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If I were Filthy Rich
By youngtafari
+64 I asked ChatGPT to plan me a vacation to Italy with a million dollar budget

Luxury Italy Itinerary: 10 Days of Coastal Splendor and Gastronomy

Budget: $1,000,000

Day 1: Arrival in Rome

• Morning: Private jet arrival at Leonardo da Vinci Airport. Chauffeured transfer to Hotel Eden (5-star).
• Afternoon: Lunch at La Pergola (3 Michelin stars) with panoramic city views.
• Evening: Private walking tour of Rome’s historic sites (Colosseum, Trevi Fountain). Dinner at Roscioli with curated wine pairing.

Day 2: Amalfi Coast – Positano

• Morning: Helicopter transfer to the Amalfi Coast. Check in to Le Sirenuse in Positano.
• Afternoon: Private boat ride along the coast, with a seafood lunch on board.
• Evening: Dine at Il San Pietro di Positano (1 Michelin star), famous for its cliffside views.

Day 3: Amalfi & Ravello

• Morning: Explore Amalfi town with a private guide, visiting historic landmarks.
• Afternoon: Michelin-starred lunch at Glicine in Amalfi.
• Evening: Drive to Ravello for a sunset concert at Villa Rufolo, followed by dinner at Palazzo Avino’s Rossellinis (2 Michelin stars).

Day 4: Capri

• Morning: Private yacht transfer to Capri. Check in to Capri Palace Jumeirah.
• Afternoon: Visit the Blue Grotto and Anacapri. Lunch at L’Olivo (2 Michelin stars).
• Evening: Dinner at Da Paolino, dining under lemon trees.

Day 5: Naples

• Morning: Yacht transfer to Naples. Guided food tour through the city’s historic districts.
• Afternoon: Lunch at L’Antica Pizzeria da Michele, famous for authentic Neapolitan pizza.
• Evening: Stay at Grand Hotel Vesuvio and enjoy fine dining at Caruso Roof Garden.

Day 6: Florence – Tuscan Countryside

• Morning: Private flight to Florence. Check in to Il Salviatino, a luxury villa overlooking the city.
• Afternoon: Winery tour in Chianti with private sommelier. Gourmet Tuscan lunch in a vineyard.
• Evening: Return to Florence for dinner at Enoteca Pinchiorri (3 Michelin stars).

Day 7: Cinque Terre

• Morning: Helicopter transfer to Cinque Terre. Stay at a private villa in Monterosso al Mare.
• Afternoon: Guided hike between villages, with stops for local Ligurian delicacies.
• Evening: Sunset seafood dinner at Ristorante Miky.

Day 8: Venice

• Morning: Train to Venice in a private cabin. Check in to Aman Venice (5-star).
• Afternoon: Gondola ride and a market tour with a private chef.
• Evening: Dinner at Quadri (1 Michelin star) overlooking Piazza San Marco.

Day 9: Verona & Lake Garda

• Morning: Private car transfer to Verona. Explore Juliet’s Balcony and the Arena.
• Afternoon: Michelin-starred lunch at Casa Perbellini.
• Evening: Luxury speedboat ride on Lake Garda. Stay at Villa Feltrinelli.

Day 10: Milan

• Morning: Helicopter transfer to Milan. Shopping tour of Via Montenapoleone with a personal stylist.
• Afternoon: Lunch at Ristorante Cracco (1 Michelin star).
• Evening: Farewell dinner at Il Luogo di Aimo e Nadia (2 Michelin stars). Private jet departure from Malpensa Airport.

Let me know if you’d like further customization or booking details!

Recent responses

+36 @ferretbusiness My gf and I had a $10,000 trip to Italy a couple years ago and stayed in cinque terre and rovello for a week each. This included a guided tour through the cinque terre towns and a private boat tour to/around Capri. If you remove the helicopters/private jets you could easily do this for way way way less than a million

+13 @Legal_Warthog_3451 Definitely a creative use of the tool, not gonna lie