After landing in Rome, allow at least 90 minutes for baggage collection and getting to Roma Termini. Take a late-morning Frecciarossa or Italo to Bari Centrale—normally around 4 hours—then change to a Trenitalia regional train for Monopoli, which takes roughly 35–50 minutes. Check the connection on the day, as September schedules can vary. Buy food and water at Termini or Bari, and keep luggage close during the connection; the regional train does not usually require a reservation. From Monopoli station, the old town is about a 20-minute walk, but with bags it is much easier to take a taxi, especially after a long travel day. Expect roughly €5–10 for the short ride, depending on luggage and time.
Once settled, make Piazza Giuseppe Garibaldi your first stop for an easy orientation to the historic center. Choose a table for an arrival Aperol and take your time watching local life gather around the square—this is exactly the kind of place where a “quick drink” becomes an hour. From there, wander through the whitewashed lanes to Cattedrale Maria Santissima della Madia, one of the town’s key landmarks. Allow about 45 minutes, checking the posted opening times because churches may close briefly in the afternoon or during services. The surrounding streets are best explored slowly rather than mapped too tightly; wear comfortable shoes, as the limestone paving can be uneven.
Reserve ahead for Osteria Perricci, particularly for a Saturday night. It is a good first taste of traditional Puglian cooking, with seafood, handmade pasta and simple local dishes; budget approximately €30–45 per person before drinks. Ask what has arrived fresh that day rather than trying to order too ambitiously. After dinner, walk down to Lungomare Santa Maria for a relaxed 45-minute stroll beside the old harbor. The best light is usually shortly after sunset, and the waterfront is ideal for a final aperitivo or gelato if everyone still has energy. Keep the evening gentle: the following days involve early trains and plenty of walking.
Start in the old port at Castello Carlo V, ideally around 9:00, before the waterfront becomes busy. The 16th-century fortress is compact and usually takes about an hour; opening hours can vary with exhibitions, so check locally or with the tourist office. From the castle, walk through the lanes of Monopoli toward Cala Porta Vecchia, the town’s most convenient swimming spot. Bring reef shoes, a towel and water—the beach is small, fills quickly, and there are limited natural shaded areas. Allow around 90 minutes for a swim and relaxed sunbathing, then pick up a light snack or granita nearby rather than having a heavy lunch before the boat.
Walk back to the harbor for your pre-booked Monopoli sea caves boat tour. A small-group outing of two to three hours is the best format, with room to swim and a slower passage along the coast; confirm the exact meeting point, whether towels and masks are supplied, and the cancellation policy for rough seas. Tours commonly run late morning or early afternoon, so reserve this in advance and leave at least 20 minutes between the beach and departure. After returning, arrange a taxi or private transfer—roughly 20–30 minutes—to a Masseria tasting experience in the Monopoli–Fasano countryside. This is much easier than trying to reach the rural masserie by bus. Expect olive oil, local cheeses, bread, cured meats and seasonal produce, with wine often available as an add-on; budget approximately €30–€55 per person and allow 90 minutes. September is olive-harvest season, so ask for a short walk among the trees and a practical explanation of how to taste oil properly.
Return to Monopoli before sunset and leave time to wander the quieter lanes around the old town’s seafront. For your evening, settle into La Locanda Don Ferrante, a beautifully atmospheric historic setting suited to an aperitivo that can turn into dinner. Reserve ahead and request a terrace or courtyard table if available; allow around €35–€60 per person for dinner, more if you add several wine pairings. Keep the evening unhurried—this is a good night for an extra Aperol Spritz, a slow seafood-focused meal and a final walk along the harbor rather than another scheduled stop.
Take a Trenitalia regional train from Monopoli around 8:30–9:00 AM; the ride to Polignano a Mare is only 10–15 minutes. From the station, it is roughly a 15-minute walk into town. Begin at Lama Monachile, the famous cove framed by limestone cliffs. The beach is pebbly rather than sandy, so bring shoes with a good grip if you plan to go down to the water. After the viewpoint, spend an hour wandering the Centro Storico di Polignano a Mare, looking for the handwritten poetry on walls and the small terraces opening suddenly onto the Adriatic. Most cafés open by 8:00–9:00 AM; viewpoints are free, while swimming conditions depend on the sea and September weather.
Have a relaxed early lunch at Pescaria, ordering one of its overflowing seafood sandwiches—expect about €15–25 per person. It is popular, so go before the main lunch rush or be prepared to queue; takeaway is useful if you would rather eat near the waterfront. After lunch, walk back to Polignano a Mare station and take a regional train to Bari Centrale, allowing roughly 25–35 minutes including the wait. Trains are frequent, but check the live departure board and validate a paper ticket before boarding if it was bought at the station.
From Bari Centrale, walk for about 20 minutes toward Bari Vecchia, passing through the lively Murat district. Explore the Basilica di San Nicola, generally open during the day with free entry, though modest clothing is expected and services may restrict access. Then lose yourselves in the medieval lanes around Strada delle Orecchiette, where local women often make pasta by hand, before continuing to the seafront near Largo Giannella. Finish around Piazza Mercantile with an Aperol and dinner—La Uascezze is a fun choice for traditional Apulian plates, while In Vino Veritas suits a more wine-focused evening. Allow about €25–40 per person for dinner. Return to Bari Centrale with a 20-minute walk or short taxi ride, and check the final regional trains to Monopoli before settling in; late-evening services become less frequent.
Leave Monopoli around 8:30 AM. For four people, a private transfer is the simplest option: it takes roughly 30 minutes and can drop you close to the historic center, avoiding the awkward connection from Ostuni railway station uphill into town. If using public transport, allow considerably longer and arrange a taxi from the station. Begin at Ostuni Cathedral, whose rose window and richly decorated interior are worth an unhurried visit; opening hours can change around services, so check the notice at the entrance. From there, spend about 90 minutes wandering the Centro Storico di Ostuni—follow the whitewashed lanes toward the belvedere viewpoints, browse small ceramic and linen shops, and pause for a coffee whenever the steep streets demand it.
Book Osteria Del Tempo Perso well ahead, especially for a Tuesday, and request one of its atmospheric cave-like dining rooms. Expect around €30–45 per person before extensive wine, with Puglian dishes such as orecchiette, burrata, local vegetables and grilled meat; allow roughly 1½ hours. After lunch, meet your pre-arranged Vespa guide—most tours collect guests in Ostuni or at an agreed meeting point just outside the center. The 3–4-hour ride is the ideal way to see the Valle d’Itria without trying to drive yourselves between scattered lanes: you’ll pass ancient olive groves, dry-stone walls and quiet farm roads before stopping at a local winery for a tasting. Confirm in advance that the tour includes helmets, insurance and the required licence or driving documentation; late September is usually warm, but bring a light layer for the ride and closed shoes.
Return to Piazza della Libertà around sunset, when the stone buildings take on a golden color and locals gather for their evening passeggiata. Settle at an outdoor table for an Aperol spritz and a few shared snacks—this is a better place to linger than to plan another formal meal. The square is close to the historic-center taxi drop-off, so arrange your return transfer to Monopoli in advance if you are not staying overnight; otherwise, enjoy one last slow walk through the illuminated lanes before heading back.
Arrange a private transfer from Ostuni at about 9:00 AM, allowing roughly 1½ hours to Matera. Ask the driver to take you directly to your accommodation for a luggage drop, then continue toward the Murgia Materana viewpoint. Wear proper walking shoes and bring water: the paths around the belvedere are uneven, exposed, and sun-baked even in late September. Give yourselves about an hour here to take in the extraordinary view across the Gravina di Matera and the cave churches scattered across the opposite plateau; avoid wandering too far from the main viewpoint unless you have a guide.
After the belvedere, head back into the historic center for a guided walk through Sasso Caveoso and Sasso Barisano. A local guide is well worth arranging, as the stepped lanes and rock-cut homes make far more sense with the stories of Matera’s former cave-dwelling communities; allow about 2½ hours, with frequent stops for photographs and explanations. Keep the pace relaxed and expect plenty of stairs. Continue to Casa Noha in Sasso Caveoso for its concise multimedia presentation, usually around 45 minutes, which provides useful context before you spend your evening simply wandering. Tickets and opening hours can vary by season, so reserve or confirm the day’s last admission in advance; the visit generally costs around €8–€10.
Finish at Trattoria del Caveoso, where the setting is as memorable as the food. Reserve ahead for four, particularly if you want an outdoor table or an atmospheric room carved into the stone. Expect approximately €25–40 per person for a traditional meal; look for local specialties such as orecchiette, cavatelli, grilled meat, and dishes featuring Matera’s famous bread. After dinner, take an unhurried walk through the illuminated lanes of the Sassi—the city is at its most magical once the day-trippers have left. Carry a little cash, as smaller bars and cafés may still prefer it, and remember that the walk back to your accommodation can involve steep cobbles rather than a straightforward flat stroll.
Arrange your private transfer from Matera for around 8:30 AM, allowing 1½ hours on the SS99/SS172. Ask the driver to stop first in Locorotondo, while taking your luggage onward to your Alberobello accommodation or arranging storage there. Begin in the Centro Storico di Locorotondo, where whitewashed lanes curve around the hilltop rather than following a conventional grid. Allow about 90 minutes to wander, looking out across the Valle d’Itria from the belvedere and noticing the distinctive cummerse roofs. It is pleasantly quiet before late-morning tour groups arrive; comfortable shoes are essential on the polished stone streets.
Take a relaxed coffee, pastry, or light lunch at Caffè della Villa, beside Villa Comunale, budgeting approximately €8–18 per person. From Locorotondo, your pre-arranged winery transfer should take you into the surrounding countryside—do not rely on taxis for the return, as rural availability is limited. A tasting normally lasts 1½–2 hours and should include local whites such as Verdeca and Minutolo, often paired with taralli, cheeses, or cured meats. Confirm in advance that the winery accepts four guests on 1 October and ask whether transport between the tasting and Alberobello is included.
Continue to Alberobello, drop bags at your accommodation, and walk to Trullo Sovrano in the Rione Monti area. This two-level trullo gives a useful look inside the architecture, and a visit takes roughly 45 minutes; allow about €3–5 per person and check the day’s closing time before setting out, as seasonal hours can change. Afterwards, spend the unhurried part of the afternoon in Rione Monti, following the sloping lanes among hundreds of trulli. It is touristy, but the quieter side streets become much more atmospheric toward sunset. Finish with an Aperol at a terrace bar overlooking the rooftops—prices are usually €7–10—and make sure your accommodation has confirmed luggage storage or check-in before the evening gets busy.