A Taste of Tuscany: Art, History & Fine Wine
Step into the soul of Tuscany with this blend of Florence’s rich Renaissance culture and the region’s sun-soaked countryside. Wander cobbled streets beneath the Duomo, sip Chianti among the vines, and soak in natural hot springs with views over rolling hills. From medieval towns to vineyard tastings and spa-side serenity, this trip is the perfect mix of art, adventure, and laid-back Italian living.
Sunset over Florence
Day 1: Arrival in Florence
Flight: UK to Florence Airport (FLR) or UK to Pisa Airport (PSA) ~2 hours 20 mins
Transfer: Car hire is the easiest method and ~1 hour 15 minutes from Pisa. Public transport links are also available.
Accommodation: Check into your hotel in Florence
Afternoon Activities: Explore the historic center: Duomo, Uffizi Gallery (advance booking), and Ponte Vecchio. Skip the lines and get a highly rated guided tour of the museums here
Evening: Dinner at a local trattoria
Day 2: Florence Sightseeing
Morning: Visit Accademia Gallery (Michelangelo’s David) if you didn’t get to it on day one, Basilica of Santa Croce, and stroll through Boboli Gardens.
Afternoon: Day trip to Fiesole for panoramic views or for something a little more involved perhaps a Pasta & Tiramisu Cooking Class with Unlimited Wine!
Evening: Aperitivo at Piazza Santo Spirito, followed by dinner.
Day 3: Travel to Siena via Chianti
Transport: Private transfer, guided tour, or rental car. You may want to schedule a stop in the Chianti region if time allows.
Accommodation: Check into hotel in Siena
Morning: Orto de’ Pecci Gardens: A beautiful, quiet public garden just a short walk from the historic Piazza del Campo, with lovely views over the Tuscan countryside and Siena’s rooftops—perfect for unwinding, reading, or having a leisurely walk with a coffee.
Afternoon: There are several amazing wine tours on offer in the region. Here are some to explore around Siena.
Evening: Back for dinner in Piazza del Campo.
Panoramic view of Siena with historic Cathedral in the background
Day 4: Val d’Orcia Day Trip
Transport: Guided tour or rental car.
All Day: Visit the ancient and picturesque towns of Pienza, Montalcino and Montepulciano. Enjoy the enchanting streets, breathtaking countryside views and local cheese and wine tastings.
Evening: Return to Siena for a relaxed evening.
Day 5: San Gimignano & Volterra
Transport: Day tour or rental car.
All Day: Explore San Gimignano’s towers medieval charm. Drive ~40 minutes to discover Volterra’s and Roman history.
Evening: Final dinner in Siena. If you still have plenty of Euros, try La Taverna di San Giuseppe at the upper end of the budget.
Day 6: Montecatini Terme & Return to Florence
Transport: Travel to Montecatini Terme (~1.5 hours from Siena)
Morning: Spa day at the stunning Terme Tettuccio.
Afternoon: Ride the funicular to Montecatini Alto for lunch with a view.
Accommodation: Check back into your Florence hotel (can be same as Day 1–2).
Evening: A relaxing stroll in Florence after dinner.
A glass of red wine poured with the city of Florence in view
Day 7: Final Day in Florence
Accommodation: Last night in Florence (if not flying out this day).
Morning: Visit missed sites (e.g., Bargello Museum or Palazzo Pitti).
Afternoon: Last-minute shopping in San Lorenzo Market or Via de' Tornabuoni.
Evening: Catch the sunset at Piazzale Michelangelo. Farewell dinner upon a romantic rooftop spot. Or if fine dining is your thing, perhaps the Michelin starred Enoteca Pinchiorri
How Much Does it Cost?
As always, there are many variables on price when it comes to holidays! So we have researched three different budgets, combining different seasonal prices, quality of accommodation, average airfares and a varying number of activities. The following includes flights, accommodation, activities, local travel and food.
Tighter Budget: £580 - £780pp
Mid-Range Budget: £800 - £1150pp
Luxury Budget: £1800 - £2750pp
Itinerary Breakdown
This itinerary has a little less downtime, in favour of experiencing the art and culture Florence and wider Tuscany has to offer.
Culture: Museums, churches, historical landmarks, art, architecture, local heritage.
Adventure: Exploratory travel (day trips), scenic drives, climbing towers, countryside tours, winery visits.
Relaxation: Spa time, scenic strolls, long lunches, wine tasting (in relaxed settings), shopping, downtime.
When Should We Go?
A summary of Tuscany’s climate.
We Recommend May - June!
Perfect balance of warm weather (20–27°C), blooming countryside, and fewer crowds than peak summer.
Ideal for vineyard visits, hiking, and outdoor dining.
Prices are moderate—cheaper than peak summer but higher than winter.
