Things to Do in Siena in May

May Weather in Siena

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Is May Right for You?

Advantages

Perfect weather for walking the city - comfortable 20-22°C (68-72°F) during prime sightseeing hours (9am-6pm) without summer's scorching heat
Peak wildflower season in Tuscany countryside - poppies and sunflowers bloom, making Val d'Orcia drives spectacular for photography
Shoulder season pricing - accommodations cost 30-40% less than June-August peak season, with better availability in historic center hotels
Palio preparation season - witness horse trials and flag-throwing practice sessions in Piazza del Campo without the July crowds and chaos

Considerations

Unpredictable spring weather - pack layers as temperatures can swing from 12°C (54°F) at dawn to 26°C (79°F) by afternoon
Occasional afternoon thunderstorms disrupt outdoor plans - brief but intense downpours happen 2-3 times per week
Restaurant terraces and outdoor dining may close unexpectedly due to weather - many establishments don't fully open outdoor seating until June

Best Activities in May

Val d'Orcia Countryside Photography Tours

May is peak wildflower season when rolling hills explode with red poppies and early sunflowers. Morning light (7-9am) is crystal clear after overnight cooling, perfect for landscape photography. Temperatures are comfortable for 3-4 hour countryside walks without summer's oppressive heat.

Booking Tip: Book 2-3 weeks ahead as this is prime season for countryside tours. Expect to pay €80-120 per person for half-day guided experiences. Look for operators offering weather guarantees and indoor alternatives. Check current tour availability in the booking section below.

Siena Cathedral Complex Climbing Tours

Cool May mornings (15-18°C/59-64°F) make climbing the 400 steps of Torre del Mangia comfortable - summer heat makes this grueling. Clear spring air offers exceptional views across Tuscany's hills. Smaller crowds mean better photo opportunities and less waiting.

Booking Tip: Reserve cathedral passes online 7-14 days ahead for €15-25. Morning slots (9-11am) offer best weather and lighting. Timed entries limit crowds compared to peak summer chaos. See current availability in the booking widget below.

Chianti Wine Estate Cycling

Perfect cycling weather with mild temperatures and firm, dry roads after winter rains. Vineyards show fresh spring growth, and many estates begin outdoor tastings in May. Cool mornings (16-20°C/61-68°F) are ideal for 20-30km (12-19 mile) rides between villages.

Booking Tip: Book bike rentals 1 week ahead for €25-35/day. E-bikes recommended for Chianti's hills. Many wine estates require advance booking for tastings - expect €15-30 per person. Check current cycling tour options in the booking section below.

Medieval Walking Food Tours

May marks the arrival of fresh spring ingredients - wild asparagus, artichokes, and new olive oil. Comfortable walking weather allows 3-4 hour food tours through Siena's contrade neighborhoods. Cool evenings (18-22°C/64-72°F) are perfect for leisurely tastings.

Booking Tip: Evening tours (5-8pm) offer best weather and atmosphere. Book 5-7 days ahead for €65-95 per person including 5-6 tastings. Look for tours focusing on seasonal spring specialties. Current food tour options available through the booking widget below.

San Gimignano Day Trips

May offers clear visibility across Tuscan valleys - perfect for photographing San Gimignano's famous towers from viewpoints. Comfortable temperatures for walking cobblestone streets and climbing medieval towers without summer's crowds and heat.

Booking Tip: Half-day trips typically cost €45-70 from Siena including transport. Book 10-14 days ahead as May is popular for countryside excursions. Morning departures (8:30-9am) return by early afternoon, avoiding potential late-day storms. See current day trip options in the booking section below.

Palio Horse Trial Viewing

May features preparatory horse trials and contrada celebrations leading to July's famous race. Witness authentic local culture without tourist crowds - practice sessions happen 2-3 times weekly in Piazza del Campo with free viewing.

Booking Tip: No advance booking needed for practice sessions, but arrive 30-45 minutes early for good viewing spots. Evening trials (6-8pm) offer best lighting and atmosphere. Local bars around the campo offer elevated viewing for €10-15. Current Palio-related experiences available through booking widget below.

May Events & Festivals

Throughout May

Maggio Musicale Senese

Month-long classical music festival featuring performances in historic venues including Santa Maria della Scala and Teatro dei Rozzi. Mix of international artists and local ensembles performing Renaissance and contemporary works.

Mid May

Sagra delle Fragole

Strawberry festival in nearby Malva celebrating Tuscan spring harvest. Local vendors offer strawberry-based dishes, wines, and traditional crafts. Authentic local experience with minimal tourist presence.

Essential Tips

What to Pack

Lightweight layering system - temperatures swing 10-12°C (18-22°F) between morning and afternoon, requiring easy add/remove pieces

Waterproof walking shoes with good grip - medieval streets become slippery when wet, and afternoon showers are common

Compact umbrella - brief but intense thunderstorms happen 2-3 times weekly, lasting 20-30 minutes

Light rain jacket or packable windbreaker - essential for countryside excursions where weather changes quickly

SPF 30+ sunscreen - UV index reaches 6, and Tuscan sun is stronger than expected at 300m (984ft) elevation

Warm layer for evenings - temperatures drop to 15°C (59°F) after sunset, making outdoor dining chilly

Comfortable walking socks - cobblestone streets and hills require proper foot protection for 8-10km (5-6 miles) daily walking

Power bank - cool weather drains phone batteries faster, essential for navigation and photography

Breathable cotton or merino wool clothing - avoid synthetic fabrics that trap moisture in 65% humidity

Small day pack - essential for carrying layers, water, and weather protection during countryside excursions

Insider Knowledge

Locals eat lunch between 1-3pm and dinner after 8pm - restaurants opening earlier cater to tourists with lower quality and higher prices

Book accommodations in Terzo di Città or Terzo di San Martino for authentic neighborhood experiences - avoid the overly touristy area immediately around Il Campo

May is truffle season transition - white truffles end but spring vegetables like wild asparagus and artichokes peak, offering better value than expensive truffle dishes

Wednesday and Saturday mornings feature the weekly market at La Lizza - locals shop here for seasonal produce and authentic prices, arriving by 8:30am for best selection