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Orvieto

Montepulciano

Siena

Florence

Lucca

Bologna

Milan

14-Day Romantic Tuscan & Northern Italy Road Trip

14 days

7 cities

81 experiences

7 hotels

7 transports

Download

Rome

Orvieto

Nov 15 – 16

Montepulciano

Nov 16 – 18

Siena

Nov 18 – 20

Florence

Nov 20 – 22

Lucca

Nov 22 – 23

Bologna

Nov 23 – 25

Milan

Nov 25 – 28

Rome

Day 1

Nov 15 – 16

Orvieto

Layla, your journey begins in the enchanting town of Orvieto, Italy, where you'll be captivated by its stunning medieval architecture and the famous Orvieto Cathedral. This stop offers a perfect blend of history and charm, with opportunities to explore underground caves and enjoy exquisite local cuisine. It's an ideal start to your Tuscan adventure, setting the tone for the romantic and culturally rich trip ahead.

Stay

Day 1

Nov 15 – 16

1 night

Palazzo Petrvs

Superior RoomBreakfast included

Non-Refundable

10.0

Wonderful33 reviews

Itinerary

Day 1

Nov 15 – 16

Day 1•Nov 15•

20°C•4 Experiences

Arrival in Orvieto and Cathedral Exploration

Day 2•Nov 16•

20°C•4 Experiences

Underground Wonders and Departure to Montepulciano

Days 2-4

Nov 16 – 18

Montepulciano

Experience the charm of Montepulciano, Italy, from November 16 to 18, where you can indulge in romantic winery stays and explore the historic hilltop town known for its Renaissance architecture and world-renowned Vino Nobile wines. This leg offers a perfect blend of scenic Tuscan landscapes and intimate boutique accommodations with queen or king-size bed options, ideal for a couple's getaway. Montepulciano serves as a serene and enchanting stop before continuing your journey to Siena.

Stay

Days 2-4

Nov 16 – 18

2 nights

Villa Cicolina

Double RoomBreakfast included

Non-Refundable

9.8

Wonderful101 reviews

Itinerary

Days 2-4

Nov 16 – 18

Day 2•Nov 16•

18°C•3 Experiences

Arrival in Montepulciano and Wine Tasting Experience

Day 3•Nov 17•

18°C•5 Experiences

Val d Orcia Landscapes and Tuscan Cooking Class

Day 4•Nov 18•

12°C•1 Experience

Departure to Siena

Days 4-6

Nov 18 – 20

Siena

Experience the charm of Siena, Italy, from November 18 to 20, where you can immerse yourself in the city's medieval architecture and historic piazzas. Enjoy the romantic ambiance perfect for couples, with opportunities to explore local cuisine and authentic Tuscan wines. This leg offers a perfect blend of culture and relaxation before heading to Florence.

Stay

Days 4-6

Nov 18 – 20

2 nights

Grand Hotel Continental Siena – Starhotels Collezione

Classic Double Room

Non-Refundable

9.2

Wonderful633 reviews

Itinerary

Days 4-6

Nov 18 – 20

Day 4•Nov 18•

13°C•5 Experiences

Arrival in Siena and Historic Heart Exploration

Day 5•Nov 19•

12°C•6 Experiences

Siena Cathedral Complex and Private Castle Wine Tasting

Day 6•Nov 20•

12°C•3 Experiences

Artistic Morning and Departure to Florence

Days 6-8

Nov 20 – 22

Florence

Experience the heart of the Renaissance in Florence, Italy, from November 20 to 22. Explore iconic landmarks like the Duomo and Uffizi Gallery, and indulge in world-class art and cuisine. This leg offers a perfect blend of cultural immersion and romantic charm, ideal for couples seeking an unforgettable Tuscan adventure.

Stay

Days 6-8

Nov 20 – 22

2 nights

Hotel Santa Maria Novella

Superior Double RoomBreakfast included

Non-Refundable

9.6

Wonderful1,015 reviews

Itinerary

Days 6-8

Nov 20 – 22

Day 6•Nov 20•

14°C•5 Experiences

Arrival in Florence and Renaissance Masterpieces

Day 7•Nov 21•

10°C•5 Experiences

Duomo Exploration and Panoramic Sunset Views

Day 8•Nov 22•

8°C•4 Experiences

Pasta Making and Departure to Lucca

Day 8

Nov 22 – 23

Lucca

Lucca is a charming Tuscan town known for its well-preserved Renaissance walls that you can walk or bike along, offering stunning views of the city. The historic center is filled with quaint streets, beautiful piazzas, and impressive churches, perfect for a romantic stroll. Don't miss the chance to explore Lucca's unique blend of history, culture, and local cuisine, making it an ideal stop between Florence and Bologna.

Stay

Day 8

Nov 22 – 23

1 night

Villino Al Dotto Country House

Panoramic Villa, Hill View

Refundable

2.0

Very poor1 reviews

Itinerary

Day 8

Nov 22 – 23

Day 8•Nov 22•

10°C•5 Experiences

Arrival in Lucca and Historic City Walls Exploration

Day 9•Nov 23•

7°C•5 Experiences

Lucca Towers and Puccini Opera before Departure

Days 9-11

Nov 23 – 25

Bologna

Your stay in Bologna from November 23 to 25 offers a perfect blend of historic charm and culinary delights. Explore the medieval architecture, indulge in the city's famous gastronomy including traditional Bolognese cuisine, and enjoy the vibrant atmosphere of this cultural hub. This leg is ideal for food lovers and history enthusiasts alike, providing a rich and authentic Italian experience before heading to Milan.

Stay

Days 9-11

Nov 23 – 25

2 nights

Hotel Brun

Deluxe Double RoomBreakfast included

Non-Refundable

9.8

Wonderful210 reviews

Itinerary

Days 9-11

Nov 23 – 25

Day 9•Nov 23•

8°C•4 Experiences

Arrival in Bologna and Historic Center Stroll

Day 10•Nov 24•

5°C•5 Experiences

Bologna City Center and Walking Tour

Day 11•Nov 25•

8°C•4 Experiences

Culinary Traditions and Departure to Milan

Days 11-14

Nov 25 – 28

Milan

Your stay in Milan from November 25 to 28 offers a perfect blend of fashion, art, and culture in Italy's stylish capital. Explore iconic landmarks like the Duomo di Milano and indulge in world-class shopping and dining experiences. This leg is ideal for soaking up the vibrant city atmosphere before your journey back home.