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Dreamy Tuscany Honeymoon Itinerary
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Dreamy Tuscany Honeymoon Itinerary
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Day 1: Arrival in Florence
Florence, Italy
3:00PM
Check-in at Hotel Brunelleschi
Immerse yourselves in luxury as you settle into your stunning hotel, housed in a former Byzantine tower.
Hotel is centrally located in Florence, just a short walk from main attractions.
EUR300, 1 hour
4:30PM
Visit the Duomo
Marvel at the iconic Florence Cathedral, a masterpiece of Renaissance architecture that boasts breathtaking views from its dome.
A 10-minute walk from your hotel.
EUR18, 2 hours
7:00PM
Dinner at La Giostra
Indulge in a romantic dinner featuring traditional Tuscan cuisine in an enchanting setting with fairy lights.
An easy 15-minute walk from the Duomo.
EUR120, 2 hours
Find Hotels in Florence
Day 2: Exploring Florence
Florence, Italy
8:00AM
Breakfast at Caffè Gilli
Start your day with buttery pastries and rich cappuccinos at this historic café.
A short 10-minute walk from your hotel.
EUR20, 1 hour
9:30AM
Uffizi Gallery Tour
Explore world-renowned artworks from the likes of Botticelli and da Vinci as you take in the history within these walls.
A direct walk of about 10 minutes.
EUR30, 2 hours
12:30PM
Lunch at Trattoria Za Za
Enjoy the rustic atmosphere and hearty meals, particularly the mushroom risotto.
Only a 5-minute walk from the Uffizi Gallery.
EUR60, 1.5 hours
2:00PM
Ponte Vecchio and Shopping
Stroll across this historic bridge, browsing the jewelry shops and soaking in romantic views.
Just a 10-minute walk from lunch.
EUR0, 1 hour
5:00PM
Gelato at Gelateria dei Neri
Cool off with artisan gelato from one of the best gelaterias in Florence.
A 15-minute walk from Ponte Vecchio.
EUR10, 30 minutes
7:00PM
Dinner at Osteria Vini e Vecchi Sapori
Savor exquisite local wines paired with homemade pasta in this charming osteria.
A 10-minute walk from your gelato stop.
EUR100, 2 hours
Find Hotels in Florence
Day 3: Charming San Gimignano
San Gimignano, Italy
8:00AM
Breakfast at hotel
Enjoy a leisurely breakfast at your hotel, featuring local cheeses and fresh fruits.
Enjoy the hotel facilities before departure.
Included, 1 hour
9:30AM
Drive to San Gimignano
Take a scenic drive through vineyards and rolling hills, arriving at the medieval town of San Gimignano.
About a 1-hour drive from Florence.
EUR50 (gas), 1 hour
10:30AM
Explore San Gimignano
Wander through this UNESCO World Heritage Site, known for its medieval towers and charming streets.
Walk up to the town center from the parking area.
EUR0, 2 hours
1:00PM
Lunch at Osteria del Carcere
Dine in a quaint osteria enjoying their renowned wild boar ragù.
Located just off the main square.
EUR70, 1.5 hours
3:00PM
Visit the Collegiata di San Gimignano
Admire beautiful frescoes and art in this historic church right in the heart of the town.
A short walk from the restaurant.
EUR5, 1 hour
5:00PM
Drive to Siena
Continue your journey to Siena, stopping for picturesque views along the way.
Approx. a 40-minute drive.
EUR50 (gas), 40 minutes
6:00PM
Check-in at Grand Hotel Continental
Relax in luxury as you arrive at your stunning hotel in the center of Siena.
Located in the heart of the city.
EUR250, 30 minutes
8:00PM
Dinner at Ristorante Il Ristorante
Enjoy a fine dining experience with a blend of modern and traditional Tuscan dishes.
Just a short walk from your hotel.
EUR120, 2 hours
Find Hotels in San Gimignano
Day 4: Discovering Siena
Siena, Italy
8:00AM
Breakfast at hotel
Start your day with a sumptuous breakfast overlooking the stunning Piazza del Campo.
Enjoy the morning views before heading out.
Included, 1 hour
9:30AM
Visit the Piazza del Campo
Explore this famous medieval square and its unique shell shape, the heart of Siena's cultural life.
Just outside the hotel.
EUR0, 1 hour
11:00AM
Explore Siena Cathedral
Admire the stunning black-and-white striped marble façade and intricate interior of this magnificent cathedral.
A walk takes 10 minutes from the square.
EUR15, 2 hours
1:00PM
Lunch at La Taverna di San Giuseppe
Enjoy traditional Tuscan fare in a cozy, rustic setting, recommended are the hand-rolled pasta.
A short walk from the cathedral.
EUR80, 1.5 hours
3:00PM
Visit the Museo dell'Opera del Duomo
Discover incredible artworks and learn about the history of Siena in this fascinating museum.
Adjacent to the cathedral.
EUR8, 1.5 hours
5:00PM
Wine Tasting at Enoteca Italiana
Experience a guided tasting of local wines, including Chianti and Brunello, as you unwind after a day of discovery.
A short drive to the wine shop.
EUR50, 2 hours
7:30PM
Dinner at Osteria La Chiacchera
Indulge in rustic Tuscan dishes, renowned for seasonal ingredients and fresh pasta.
A 10-minute drive back to central Siena.
EUR100, 2 hours
Find Hotels in Siena
Day 5: Luxurious Chianti
Chianti, Italy
8:00AM
Breakfast at hotel
Enjoy a relaxed breakfast while overlooking the stunning Tuscan landscape.
Current location, enjoy the views.
Included, 1 hour
9:30AM
Drive to Chianti
Cruise through the idyllic Chianti wine region, stopping at vineyards along the way.
A short 30-minute drive from Siena.
EUR40 (gas), 30 minutes
10:00AM
Wine Tour at Antinori nel Chianti Classico
Embark on a private tour of this captivating winery, indulging in exceptional wines and breathtaking views.
Located in the heart of Chianti.
EUR75, 2 hours
12:30PM
Lunch at Ristorante Badia a Coltibuono
Experience gourmet dining with an emphasis on local produce featuring seasonal specialties.
A 30-minute drive to the restaurant.
EUR90, 1.5 hours
2:30PM
Relaxation Time at the Villa
Return to your luxurious villa for some downtime, perhaps testing the private pool.
Back to the Chianti villa.
EUR0, 2 hours
5:00PM
Dinner at Ristorante La Cantina
Savor a delightful dinner with local dishes while enjoying the countryside views.
In close proximity to your villa.
EUR100, 2 hours
Find Hotels in Chianti
Day 6: Historical Lucca
Lucca, Italy
8:00AM
Breakfast at villa
Enjoy an al fresco breakfast surrounded by nature.
Beverages and local pastries served at the villa.
Included, 1 hour
9:30AM
Drive to Lucca
Venture into Lucca, a city known for its Renaissance walls.
A 1-hour drive from Chianti.
EUR50 (gas), 1 hour
10:30AM
Explore the Lucca Walls
Walk or bike along the serene Lucca walls, enjoying panoramic views of the city.
Start at the main gate entry into the walls.
EUR5, 2 hours
1:00PM
Lunch at Ristorante Da Leo
Feast on delicious local dishes, pairing your meal with a glass of Lucca wine.
Located within the city center.
EUR80, 1.5 hours
3:00PM
Visit the Puccini Museum
Discover the life and works of the famous composer Giacomo Puccini in this charming museum.
A short walk from the restaurant.
EUR10, 1.5 hours
5:00PM
Relax at Villa Bottini Gardens
Revel in the beautiful gardens of Villa Bottini, enjoying a quiet moment together.
A short walk from the museum.
EUR0, 1 hour
7:00PM
Dinner at A Due Passi dal Cielo
Indulge in fine dining in a beautifully arranged restaurant with a romantic atmosphere.
A short walk from your garden stop.
EUR120, 2 hours
Find Hotels in Lucca
Day 7: Scenic Cortona
Cortona, Italy
8:00AM
Breakfast at villa
Savor a relaxed breakfast with Tuscan pastries and coffee.
Enjoy the amenities of your villa.
Included, 1 hour
9:30AM
Drive to Cortona
Make your way to Cortona, a picturesque hill town known for its art and vistas.
It's about a 1-hour drive from Lucca.
EUR50 (gas), 1 hour
10:30AM
Explore Cortona’s Historic Center
Wander through charming alleys, local shops, and galleries as you admire the town's rich history.
Walking through the traffic-free center.
EUR0, 2 hours
1:00PM
Lunch at Ristorante La Bucaccia
Enjoy authentic Tuscan cuisine made with locally sourced ingredients in a rustic setting.
Located near the main square.
EUR70, 1.5 hours
3:00PM
Visit Diocesan Museum
Learn about the local art and history within the charming galleries of the museum.
A short walk from the restaurant.
EUR8, 1.5 hours
5:00PM
Relax at the Fortress of Girifalco
Take in panoramic views of the Valdichiana from this historic fortress as you reflect on the beauty of Cortona.
A 15-minute walk uphill from the museum.
EUR0, 1.5 hours
7:00PM
Dinner at Osteria del Teatro
Round off the day with a delightful dinner characterized by delicious Tuscan specialties.
A lovely 10-minute downhill walk.
EUR100, 2 hours
Find Hotels in Cortona
Day 8: Farewell Florence
Florence, Italy
8:00AM
Breakfast at villa
Celebrate your final breakfast in Tuscany with local cheeses and sweet pastries.
At your villa, enjoy the morning sun.
Included, 1 hour
9:30AM
Drive back to Florence
Return to Florence, where your adventure began, reflecting on your lovely journey.
A 1-hour drive from Cortona.
EUR50 (gas), 1 hour
11:00AM
Free Time for Last-minute Shopping
Last chance to pick up souvenirs or gifts from Florence, visiting the markets or boutiques.
A walk from your hotel.
EUR0, 2 hours
1:00PM
Lunch at Mercato Centrale
Explore a wide range of local delicacies within this vibrant market before your flight.
A short walk from the shopping area.
EUR40, 1.5 hours
3:00PM
Departure from Florence
Bid farewell to Tuscany, cherishing the remarkable memories created during your honeymoon.
Make your way to the airport.
Fleet service arranged for departure., 1 hour
Find Hotels in Florence
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Itinerary created by
Plantrip Team
January 8, 2025
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