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Siena - Things to Do in Siena in May

Things to Do in Siena in May

May weather, activities, events & insider tips

May Weather in Siena

22°C (72°F) High Temp
11°C (52°F) Low Temp
71mm (2.8 inches) Rainfall
70% Humidity

Is May Right for You?

Advantages

  • Perfect shoulder season temperatures - you'll get warm afternoons around 22°C (72°F) without the crushing July-August heat that sends locals indoors. Mornings start cool at 11°C (52°F), ideal for walking Siena's steep medieval streets before the sun climbs higher.
  • Significantly fewer tourists than summer months, meaning you can actually experience the Duomo and Piazza del Campo without fighting through tour groups. Hotels typically run 25-35% cheaper than June-August rates, and restaurant reservations are easier to secure with just 2-3 days notice rather than weeks ahead.
  • The Tuscan countryside hits peak green after spring rains - vineyards are lush, wildflowers blanket the hillsides, and the famous cypress-lined roads look exactly like those Renaissance paintings. This is arguably the most photogenic month before everything turns golden-brown in summer.
  • Local life is in full swing without tourist-season chaos. You'll see actual Sienese going about their daily routines in the contrade neighborhoods, markets are stocked with spring produce like fresh fava beans and artichokes, and outdoor cafes fill with locals rather than just visitors.

Considerations

  • Rain is genuinely unpredictable - those 10 rainy days don't follow a pattern, and May storms can arrive suddenly in the afternoon. You might get three gorgeous days followed by two wet ones, which makes planning outdoor activities in the countryside a bit of a gamble. The humidity at 70% means things don't dry quickly either.
  • It's too early for the Palio (July 2 and August 16), which is honestly what many visitors want to experience. If you're coming specifically for that electric atmosphere when the entire city revolves around the horse race, May will feel relatively quiet by comparison.
  • Evenings can be surprisingly chilly - that 11°C (52°F) low isn't just theoretical. After sunset around 8:30pm, you'll want layers for outdoor dining. Many restaurants haven't fully transitioned to summer hours yet, and some rooftop terraces remain closed until June.

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Best Activities in May

Val d'Orcia countryside cycling and hill town tours

May is genuinely the best month for exploring the UNESCO-protected Val d'Orcia valley south of Siena. The landscape is still green from spring rains, temperatures sit in that perfect 18-22°C (64-72°F) range for cycling, and towns like Pienza and Montalcino haven't yet filled with summer tour buses. The morning light on those famous cypress groves is extraordinary right now. Most tours cover 25-40km (15-25 miles) through rolling hills, which is manageable in cooler weather but becomes brutal in July-August heat.

Booking Tip: Tours typically run 65-95 euros including bike rental and sometimes wine tastings. Book 7-10 days ahead through licensed operators - look for ones that provide e-bikes as an option since those hills are steeper than they look in photos. Morning departures around 9am work best to avoid afternoon rain chances. See current tour options in the booking section below.

Chianti wine estate visits and tastings

May hits a sweet spot in the wine calendar - the vines are actively growing with bright green leaves, but harvest chaos is months away so winemakers actually have time to talk with visitors. Estates are less crowded than summer, and the 70% humidity actually helps your nose pick up wine aromas better than in dry conditions. The countryside drive between Siena and Chianti estates like those around Castellina or Gaiole is spectacular right now with wildflowers everywhere. You'll taste primarily previous vintages since 2025 wines are still aging.

Booking Tip: Estate visits range from 25-60 euros depending on the number of wines and food pairings. Book at least 5-7 days ahead as many estates require reservations and limit daily visitors. Afternoon slots from 2-4pm tend to have better availability. Look for tours that include transportation if you want to taste properly - Chianti roads are narrow and winding. Check the booking widget below for current options with transport included.

Siena historic center walking tours and contrade exploration

May weather is ideal for spending 3-4 hours walking Siena's medieval streets without overheating. The city's built on three hills, so there's constant climbing, and you'll appreciate doing this in 20°C (68°F) rather than 35°C (95°F). Each of Siena's 17 contrade neighborhoods has its own museum, fountain, and identity - visiting these small museums gives you context for the Palio rivalry even if you're not here for race day. The Duomo's marble floors are fully uncovered in May, which only happens certain months, and the cathedral complex is significantly less crowded than summer.

Booking Tip: Guided walking tours run 25-45 euros for 2-3 hours. You can easily do this self-guided with a good map, but a local guide adds tremendous context about contrade politics and Palio history that you'd otherwise miss. Duomo admission is 15 euros for the basic ticket, 20 euros for the complete pass including museum and baptistery. Book Duomo tickets online 2-3 days ahead to skip lines. Morning tours starting around 10am work well after the chill burns off.

San Gimignano and Volterra day trips

These two medieval hill towns make perfect May day trips from Siena - San Gimignano with its famous towers is 38km (24 miles) northwest, Volterra with Etruscan ruins is 50km (31 miles) west. May means you'll experience them without the oppressive summer crowds, and the alabaster workshops in Volterra are more pleasant to visit when it's not sweltering. The dramatic hilltop positions of both towns means they catch wind and stay cooler. Spring wildflowers along the approach roads are outstanding. You can combine both in one long day or dedicate a half-day to each.

Booking Tip: Organized day trips covering both towns typically cost 70-110 euros including transport and sometimes a lunch stop. Alternatively, rent a car for 45-65 euros per day and go independently for more flexibility. Public buses exist but are slow and infrequent. If driving yourself, parking in both towns requires walking uphill 400-600m (0.25-0.37 miles) from lots to historic centers. Check current guided tour options in the booking section below.

Siena cooking classes and food market tours

May brings excellent seasonal produce to Siena's markets - fresh fava beans, artichokes, asparagus, and the first cherries appear now. Cooking classes in May focus on spring dishes like pici pasta with asparagus or fava bean soups that you won't see taught in other seasons. The humidity actually helps pasta-making since dough doesn't dry out as quickly. Market tours typically start at Mercato di La Lizza on Wednesday mornings or the smaller daily markets, then move to a kitchen for hands-on cooking. You'll avoid the intense heat that makes standing over stoves miserable in summer.

Booking Tip: Half-day cooking classes with market visits run 85-140 euros per person, usually including the meal you prepare plus wine. Book 5-10 days ahead as class sizes stay small, typically 6-12 people. Morning classes starting around 9:30am are most common since markets are freshest early. Look for classes in actual homes or small cooking schools rather than restaurant kitchens for a more authentic experience. See booking options below for current availability.

Monte Oliveto Maggiore and Sant'Antimo abbey visits

May is excellent for visiting Tuscany's monasteries and abbeys, which offer peaceful contrast to busy tourist towns. Monte Oliveto Maggiore, 35km (22 miles) southeast of Siena, sits isolated among eroded clay hills with remarkable Renaissance frescoes and Gregorian chanting at services. Sant'Antimo near Montalcino, 40km (25 miles) south, is a Romanesque abbey in a valley setting that's achingly beautiful in spring green. Both locations involve outdoor walking between buildings, which is far more pleasant now than in summer heat. The contemplative atmosphere suits May's variable weather when you want meaningful indoor-outdoor experiences.

Booking Tip: Both abbeys are free to enter though donations are appreciated, typically 3-5 euros. They're best reached by car as public transport is extremely limited - figure 45-60 minutes driving from Siena to either location. Organized tours combining both abbeys with Montalcino wine tastings run 90-130 euros. Visit mid-morning or late afternoon to potentially hear monks chanting. Dress modestly with covered shoulders and knees. Check the booking widget for current tour combinations.

May Events & Festivals

Late May

Cantine Aperte - Open Cellars Weekend

This nationwide event happens the last weekend of May across Italian wine regions, including dozens of estates in Chianti and the Siena area. Wineries open their cellars for tastings, tours, and often food pairings or live music, many waiving normal reservation requirements just for this weekend. It's a genuine local event, not a tourist creation, and you'll meet Italian wine enthusiasts traveling from other regions. Participating estates post schedules in early May, and you can visit multiple locations in a day though driving between tastings requires a designated driver.

Throughout May

Maggio Musicale Fiorentino spillover concerts

While the main festival happens in Florence, some performances and associated events occasionally take place in Siena venues like Teatro dei Rozzi. Worth checking 2026 programming if you're interested in classical music, opera, or contemporary performances. The festival runs throughout May and into June, and Siena shows tend to be easier to get tickets for than the Florence venues.

Essential Tips

What to Pack

Layering pieces are essential - that 11°C (52°F) morning temperature climbs to 22°C (72°F) by afternoon, meaning you'll be constantly adding and removing layers. Pack a light merino wool or synthetic base layer, a medium-weight cardigan or fleece, and a windbreaker. Avoid cotton which stays damp in 70% humidity.
Waterproof jacket with a hood, not just an umbrella - Siena's steep, narrow streets create wind tunnels that make umbrellas useless. Those 10 rainy days often bring sudden afternoon storms. Look for something packable that you can stuff in a daypack. Waterproof doesn't mean heavy - a 200g (7oz) rain shell works perfectly.
Comfortable broken-in walking shoes with good grip - Siena's streets are steep medieval stone and marble that gets slippery when wet. You'll easily walk 8-12km (5-7.5 miles) daily just exploring the city and contrade neighborhoods. Skip new shoes that will give you blisters. Ankle support helps on those hills.
Sunscreen SPF 50 or higher - that UV index of 8 is serious, and the variable weather means you might not realize how much sun exposure you're getting between clouds. The high altitude of Siena at 322m (1,056 ft) increases UV intensity. Reapply every 2-3 hours if you're outside continuously.
Sunglasses and a packable sun hat - May sun is strong during clear periods, and you'll spend hours walking exposed in Piazza del Campo or along city walls. A hat that folds or crushes for packing works better than rigid styles. Polarized sunglasses help with glare off those light-colored medieval buildings.
Light scarf or pashmina - serves multiple purposes in May. Covers shoulders for church visits, provides warmth in cool morning air, protects neck from sun, and adds a layer for breezy evenings. The 70% humidity means you want natural fabrics like cotton, linen, or silk that breathe.
Small daypack or crossbody bag - you'll be carrying that rain jacket, extra layers, water bottle, and camera around all day. Keep hands free for climbing Siena's hills and stairs. Something 15-20L (900-1,200 cubic inches) capacity with water-resistant material works well.
Reusable water bottle - Siena has drinking fountains throughout the historic center with excellent water. Staying hydrated in 70% humidity matters even if temperatures seem moderate. A 750ml (25oz) bottle is enough since you can refill easily.
Dressier outfit for nice dinners - Sienese dress well for evening meals, and you'll feel out of place in hiking gear at better restaurants. Nothing formal required, but clean dark jeans or casual trousers with a collared shirt or nice blouse fits local standards. Remember that evening layer for outdoor seating.
Power adapter for Italy (Type L, 230V) and perhaps a portable charger - you'll use your phone constantly for photos, maps, and translation. Churches and museums often don't allow charging, so a portable battery pack keeps you functional during long days out.

Insider Knowledge

Book accommodations within or just outside the ZTL limited traffic zone - Siena's historic center is largely car-free, and staying inside means you're already where you want to be. Hotels outside the walls often advertise free parking as an advantage, but you'll end up walking uphill 800-1,200m (0.5-0.75 miles) with luggage or taking taxis. In May, you can still find good rates 3-4 weeks out, but popular places near Piazza del Campo book earlier.
The Duomo floor panels are fully visible in May, which only happens during specific periods when protective coverings are removed. These intricate marble inlay panels from the 14th-16th centuries are genuinely extraordinary and many visitors have no idea they're often covered. This alone makes May special for cathedral visits.
Eat lunch at 1-2pm, dinner after 8pm to match local schedules - restaurants serving at noon or 6pm are targeting tourists and quality often suffers. In May, sunset happens around 8:30pm, so dining at 8:30 or 9pm means you catch beautiful evening light in outdoor seating. Many kitchens close between lunch and dinner service, roughly 3-7pm.
Skip the expensive wine shops on Via di Città and head to Enoteca Italiana in the Fortezza Medicea for better selection and prices. This national wine library has hundreds of Italian wines available for tasting and purchase at near-retail prices. The fortress setting is also a pleasant 10-minute walk from the Campo where locals actually go.
Wednesday morning market at La Lizza brings locals shopping for produce, cheese, and household goods - it's not a tourist market, which makes it far more interesting. You'll see actual Sienese selecting their vegetables and arguing with vendors. Good for people-watching and understanding daily life beyond the medieval tourist center.
The Porta Tufi area southeast of the center has several excellent restaurants where you'll hear Italian conversations rather than English. It's a 12-15 minute walk from Piazza del Campo but still within the walls. Locals know this neighborhood for authentic food at 25-30% lower prices than restaurants directly on the Campo.
May mornings can be genuinely cold until 10am - that 11°C (52°F) low isn't just at dawn, it lingers. Plan museum visits or indoor activities for early hours, then shift to outdoor walking and countryside trips as temperatures climb into the comfortable range by late morning.

Avoid These Mistakes

Underestimating how much walking you'll do on steep hills - Siena isn't flat Florence. First-timers often book accommodations based on map distance without realizing a 400m (0.25 mile) walk might involve climbing 30m (100 ft) elevation on medieval stairs. This matters when you're doing it multiple times daily with tired legs. Check elevation profiles, not just distances.
Assuming May weather will be consistently warm and leaving warm layers at home - those cool mornings and chilly evenings after 8:30pm catch people unprepared. You'll see tourists shivering at outdoor restaurant tables in t-shirts while locals wear light jackets. That 11-degree temperature swing between day and night is real.
Renting a car for their entire stay including Siena days - you cannot drive in the historic center, parking is expensive at 25-35 euros per day, and walking is faster than driving the narrow surrounding streets anyway. Rent a car only for countryside day trips, picking it up the morning you leave Siena and returning it when you come back. You'll save 60-100 euros and considerable frustration.
Booking Duomo tickets for early morning then finding it closed - the cathedral complex opens at 10:30am most days, later than many visitors expect. People book 9am tickets and show up to locked doors. Check current 2026 hours when booking, and remember that religious services can occasionally close sections without much notice.

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June

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Weather and seasonal patterns for Siena

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