🌍 Hey, I'm Layla, your AI trip planner.

This is a sample trip — I can add cities, find flights, activities, and local tips.

Tell me your style and budget, and I'll design a trip just for you.

Can you make this trip cheaper?Find me restaurants with local foodSwitch to a 4-star hotelCan you make this trip cheaper?Find me restaurants with local foodSwitch to a 4-star hotelCan you make this trip cheaper?

Instant replies, no wait time ⚡

Florence

San Gimignano

Siena

5-Day Tuscany Wine and Views Road Trip

5 days

3 cities

36 experiences

3 hotels

3 transports

Download

Stare Babice

Florence

May 12 – 14

San Gimignano

May 14 – 15

Siena

May 15 – 16

Stare Babice

Days 1-3

May 12 – 14

Florence

Dear traveler, your stay in Florence from May 12 to May 14, 2027, promises an unforgettable immersion into the heart of Tuscany's art and culture. Explore the Renaissance masterpieces, stroll through the charming historic streets, and savor the authentic Tuscan cuisine and wines. This leg perfectly blends your love for wine and stunning views with the rich heritage of Florence, making it a highlight of your 5-day Tuscan adventure.

Car Rental

May 12

Toyota Aygo

Mini Elite • Manual • 4-5 Door

Stay

Days 1-3

May 12 – 14

2 nights

Bernini Palace

Basic Double Room, 1 Queen BedBreakfast included

9.8

Wonderful1,004 reviews

Itinerary

Days 1-3

May 12 – 14

Day 1•May 12•

22°C•3 Experiences

Arrival and Sunset Views over Florence

Day 2•May 13•

20°C•7 Experiences

Renaissance Masterpieces and Iconic Landmarks

Day 3•May 14•

21°C•5 Experiences

Artistic Treasures and Riverside Charm

Day 3

May 14 – 15

San Gimignano

Experience the charm of San Gimignano, a medieval town famous for its towering skyline and stunning views over the Tuscan countryside. Enjoy a romantic day exploring its historic streets, artisan shops, and tasting the renowned Vernaccia wine. This leg perfectly blends culture, wine, and breathtaking landscapes for a memorable couple's escape.

Stay

Day 3

May 14 – 15

1 night

Relais Santa Chiara Hotel by Double Hospitality

Basic RoomBreakfast included

8.8

Very Good458 reviews

Itinerary

Day 3

May 14 – 15

Day 3•May 14•

20°C•5 Experiences

Medieval Charm and Tuscan Flavors in San Gimignano

Day 4•May 15•

13°C•4 Experiences

Wine Tasting and Departure to Siena

Day 4

May 15 – 16

Siena

Experience the charm of Siena, a medieval city renowned for its stunning Gothic architecture and the famous Piazza del Campo, where the thrilling Palio horse race takes place. Enjoy romantic strolls through narrow cobblestone streets, savoring local Tuscan cuisine and wines in intimate trattorias. This leg offers a perfect blend of history, culture, and scenic views, ideal for a couple seeking an authentic Tuscan experience.