden olive oil, and meats raised just steps away. Paired with local wines, each course celebrates the rustic flavors of Umbria. Surrounded by the sights and sounds of the countryside, this farm-to-table feast is a joyful immersion into authentic Italian life.
Day 5
Wake up early, grab a quick breakfast, then hit the road to make the most of the day—tour, taste, and explore from morning to night, with time to recharge before dinner and a well-earned evening under the stars.
Montone, Italy
Early Bird Umbrian-Inspired Breakfast at Hotel SPA Fortebraccio
Begin your day with a nourishing breakfast served on the terrace overlooking the Umbrian hills. Enjoy fresh-baked pastries, farm eggs, prosciutto, pecorino, ripe fruit, and strong Italian coffee. It’s the perfect start to your day of inspiration and relaxation.
Morning
Choose Your Passion- Signature Experiences
Premier Italian Golf Escape
Golf the 18 hole Championship Golf Course of Antognolla, designed by the famous course architect Robert Trent Jones jr. - framed by Umbrian hills – tee off against a backdrop of rolling green landscapes, where every swing comes with panoramic views of medieval hill towns and vineyards stretching into the horizon.
Italian Galleria Shopping Escape
The Valdichiana Village houses over 140 famous designer and brand shops that offer 30 – 70% discounts all year round and during sales periods further discounts and offers are made. The Village offers a pleasant and relaxing atmosphere; it has several facilities and services such as the beauty center, the playground, the library, and several food courts where the best local food and wines are offered. The visitors choose Valdichiana Outlet Village situated in Foiano for a unique“shopping experience” characterized by quality and convenience.
Vespa & E-Bike Countryside Escape
Vespa-It’s not just a ride; it’s a slow, joyful way of experiencing Umbria’s beauty.. the scent of cypress and wild herbs, and panoramic views that seem to appear around every curve. It’s an effortless, charming way to explore nearby towns, vineyards, and quiet country roads while soaking up the rhythm of rural Italy.
E-biking along countryside trails and medieval villages – Glide effortlessly along scenic paths, weaving through stone-paved streets and centuries-old villages, with every turn offering a new glimpse into the timeless charm of rural Italy.
Hike through olive groves and vineyards, soaking in the quiet rhythm of Italy’s heartland – troll under the silver-green canopy of ancient olive trees and past rows of sun-drenched vines, where the only soundtrack is the whisper of the breeze and the soft crunch of gravel underfoot.
"The Art of Reawakening"
Let the tension melt away. This afternoon the Signature Massage Suite is reserved to receive a 50 minute customized treatment designed to soothe sore muscles and banish jetlag. Whether you choose deep tissue or aromatherapy, you’ll emerge refreshed and rebalanced. Sessions available at 9:00AM, 10:00AM, and 11:00AM.
Montepulciano, Italy
10:30 am
Return to Hotel SPA Fortebraccio
After a generous lunch and flowing wine, return to the hotel to rest, read, swim, or simply take in the view from your balcony. The pace is slow, the air is still, and the afternoon is yours.
Evening
Barbecue Under the Stars
Tonight, everyone reunites for a festive barbecue dinner by the pool at Hotel SPA Fortebraccio. Savor flame-grilled meats, garden-fresh vegetables, and rustic Umbrian specialties paired with regional wines and chilled beers. With twinkling lights reflecting off the water and soft music in the background, it’s the perfect evening of laughter, stories, and togetherness under the Italian night sky.
Mid-Day
Wine Cellar Tour & Grand Lunch at Cantina Blasi
Just a short drive from Montone, Cantina Blasi is a family-owned winery known for bold reds, crisp whites, and ancient underground cellars dating back centuries.
What to Expect:
• A guided tour through the historic wine cellars, where time and temperature shape each bottle
• Stories of the land, the vines, and the Blasi family legacy
• A long, memorable Umbrian lunch—homemade pastas, roasted meats, truffle-scented dishes—paired with multiple wine tastings, laughter, and toasts
Founded in 1893 and set among rolling hills and 30 hectares of vineyards, Cantina Blasi blends winemaking with a long tradition in butchery and artisanal food production. The winery is celebrated for sustainable practices and produces an exclusive private-label wine for Villa Destino, part of our broader hospitality family with Hotel SPA Fortebraccio and L’Antica Osteria.
Day 6
Spend a day in Florence—golf-cart the Renaissance, dine at historic Gilli’s, skip the line for Michelangelo’s David, then return for pizza in Montone’s piazza.
Montone, Italy
Morning
Depart for Florence
After an early breakfast at Hotel SPA Fortebraccio, depart for a full-day adventure to one of the most culturally rich cities in the world—Florence. Enjoy the scenic 2-hour drive through the rolling hills of Umbria and into the heart of Tuscany.
Florence, Italy
10:30 am
Arrival in Florence & Golf Cart City Tour
To save your feet from the cobblestone maze of Florence, enjoy the city’s most relaxed and stylish sightseeing experience: a guided golf cart tour through the heart of the Renaissance.
Your 2-hour guided ride includes stops and stories at Florence’s most iconic sites:
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Piazza della Signoria – The political heart of Florence, flanked by sculptures and the Palazzo Vecchio
-
The Duomo & Baptistery – Marvel at Brunelleschi’s dome and the Gates of Paradise
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Santa Croce – Final resting place of Michelangelo, Galileo, and Machiavelli
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Ponte Vecchio – The famous medieval bridge lined with goldsmith shops
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Piazzale Michelangelo – Enjoy a panoramic view of the city’s skyline
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San Lorenzo Market – Glimpse local life with leather, food, and artisan stalls
The tour ends at the doorstep of a legendary culinary experience…
Mid-Day
Lunch at Gilli's Restaurant
Gather at Gilli’s, Florence’s oldest café and a symbol of elegance since 1733. Located on Piazza della Repubblica, it’s the perfect place to enjoy a refined Tuscan lunch in a historic setting, surrounded by marble columns, mirrored walls, and the charm of old Florence.
Afternoon
Skip-the-Line Private Tour: Michelangelo's David
Meet your private guide at the Galleria dell’Accademia for a reserved entry and intimate look at one of the most celebrated sculptures in the world—Michelangelo’s David. Learn the story behind the masterpiece, explore the museum’s highlights, and absorb the genius of Renaissance artistry.
Late-Afternoon
Depart Florence for Montone
After a full day of beauty, history, and unforgettable food, relax and unwind on the scenic drive back to Umbria.
Montone, Italy
Evening
Return to Hotel SPA Fortebraccio
Arrive at the hotel to freshen up. Choose to sip wine on the terrace, or simply unwind after a day well spent in the cradle of the Renaissance.
Montone, Italy
Evening
Pizza at the Piazza
Enjoy the best Pizza and Calzone at the local piazza in Montone.
Day 7
Ease into the morning; ladies roll fresh pasta over Prosecco while gentlemen choose golf, e-biking or vineyards hikes—reunite poolside for a festive barbecue under the stars.
Montone, Italy
Morning
Leisurely Breakfast
After an early breakfast at Hotel SPA Fortebraccio, depart for a full-day adventure to one of the most culturally rich cities in the world—Florence. Enjoy the scenic 2-hour drive through the rolling hills of Umbria and into the heart of Tuscany.
Florence, Italy
Morning
Truffle Hunt and Lunch
Birds calling overhead, leaves crunching underfoot, sunlight filtering into green-gold patches. Your guide explains the difference between black and white truffles, how the earth must be read like a map, and why the best finds rely on trust between human and dog.
Lunch is built around the morning’s treasure. Plates arrive simple and perfect: warm bruschetta with shaved truffle, fresh tagliatelle swirled with butter and generous ribbons of black truffle, a local Sangiovese or Sagrantino wine deep enough to stand beside the dish. The flavors are earthy, rich, but somehow delicate—Umbria on a plate. It feels like the forest, the hunt, and the lunch have blended into a single Umbrian memory—quiet, authentic, and deeply satisfying.
Mid-Day
Return to Hotel SPA Fortebraccio
Mid-Day
Signature Experience: The Art of Reawakening, Massage and Spa OR Vespa/E-Bike Countryside
The Art of Reawakening, Massage and Spa
Let the tension melt away. This afternoon the Signature Massage Suite is reserved for a 50 minute customized treatment designed to soothe sore muscles. Whether you choose deep tissue or aromatherapy, you’ll emerge refreshed and rebalanced. Sessions available at 1:00PM, 2:00PM, and 3:00PM.
Vespa and E-Bike Country Side
Vespa-It’s not just a ride; it’s a slow, joyful way of experiencing Umbria’s beauty.. the scent of cypress and wild herbs, and panoramic views that seem to appear around every curve. It’s an effortless, charming way to explore nearby towns, vineyards, and quiet country roads while soaking up the rhythm of rural Italy.
E-biking along countryside trails and medieval villages – Glide effortlessly along scenic paths, weaving through stone-paved streets and centuries-old villages, with every turn offering a new glimpse into the timeless charm of rural Italy.
Hike through olive groves and vineyards, soaking in the quiet rhythm of Italy’s heartland – troll under the silver-green canopy of ancient olive trees and past rows of sun-drenched vines, where the only soundtrack is the whisper of the breeze and the soft crunch of gravel underfoot.
Late - Afternoon
Signature Experience: Italian Cooking Class
Gather in Hotel Fortebraccio’s new culinary studio for a hands-on cooking immersion. Under the guidance of a local chef, you’ll roll fresh pasta by hand, stir age-old sauces, and raise a glass of Prosecco to toast your creations. This joyful class concludes with a shared dinner featuring the very dishes you’ve prepared—an authentic, delicious celebration of Italian culinary tradition.
Evening
Amore al Gelato Cart
Your evening concludes with a magical touch: your very own private gelato cart experience, included exclusively for your group.
After an unforgettable dinner and the warm glow of Italian hospitality, the night takes a sweet turn. Just as the meal winds down, a charming vintage gelato cart rolls in, its soft pastel colors glowing under the evening lights.
Your personal gelato lifts the lid to reveal small-batch, handcrafted flavors made that very day: velvety pistachio from Bronte, bright Amalfi lemon, rich dark chocolate, and classic stracciatella. You’re invited to sample, choose, and savor as the stories behind each flavor are shared with you.
It’s the perfect finale to a perfect evening—your own taste of dolce vita, created just for your group and included in your Amore Italy journey.
Day 8
Explore Deruta’s centuries-old majolica craft with a family-run studio demo, shop vibrant ceramics, then toast your journey at a heartfelt farewell dinner in Montone.
Montone, Italy
Morning
Breaksfast at Hotel SPA Fortebraccio
Start your day with a hearty breakfast on the terrace. Fresh baked cornetti, local yogurt, honey from the valley, and madeto-
order cappuccinos await as the morning mist lifts from the hills of Montone
Florence, Italy
Morning
Depart for Deruta: The Heart of Umbrian Ceramics
Enjoy a scenic drive through the Umbrian countryside as you make your way to Deruta, Italy’s world-famous ceramics capital—home to a centuries-old tradition of majolica pottery.
Deruta, Italy
Mid-Morning
The Deruta Experience: Where Clay Meets Craft
Warm Welcome at El Frate Ceramics with the Giovanna Family
Arrive at the family-run El Frate Ceramics Studio, where you’ll be greeted with morning refreshments and warm Umbrian
hospitality from the Giovanna family. Savor coffee, pastries, and local delights as you settle into the heart of Deruta.
Ceramics Demonstration: From Earth to Art
Watch as skilled artisans bring clay to life before your eyes—shaping, painting, and glazing each piece with precision and
passion. This is true craftsmanship, preserved through generations and proudly shared with guests.
Showroom Tour: A Feast of Color and Tradition
Step into the El Frate showroom, where shelves overflow with exquisite hand-painted plates, tiles, vases, and custom
pieces. This is your chance to browse, ask questions, and even shop for one-of-a-kind souvenirs or gifts that carry the spirit
of Umbria home with you.
Mid-Day
Lunch in Deruta
Just next door, enjoy a relaxed lunch at a local trattoria—a perfect pairing of artisan and appetite. Savor traditional Umbrian dishes and house wine in a cozy setting where locals dine and laughter lingers.
Afternoon
Return to Hotel SPA Fortebraccio
Head back to Montone for some well-earned rest and reflection. Take a dip in the pool, enjoy a book on the terrace, or schedule a massage if you're in the mood for extra indulgence.
Montone, Italy
Evening
Farewell Dinner at L'Antica Osteria in Montone
As the stars come out over the medieval village of Montone, gather one last time at the beloved L’Antica Osteria, hosted by Meik and Belinda Andriani. Raise a glass to an unforgettable week of friendship, flavor, and discovery. A multi-course farewell feast will bring your Umbrian journey to a perfect close.
Day 9
Rise before dawn for a private transfer through rolling hills back to Rome Fiumicino—arrivederci Italy, until next time.
Montone, Italy
Morning
Early Morning Departure from Hotel SPA Fortebraccio
Your journey home begins with an early departure from Montone (box breakfast will be ready for you). Board your private Mercedes Van for a comfortable transfer to Rome Fiumicino Airport (FCO). Estimated drive time: 2.5 hours.
Rome, Italy
Morning
Florence, Italy
Arrive with plenty of time to check in, pass through security, and prepare for your mid-morning international flight home.
Arrive at Rome Fiumicino Airport
Morning
Depart Rome for the U.S.
As you take off from the Eternal City, carry with you a week’s worth of memories—meals shared, wine savored, landscapes wandered, and friendships formed.
Florence, Italy
