Romantic Honeymoon in Tuscany: A 7-Day Luxury Road Trip Itinerary

Day 1: Exploring Florence

Florence, Italy

9:00AM

Breakfast at Caffè Gilli

Start your honeymoon with a delightful breakfast at Caffè Gilli, renowned for its exquisite pastries and fresh coffee.
Located in the heart of Florence, just a short walk from your hotel.
EUR20, 1 hour

10:30AM

Visit the Uffizi Gallery

Immerse yourselves in art as you explore the Uffizi Gallery, home to masterpieces by Michelangelo and Botticelli.
A quick 10-minute walk from Caffè Gilli.
EUR24, 2 hours

1:00PM

Lunch at Trattoria Mario

Enjoy a rustic yet romantic lunch featuring Tuscan cuisine at Trattoria Mario, a local favourite.
An easy 15-minute stroll from the Uffizi Gallery.
EUR40, 1 hour

2:30PM

Explore the Florence Cathedral

Take in the stunning architecture of Florence Cathedral and climb to the dome for panoramic views of the city.
A short 10-minute walk from Trattoria Mario.
EUR20, 1.5 hours

4:00PM

Stroll across Ponte Vecchio

Wander across the famous Ponte Vecchio, experiencing the charming shops and picturesque views of the Arno River.
A 10-minute walk from the cathedral.
Free, 1 hour

7:00PM

Dinner at Osteria Vini e Vecchi Sapori

Indulge in an elegant dinner at this intimate restaurant, known for its homemade pastas and fine wine.
Located 15 minutes away on foot from Ponte Vecchio.
EUR100, 2 hours
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Day 2: Wine Tasting in Chianti

Chianti, Italy

8:00AM

Breakfast at your hotel

Savour a luxurious breakfast to fuel your adventure in Tuscany.
N/A - Enjoy breakfast at your hotel.
EUR30, 1 hour

9:30AM

Drive to Chianti

Scenic drive to Chianti, which offers breathtaking landscapes of vineyards and olive groves.
Take the SR222 road for an hour.
N/A, 1 hour

10:30AM

Wine Tasting at Castello di Verrazzano

Enjoy a private wine tasting at Castello di Verrazzano with a guided tour of the winery.
A short drive within Chianti region.
EUR45, 2 hours

1:00PM

Lunch at Ristorante Pizzeria il Visconte

Relax with a light lunch featuring locally-sourced ingredients and delicious pizzas.
Drive 15 minutes from the winery.
EUR50, 1 hour

2:30PM

Explore the Vineyards

Take a romantic stroll through picturesque vineyards and bask in Tuscany’s scenery.
Located around the Ristorante, perfect for walking.
Free, 2 hours

5:00PM

Drive to San Gimignano

Wind your way through the hills to reach the medieval town of San Gimignano.
A scenic 45-minute drive.
N/A, 45 minutes

7:00PM

Dinner at La Mandragola

Enjoy a romantic dinner at La Mandragola, renowned for its authentic Tuscan dishes.
Close to where you park in San Gimignano.
EUR80, 2 hours
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Day 3: Charming San Gimignano

San Gimignano, Italy

8:00AM

Breakfast at your hotel

Relish a hearty breakfast at your hotel and fuel up for a day of exploration.
N/A - Breakfast at your hotel.
EUR30, 1 hour

9:30AM

Visit the Towers of San Gimignano

Climb up the famous towers for sweeping views of the countryside.
Just a few minutes' walk from your hotel.
EUR10, 1 hour

11:00AM

Wine Tasting at Podere La Marronaia

Enjoy an exclusive wine tasting session paired with local cheeses.
A short drive or stroll away.
EUR35, 1.5 hours

1:00PM

Lunch at Osteria dei Lippi

Experience Tuscan flavours with a rustic lunch at this local gem.
A quick 10-minute walk from Podere La Marronaia.
EUR60, 1 hour

2:30PM

Explore the Local Shops

Wander the charming streets and indulge in delightful local shops filled with artisan products.
Stroll through San Gimignano's historic centre.
Free, 2 hours

5:00PM

Drive to Siena

Travel through delightful landscapes as you head to the breathtaking city of Siena.
A scenic 45-minute drive.
N/A, 45 minutes

7:00PM

Dinner at Sotto le Fonti

Dine in style with traditional Siena dishes at this popular restaurant.
Short walk from the parking area in Siena.
EUR85, 2 hours
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Day 4: Discovering Siena

Siena, Italy

8:00AM

Breakfast at your hotel

Start with a delightful breakfast at your hotel, preparing for a day in stunning Siena.
N/A - Breakfast at your hotel.
EUR30, 1 hour

9:30AM

Visit Piazza del Campo

Admire the iconic square of Siena and visit the magnificent Palazzo Pubblico.
Located in the heart of Siena, just a short walk from your hotel.
Free, 1 hour

11:00AM

Tour the Siena Cathedral

Explore the stunning Gothic architecture of Siena Cathedral and its remarkable interior.
A quick 5-minute walk from Piazza del Campo.
EUR15, 1.5 hours

1:00PM

Lunch at Osteria Le Logge

Delight in seasonal dishes at this beautiful restaurant overlooking the square.
Next to the cathedral.
EUR70, 1.5 hours

2:30PM

Visit the Pinacoteca Nazionale

Discover Siena’s art history at the Pinacoteca Nazionale, featuring works from the 12th to 16th centuries.
A 10-minute walk from your lunch spot.
EUR8, 1.5 hours

4:30PM

Drive to Montepulciano

Head to the charming hilltop town of Montepulciano, known for its incredible wines.
A 1-hour drive through stunning landscapes.
N/A, 1 hour

7:00PM

Dinner at La Grotta

Indulge in fine dining with exquisite dishes at La Grotta, located in a historic cellar.
Close to the main square in Montepulciano.
EUR100, 2 hours
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Day 5: Wine and Views in Montepulciano

Montepulciano, Italy

8:00AM

Breakfast at your hotel

Enjoy a refreshing breakfast at your hotel, setting the tone for another exhilarating day.
N/A - Breakfast at your hotel.
EUR30, 1 hour

9:30AM

Explore Montepulciano's Historic Center

Wander the charming streets of Montepulciano, rich in history and stunning architecture.
Easily walk around the town centre.
Free, 2 hours

11:30AM

Wine Tasting at Contucci Winery

Partake in a wine tasting session at the historic Contucci Winery, tasting their renowned Nobile di Montepulciano.
Located a short walk from the historic centre.
EUR25, 1.5 hours

1:00PM

Lunch at Osteria Acquacheta

Savour hearty Tuscan fare at this beloved local eatery, famous for its pici pasta.
Just a short walk from Contucci Winery.
EUR40, 1.5 hours

2:30PM

Visit Tempio di San Biagio

Explore the stunning church of San Biagio with beautiful views over the countryside.
A short drive outside of Montepulciano.
Free, 1 hour

5:00PM

Drive to Cortona

Enjoy the beautiful scenery as you make your way to the charming town of Cortona.
A 30-minute drive.
N/A, 30 minutes

7:00PM

Dinner at Osteria del Teatro

Dig into traditional Tuscan dishes in this welcoming atmosphere in Cortona.
In the town centre, easy to find.
EUR85, 2 hours
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Day 6: Charming Cortona

Cortona, Italy

8:00AM

Breakfast at your hotel

Begin your day with a scrumptious breakfast at your hotel in beautiful Cortona.
N/A - Breakfast at your hotel.
EUR30, 1 hour

9:30AM

Visit the Etruscan Academy Museum

Explore Etruscan history and artifacts in this fascinating museum.
Located in the center of Cortona.
EUR10, 1.5 hours

11:00AM

Explore Cortona's Beautiful Streets

Wander through the picturesque old town with its dramatic landscapes and charming shops.
Easily accessible on foot from the museum.
Free, 1.5 hours

1:00PM

Lunch at Caffe Edy

Enjoy a delicious lunch at the delightful Caffe Edy, known for its local delicacies.
Close to the museum.
EUR40, 1 hour

3:00PM

Visit the Diocesan Museum

Marvel at the exquisite art showcased in the Diocesan Museum of Cortona.
A 10-minute walk from Caffe Edy.
EUR8, 1 hour

4:30PM

Relax at Parterre Park

Spend a leisurely afternoon at Parterre Park, enjoying stunning views over the hills.
A short walk from the museum.
Free, 1 hour

6:00PM

Drive to Lucca

Travel to Lucca for your next destination, famous for its well-preserved Renaissance walls.
A 1.5-hour drive.
N/A, 1.5 hours

8:00PM

Dinner at Ristorante Giglio

Savour your final dinner in Tuscany with delectable Italian cuisine at this celebrated local restaurant.
Located in the heart of Lucca.
EUR90, 2 hours
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Day 7: Explore Pisa

Pisa, Italy

8:00AM

Breakfast at your hotel

Start your last day in Tuscany with a satisfying breakfast at your hotel.
N/A - Breakfast at your hotel.
EUR30, 1 hour

9:30AM

Visit the Leaning Tower of Pisa

Climb the iconic Leaning Tower of Pisa and take in the breathtaking views.
A short drive to Piazza dei Miracoli.
EUR25, 1.5 hours

11:30AM

Explore Piazza dei Miracoli

Stroll through the beautiful architecture of the Baptistery and the Cathedral around the square.
All within walking distance.
Free, 1 hour

1:00PM

Lunch at Ristorante da Rocco

Enjoy classic Italian dishes with a local twist at Ristorante da Rocco.
A short walk from Piazza dei Miracoli.
EUR50, 1.5 hours

2:30PM

Drive back to Florence

Return to Florence, enjoying the lovely Tuscan countryside on your way.
A 1-hour drive.
N/A, 1 hour

4:00PM

Last-minute Shopping in Florence

Explore the local shops for souvenirs and gifts to take back home.
Return to the Florence city centre.
Free, 2 hours

7:00PM

Farewell Dinner at Enoteca Pinchiorri

End your magical honeymoon with an unforgettable dinner at this Michelin-starred restaurant.
A short drive back to the centre of Florence.
EUR200, 2.5 hours
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