Luxury 14-Day Italy Itinerary: Culture, Cuisine, Wine & Wellness

Day 1: Arrival & Relax

Rome, Italy on May 1, 2025

9:00am

Check-in at Hotel de Russie

Settle into this luxurious hotel located near Piazza del Popolo known for its beautiful secret garden and elegant spa facilities.
EUR800, 1h0m

10:30am

Breakfast at Caffè Propaganda

Enjoy a stylish breakfast featuring Italian cappuccino and fresh pastries in a chic atmosphere with views of the Colosseum.
EUR50, 1h0m

11:30am

Visit the Colosseum and Roman Forum

Explore the iconic ancient Roman amphitheater and nearby Forum for a deep dive into Rome’s imperial history. Open 8:30am to 7:00pm.
EUR30, 2h30m

2:30pm

Lunch at Aroma Restaurant

Dine with a magnificent panoramic view of the Colosseum while tasting refined Roman cuisine and fine wines.
EUR150, 1h30m

4:00pm

Spa session at Hotel de Russie's Le Jardin de Russie

Relax with a signature massage and wellness treatments in the tranquil garden spa to rejuvenate after travel.
EUR250, 2h0m

7:30pm

Dinner at Il Pagliaccio

Experience an intimate two Michelin-star dining experience that blends creative Italian flavors in a luxurious setting.
EUR300, 2h30m
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Day 2: Rome Culture Day

Rome, Italy on May 2, 2025

8:00am

Breakfast at Roscioli Caffè

Savor freshly baked bread and expertly brewed espresso to begin the day with authentic Roman taste.
EUR40, 1h0m

9:30am

Vatican Museums and Sistine Chapel tour

Explore the Vatican’s remarkable art collections including Michelangelo’s Sistine Chapel ceiling. Open 9:00am to 6:00pm (closed Sundays except last Sunday monthly).
EUR45, 3h0m

1:00pm

Lunch at Pizzeria La Montecarlo

Relish some of Rome’s best traditional pizzas in a casual but beloved local eatery.
EUR30, 1h0m

2:30pm

Stroll through Trastevere neighborhood

Enjoy a leisurely walk exploring colorful streets, artisan shops, and historic churches in one of Rome’s most charming areas.
Free, 2h0m

5:00pm

Gelato at Gelateria del Viale

Indulge in some gourmet gelato before heading to evening activities.
EUR10, 30m

7:00pm

Special Birthday Dinner at La Pergola

Celebrate with a Michelin three-star experience at Rome’s finest rooftop restaurant featuring spectacular city views, exquisite dishes, and an extensive wine cellar. Reservations required.
EUR700, 3h0m
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Day 3: Florence Art & Cuisine

Florence, Italy on May 3, 2025

7:30am

Travel from Rome to Florence by high-speed train

A swift 1.5 hour journey on the Italotreno or Frecciarossa train connecting two cultural capitals of Italy.
EUR80, 1h30m

9:30am

Check-in at Four Seasons Hotel Firenze

Stay at a Renaissance palace turned into a luxury hotel with stunning gardens and a luxurious spa.
EUR700, 1h0m

10:30am

Breakfast at Rivoire

Taste famous Florentine pastries and hot drinks overlooking the Piazza della Signoria.
EUR45, 1h0m

11:30am

Uffizi Gallery exploring Renaissance masterpieces

Visit one of the world’s most important art museums to see works by Botticelli, Michelangelo, and Leonardo da Vinci. Open 8:15am to 6:50pm.
EUR30, 2h30m

2:30pm

Lunch at Trattoria Mario

Enjoy authentic Tuscan dishes like ribollita and bistecca alla fiorentina in a lively local favorite spot.
EUR50, 1h30m

4:00pm

Stroll through Boboli Gardens

Relax in this grand Renaissance garden behind the Pitti Palace offering spectacular views and lush surroundings.
EUR15, 1h30m

6:00pm

Spa treatment at 4 Seasons Wellness Center

Soothe your muscles with a deluxe massage and access to the indoor pool and sauna.
EUR200, 2h0m

8:30pm

Dinner at Enoteca Pinchiorri

Dine at a three Michelin-star restaurant renowned for its superb wine list and innovative Italian cuisine.
EUR350, 2h30m
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Day 4: Tuscan Wine Tour

Tuscany region, Italy on May 4, 2025

8:00am

Breakfast at hotel

Light and elegant breakfast served at Four Seasons before heading into the countryside.
Included, 1h0m

9:00am

Private guided wine tour through Chianti

Explore vineyards and wineries of Chianti, enjoy wine tastings of acclaimed Chianti Classico, Brunello, and Vernaccia wines with expert guides.
EUR350, 6h0m

3:00pm

Lunch at Castello di Ama winery

Savor Tuscan specialties paired with estate wines in a prestigious winery setting with art installations.
EUR120, 1h30m

5:00pm

Return to Florence

Relax during transfer back to the city.
Included, 1h0m

7:00pm

Dinner at Osteria Vini e Vecchi Sapori

An intimate dining experience focusing on traditional Tuscan comfort food in a cozy atmosphere.
EUR70, 2h0m
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Day 5: Cinque Terre Scenic Day

Cinque Terre, Italy on May 5, 2025

7:00am

Travel to Cinque Terre via train

Scenic 2.5 hour train ride along the Ligurian coast to reach the five picturesque villages.
EUR40, 2h30m

10:00am

Check-in at Hotel Porto Roca in Monterosso al Mare

Stay at a luxury cliffside hotel offering stunning sea views and spa facilities.
EUR400, 1h0m

11:00am

Hiking the Blue Trail (Sentiero Azzurro)

Enjoy a beautiful coastal hike linking Monterosso with Vernazza and Corniglia. Allow 3 to 4 hours for a leisurely pace.
EUR7, 4h0m

3:30pm

Seafood lunch at Ristorante Miky

Dine on fresh, locally caught seafood with Ligurian flavors in Monterosso's harbor area.
EUR90, 1h30m

5:30pm

Relaxation & Spa at Hotel Porto Roca

Unwind with a spa session featuring massage treatments and panoramic sea views.
EUR150, 2h0m

8:00pm

Dinner at Ristorante Belvedere

Enjoy an elegant dinner on the terrace with breathtaking views of the Ligurian sea and villages.
EUR130, 2h0m
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Day 6: Milan City Highlights

Milan, Italy on May 6, 2025

7:00am

Travel to Milan by train

Fast train takes about 3 hours from Cinque Terre via La Spezia or Pisa.
EUR70, 3h0m

10:30am

Check-in at Armani Hotel Milano

Experience Milanese elegance at this designer luxury hotel located in the heart of Milan's fashion district.
EUR600, 1h0m

11:30am

Breakfast at Marchesi 1824

Start your day with Italian pastries and coffee at this historic and refined café in Milan.
EUR50, 1h0m

12:30pm

Visit the Duomo and rooftop terrace

Explore Milan’s Gothic cathedral and enjoy panoramic views of the city from the rooftop. Open 9:00am to 7:00pm.
EUR15, 2h0m

3:00pm

Lunch at Ristorante Cracco

Sample modern Italian cuisine by a celebrity chef in an elegant setting near the Duomo.
EUR130, 1h30m

5:00pm

La Scala Opera House tour

Tour the famous opera house museum and backstage areas. Open generally 9:00am - 5:00pm (verify special schedules).
EUR15, 1h0m

7:00pm

Relaxing spa session at Armani/Spa

Indulge in a luxurious spa treatment including massages and wellness therapies in a sophisticated environment.
EUR250, 2h0m

9:30pm

Dinner at Il Luogo di Aimo e Nadia

Experience two Michelin-starred contemporary Tuscan cuisine in a refined setting.
EUR300, 2h0m
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Day 7: Lake Como Luxury

Lake Como, Italy on May 7, 2025

8:00am

Travel from Milan to Lake Como by private car

A scenic 1.5 hour drive to the glamorous lake area favored by celebrities.
EUR350, 1h30m

9:30am

Check-in at Villa d’Este Hotel

Settle into one of Italy’s most opulent lakeside hotels featuring magnificent gardens and a world-class spa.
EUR900, 1h0m

10:30am

Breakfast at hotel terrace

Enjoy breakfast with spectacular views over Lake Como featuring fresh local ingredients.
Included, 1h0m

11:30am

Private boat tour on Lake Como

Cruise past charming lakeside villas, quaint towns like Bellagio, and scenic landscapes.
EUR400, 3h0m

3:00pm

Lunch at Ristorante Mistral

Dine at a Michelin-starred lakeside restaurant offering creative Italian cuisine with lake views.
EUR150, 1h30m

5:00pm

Spa and wellness treatments at Villa d’Este

Relax with massages, sauna, and wellness therapies in the hotel’s luxury spa.
EUR300, 2h0m

8:00pm

Dinner at La Veranda

Enjoy an exclusive lakeside fine dining experience with exquisite local ingredients and elegant ambiance.
EUR200, 2h0m
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Day 8: Venice Charm & Relaxation

Venice, Italy on May 8, 2025

8:00am

Travel to Venice by private car and water taxi

Comfortable 3 hour trip including water taxi to your hotel in Venice’s historic center.
EUR500, 3h0m

11:00am

Check-in at The Gritti Palace

Stay in this luxurious palazzo on the Grand Canal featuring Venetian elegance and wellness amenities.
EUR1000, 1h0m

12:00pm

Lunch at Osteria alle Testiere

Savor fresh Venetian seafood dishes in one of the city’s most sought-after intimate restaurants.
EUR120, 1h30m

2:00pm

Visit Doge’s Palace and St. Mark’s Basilica

Tour these iconic Venetian landmarks showcasing rich history, opulent architecture, and art. Open 9:30am - 5:00pm.
EUR35, 3h0m

5:30pm

Relaxation at hotel spa

Unwind with exclusive spa treatments designed to rejuvenate your body and mind.
EUR250, 2h0m

8:00pm

Dinner at Quadri Restaurant

Celebrate Venetian haute cuisine with views over St. Mark’s Square in this Michelin-starred restaurant.
EUR300, 2h30m
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Day 9: Venice & Departure

Venice, Italy on May 9, 2025

8:00am

Breakfast at hotel

Elegant breakfast to start your morning overlooking the Grand Canal.
Included, 1h0m

9:30am

Morning Gondola Ride

Enjoy a serene gondola ride through Venice’s canals to experience the romantic charm of the city from the water.
EUR120, 1h0m

11:00am

Visit Peggy Guggenheim Collection

Explore modern art in this unique museum located in the former home of the famous American heiress. Open 10:00am - 6:00pm.
EUR15, 1h30m

1:00pm

Lunch at Ristorante La Caravella

Enjoy Venetian and Adriatic seafood specialties in a refined atmosphere.
EUR100, 1h30m

3:00pm

Departure

Transfer to Venice Marco Polo Airport for your onward journey.
EUR100, 1h0m
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