Shoulder Season Charm: Exploring the Beauty of Tuscany in Late Spring/Early Summer.

When you picture Tuscany, images of golden hills, cypress-lined roads, and sun-drenched vineyards likely come to mind. While summer is undoubtedly a popular time to visit, the true magic of this Italian region reveals itself during the shoulder season—specifically late spring and early summer (May to mid-June). Fewer tourists, blooming landscapes, and mild temperatures make this period ideal for an immersive Tuscan experience.

In this guide, we’ll explore why the shoulder season is the best-kept secret for Tuscany travel and outline must-see destinations, events, and practical tips to make the most of your trip.

Why Visit Tuscany in the Shoulder Season?

1. Pleasant Weather Without the Heat

Late spring and early summer bring sunny days and comfortable temperatures ranging from 15°C to 28°C (59°F to 82°F). Unlike the often-intense heat of July and August, this period is ideal for outdoor exploration, from hiking to vineyard tours.

2. Fewer Crowds

The high summer season draws travelers from all over the world, leading to packed piazzas and long queues. In contrast, visiting in May or early June allows for uncrowded museums, quieter countryside, and more intimate dining experiences.

3. Affordable Accommodations

Hotels, agriturismos (farm stays), and vacation rentals often offer better rates before the summer peak. You’ll also have more flexibility in choosing scenic or centrally located stays.

4. Natural Beauty in Full Bloom

Fields of poppies, sunflowers, and wild herbs burst into bloom, painting the Tuscan countryside in vibrant hues. Vineyards begin to show signs of summer abundance, and landscapes are lush and photogenic.

Top Destinations to Explore in Late Spring/Early Summer

1. Florence – The Cradle of the Renaissance

Florence is more enjoyable when you’re not elbowing your way through summer crowds.

Highlights:

Climb the Duomo or Giotto’s Campanile for panoramic views.
Stroll the Boboli Gardens, where spring flowers are in full display.
Visit the Uffizi Gallery or Accademia with shorter wait times.

Local Tip: Enjoy aperitivo at a rooftop bar like La Terrazza while the sun sets over the Arno River.

2. Siena – Medieval Splendor

Siena’s Gothic architecture and winding streets feel like a step back in time.

Highlights:

Marvel at the Duomo di Siena, one of Italy’s most ornate cathedrals.
Relax in Piazza del Campo, home of the famous Palio horse race (held in July, but preparations begin early).
Visit local enotecas (wine bars) for early-season samplings of Chianti and Brunello di Montalcino.

3. Val d’Orcia – The Heart of Tuscany’s Countryside

This UNESCO World Heritage Site is famed for its rolling hills, photogenic landscapes, and small villages.

Highlights:

Explore Pienza, known for its pecorino cheese and Renaissance layout.
Wander through Montalcino and enjoy wine tastings at Brunello vineyards.
Drive or bike the scenic route through cypress-lined roads and poppy-covered fields.

Local Tip: Visit in May for flower festivals that transform the villages into botanical wonders.

4. Lucca – Walled Charm

Lucca offers a quieter, lesser-known escape filled with architectural gems.

Highlights:

Walk or cycle along the Renaissance-era city walls.
Enjoy concerts in honor of Lucca’s most famous son, Giacomo Puccini.
Browse local markets for olive oil, handmade textiles, and seasonal produce.

5. San Gimignano – The Town of Fine Towers

Known for its medieval towers, this town is striking in the soft light of spring.

Highlights:

Climb Torre Grossa for views of the verdant countryside.
Sample the region’s signature white wine, Vernaccia di San Gimignano.
Explore artisan shops selling ceramics, leather, and lace.

Events & Festivals During Late Spring and Early Summer

1. Infiorata Festivals (May–June)

Towns like Spello, Pienza, and Pitigliano celebrate the feast of Corpus Christi with elaborate flower carpets lining the streets.

2. Cantine Aperte (Last Weekend of May)

This national “open cellar” event invites visitors to tour and taste at participating wineries—perfect for wine lovers.

3. Lucca Summer Festival (Early June)

A renowned music event that kicks off in early summer, featuring international artists in a historic piazza.

4. Sagra della Fragola (Strawberry Festival)

In small towns like Terricciola, enjoy strawberry-themed dishes, desserts, and wines during May.

Outdoor Activities to Enjoy in Shoulder Season

1. Cycling and Hiking

The milder climate is ideal for outdoor sports. Routes around Chianti, Cortona, and Montepulciano offer scenic climbs and vineyard views.

2. Truffle Hunting

Join a local guide and dog for a truffle hunt—especially in areas like San Miniato or the Crete Senesi.

3. Cooking Classes and Farm Tours

Learn to make fresh pasta or tour a working olive oil mill. Farms are especially lively in spring.

4. Hot Springs

Soak in natural thermal baths like Bagno Vignoni or Saturnia, which are less crowded and more enjoyable in moderate weather.

What to Eat in Late Spring and Early Summer

Tuscany’s seasonal cuisine shines this time of year. Don’t miss:

Pappardelle al cinghiale (wide pasta with wild boar ragu)
Fava beans and pecorino – a classic springtime antipasto
Bistecca alla Fiorentina – grilled T-bone steak served rare
Strawberries, cherries, and apricots fresh from the market
Gelato al limone or fragola (lemon or strawberry gelato) to beat the afternoon warmth

Pair meals with regional wines like Chianti Classico, Rosso di Montepulciano, or Vernaccia.

Practical Tips for Traveling in Shoulder Season

Packing Essentials: Bring layers, as mornings and evenings can be cool. Don’t forget sunblock, a hat, and comfortable walking shoes.
Transport: Renting a car is ideal for exploring the countryside, but train service connects major towns like Florence, Siena, and Pisa.
Reservations: While crowds are lighter, it’s still smart to book winery tours, cooking classes, and museum entries in advance.
Language: English is widely spoken in tourist areas, but basic Italian greetings go a long way with locals.

Sustainable Travel Tip

Support locally owned agriturismos and family-run trattorias. Buy local produce and crafts, and be respectful of the region’s slower, more deliberate pace of life.

Conclusion

Late spring and early summer in Tuscany offer the perfect blend of natural beauty, cultural experiences, and relaxed ambiance—without the heat and crowds of high season. From Florence’s art to Val d’Orcia’s open fields, this shoulder season provides a more authentic and enjoyable way to fall in love with Tuscany.

Plan ahead, pack smart, and prepare for unforgettable moments beneath the Tuscan sun—just before everyone else gets there.