Three weeks at each villa gives you the rare luxury of becoming a temporary local — shopping at the same stalls, greeting the same baristas, and knowing which lane to take for the best evening light. This guide leans into that rhythm.
🌊 Part One · Ostuni, Puglia
🏛 Part Two · Pergine Valdarno / Arezzo
Part One
Ostuni, Puglia
May 11 – June 1 · Villa Saracena
Arriving before peak summer means May and June give you warm weather, open restaurants, the sea just reaching swimmable temperatures, and a town that still belongs to the people who live in it. The centro storico is entirely whitewashed and best explored on foot in the early morning or around the passeggiata hour (18:00–20:00). The countryside around the villa — ancient dry-stone walls, trulli-style structures, olive groves up to 1,000 years old — is made for slow exploration.
15–20 min drive
🏖 Nearby Beaches
Torre Guaceto
~12 km
A protected marine and nature reserve. Gorgeous clear water, walking trails through dunes and wetlands. One of the finest beaches in all of Puglia — strict protections keep it pristine.
Rosa Marina / Torre Canne
~15 km
Gentle sandy beaches in a pine-shaded resort village. Calm water, easygoing atmosphere, good for long lazy afternoons.
Costa Merlata
~18 km
Rocky coves north of Ostuni with crystal water. Less developed, more local feel — bring a snorkel.
Not Tourism — Living
✨ Local Experiences
Olive Oil Tasting
Masseria Il Frantoio, 10 min from the villa on SP 29. Working olive oil press, tastings, and dinner in the garden. Genuinely local, not staged. Reservations helpful.
Bio Solequo Coop
A historic vegetable garden restored to its original purpose. Open Thursday mornings — walk the garden and buy their seasonal organic produce directly. A quiet, beautiful ritual.
Saturday Market
Via Nino Sansone, 08:00–12:00. Clothes, housewares, fruits, vegetables, cheeses. Go early. This is where Ostuni actually shops.
Valle d'Itria Drive
Any afternoon — take the car south. The landscape of trulli, vineyards and whitewashed villages is unlike anywhere else in Europe. Stop whenever something catches your eye.
Pasta / Cooking Class
Several masserias near Ostuni offer half-day pasta-making experiences. Good rainy-morning activity and you eat what you make. Ask host Andrea for a local recommendation.
Multi-week rates available
🚲 E-Bike Rentals
For a 3-week stay, contact each shop directly — all are open to multi-week arrangements and will negotiate a flat rate. Delivery to the villa is available from most operators.
Cristal E-Bike
E-bikes and mountain bikes for Valle d'Itria and Salento. From €10/day — contact for 3-week flat rate. English spoken.
Wide range including e-bikes, mountain bikes, and children's bikes. Offers delivery directly to the villa. Contact for multi-week pricing.
martinobike.it
CCT Bike Rental
E-bikes, trekking and road bikes. Delivery to Ostuni €40. Explicitly offers discounted rates for rentals over 1 week — email for a 3-week quote. Book at least 3 days ahead.
cctbikerental.com
Apulia Bike Rental
Operates across Valle d'Itria including Ostuni. Good for renting multiple bikes at once (group of 8). "For rental requests of more than a week, contact us for a discounted quote."
apuliabikerental.com
Primitivo · Negroamaro · Ostuni DOC
🍷 Wine — Enoteca & Local Wineries
Puglia produces some of Italy's most characterful wines. Expect €5–12 for excellent everyday bottles. Two enotecas in town for daily bottles; two local wineries for buying direct from the producer.
Enoteca Vini di Puglia
Best dedicated wine shop near the villa. Excellent range of Pugliese labels — Primitivo, Negroamaro, Nero di Troia, passito — plus local olive oil, pasta, and taralli. Staff know their wines. Can arrange shipping. Closed during afternoon pausa.
Via Cav. di Vitt. Veneto 61 · near Famila supermarket
Le Bontà di Bacco
One of Ostuni's most established enotecas, right in the old town. Good selection of regional bottles including less-common local labels. Worth a visit on an Ostuni centro storico walk.
Corso Vittorio Emanuele II 230/D · Mon–Sat 8:00–13:00 & 16:00–20:00 · Sun 9:00–17:00
★ Amalberga Winery
Local winery making wines under the rare Ostuni DOC — white Bianchetto Gentile and red Ottavianello (Cinsault). Tasting room in an ancient trullo open every day 9:30–22:30. Natural wine ethos, very local.
Family winery in the Valle d'Itria hills between Fasano and Ostuni, growing Primitivo, Negroamaro, Verdeca, and Fiano Minutolo. Wines available direct at the cantina. Contact via website to arrange a visit.
Contrada Sant'Angelo, Fasano (BR) · tagaro.it
Burrata · Orecchiette · Fresh Fish · Olive Oil
🛒 Groceries & Fresh Produce
Famila Supermarket
The largest supermarket, a genuine local favourite. Good range of regional products, well-stocked deli and cheese counters.
Via Pietro de Laurentis (main Ostuni ring road)
Carrefour Market
Spacious, good fresh seafood counter and deli. Reliable for everyday needs.
Multiple locations including Piazza Italia
Saturday Mercato
Vegetables and fruit here will be fresher and cheaper than any supermarket. Make it a Saturday morning habit.
Via Nino Sansone · 08:00–12:00 weekly
Bottega Italiana
Local shop selling km0 (zero-kilometre) products — local olive oils, pastas, preserves, cheeses. Worth exploring for quality ingredients and gifts.
Bio Solequo Coop
Thursday mornings — organic seasonal vegetables direct from their garden. Exceptional quality.
Local Butcher / Macelleria
Ask host Andrea for the nearest macelleria. Local Puglian sausages and cuts are excellent and worth seeking out.
Where locals eat
☕ Cafés & Local Eateries
Ostuni has good restaurants but also its share of tourist-facing places. The following are where the town's own people eat and drink.
Osteria CasaCiaccia
One of those places that feels like a local secret. Home-style Puglian cooking: handmade pastas, fresh seasonal vegetables, no frills. The kind of table you return to every few days.
Osteria Monacelle
A dependable dinner choice, nestled in the old town. Classic regional dishes done consistently well. Locals eat here without fanfare — which is the best recommendation.
Osteria Cattedrale
Tiny — just six tables — run by a husband and wife duo. Set menus from ~€30 for three generous courses. Book ahead.
Il Gatto Rosso
Fills up with locals ordering their usuals, chatting to friends at the next table. Relaxed, local, honest. No website needed — just show up.
Ostuni Bistrot
On the piazza. Good value lunch spot popular with locals throughout the week. Friendly service and solid local cooking.
Trattoria Il Cortiletto — Speziale
A personal recommendation from Dave's Italian tutor's family — about as local as it gets. Authentic Puglian cooking driven by the season and the land: orecchiette, burnt wheat pasta, cicoria e fave, lamb in foil. Dine in the courtyard or, best of all, in the orange grove under the stars. About 20 minutes from Ostuni. Closed Monday and Sunday evenings. trattoriailcortiletto.it · +39 080 4810 758
☕ Morning Bar Ritual
Pick any bar in the old town that looks full of Italians at 08:00. Order a cornetto and cappuccino standing at the counter. This is the best €2 you will spend in Italy.
Part Two
Pergine Valdarno / Arezzo
June 1 – 22 · Villa, Pergine Valdarno
This is arguably the most unrushed, genuinely local part of Tuscany — the Valdarno and Valdichiana valleys sit between the big-name tourist circuits (Florence, Siena, Chianti) without being reached by the tour buses. Pergine Valdarno itself is a tiny medieval hilltop village — the villa, the pool, the views, and the quiet are the point. After a few days you will know the bar owner, the baker, and the woman who runs the fruit stall.
Not Tourism — Living
✨ Local Experiences
Piero della Francesca Frescoes
Basilica of San Francesco, Arezzo. The Legend of the True Cross cycle is stunning and undervisited. Book timed entry (€8) in advance — groups kept small. Allow an hour minimum. Among the greatest cycles of Renaissance painting in Italy.
Arezzo, 15 km from villa
Arezzo Antique Market
First weekend of every month, Piazza Grande. One of Italy's best antique markets spreads across the piazza and medieval streets. Arrive early, leave late — ideal for a full Saturday.
Pratomagno Ridge Drive
The Pratomagno mountain ridge runs along the eastern edge of the Valdarno. Take the road up through chestnut and beech forest for panoramic views over both valleys and the Apennines. Perfect for a morning drive or bike ride.
Loro Ciuffenna
A beautiful small town 10 km from Pergine, set above a rushing stream. Medieval mill still working. Small caffè, slow pace. The drive there through vineyards and olive groves is half the pleasure.
Walking the Village
Pergine Valdarno itself is worth exploring thoroughly. The church of San Michele Arcangelo has a frescoed barrel-vault ceiling; the castle ruins give views over the Valdarno. The locals are genuinely welcoming — buongiorno counts for a lot.
Cycling / E-Bike
Rent an e-bike in Montevarchi or San Giovanni Valdarno and take the riverside route along the Arno. Flat, scenic, and peaceful.
Multi-week rates available
🚲 E-Bike Rentals
The closest rental shop is just 10 km away in Loro Ciuffenna. Contact each shop in advance to arrange a 3-week flat rate — most offer delivery to your accommodation.
★ Energy E-Bike
Dedicated e-bike shop — sales, rentals, and guided tours. Also listed on the Valdarno Bike Road cycling network. The natural starting point for a 3-week arrangement; email or call in advance.
Via Giuseppe Saragat 9, Loro Ciuffenna · ~10 km from villa · +39 389 001 0667 · energyebike.it
On the Tuscan Bike
Rents classic mountain bikes and e-bikes for Tuscan countryside exploration. Based in the Valdarno. Contact for multi-week rates.
Via G. Dal Borro 14B, San Giustino Valdarno · onthetuscanbike.it
Veloce Bike Rental
Regional operator serving Arezzo, Loro Ciuffenna, Montevarchi and surrounding towns. Delivers and collects at your accommodation — will bring bikes to the villa. Advance booking discounts available.
rentalbikeitaly.com
Chianti Colli Aretini · Valdarno di Sopra DOC
🍷 Wine — Enoteca & Local Wineries
Remarkable find: Vini Guerrini is at Via Querceto 24 — literally next door to the villa at Via Querceto 26.
★ Vini Guerrini — Next Door
The villa is at Via Querceto 26 — this producer is literally next door. Makes wine, extra virgin olive oil, pecorino, and cured meats from their own land. Buy direct; online shop also available. An exceptional convenience — knock on the door for local Sangiovese and olive oil.
Via Querceto 24, Pergine Valdarno · viniguerrini.it
Cantine Terredagoli
Family winery in business since 1915, right in the same municipality. Makes Chianti DOCG, Chianti Riserva DOCG, and Chianti Classico Riserva DOCG. Wine shop inside the winery — buy direct. Call ahead to confirm a visit.
Beautiful estate in the Val d'Ambra (~15–20 min). Valdarno di Sopra DOC and Chianti DOCG. The Bossini-Gori family welcome visitors for tastings, cellar tours, and direct purchase. Book in advance for a sommelier-guided tasting with a charcuterie board.
Loc. Poggio Molina, Bucine (AR) · poggiomolina.it
Nettare di Vino
A proper bulk-wine enoteca (vini sfusi) — bring your own bottle or buy a container there. Excellent everyday Tuscan table wine at very low prices. Also carries labelled bottles, sparkling wine, and grappa. Perfect for stocking the villa on a market-day trip.
Via Roma, San Giovanni Valdarno · ~20 min from villa
Chianina beef · Pecorino · Porcini · Tuscan wine
🛒 Groceries & Fresh Produce
Pergine Valdarno Village
The village itself has a supermarket, butcher, bakery, and fruit & vegetable stall. For daily needs this is perfect — and shopping here keeps your money in the village.
Friday Market — Pergine
Every Friday morning. Fresh produce, cheese, local specialties, and crafts. Small but authentic. Make it a weekly ritual.
Mercato Coperto — Montevarchi
Covered market open Mon–Sat 08:30. Local produce, vegetables, Valdarno cheeses, typical cold cuts, and a wide selection of regional wines and extra-virgin olive oil. Excellent quality.
Via Trieste 30, Montevarchi (~8 km)
Slow Food Earth Market — Montevarchi
Artisan and small-producer market. Seasonal, curated — the kind of place where you discover a local honey or cheese you will try to import for years afterwards.
Saturday Market — Arezzo
Big weekly market in Arezzo city. Combine with an early morning visit and a coffee at Caffè dei Bastioni.
Saturday Market — San Giovanni Valdarno
Another big weekly market close by. Good for produce, clothing, and housewares.
Where locals eat
☕ Cafés & Local Eateries
Arezzo has a very local food culture — not Florence, not Chianti — and is all the better for it. Many are simply where people eat on a Tuesday.
Caffè dei Bastioni — Arezzo
Historic café dating to 1804 on the ancient city walls. Excellent cappuccino, cornetto, and atmosphere. This is where Arezzo has its morning. No website — just walk in.
Pasticceria Filli Bruschi — Arezzo
Family-run since 1937. Come for pastries, local cakes, and a coffee at the counter. A proper neighbourhood pasticceria.
Osteria dell'Acquolina — Arezzo
Owner Paolo Tizzanini's commitment to authentic Tuscan cuisine is total — nothing imported, everything regional. Ribollita, pappardelle al cinghiale, bistecca. Reserve for dinner.
Osteria del Borghicciolo — Arezzo
Rich soups, handmade pasta, Tuscan wines by the glass. Reliable local trattoria where you feel the rhythm of ordinary Arezzo life.
★ Castellucci — Montevarchi
Widely regarded as the best place in the Valdarno for bistecca alla Fiorentina — the great Tuscan T-bone from Chianina cattle. Go once for the full experience. Reserve ahead.
La Tua Piadina — Arezzo
A sandwich shop perpetually full of locals. Piadine (flatbread wraps) stuffed with local ingredients, fast and delicious. No tourists. Zero fuss. Excellent lunch.
☕ Bar in Pergine Village
The village caffè is your daily anchor. Walk in, learn the barista's name by day two, and let this become your morning.