Tuscany is synonymous with timeless beauty, rich culture, and exceptional living, making it an ideal destination for a luxury vacation. Home to romantic stone farmhouses surrounded by olive groves and cypress trees, medieval hilltop towns, coastal villages, and world-class wineries, it’s easy to see why the region is a favorite among adventure seekers, luxury travelers, and our Equity Estates Investors.
For those dreaming of a more refined, less hurried experience in the Tuscan countryside, shoulder season is an exceptional time to visit. Shoulder season in Tuscany typically refers to the months just outside of the peak summer tourist season — usually early April to early June and September to October. These months strike the perfect balance between beautiful weather, smaller crowds, and authentic experiences.
Here we’ve highlighted our top three reasons to plan your Tuscan getaway during one of those golden windows.
CULTURE, CUISINE, AND CHARM
Fewer Crowds and a Slower Pace
Avoid the peak summer influx of tourists and enjoy Tuscany at a deliciously slower pace. Whether you’re wandering through Florence’s Uffizi Gallery or sipping wine in a hilltop village like Montepulciano, shorter lines and less congestion make for more personal, unhurried experiences.
- Stroll through Florence’s Uffizi Gallery without the long lines and enjoy world-famous works like Botticelli’s The Birth of Venus up close and at your own pace.
- Take a short road trip to savor a quiet afternoon in Siena’s Piazza del Campo, sipping espresso or enjoying gelato while soaking in the medieval architecture — no jostling tour groups in sight.
- Have lunch and visit the Museo del Vino in Greve, then enjoy a leisurely afternoon of shopping and sightseeing in the town’s unique Piazza Matteotti.
- Secure coveted reservations at Michelin-starred restaurants like Osteria di Passignano or Santa Elisabetta, which are more accessible outside of peak months.
Milder Weather for Outdoor Exploration
Spring months and early fall offer milder temperatures, perfect for walking tours, biking through the countryside, or enjoying a long al fresco lunch without the sweltering heat of July and August. Vineyards, olive groves, and fields of wild poppies and other blooms are lush and vibrant in late spring, while fall brings golden light and grape harvesting.
With daytime highs typically in the 60s and 70s°F (15–25°C), shoulder season is perfect for enjoying time outdoors without overheating.
- Bike through the Chianti hills, stopping at vineyards and small villages along the way to sample local wines and regional cheeses.
- Explore peaceful trails and wooded hills with a waterfall hike in the Vallombrosa Biogenetic State Nature Reserve.
- Join a truffle hunt near San Miniato in the fall, followed by a chef-prepared lunch featuring your finds alongside local wine pairings.
- Take a scenic drive along the famed Strada Statale 222 Chiantigiana, where vast fields, cypress trees, historic castles, and rolling green hills are even more breathtaking in the gentle spring or autumn light.
Seasonal Food, Wine, and Festivals
Tuscany’s seasonal rhythms are on full display in spring and fall, with some of the region’s best culinary and cultural events taking place, offering travelers a chance to experience the deep flavors and festivities of the region.
Springtime brings a bounty of fresh ingredients. Enjoy fava beans, artichokes, lamb, spring pea risottos and pecorino cheese, showcased in seasonal dishes.
In the fall, Tuscany comes alive with la vendemmia (the grape harvest), truffle festivals, and the olive oil pressing season. If you are in-house during harvest season, you’ll have the opportunity to participate in the harvest at your Equity Estates villa.
Visiting during either end of shoulder season lets you experience regional cuisine at its freshest.
- Spend a day at a boutique winery during harvest season to experience grape picking, cellar tours, and barrel tastings — often hosted by the winemakers themselves.
- Immerse yourself in a private Cooking Class at Querceto di Castellina beginning with a trip to the local butcher and market for seasonal ingredients, followed by step-by-step guidance through the cooking process, and ending by enjoying the finished meal on the estate’s sun-drenched terrace.
- Take the popular, four-hour Taste Florence Food Tour — a fantastic way to see the sights and experience some of the city’s best food and drinks with an English-speaking guide leading the way.
- Experience the Chianti Classico Wine Expo in Greve in September for artistic events, activities, tastings, and encounters with local winemakers
At Home in Tuscany with Equity Estates
Our grand Tuscany I vacation home is set on over nine beautifully landscaped acres in the heart of the Florentine countryside, providing convenient access to Florence and the towns of Greve and Strada in Chianti — making it a strategic home base for both city and rural adventures.
Set above a rolling landscape dotted with olive groves, Tuscany II, one of our reciprocal properties, is another conveniently located, luxurious home with lush, gorgeous surroundings that’s available for a relaxing Tuscan retreat.
Ask your Destination Manager for shoulder season suggestions, including vineyard reservations, local food festivals, guided tours, or seasonal cooking classes.
Travel with Equity Estates for a unique and memorable experience. If you would like more information about investing with Equity Estates, please reach out to our Investor Relations team at 404.445.8501 or click to schedule a call.
