A trip to Italy through Tuscany and the Amalfi Coast becomes a living, tasting story, where every moment is crafted around flavor, culture, and connection. Savor sun-ripened tomatoes at a family table, uncover cellar secrets with artisan winemakers, and stroll coastal lanes with a private guide who shapes each experience to your interests.
Designed for travelers who value authentic, tailor-made journeys, this gastronomic adventure awakens your senses and transforms curiosity into lasting memories. Start planning your personalized itinerary today, and let us craft the meals, encounters, and hidden moments that make Italy feel entirely your own.
| Day | Morning | Afternoon | Evening |
|---|---|---|---|
| Day 1 | Arrival in Florence; private transfer to hotel | Artisan walk in Oltrarno with local guide | Free time to relax or explore |
| Day 2 | Guided hike in Chianti with olive oil tasting | Cellar tour and lunch at boutique winery | Evening at leisure |
| Day 3 | Market visit and food tour with a chef | Cooking class with wine pairings | Free evening or recipe booklet takeaway |
| Day 4 | Transfer to Montalcino; explore medieval town | Brunello tasting with multi-course lunch | Return to Florence and rest |
| Day 5 | Train from Florence to Naples | Naples street food tour with local guide | Evening at leisure |
| Day 6 | Guided tour of Pompeii ruins | Wine tasting lunch on Mt. Vesuvius and crater hike | Return to Naples and relax |
| Day 7 | Private transfer to Positano | Free time to explore or relax | Optional tastings or seaside dinner |
| Day 8 | Amalfi Coast scenic drive with guide | Explore Amalfi and Positano | Gelato or sunset walk |
| Day 9 | Hike the Path of the Gods with guide | Return to hotel and relax | Free evening |
| Day 10 | Private boat to Capri | Free time to explore the island | Optional shopping or limoncello |
| Day 11 | Breakfast and check-out | Private transfer to Naples Airport | Departure |
A private car transfer from Florence Airport to your accommodation ensures a smooth, personalized start to your Italy travel experience.
In the afternoon, meet your local host Mirka for a walking tour of the Oltrarno district, where you'll visit centuries-old botteghe: hatters, gilders, confectioners, carpenters, instrument makers, and jewelers.
Learn traditional techniques, sample local specialties, and immerse yourself in the authentic craft culture that defines this Tuscany and Amalfi Coast trip.

After breakfast, meet in Florence and take a 20-minute shuttle into the Chianti wine region for a guided hike through the Tuscan countryside. Along the way, stop at an olive oil mill on a historic estate for a tour and tasting, led by an environmental guide who highlights local vines, olive groves, hidden churches, and medieval towers.
The hike ends at a boutique winery, where you’ll enjoy a cellar tour and tasting, followed by a tailor-made Tuscan lunch paired with regional wines.

Join a tailored small-group Italy trip experience: a guided food tour through Florence’s historic center and Oltrarno, led by a professional chef. Visit authentic botteghe to taste and shop for fresh Tuscan ingredients, then head to a hands-on cooking class in an exclusive Florence location.
Learn to make potato gnocchi with pesto, eggplant parmigiana, and cantuccini to dip in Vinsanto, all paired with fine Tuscan wines. You’ll take home a recipe booklet and the skills to recreate this delicious chapter of your Tuscany and the Amalfi Coast trip.

Join a semi-private full-day trip to Montalcino for an authentic, tailor-made wine experience. Wander the medieval streets of this charming UNESCO-listed hilltop town, exploring winding alleys and scenic viewpoints while hearing local stories that bring the place to life.
Visit two distinctive Sangiovese-based cellars, plus a boutique winery for a Brunello di Montalcino DOCG tasting, paired with a generous multi-course Tuscan lunch. Along the way, learn about Brunello’s five-year aging process and the remarkable longevity that makes it one of Italy’s most prestigious wines.


Tips from Fabio
Italy Travel Expert

Before or after your wine tastings, climb the walls of Montalcino’s 14th-century fortress (Fortezza di Montalcino) for panoramic views over the Val d’Orcia, then stop at the small enoteca inside for a hidden gem: rare vintage Brunellos by the glass, often poured by locals who love to share a story or two.
Start your day with a morning train from Florence to Naples. After breakfast and check-out, arrive at your accommodation near the station and get settled, ready to explore Naples.
In the afternoon, meet your local host for an authentic street food tour through the historic center. Taste iconic bites like pizza, sfogliatella, and market specialties while hearing lively local stories and the culinary traditions that make Naples unforgettable.
Spend the evening at your leisure, exploring more of the city or relaxing with a view.

Join a small-group coach tour to the legendary archaeological site of Pompeii. With an expert guide, uncover the story of Mount Vesuvius’s eruption in 79 AD as you walk the city’s remarkably preserved streets, villas, and frescoes.
Then head to the slopes of Vesuvius for an exclusive lunch and wine tasting at a top local producer. Enjoy a three-course meal featuring regional cheeses, cured meats, pasta with piennolo tomatoes, and pastiera for dessert.
After lunch, take a 20-minute hike to the crater for panoramic views over the Bay of Naples, a dramatic finale to a day steeped in history, flavor, and landscape.

Check out of your hotel in Naples and enjoy a private transfer to Positano. Relax on the scenic coastal drive as your driver takes you to your new accommodation overlooking the sea.
The rest of the day is yours for authentic, tailor-made travel: wander Positano’s cliffside lanes, sample fresh seafood and limoncello, unwind on the pebble beach, or browse local ceramic shops. Optional guided tastings, boat excursions, and custom experiences can be arranged to match your interests.

Meet your driver and travel by comfortable coach along the breathtaking Amalfi Coast, pausing at scenic viewpoints for photos and sweeping coastal panoramas.
Wander Positano’s steep lanes and colorful boutiques, then stroll through Amalfi’s historic piazza and visit its striking cathedral. There’s also time for a relaxed seaside walk or a gelato with a view.
This journey is all about sensory pleasures: lemon-scented breezes, vibrant majolica domes, and the charm of cliffside villages perched above the sea.

Hike the Path of the Gods with a professional guide and experience one of the Amalfi Coast’s most iconic trails. This round-trip route from Bomerano takes about 3.5 hours, leading you along dramatic cliffside paths with sweeping views of the coastline.
Along the way, your guide shares local stories and regional insights that make your Italy trip feel truly authentic and tailor-made.
Return to your hotel in the afternoon and enjoy the rest of the day at leisure.

Set off by private boat to Capri, arriving with plenty of time to explore the island at your own pace. Stroll through the Piazzetta, take in coastal views, unwind in hidden coves, or sip limoncello at a seaside café.
Your tailor-made Italy trip continues with experiences suited to your style: choose scenic hikes with panoramic vistas or enjoy a leisurely day of shopping and local discovery.

After breakfast and check-out, a private car transfer will take you to Naples Airport, providing a smooth and personalized end to your Italy trip.
Enjoy a relaxed departure, and arrivederci until next time!
