Amalfi Coast · Rome · Tuscany · Florence
15 days across four of Italy's most extraordinary regions — from the cliffside splendor of the Amalfi Coast, through the eternal city of Rome, into the rolling hills of Tuscany, and finishing in Renaissance Florence. Private drivers, VIP access, world-class hotels, and once-in-a-lifetime experiences throughout.
| Hotel | Dates | Nights | Region |
|---|---|---|---|
| Il San Pietro di Positano | May 13 – 17 | 4 | Amalfi Coast |
| Hotel de Russie | May 17 – 20 | 3 | Rome |
| COMO Castello del Nero | May 20 – 24 | 4 | Tuscany |
| Four Seasons Hotel Firenze | May 24 – 27 | 3 | Florence |
LH429 Charlotte (CLT) → Munich (MUC) — 6:40 PM, arriving 9:15 AM +1
LH1876 Munich (MUC) → Naples (NAP) — 10:30 AM, arriving 12:15 PM
VIP meet & greet in Munich + Naples. Private transfer to Positano (1h 30m).
LH9437 Florence (FLR) → Munich (MUC) — 9:50 AM, arriving 11:05 AM
LH428 Munich (MUC) → Charlotte (CLT) — 1:05 PM, arriving 4:45 PM
VIP airport assistance at Florence & Munich.
Essential tips for first-timers & what NOT to do
Positano, Ravello, Capri, Sorrento & Amalfi
2026 travel itinerary
Tuesday, May 12 — Charlotte to Munich
International flights — arrive 3 hours early. Terminal B handles Lufthansa. Check in, clear security, and settle into the lounge.
Overnight flight. Arriving 9:15 AM local time May 13. Flight time approximately 9 hours.
Wednesday, May 13 — Arrival & Transfer to Positano
VIP greeter meets you at the aircraft/air bridge. Fast-track through immigration and security. Escort directly to connecting gate. 1 hour 15 minute connection.
Short 1h 45m hop to Naples. Luggage checked through from Charlotte.
VIP meet & greet with expedited arrival assistance. Your private driver will be waiting.
90-minute scenic drive along the Amalfi Coast. One of the most dramatic drives in the world — the road hugs sheer cliffs above the Tyrrhenian Sea.
Take a nap if needed, explore the hotel, take the private elevator down to the beach. Dinner at the hotel's Michelin-starred restaurant or in Positano town.
Panoramic rooftop restaurant and cocktail bar on Viale Pasitea. Bougainvillea-covered terrace with sweeping views over Positano and the Amalfi Coast. Classic Mediterranean cuisine. A relaxed and beautiful first evening in Italy.
Note: Reservations open 14 days in advance — confirm closer to the date.
Luxury cliffside hotel tour
4K travel guide
Thursday, May 14 — Full Day Amalfi Coast Exploration
Full-day exploration begins. Driver only — no guide. Wear comfortable walking shoes.
Wander the historic streets. Visit the stunning 9th-century Amalfi Cathedral (Duomo di Sant'Andrea) in Piazza del Duomo. Browse the paper-making shops — Amalfi has been making paper since the 13th century.
Visit a centuries-old vineyard estate for a guided wine tasting and countryside lunch. Expect local varietals like Falanghina and Aglianico with fresh coastal cuisine.
Perched 1,200 feet above the sea. Visit the famous gardens of Villa Rufolo and Villa Cimbrone (the "Terrace of Infinity" has one of the most photographed views in Italy). Wander the quiet, elegant piazzas.
Back to Il San Pietro for sunset drinks and dinner.
One of the Amalfi Coast's most celebrated restaurants — candlelit each evening with hundreds of candles on a terrace with sweeping Positano views. Confirmed by Il San Pietro Concierge.
Dress code: Elegant casual. Long trousers required for gentlemen.
What to do, when to visit, cost
Friday, May 15 — Full-Day Yacht Charter
Board the Princess V65 yacht. Full circumnavigation of Capri included. Soft drinks, towels, and beverages onboard.
Pass the famous Faraglioni rock formations, iconic sea stacks rising from the water. See celebrity villas, hidden coves, and the dramatic cliff faces.
If tides are favorable, visit the Blue Grotto — a stunning sea cave where sunlight creates an ethereal blue glow. €18/person paid on-site. Transfer to a small rowing boat at the cave entrance.
Swim in crystal-clear water, stop at a beach club for lunch, or go ashore to explore Capri town and the famous Piazzetta.
Cruise back along the coast with the setting sun behind you.
A legendary seaside restaurant and beach club set directly beneath the Faraglioni rock formations — one of the most iconic lunch settings on Capri. Confirmed by Il San Pietro Concierge.
Evening dinner: La Taverna Del Leone · 7:30 PM (confirmed) — Via Laurito, 43. Relaxed family-run restaurant just outside Positano, a short distance from Il San Pietro. Confirmed by the restaurant. Cancellation: €50/person within 24 hours.
Complete day trip guide
Anacapri, Monte Solaro & more
Saturday, May 16 — Marisa Cuomo Wine Tasting & Zass Dinner
The terrace, the private beach club, or a long breakfast. No agenda — enjoy the hotel at its finest.
Private 3-hour wine tasting and lunch confirmed for Sharon & Steve Campbell by Maria Giovanna Esposito, Tour & Tasting Manager. Marisa Cuomo produces what many consider the finest white wine on the Amalfi Coast — her Fiorduva, grown on vertiginous terraced slopes. Menu: €110 per person (4 courses, 4 wines). Payment taken onsite (credit card provided as guarantee).
Short drive back to Positano. Time to freshen up before a special evening.
A Michelin-starred restaurant set on a dramatic cliffside terrace at your own hotel, with sweeping Amalfi Coast views. Refined, modern Italian cuisine with a strong focus on seasonal ingredients. Confirmed by Il San Pietro Concierge. Dress code: elegant casual; long trousers required for gentlemen.
Sunday, May 17 — Transfer via Naples to Rome
Check out of Il San Pietro. Driver meets in hotel lobby. Mercedes V-Class, €1,220 prepaid. Your driver is a Naples local and will recommend an exceptional pizza stop en route.
Your driver's personal recommendation. As the saying goes in Naples: there's no such thing as average pizza — if it's not good, the restaurant doesn't last long. Time to walk around if you wish.
Door to door, no connections to manage.
Check-in 3:00 PM, check-out May 20 at 12:00 PM. Set between the Spanish Steps and Piazza del Popolo. Walk to Via Condotti, Trevi Fountain, Piazza Navona, and the Vatican. The tiered Secret Garden is the standout feature — ideal for breakfast, aperitivo, or dinner at Le Jardin de Russie.
Via dell'Oca, 43 — a cozy traditional Roman osteria serving classic dishes in a warm, no-frills setting. 2-minute walk from the hotel. Confirmed by Hotel de Russie Concierge.
Your Naples local driver will stop en route for an excellent pizza lunch. Trust the recommendation — as the saying goes in Naples, there's no such thing as average pizza. If it's not good, the restaurant doesn't last long.
Via dell'Oca, 43 — a cozy traditional Roman osteria just 2 minutes' walk from Hotel de Russie. Classic Roman dishes in a warm, no-frills setting. Confirmed by Hotel de Russie Concierge.
Monday, May 18 — Masterclass at Stravinskij & E-Tuk Sunset Tour
Colline Emiliane (15-min walk) — long-standing trattoria near the Trevi Fountain specializing in Emilia-Romagna cuisine; house-made egg pastas like tagliatelle alla bolognese and tortelli. Hosteria Grappolo d'Oro (25-min walk) — relaxed trattoria near Campo de' Fiori with seasonal Roman classics. Food Tour option: ask Scouted about a guided food tour of Trastevere, Testaccio, or Centro Storico.
Private 1-hour cocktail masterclass with Mattia Capezzuoli, Mixologist, at the Stravinskij Bar in the Hotel de Russie Secret Garden — one of Rome's finest hotel bars. Confirmed for Sharon & Steve. €100/person, charged to hotel room bill.
Hotel lobby meetup. 2-hour private E-Tuk tour — a romantic aperitivo from one of Rome's most beautiful panoramic terraces overlooking the eternal city at sunset. Cancellation policy: no penalty until 24 hrs before; 50% between 23–6 hrs; 100% within 6 hrs.
Tuesday, May 19 — Barbara Lessona · Vatican Apostolic Palace · Orma Roma
Meet Barbara in the hotel lobby at 10am. 4 hours through some of Rome's most unique ateliers — art, furniture, fashion, and leather goods. Lunch at Barbara's recommendation based on your location. If you'd like to extend, just let her know directly. €500.
Meet your private guide and driver in the hotel lobby at 5:30pm. After-hours visit confirmed by Hotel de Russie Concierge. €13,000 for the experience.
Second Loggia — Raphael designs; one of the masterpieces of the Italian Renaissance. Clementine Hall and Redemptoris Mater Chapel (striking Byzantine-style mosaics). Sistine Chapel — just the two of you in silence. Treasure Room — extraordinary collection of papal artifacts accumulated over centuries. Driver drops you at dinner.
Via Boncompagni, 31. Contemporary fine dining with creative, ingredient-driven tasting menus and a modern, minimalist feel. Confirmed directly by the restaurant for Sharon Campbell. Menu: 5 courses €150/person (7-course upgrade €190 available — advise in advance). Optional wine pairing available. Cancellation: €100/person within 24 hours.
Wednesday, May 20 — Rome to Tuscan Countryside
Check out and meet your driver in the lobby. Full private transfer including stopping time for lunch.
A medieval and Renaissance hilltop town perched above the Val d'Orcia, renowned for its Vino Nobile. A natural and scenic break en route to COMO.
Private tour of Cantina De' Ricci's historic cellars, followed by a wine tasting and relaxed vineyard lunch. Confirmed for Sharon & Steve. €180 for 2.
Arriving mid-afternoon.
Check-out May 24 at 11:00 AM. 12th-century castle on 740 acres. The Tavarnelle Suite blends frescoes and vaulted ceilings with COMO's contemporary aesthetic. Amenities include daily breakfast, USD100 resort credit, complimentary yoga/pilates, and shuttle to Florence or Siena.
A relaxed first evening at COMO's Pavilion restaurant — outdoor seating with sweeping views over the Tuscan countryside. Confirmed by COMO Concierge.
A relaxed first evening at COMO's Pavilion restaurant — outdoor seating with sweeping views over the Tuscan countryside. The perfect welcome after a long travel day. Save La Torre (Michelin-starred) for a night when you have more energy to appreciate it fully. Confirmed by COMO Concierge.
4K travel guide
12th-century castle retreat in Tuscany
Thursday, May 21 — COMO Shambhala · Siena · Osteria Le Logge
A restorative morning at the COMO Shambhala spa — treatments, yoga, pool, and wellness facilities. Ask the concierge to arrange a treatment suited to the morning before your Siena departure. Advance booking likely required.
~45-minute drive from COMO. The Duomo and Piazza del Campo — the extraordinary medieval shell-shaped square — are the anchors. Sit at a café on the campo and let the space settle around you. Optional: Santa Maria della Scala museum or a contrada museum for a glimpse into the city's Palio traditions.
Proper aperitivo before dinner.
Via del Porrione, 33. A charming osteria in Siena's historic center, blending old-world character with refined, modern Tuscan cooking. Confirmed by COMO Concierge for Sharon & Steve.
Tuscany's luxury castle haven
Rick Steves' Europe Travel Guide
Countryside riding & The David
Friday, May 22 — World-Class Wine, Helicopter & Estate Dinner
Driver meets at hotel lobby. Charged to hotel room bill. At disposal for 4 hours; additional hours €50/hour.
Confirmed for Sharon Campbell by Antinori. Arrive at reception by 11:45 AM — 15 minutes early required to complete arrival formalities. Group experience. Via Cassia per Siena, 133, Bargino. Tignanello and Solaia tasted side by side, followed by lunch at Rinuccio 1180 rooftop restaurant.
4 passengers. Shuttle departs COMO at 6:30 PM.
Confirmed by Francesca at Tenuta Torciano Winery. Prepaid. Cancellation: 30% (30+ days), 40% (29–15 days), 70% (14–5 days), non-refundable within 5 days.
Dinner at the estate following the helicopter flight. Shuttle returns all 4 guests to COMO after dinner.
Included in the €140 round-trip prepaid.
Tuscany's iconic wine estate
Rick Steves' Tuscany travel guide
Italy's wine heartland
Saturday, May 23 — Leisure & Fine Dining
A full day to enjoy the castle estate and Tuscan countryside at your own pace. This is your last full day at COMO Castello del Nero before heading to Florence tomorrow.
Holistic spa treatments in the castle's restored frescoed rooms. Signature COMO Shambhala massage, facials, and body treatments. Book ahead.
740 acres of vineyards, olive groves, and gardens to explore. The infinity pool has sweeping views of the Tuscan hills. Perfect for reading and relaxing.
The hotel offers hands-on Tuscan cooking classes. Learn to make fresh pasta, regional sauces, and traditional dishes with their chef.
Siena (45 min), San Gimignano (30 min), or the charming village of Tavarnelle Val di Pesa right nearby for a genuine local experience.
Private Vespa tour arranged through COMO Concierge. Experienced local guide, helmets and Vespas provided. Route through vineyard-lined backroads, hilltop villages, and cypress-lined drives. Lunch at a family-run trattoria en route. Confirmed by COMO Concierge for all four guests.
La Torre at Castello del Nero — Confirmed for Sharon, Steve, Sarah & Moriah by COMO Concierge. Michelin-starred Tuscan fine dining. Cancellation policy: Amendments or cancellations must be made at least 48 hours in advance — €150/person fee after that. The restaurant has been informed of Sharon's food allergies; please advise if any other guests have dietary requirements.
Tuscan experiences at the castle
Travel guide for nearby day trips
Sunday, May 24 — Tuscany to the Renaissance City
Short 45-minute transfer to Florence ahead.
Hotel will hold luggage. Use the gap for one of Florence's greatest pleasures: a sandwich from All'Antico Vinaio on Via dei Neri (queue moves fast), or quieter alternatives La Fettunta or Fermentino. Then explore the Ponte Vecchio neighborhood on foot.
Check-out May 27 at 12:00 PM. Palazzo della Gherardesca. 11-acre private garden (largest in Florence). Michelin-starred Il Palagio, Al Fresco garden restaurant, Atrium Bar. Full-service spa and outdoor pool.
Via della Spada, 27R. A classic Florentine trattoria serving traditional Tuscan dishes in a lively, welcoming setting. A perfect first dinner in Florence — unfussy, local, and excellent. 15-minute walk from the hotel. Confirmed by Four Seasons Concierge.
Via della Spada, 27R. A classic Florentine trattoria serving traditional Tuscan dishes in a lively, welcoming setting. A perfect first dinner in Florence — unfussy, local, and excellent. 15-minute walk from the Four Seasons. Confirmed by Four Seasons Concierge for Sharon Campbell.
The most luxurious hotel — pure class
2025 travel guide
Walk & explore the historic center
Monday, May 25 — Cooking Class · Private Shopping · Vini e Vecchi Sapori
Your chef meets at the hotel at 10am and accompanies you to the market, then continues to a hands-on cooking class in a lovely kitchen near Ponte Vecchio. 4 hours total. Cancellation: No penalty up to 7 days prior. Full charge within 6–1 days or no-shows.
A curated 3-hour private shopping experience through Florence's artisan boutiques — leather goods, handmade paper, ceramics, perfumery, jewelry, and silk. Confirmed for Sharon & Steve. Prepaid.
Via dei Magazzini, 3/r — a tiny, no-frills trattoria just off Piazza della Signoria. Traditional Tuscan dishes and a lively, local atmosphere. A 15-minute walk from the Four Seasons. Confirmed by Four Seasons Concierge for Sharon Campbell.
Local expert recommendations
Hidden gems of Italy
Tuesday, May 26 — Florence Duomo Opening · Sergio Gozzi · Cibrèo
Meet your expert guide outside the main entrance of the Duomo at 6:45am. Early access small-group guided visit — before the general public enters.
Enter with the key master (chiavigero) as the cathedral is unlocked. Watch the lights switch on, illuminating the vast frescoed interior overhead — the 3,600-square-meter dome painted by Vasari and Zuccari. Tour the interior largely crowd-free.
463 steps (no elevator) through the tight winding staircase between the dome's inner and outer shells. Midway stop on the interior balcony up close to Vasari's Last Judgement fresco. Final ascent opens to panoramic views over Florence. Physical but very doable — more about tight spaces than endurance. If you don't feel like climbing, leave after the interior visit. The hotel is a short walk away.
Done by 9:15am. The city is still quiet. Return to the Four Seasons for breakfast before the rest of the day opens up.
A simple, family-run Florentine institution in the city center — only open for lunch. After an early start and a dome climb, a proper sit-down lunch is exactly the right call. 20-minute walk from the Four Seasons. Ino (high-quality panini under the Uffizi) remains a good backup if a reservation cannot be secured.
No fixed plans. Explore at your own pace — the Oltrarno, Piazza della Signoria, a final gelato, or simply sit in the Four Seasons gardens.
Via Andrea del Verrocchio, 8r. Seasonal, ingredient-driven Tuscan cooking with a strong wine focus — refined yet still relaxed. A 10-minute walk from the Four Seasons. Confirmed for Sharon & Steve by Four Seasons Concierge.
463 steps to the top of the Duomo
Cathedral Santa Maria del Fiore
Hidden luxury in the heart of the city (4K)
Wednesday, May 27 — Departure Day
Driver meets at hotel. Check out the evening before or arrange early departure with the front desk. Pack the night before — this is an early morning after what may be a late last evening.
Confirmed for Sharon & Steve Campbell. Flight LH9437. Greeter coordinates with your driver and meets you curbside. Porterage included for up to 6 suitcases. Escort to check-in, through security and customs, and to the departure lounge (if applicable) and gate.
Arriving Munich 11:05 AM.
Confirmed for Sharon & Steve Campbell by Royal Airport Concierge. Connection LH9437 → LH428. Greeter meets at aircraft or air bridge with identifying signs. Escort to lounge (if applicable) and to connecting gate. Card charged after service. Cancellation: full charge within 48 hours.
Arriving 4:45 PM. You'll be home for dinner — though your body will think it's close to midnight. Benvenuto a casa.
Essential Phrases for Your Italy Adventure
| Buongiorno | Good morning / Hello (formal) |
| Buonasera | Good evening |
| Buonanotte | Good night |
| Ciao | Hi / Goodbye (informal) |
| Per favore | Please |
| Grazie | Thank you |
| Grazie mille | Thank you very much |
| Prego | You're welcome |
| Mi scusi | Excuse me / I'm sorry |
| Non parlo italiano | I don't speak Italian |
| Parla inglese? | Do you speak English? |
| Mi chiamo... | My name is... |
| Un tavolo per due | A table for two |
| Il menu per favore | The menu please |
| Vorrei... | I would like... |
| Qual è il piatto speciale? | What is the special dish? |
| Posso avere...? | Can I have...? |
| Acqua naturale | Still water |
| Acqua frizzante | Sparkling water |
| Vino rosso | Red wine |
| Vino bianco | White wine |
| Birra | Beer |
| Il conto per favore | The check please |
| Era delizioso | That was delicious |
| Dov'è il bagno? | Where's the bathroom? |
| Quanto costa? | How much does it cost? |
| Dov'è...? | Where is...? |
| A destra | To the right |
| A sinistra | To the left |
| Dritto | Straight ahead |
| La stazione | The train station |
| L'aeroporto | The airport |
| Un biglietto per... | A ticket to... |
| Mi può portare a...? | Can you take me to...? |
| Quanto tempo? | How long? |
| Taxi! | Taxi! (to hail a cab) |
| Posso provare? | Can I try this on? |
| Troppo caro | Too expensive |
| Avete una taglia più grande? | Do you have a larger size? |
| Avete una taglia più piccola? | Do you have a smaller size? |
| Quanto costa questo? | How much is this? |
| Accettate carte di credito? | Do you accept credit cards? |
| Ho contanti | I have cash |
| Aiuto! | Help! |
| Ho bisogno di un medico | I need a doctor |
| Chiamate la polizia | Call the police |
| Ospedale | Hospital |
| Mi sono perso/a | I'm lost (male/female) |
| Dove posso trovare un farmacista? | Where can I find a pharmacist? |
| Ho perso il passaporto | I lost my passport |
| Uno | 1 |
| Due | 2 |
| Tre | 3 |
| Quattro | 4 |
| Cinque | 5 |
| Sei | 6 |
| Sette | 7 |
| Otto | 8 |
| Nove | 9 |
| Dieci | 10 |
| Lunedì | Monday |
| Martedì | Tuesday |
| Mercoledì | Wednesday |
| Giovedì | Thursday |
| Venerdì | Friday |
| Sabato | Saturday |
| Domenica | Sunday |
Important Numbers, Embassies & Safety Info
Police, Fire, Ambulance
112Works from any phone, even without SIM
Ambulance / First Aid
118Military Police
112State Police
113Vigili del Fuoco
115Via Vittorio Veneto, 121
+39 06 46741After hours emergency: same number
Lungarno Amerigo Vespucci, 38
+39 055 266 951Visa: +1-303-967-1096
Mastercard: +1-636-722-7111
Amex: +1-336-393-1111
Everything you need for your Italian adventure
Get everything sorted before departure
Confirm all hotel reservations
Due by April 15
Notify bank/credit card companies of Italy travel
Due by April 30
Check passport expiration — must be valid 6+ months past return
Due by March 15
Enroll in STEP program (Smart Traveler Enrollment)
Due by April 15
Confirm private driver/transfer arrangements
Due by April 30
Book restaurant reservations — La Pergola needs months ahead, others 2–4 weeks
Due by April 15
Print backup copies of all confirmations
Due by May 1
Purchase travel insurance if not done
Due by April 1
Buy universal power adapters
Due by May 1
Download offline maps for all regions
Due by May 10
Get euros from bank — better rate than airport
Due by May 8
Practice key Italian phrases
Ongoing
Research VAT refund process for shopping
Due by May 1
Create shared photo album for trip
Due by May 10
Pack bags — use the packing checklist!
Due by May 11
Arrange pet/house sitter if needed
Due by April 15
Weather & climate for each destination
May 13–17
68–79°F / 20–26°C
May 17–20
61–77°F / 16–25°C
May 20–24
57–75°F / 14–24°C
May 24–27
59–79°F / 15–26°C
May is ideal for Italy — warm but not peak summer heat. Evenings can be cool (mid-50s°F), especially in Tuscany, so a light jacket is essential. The sun is strong — wear SPF even on cloudy days. Brief rain showers are possible but rare and pass quickly.
Money matters for your trip
Approximate rate: $1 USD ≈ €0.92 EUR (check current rate before travel)
Service charge (coperto) of €1–3 is standard and is NOT a tip. Tipping is not expected but appreciated. For exceptional service, round up or leave 5–10%.
€10–20 per day is customary for your private driver. Give at end of each segment or at trip's end.
€1–2 per bag for porters. €1–2 per night for housekeeping (leave daily). Concierge €5–10 for special arrangements.
€5–10 per person for half-day tours, €10–20 for full-day. For exceptional private guides, up to €20–30.
Not expected. You can leave coins on the counter. Standing at the bar is cheaper than sitting at a table.
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