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15-Day Romantic Italy Itinerary: Milan, Dolomites, Lake Como & Tuscany

Viewed by 178 travelers

Day Day 1: Arrival & Milan

Milan, Italy on August 10, 2025

2:00 PM

Arrive at Milan Malpensa Airport

Transfer to hotel, check-in, and relax after your flight.
CURRENCY0, 1h

4:00 PM

Exploring Milan

Stroll around Piazza del Duomo and see the iconic Milan Cathedral. Enjoy the lively atmosphere and maybe some window shopping at Galleria Vittorio Emanuele II.
CURRENCY0, 2h

7:00 PM

Dinner at Trattoria Milanese

Savor traditional Milanese dishes like Risotto alla Milanese in a cozy local setting.
CURRENCY50, 2h
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Day Day 2: Milan Sightseeing

Milan, Italy on August 11, 2025

9:00 AM

Visit Sforza Castle & Parco Sempione

Discover this historic fortress and enjoy a calming walk in the surrounding park.
CURRENCY0, 2h

12:00 PM

Lunch at Peck Milano

Enjoy gourmet Italian cuisine and local delicacies at this renowned deli restaurant.
CURRENCY40, 1.5h

2:00 PM

Visit The Last Supper (reservation needed)

See Leonardo da Vinci's masterpiece at Santa Maria delle Grazie. Book tickets well in advance.
CURRENCY40, 2h

6:00 PM

Relax & Dinner near hotel

Enjoy casual dining with local wines and Italian antipasti at a nearby trattoria.
CURRENCY50, 2h
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Day Day 3: Journey to Dolomites

Milan to Cortina d'Ampezzo on August 12, 2025

8:00 AM

Train/drive to Dolomites

Travel from Milan to Cortina d'Ampezzo via train or rental car, approx 4-5 hours.
CURRENCY100, 5h

2:00 PM

Check-in & relax

Check into your mountain lodge or hotel, unwind and enjoy the breathtaking scenery.
CURRENCY0, 1h

4:00 PM

Explore Cortina d'Ampezzo

Stroll through the picturesque town, visit local shops, and enjoy mountain views.
CURRENCY0, 2h

7:00 PM

Dinner at Ristorante Al Camin

Taste local alpine specialties in a cozy mountain setting.
CURRENCY60, 2h
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Day Day 4: Dolomites: Cortina & Sesto

Cortina d'Ampezzo, Italy on August 13, 2025

8:00 AM

Cable car ride to Tre Cime di Lavaredo

Hike and enjoy the stunning views of the iconic mountain peaks, ideal for photography and nature walks.
CURRENCY20, 4h

12:00 PM

Lunch at rifugio

Enjoy hearty mountain fare with panoramic views at a mountain hut.
CURRENCY30, 1.5h

2:00 PM

Drive to Sexten & Explore

Discover charming Sexten village, known for emerald lakes and mountain trails.
CURRENCY0, 2h

6:00 PM

Relax & Dinner in Sexten

Savor local alpine dishes and unwind after outdoor activities.
CURRENCY60, 2h
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Day Day 5: Dolomites: Scenic & Leisure Day

Sexten & surroundings on August 14, 2025

8:00 AM

Hiking or cable car to Monte Elmo

Enjoy a scenic hike or panoramic views from the mountain top.
CURRENCY20, 4h

12:00 PM

Lunch in Sexten

Relax with delicious local cuisine and mountain views.
CURRENCY30, 1.5h

2:00 PM

Visit San Candido & local sights

Explore nearby charming towns, boutiques, and picturesque streets.
CURRENCY0, 2h

6:00 PM

Dinner & relax

Enjoy your evening at leisure with hearty Italian mountain fare.
CURRENCY60, 2h
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Day Day 6: Transfer to Lake Como

Sexten to Lake Como on August 15, 2025

8:00 AM

Drive or train to Lake Como

Journey south, approximately 4-5 hours, with scenic stops as desired.
CURRENCY120, 5h

2:00 PM

Check-in at Como or Bellagio

Settle into your lakeside hotel and enjoy the views.
CURRENCY0, 1h

4:00 PM

Explore Como Town or Bellagio

Relax by the lake, stroll through historic streets, and enjoy sunset views.
CURRENCY0, 2h

7:00 PM

Dinner at Locanda La Vista

Dine at a lakeside restaurant offering local fish and Italian wines.
CURRENCY70, 2h
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Day Day 7: Lake Como: Leisure & Islands

Lake Como, Italy on August 16, 2025

8:30 AM

Boat tour of Lake Como

Visit picturesque villages like Varenna, Menaggio, and the famous Bellagio island.
CURRENCY50, 4h

1:00 PM

Lunch in Bellagio

Enjoy lunch at a lakefront café with stunning views.
CURRENCY40, 1.5h

3:30 PM

Relax & explore locally

Walk along lakeside paths, shop for local crafts, or relax at your hotel.
CURRENCY0, 2h

6:30 PM

Dinner in Como or Bellagio

Experience fine dining with lakeside scenery and authentic Italian flavors.
CURRENCY70, 2h
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Day Day 8: Travel to Tuscany - Florence

Lake Como to Florence on August 17, 2025

8:00 AM

Drive or train to Florence

Travel approximately 3-4 hours south, enjoying scenic views en route.
CURRENCY100, 4h

1:00 PM

Check-in & Lunch at Trattoria Mario

Relax and enjoy a local Tuscan meal in Florence's historic center.
CURRENCY50, 1.5h

3:00 PM

Visit Florence Cathedral & Baptistery

Explore this icon of Renaissance art and architecture, including climbing the Duomo for city views.
CURRENCY20, 2h

6:00 PM

Stroll Ponte Vecchio & evening walk

Enjoy the charming bridge with shops and sunset views over the Arno River.
CURRENCY0, 2h
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Day Day 9: Florence & Art Highlights

Florence, Italy on August 18, 2025

9:00 AM

Visit Uffizi Gallery

Admire masterpieces by Botticelli, Michelangelo, and Leonardo in this world-famous art museum.
CURRENCY30, 3h

1:00 PM

Lunch at Mercato Centrale

Sample fresh Italian street food and local produce at this vibrant market.
CURRENCY25, 1.5h

3:00 PM

Palazzo Pitti & Boboli Gardens

Visit the historic palace and enjoy a relaxing walk in the exquisite gardens.
CURRENCY20, 2h

6:00 PM

Dinner in Florence city center

Savor Tuscan specialties like Bistecca alla Fiorentina in a renowned local restaurant.
CURRENCY60, 2h
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Day Day 10: Day trip to Siena & Chianti

Florence, Italy on August 19, 2025

8:00 AM

Travel to Siena

Drive or take a day tour (~1.5 hours), explore the medieval city, Piazza del Campo, and Duomo.
CURRENCY50, 4h

12:30 PM

Lunch in Siena

Enjoy local Tuscan dishes in a charming trattoria.
CURRENCY30, 1.5h

2:00 PM

Visit Chianti vineyards

Tour vineyards, sample wines, and enjoy scenic countryside views.
CURRENCY50, 3h

6:00 PM

Return to Florence

Relax and prepare for the next day or dinner nearby.
CURRENCY0, 1h
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Day Day 11: Leisure & Exploration in Tuscany

Florence & surroundings on August 20, 2025

8:30 AM

Visit San Gimignano

Explore historic towers and medieval streets, known as the 'Manhattan of the Middle Ages'.
CURRENCY20, 3h

12:00 PM

Lunch in San Gimignano

Taste local Vernaccia wine and regional pasta dishes.
CURRENCY25, 1.5h

2:00 PM

Relax at your villa or hotel pool

Enjoy the afternoon at leisure, relaxing by the pool or exploring nearby villages.
CURRENCY0, 3h

6:00 PM

Dinner in Florence

Indulge in authentic Tuscan cuisine in a cozy trattoria or osteria.
CURRENCY60, 2h
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Day Day 12: Travel to Pisa & Lucca

Florence to Pisa & Lucca on August 21, 2025

8:00 AM

Drive/train to Pisa

Visit the Leaning Tower and Piazza dei Miracoli, then continue to Lucca for the afternoon (total travel ~2 hours).
CURRENCY50, 4h

12:00 PM

Lunch in Lucca

Enjoy Tuscan cuisine in this charming walled city known for its intact city walls and towers.
CURRENCY30, 1.5h

2:30 PM

Bike ride on Lucca walls

Cycle along the historic city walls and soak in views of the surrounding countryside.
CURRENCY10, 2h

6:00 PM

Return to Florence

Relax and enjoy your last evening in Tuscany with a nice dinner.
CURRENCY0, 1h
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Day Day 13: Transfer to Milan or Explore Tuscany

Florence to Milan or stay local on August 22, 2025

8:00 AM

Travel to Milan or Leisure day

Optionally, return to Milan (~3 hours) for last-minute shopping or relax in Tuscany.
CURRENCY100, 3h

1:00 PM

Lunch depending on your choice

Taste your final Italian meal, either in Milan or Tuscan countryside.
CURRENCY50, 1.5h

3:00 PM

Relax or last sightseeing

Enjoy your last hours exploring or relaxing, packed bags for your trip home.
CURRENCY0, 2h

6:00 PM

Farewell dinner

Celebrate your trip with a memorable dinner featuring Italian classics.
CURRENCY70, 2h
Find Hotels in Florence to Milan or stay local

Day Day 14: Departure Day

Florence or Milan on August 23, 2025

8:00 AM

Transfer to airport

Head to Milan Malpensa or Florence airport for your flight back to Dubai.
CURRENCY0, 2h

10:00 AM

Fly home

Catch your flight, taking wonderful memories of your Italian adventure.
CURRENCY0
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