Siena in 2 Days for Couples - Sunset wine tasting on the Fortezza Medicea terrace
A slow-paced, intimate 48 hours in medieval Siena: candlelit dinners, golden-hour views, quiet gardens and hands‑on wine tasting. Designed for couples who want history, scenic moments and relaxed romance in spring.
Highlights
- Sunset wine tasting on the Fortezza Medicea terrace
- Climb Torre del Mangia at golden hour for sweeping city views
- Private moments in the Duomo and Santa Maria della Scala
- Cozy pastry breakfasts and candlelit Tuscan dinners
- Quiet garden strolls and boutique shopping on Banchi di Sopra
Itinerary
Day 1
Arrival morning, historic centre immersion, sunset wine tasting and intimate dinner.
Breakfast at Pasticceria Nannini
Start your day with traditional pastries, cappuccino and a quiet corner seat — a sweet, intimate morning ritual.
Tips from local experts:
- Ask for a table by the window to watch the morning light on Banchi di Sopra — perfect for a couples' photo.
- Try a 'biscotti di Siena' or ricciarelli with your cappuccino; share pieces to taste more specialties.
- Small shop — arrive by 09:00 to avoid the midday queue and secure a relaxed start.
Duomo di Siena & Piccolomini Library (Cattedrale di Santa Maria Assunta)
Explore Siena's masterpiece cathedral: inlaid marble floor panels, frescoes and the intimate Piccolomini Library's vivid colors.
Tips from local experts:
- Reserve tickets or arrive early — the cathedral and library are best enjoyed slowly and are less crowded mid-morning.
- For a romantic pause, stand near the marble inlay of the zodiac panels and take in the centuries-old craftsmanship together.
- The cathedral has steps and uneven floors; bring comfortable shoes and note limited accessibility to some areas.
Lunch at La Taverna di San Giuseppe
Cozy 13th-century dining room offering hearty Tuscan dishes — a warm, candlelit vibe even at midday.
Tips from local experts:
- Book a table in advance and request a quiet table for two in the cellar rooms for extra intimacy.
- Share a primi and a main plus a local Chianti to keep the meal leisurely and romantic.
- Ask the staff for their recommended dessert pairing — the house specialties pair beautifully with a small dessert wine.
Stroll: Banchi di Sopra and Fontebranda
Wander the elegant Banchi di Sopra shopping street and explore the ancient Fontebranda fountain — quiet corners perfect for lingering conversations.
Tips from local experts:
- Browse small artisan shops on Banchi di Sopra for a keepsake; look for local paper shops and leather makers.
- Stop at Fontebranda to rest on the stone edges — it's a secluded, historic spot to sit together and people-watch.
- May is mild: bring a light layer for shaded stone streets which stay cool even in spring sunshine.
Afternoon break in Parco della Lizza
A short, green respite near the city walls — ideal for a quiet sit-down on a bench or a shaded kiss under the pines.
Tips from local experts:
- Bring a small picnic blanket or sit on the benches facing the city walls for a private moment.
- The park paths are gentle — good if either partner prefers a lower‑impact stroll.
- Look out for local joggers and dogs; pick a quieter corner toward the edges for more privacy.
Special Moment — Wine tasting at Enoteca Italiana (Fortezza Medicea)
A curated tasting of Tuscan wines on the Fortezza's terrace: sunset light, panoramic views and an intimate tasting room.
Tips from local experts:
- Reserve the tasting in advance and request a terrace table for sunset views across the Val d'Arbia.
- Ask for a tasting focused on local Sangiovese/Chianti Classico wines and taste slowly — sip, share notes, and compare favorites.
- The fortress terrace can be breezy in May evenings; bring a light wrap for a cozy cuddle between pours.
Candlelit dinner at Osteria Le Logge
An elegant, intimate dinner in a softly lit dining room — refined Tuscan cuisine ideal for a romantic night.
Tips from local experts:
- Reserve a quiet table and mention it's a special evening; the staff often adds a small, personalized touch.
- Order a bottle to share — the sommelier can suggest a romantic pairing based on your earlier tasting.
- End the meal with a slow stroll back through the lit streets of the historic center for a perfect post‑dinner moment.
Day 2
Slow morning, museum visit, garden break, golden-hour tower climb and rooftop cocktails followed by a romantic farewell dinner.
Morning coffee & quiet hour at Piazza del Campo
Enjoy a calm morning in the shell-shaped heart of Siena — coffee on a bench, people-watching and planning the day together.
Tips from local experts:
- Find an early-morning bench near the Torre for expansive views before the piazza fills with visitors.
- Capture a photo from the west side steps for soft morning light and fewer crowds.
- Piazza stones can be uneven; if you want to sit, bring a light travel blanket or choose a café terrace seat.
Santa Maria della Scala (museum complex)
Explore this atmospheric former hospital turned museum: frescoed halls, intimate chapels and rooftop views over the cathedral.
Tips from local experts:
- Buy a combined ticket with the Duomo Complex if you didn't earlier — it's a quieter cultural gem for couples.
- Climb to the rooftop terraces for private skyline views — great for a soft, photo-friendly moment.
- Wear comfortable shoes: the complex is sprawling and best enjoyed unhurried; benches in galleries invite restful pauses together.
Lunch at Antica Osteria da Divo
Dine in atmospheric vaulted rooms carved from the rock — a dramatic setting that remains cosy for two.
Tips from local experts:
- Request one of the tucked-away vault tables for an intimate atmosphere and dramatic candlelit feeling even at lunch.
- Share antipasti and a primi to leave room for dessert and a leisurely coffee afterwards.
- The restaurant is popular; reserve ahead and mention your preference for a quieter table.
Orto Botanico dell'Università di Siena (Botanical Garden)
A calm one-hour walk through ordered Mediterranean plantings — small greenhouses, fragrant herbs and a secluded mood.
Tips from local experts:
- May is in bloom — sniff the herbs and find a secluded bench for a quiet, intimate moment.
- The garden paths are compact and easy to walk; perfect for a gentle post-lunch stroll.
- Bring a light jacket for shaded areas that stay cooler; the garden is a lovely spot for candid couple photos.
Leisurely shopping & window browsing on Via di Città
Browse artisan shops and small boutiques together — pick a meaningful souvenir or a shared gift.
Tips from local experts:
- Look for local paper-makers, small jewelry shops and leather artisans for unique, romantic keepsakes.
- Take breaks at little ateliers and ask shop owners about the crafts — conversations often lead to story-rich purchases.
- Carry a small tote for souvenirs so you can keep hands free for wandering and holding hands.
Special Moment — Climb Torre del Mangia for golden-hour views
Ascend the Torre del Mangia together for an unforgettable panorama of Siena and the surrounding hills at late afternoon.
Tips from local experts:
- Book tickets in advance for a late-afternoon slot to catch warming late-spring light across the rooftops.
- There are many steep steps and narrow passages — not ideal for those with limited mobility; hold hands and take your time.
- Bring a light wrap; the top can be breezy. Pause at the viewpoint to share the cityscape and a quiet toast (non-alcoholic if preferred).
Rooftop cocktail at Hotel Athena terrace
A relaxed rooftop drink to watch sunset colors deepen over Siena — intimate atmosphere and panoramic views.
Tips from local experts:
- Reserve a terrace seat and ask for a quieter corner; the terrace is popular at sunset in May.
- Order a locally inspired cocktail or a glass of Tuscan rosé to toast the view and the moment.
- If you prefer more privacy, request a seat away from the bar area — a small note when booking helps.
Farewell dinner at Antica Taverna di San Giuseppe or similar intimate restaurant
End your stay with a slow, romantic dinner in Siena's warm evening light — savour another chapter of Tuscan cuisine together.
Tips from local experts:
- Choose a quiet restaurant room or book a tasting menu to make the evening feel ceremonial and unhurried.
- Ask for a dessert to share and request the staff to pair it with a small local dessert wine for a sweet finish.
- Take a post-dinner moonlit walk back through the historic streets; the city takes on a remarkably intimate character at night.
Itinerary Attributes
| Days | 2 |
| Highlights | 5 |
| Season | - |
| Month | - |
| Persona | Couples |
| Transfers | - |
| Restaurants | 5 |
| Total Activities | 15 |
| Total Places | 15 |
| Activities Types | Meal, Culture, Restaurant, Neighborhood, Break, Experience, Outdoor, Shopping, Attraction, Nightlife |
