Quick Stats

• Best Time to Go: April – June & September (pleasant weather, fewer crowds
• Trip Type: Culinary & Cultural Immersion
• Pricing Range: Luxury ($5,000–$7,000 per person excluding flights)
• Who It’s For: Couples seeking food, wine, history, and romance in shoulder season

Where You’ll Go

• Rome – 3 nights
• Florence – 2 nights
• Tuscany (Chianti Region) – 2 nights
• Venice – 2 nights

Day-by-Day Itinerary

Day 1: Arrive in Rome – Welcome to the Eternal City
Feel the thrill of arriving in Rome, where ancient history greets you at every turn. After a private airport transfer, settle into your boutique hotel in the heart of the city. Spend the evening with a sunset stroll past the Spanish Steps and a welcome dinner at a hidden trattoria known for handmade cacio e pepe.

✓ Highlights

• Arrival & private transfer
  
• Boutique hotel check-in
  
• Dinner in Trastevere

Day 2: Roman Empire & Hidden Flavors
Walk in the footsteps of emperors with a private early access tour of the Colosseum and Roman Forum. Later, join a culinary walking tour through the Jewish Ghetto and Campo de’ Fiori, sampling supplì, artichokes, and gelato. The evening is yours to discover a rooftop bar with a view.

✓ Highlights

• Private Colosseum & Forum tour
  
• Food tour with tastings
  
• Optional rooftop aperitivo
  

Day 3: Vatican Wonders & Romantic Piazza Nights
Explore the Vatican Museums, Sistine Chapel, and St. Peter’s Basilica with a private guide. After a light lunch, enjoy an afternoon at leisure – perhaps visit the Villa Borghese gardens or sip espresso at a historic café. Tonight, dine alfresco in Piazza Navona.

✓ Highlights

• Private Vatican tour
  
• Free afternoon
• Dinner in Piazza Navona

Day 4: High-Speed to Florence – Renaissance Awakened
Travel by high-speed train to Florence (approx. 1.5 hrs). Check into a restored palazzo near the Duomo. Spend the afternoon with a private guide exploring the Uffizi Gallery and Accademia, home of Michelangelo’s David. In the evening, watch the sunset from Piazzale Michelangelo.

✓ Highlights

• Train to Florence
  
• Guided museum visits
  
• City view at sunset

Day 5: Tuscan Treasures
Spend the day in the Chianti countryside. Your private driver-guide takes you to two vineyards for tastings, a cellar tour, and a leisurely lunch under the vines. Stop by a hilltop village for gelato before returning to Florence for a relaxed evening.

✓ Highlights

• Chianti wine tour
  
• Vineyard lunch
  
• Hilltop village stroll

Day 6: Into the Hills of Tuscany
Transfer to a countryside villa for a two-night stay. Enjoy an afternoon cooking class in a farmhouse kitchen, learning to make pasta, sauces, and tiramisù. Dine on your creations with local wine.

✓ Highlights

• Countryside villa check-in
  
• Tuscan cooking class
  
• Wine-paired dinner

Day 7: Leisure & Lavender Fields
This day is yours to relax. Lounge by the villa pool, wander nearby fields, or visit a nearby spa town. For dinner, we arrange a romantic candlelit table overlooking the vineyards.

✓ Highlights

• Free day for relaxation
  
• Optional spa visit

Day 8: Venice Beckons
Travel to Venice by train (via Florence, approx. 3.5 hrs). Arrive at your canal-side hotel via private boat transfer. Spend the afternoon exploring the Rialto market and sipping wine at a traditional bacaro. Evening gondola ride included.

✓ Highlights

• Train to Venice
  
• Bacaro wine stop
  
• Gondola ride

Day 9: Art, Islands & Aperitivi
Discover St. Mark’s Basilica and the Doge’s Palace with skip-the-line access. After lunch, cruise to Murano and Burano for glassblowing and colorful facades. Celebrate your final night with aperitivo on a hidden terrace.

✓ Highlights

• Skip-the-line Venice sites
  
• Island visits
  
• Farewell aperitivo

Day 10: Departure
Transfer to the airport via private water taxi. Arrivederci, Italia — you leave with full hearts, fuller bellies, and timeless memories.

✓ Highlights

• Private transfer

Departure

Add-On Experiences

• Private Yacht Day on the Amalfi Coast – Extend your trip south to sail the Amalfi Coast in style with prosecco and fresh seafood.
  
• Truffle Hunting in Piedmont – Join a guide and trained dog in search of white truffles, followed by a gourmet lunch.
  
• Florence Artisan Workshop Tour – Explore small studios making leather goods, mosaics, and perfumes.

Pro Tips

• Skip the Crowds: Visit popular sites like the Vatican or Uffizi right at opening hours for a quieter experience.
  
• Dress the Part: Modest attire is needed for churches (shoulders and knees covered).
  
• Train Travel: First-class rail in Italy is affordable and adds comfort – reserve early.
  
• Foodie Finds: Trastevere in Rome and Oltrarno in Florence offer amazing local restaurants away from tourist zones.
  
• Luggage Tip: Pack light with a rolling carry-on for cobblestone streets and train transfers.

What to Pack

• Comfortable walking shoes (cobblestones are no joke)
  
• Smart-casual dinner outfit
  
• Lightweight scarf or shawl (for church entry and evenings)
  
• Reusable water bottle
  
• Universal power adapter
  
• Travel-sized sunscreen
• Digital and printed copies of travel documents