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Florence, Italy
🗓️ Day 1: Florence City Highlights + Wine Windows + Aperitivo
🕘 Morning
• Duomo di Firenze & Climb the Dome: Start at Florence’s iconic cathedral, climb Brunelleschi’s dome for stunning views.
• Baptistery & Giotto’s Bell Tower nearby — worth a visit (get a combined ticket).
🕛 Lunch
• Eat at La Ménagère or Trattoria ZaZa (Tuscan cuisine with great wine).
• Visit your first wine window (buchetta del vino) — there’s one at Buca del Vino near Palazzo Vecchio.
🕓 Afternoon
• Uffizi Gallery: Masterpieces from Botticelli, Leonardo da Vinci, Caravaggio.
• Stroll along the Arno River to Ponte Vecchio.
🕡 Aperitivo & Wine
• Le Volpi e l’Uva – small, cozy wine bar with curated regional wines.
• Enjoy an aperitivo platter with cured meats, cheese, and crostini.
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🗓️ Day 2: Tuscan Wine Day Trip (Chianti Region)
🍇 Full-day wine tour options (book in advance)
• Chianti Classico Tour with stops at 2–3 wineries.
• Sample wines like Chianti Classico, Super Tuscan, and Vinsanto.
• Visit Greve in Chianti or Castellina in Chianti.
Alternative DIY Option:
• Rent a car or book a private driver.
• Visit Antinori nel Chianti Classico – a famous modern winery just 30 minutes from Florence.
🕗 Evening (Back in Florence)
• Dinner at La Giostra – romantic setting, good wine list.
• Stop by Wine Window #2: Cantina de’ Pucci (they still serve wine via the little door!).
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🗓️ Day 3: Optional Rome Day Trip (Colosseum) OR Florence Art & Relax
✨ Option A: Day Trip to Rome
• Take a high-speed train (Firenze S.M.N. → Roma Termini, 1h30–2h).
• Book a Colosseum + Roman Forum + Palatine Hill ticket in advance.
• Quick stroll past Trevi Fountain or Spanish Steps.
• Return to Florence in the evening.
🕘 Suggested train:
• 7:00 AM to Rome
• 7:00 PM return to Florence
🍷 Option B: Stay in Florence
• Morning at Accademia Gallery – See Michelangelo’s David.
• Visit Santa Croce or stroll around Oltrarno (less touristy, artsy area).
• Lunch & your 3rd wine window: Babae (modern, still serves wine through the window!).
🍝 Farewell Dinner
• Eat at Trattoria Cammillo or Osteria Vini e Vecchi Sapori.
• Toast with a final glass of Brunello di Montalcino or Vino Nobile di Montepulciano.
- Santa Maria del Fiore
- Accademia Gallery
- Giotto's Campanile
- Florence Baptistery of St. John
- Fountain of Neptune
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Bagno Vignoni, Italy
Day 1 (Afternoon arrival)
• Arrive by taxi from Chiusi
• Check in and relax at the spa
• Walk around the thermal square (Piazza delle Sorgenti)
• Enjoy a Tuscan dinner with wine (try local Rosso di Montalcino or Nobile di Montepulciano)
Day 2 (Morning)
• Another spa session or walk the Parco dei Mulini trail – a peaceful path near ancient water mills
• Enjoy breakfast with a view
• Taxi back to Chiusi or onward to Rome or Florence
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Rome, Italy
🏛️ Morning – Colosseum, Roman Forum, Palatine Hill
• Start early (pre-book a skip-the-line ticket or guided tour)
• Walk the Roman Forum ruins — temples, arches, and basilicas
• Climb Palatine Hill for views over the Forum and Circus Maximus
🍕 Lunch:
• Trattoria Luzzi (casual, Roman food near Colosseum)
• Or: PastaChef (fast, gourmet pasta)
🏛️ Afternoon – Pantheon & Piazza Navona
• Walk to Piazza Venezia & Altare della Patria (massive white monument)
• Explore the Pantheon (ancient Roman temple)
• Chill at Piazza Navona with street artists & fountains
🍷 Evening:
• Aperitivo at Il Goccetto (local wine bar)
• Dinner in Campo de’ Fiori or Trastevere
• Try Da Enzo al 29 (authentic Roman dishes) or Tonnarello
• Optional: Stroll along the Tiber River at night
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🗓️ Day 2 – Vatican & Viewpoints
🏛️ Morning – Vatican Museums + Sistine Chapel + St. Peter’s Basilica
• Book early morning Vatican Museum tickets (to avoid crowds)
• See the Sistine Chapel, Raphael Rooms, and more
• Walk to St. Peter’s Basilica and climb the dome for city views
🥗 Lunch:
• Pizzarium Bonci (legendary pizza by the slice, 10-min walk from Vatican)
🏞️ Afternoon – Castel Sant’Angelo & Stroll
• Walk or bike along the Tiber River
• Visit Castel Sant’Angelo (rooftop views + history)
• Optional chill time in Villa Borghese park (rent a bike or relax by the lake)
🍝 Dinner:
• Head to Monti (hip neighborhood near Colosseum)
• Try Trattoria al 42 or Ai Tre Scalini
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🗓️ Day 3 – Hidden Gems & Local Vibes
🌿 Morning – Appian Way (Via Appia Antica)
• Rent a bike and ride along this ancient Roman road lined with pines, ruins, aqueducts
• Visit Catacombs of San Sebastiano or San Callisto
🥪 Lunch:
• Picnic on the Appian Way, or eat at Hostaria Antica Roma
🎨 Afternoon – Jewish Ghetto + Largo Argentina + Shopping
• Explore Jewish Ghetto – quiet, historic, with unique Roman-Jewish food
• Stop by Turtle Fountain, Largo Argentina (cat sanctuary + ruins), or wander Via del Governo Vecchio for boutiques
🍷 Final Dinner:
• Roscioli (wine bar + gourmet Roman cuisine) – best for a last-night splurge
• Optional: Grab gelato at Gelateria del Teatro
- Vatican Museums & Sistine Chapel Entrance Ticket
- Rome: Colosseum, Roman Forum, Palatine Hill Priority Tickets
- Pantheon
- Roman Forum
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Sessa Aurunca - Roccamonfina - Cellole, Italy
🧳 Day 1 – Arrival & Horse Riding
• 🚆 Take morning train to Sessa Aurunca – Roccamonfina station
• 🚕 Taxi or pickup (ask riding center or agriturismo to help)
• 🐴 Afternoon: Horseback trail ride through hills, vineyards, chestnut forests
• 🍷 Dinner at your agriturismo (home-cooked local food and wine)
• 🌌 Relax in silence, under stars
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🥾 Day 2 – Hiking & Views
• 🥐 Breakfast with local products
• 🥾 Hike in Parco di Roccamonfina-Foce Garigliano (moderate forest trails, old lava flows, panoramic ridges)
• 🧘♀️ Optional: Visit nearby natural springs or viewpoints
• 🧺 Picnic or lunch in nature
• 🍽 Dinner in Sessa Aurunca’s historic town (views + medieval charm)
Optional Day 3:
• Slow breakfast, then train to Naples (or Rome)
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🛌 Where to Stay (Riding + Nature)
🐎 Option 1: Agriturismo San Tommaso
• Offers horseback riding, hiking info, meals
• Rural, calm, and welcoming
• Can assist with station transfers
🌄 Option 2: Agriturismo Cerreto
• Between vineyards and forest trails
• Great food, peaceful rooms, and lovely views
• Near hiking paths and riding centers
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Naples, Italy
Day 1 — Historic Core + Pizza & Views
Morning
• Spaccanapoli Walk — dive into the heartbeat of Naples through its narrow streets
• Visit Naples Cathedral (Duomo di San Gennaro)
• Explore Via San Gregorio Armeno (nativity artisans)
• Optional: Quick visit to Napoli Sotterranea (underground city tour, 1.5 hrs)
Lunch
• Legendary pizza at L’Antica Pizzeria da Michele or Sorbillo
Afternoon
• Visit Museo Archeologico Nazionale — Pompeii artifacts & Roman treasures
• Walk to Piazza del Plebiscito and see Palazzo Reale
• Stroll the Lungomare promenade for seaside views & photos
Dinner
• Dinner in Quartieri Spagnoli (try Trattoria Nennella or seafood spots)
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Day 2 — Pompeii or Vesuvius + Castles
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Option 1: Pompeii + Vesuvius Vineyards
• Morning train to Pompeii (~40 mins)
• Explore the ruins (~2-3 hours)
• Afternoon taxi or arranged transfer to a vineyard on Mt. Vesuvius for wine tasting & views
• Evening back in Naples for dinner
Option 2: Climb Mt. Vesuvius + Explore Naples Castles
• Morning hike to Vesuvius crater (bus from Naples or Pompeii)
• Afternoon visit Castel dell’Ovo (sea castle) and Pio Monte della Misericordia (Caravaggio art)
• Evening: relax with seafood dinner on the Lungomare
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Where to Stay
• Centro Storico — lively and close to most sights
• Chiaia — more upscale, near the sea and nightlife
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Tips
• Use the Circumvesuviana train for Pompeii or Vesuvius area (buy tickets in station)
• Try sfogliatella (pastry) and espresso at a local café
• Stay aware of your belongings, especially in crowded areas
- Pompeii Reserved Entry Ticket
- Herculaneum Priority Entrance Ticket
- Piazza del Plebiscito
- Castel dell'Ovo
- Cathedral of the Assumption of Mary
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Procida, Italy
🏝️ Procida in 1 Day (Late Afternoon Arrival)
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Afternoon Arrival (from Naples)
• Catch a ferry from Naples Beverello port around 4–5 PM
• Ferry ride ~1 hour; enjoy sunset views arriving on Procida
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Evening & Night on Procida
• Check-in to your accommodation
• Take a gentle stroll around Marina Corricella, the iconic colorful fishing harbor — perfect for photos in the golden hour
• Dinner at a cozy trattoria by the water — I recommend Da Teresa or La Lampara for fresh seafood and local wine
• Walk up to Terra Murata (the medieval village on the hill) if you have energy — it’s beautifully lit at night with panoramic views of the bay
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Next Morning (Optional)
• Early morning walk or bike rental to explore beaches like Chiaiolella
• Grab a limoncello or coffee at a seaside café
• Catch a late morning or early afternoon ferry back to Naples (ferries run frequently)
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Ferry Tips
• Check the return ferry schedule the night before
• Purchase tickets in advance online or at the port to avoid lines
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Capri, Italy
When most people think of a vacation to Italy, they picture Rome or Florence,
perhaps Venice or Milan. While these larger cities have a lot to offer, they
tend to be crowded and overrun with tourists. Instead, consider heading south to
Capri instead.
- From Sorrento: Amalfi and Positano Full-Day Shared Boat Tour
- Blue Grotto
- Mount Solaro
- Via Krupp
- Faraglioni
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Sorrento, Italy
This beautiful town is home to what many people consider to be one of the most
beautiful beaches in all of Italy. It’s also where you can find delicious
restaurants and charming hotels. If your plans include exploring Amalfi Coast,
then staying here is a great idea! Check out Hotel Villa Adriano or Le Chic
Sorrento for a taste of Sorrento hospitality.
- Positano Beach
- Fiordo di Crapolla
- Herculaneum Priority Entrance Ticket
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Ravello, Italy
One of The Most Beautiful Villages in Italy: While taking a tour of Southern
Italy, I stumbled upon Ravello. This historic town is one of my favorite places
to visit, and here’s why...
- Amalfi Cathedral
- Villa Rufolo
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Salerno, Italy
Taking a detour from Rome and Naples, Salerno is one of my favorite cities in
southern Italy. It’s not only an excellent base for touring nearby Amalfi Coast
but it’s got a rich history of its own—which was immortalized by Federico
Fellini himself. Although Fascist dictator Benito Mussolini had some ambitious
plans to change Salerno (he wanted to build a replica Rome), he never managed to
carry them out before World War II intervened.
- Salerno Cathedral
- Castello di Arechi
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Matera, Italy
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Bari, Italy