Luxury One-Week Tuscany Itinerary: A Five-Star Experience through Florence, Siena, and Chianti

Day 1: Arrival & Florence

Florence, Italy on April 27, 2025

10:00am

Arrive and Check-in at Four Seasons Hotel Firenze

Experience luxury at the Four Seasons, a historic palace with stunning gardens and impeccable service, your base for the Tuscan adventure.
EUR500, 1h

12:00pm

Lunch at Enoteca Pinchiorri

Enjoy a refined Tuscan lunch at this celebrated Michelin 3-star restaurant known for its exquisite wine cellar and gourmet cuisine.
EUR150, 2h

2:30pm

Private Guided Tour of Florence Cathedral and Uffizi Gallery

Discover Renaissance masterpieces with a private expert guide at the iconic Duomo and Uffizi Gallery, open 8:15am-6:50pm.
EUR100, 3h

6:00pm

Stroll on Ponte Vecchio

Enjoy a relaxed evening walk along the historic Ponte Vecchio with its artisan shops and picturesque views at sunset.
Free, 1h

7:30pm

Dinner at Il Palagio, Four Seasons

Dine in style at Il Palagio, offering refined Tuscan fare with organic ingredients in an elegant setting.
EUR120, 2h
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Day 2: Art & Culture

Florence, Italy on April 28, 2025

8:00am

Breakfast at Hotel

Start your day with a gourmet breakfast buffet featuring fresh Italian pastries and espresso at the hotel restaurant.
Included, 1h

9:30am

Accademia Gallery & Michelangelo’s David

Visit the Accademia Gallery to see Michelangelo’s iconic David sculpture, open from 8:15am to 6:50pm.
EUR20, 2h

12:00pm

Lunch at Osteria di Giovanni

Enjoy authentic Tuscan dishes in a cosy, traditional setting near Florence’s historic centre.
EUR60, 1.5h

2:00pm

Boboli Gardens and Pitti Palace

Explore the lush Boboli Gardens and the grand Pitti Palace with art collections, open 8:15am to 6:30pm.
EUR25, 3h

6:00pm

Sunset Aperitivo at La Terrazza Rooftop Bar

Sip a cocktail while overlooking the Florence skyline and the Duomo in a stylish rooftop setting.
EUR25, 1h

7:30pm

Dinner at Enoteca Fuori Porta

Savour a contemporary Tuscan menu paired with an excellent wine selection in a sophisticated atmosphere.
EUR90, 2h
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Day 3: Chianti Wine Tour

Chianti, Tuscany, Italy on April 29, 2025

8:00am

Breakfast at Hotel

Enjoy a leisurely hotel breakfast before embarking on your countryside adventure.
Included, 1h

9:30am

Private Chianti Wine Region Tour

Travel to the Chianti region for guided visits to historic wineries including Castello di Ama and Castello di Brolio. Tastings and vineyard walks included, tours run typically 9am-5pm.
EUR250, 6h

4:00pm

Check-in at Castello di Casole

Indulge in countryside luxury at this 5-star estate nestled among Chianti’s rolling hills.
EUR600, 1h

7:30pm

Dinner at Castello di Casole Restaurant

Dine on gourmet Tuscan cuisine prepared with local ingredients in a romantic castle setting.
EUR100, 2h
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Day 4: Siena & History

Siena, Italy on April 30, 2025

8:00am

Breakfast at Castello di Casole

Savour a hearty breakfast with views over vineyards and olive groves in the luxurious estate.
Included, 1h

9:30am

Travel to Siena

Scenic 1.5-hour drive to Siena, a medieval Tuscan city famous for its Piazza del Campo and Gothic architecture.
Private transfer EUR150, 1.5h

11:00am

Explore Piazza del Campo and Siena Cathedral

Visit Siena’s famous shell-shaped square and marvel at the intricate Gothic Siena Cathedral (Maria Assunta), open 10am-7pm.
EUR20, 2h

1:00pm

Lunch at La Taverna di San Giuseppe

Enjoy traditional Sienese dishes such as pici pasta in a charming rustic setting.
EUR70, 1.5h

3:00pm

Visit Museo dell’Opera del Duomo

Discover art and history related to Siena Cathedral’s construction and treasures, open 10am-7pm.
EUR15, 1.5h

5:00pm

Return to Castello di Casole

Relax en route back to the castle estate in the serene Tuscan countryside.
Included in transfer, 1.5h

8:00pm

Dinner at Castello di Casole

Gourmet dinner featuring seasonal ingredients and paired with renowned Chianti wines.
EUR100, 2h
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Day 5: Val d’Orcia Day Trip

Val d’Orcia, Tuscany, Italy on May 1, 2025

7:30am

Early Breakfast at Castello di Casole

Enjoy an early healthy breakfast to fuel your day exploring one of Tuscany’s most scenic regions.
Included, 1h

8:30am

Full Day Private Tour of Val d’Orcia

Visit iconic towns such as Pienza, Montalcino, and Montepulciano, with stops for tasting local Pecorino cheese and Brunello wine. Tours operate 9am-6pm.
EUR300, 8h

5:00pm

Return to Castello di Casole

Relax after a scenic day with views of rolling hills and cypress-lined roads.
Included, 1h

7:30pm

Dinner at Castello di Casole

Indulge in a refined menu highlighting local flavours and ingredients, paired with estate wines.
EUR100, 2h
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Day 6: Lucca & Relaxation

Lucca, Italy on May 2, 2025

8:00am

Breakfast at Castello di Casole

Enjoy a slow breakfast soaking in the views of Tuscan countryside.
Included, 1h

9:30am

Drive to Lucca

Luxurious private transfer for a 2-hour scenic drive to the historic walled city of Lucca.
EUR200, 2h

11:30am

Bike Ride on Lucca’s Historic City Walls

Ride atop the well-preserved Renaissance walls offering stunning views over the terracotta rooftops.
EUR25, 1h

12:30pm

Lunch at Buca di Sant'Antonio

Experience traditional Lucchese cuisine at one of Lucca’s oldest fine dining restaurants.
EUR80, 1.5h

2:30pm

Visit the Guinigi Tower and San Michele in Foro

Explore notable landmarks including the tower with rooftop trees and the beautiful central piazza church.
EUR18, 2h

5:00pm

Return to Florence and Check-in at Hotel Savoy

Drive back to Florence for your final night, staying at the chic Hotel Savoy in the city centre.
EUR350, 2h

7:30pm

Dinner at Borgo San Jacopo

Conclude your trip with Michelin-starred creative Tuscan cuisine on the Arno riverbank.
EUR140, 2h
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Day 7: Departure

Florence, Italy on May 3, 2025

8:00am

Breakfast at Hotel Savoy

Enjoy your final breakfast in Tuscany with a selection of fresh pastries and coffee.
Included, 1h

10:00am

Last-minute Shopping and Stroll

Spend a relaxed morning wandering Florence’s luxury boutiques and artisan shops near Piazza della Repubblica.
Free, 2h

12:30pm

Private Transfer to Florence Airport

Arrive in comfort at Florence Airport for your onward journey.
EUR100, 30m
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