Start with an easy wander through Bari Vecchia, where the point is less “seeing sights” and more letting the old town set the pace. The lanes are tight, chalky, and full of laundry lines, tiny shrines, and kids kicking balls out to the seafront edge. It’s especially nice around dusk, when the light softens over the limestone and the promenade near the old walls gets that breezy Adriatic feel. Give yourself about 90 minutes here to drift without a fixed route, then head into the heart of the old quarter on foot.
From there, continue to the Basilica di San Nicola, one of the city’s most important landmarks and still very much alive with pilgrims and local devotion. Inside, the atmosphere is calm and slightly dim, and the Romanesque stonework feels especially strong in the evening quiet. Entry is usually free, though modest donations are appreciated, and it’s worth dressing respectfully since this is an active place of worship. Afterward, make the short walk to Orecchiette Street (Strada Arco Basso), where the famous pasta ladies often sit outside their doors shaping fresh orecchiette by hand — it’s one of those very Bari moments that feels almost unchanged. If you want a small taste or to buy a bag to take away, expect a few euros for a portion, and come with cash.
Finish with dinner at La Cecchina, a dependable local stop in Bari Vecchia for Apulian seafood and pasta. This is a good place to slow down after the wandering: think orecchiette with vegetables, grilled fish, or a simple seafood starter, with a typical spend of about €25–40 per person depending on wine and extras. Since it’s a popular area for an evening stroll, it’s smart to book ahead or show up on the earlier side of dinner service, especially in May when the old town starts to fill up again after work.
Arrive on Capri with enough cushion to settle into the island’s rhythm, then head straight to Piazzetta di Capri — the little square everyone talks about, and for once the cliché is deserved. It’s the best place to get your bearings: cafés spilling onto the pavement, locals cutting through on their way to errands, and that constant sense that you’re in the middle of a very small, very glamorous island. Grab an espresso at Bar Tiberio or Gran Caffè Vuotto if you want to do it properly, then stroll the lanes for a few minutes before moving on. From the square, it’s an easy uphill walk to Giardini di Augusto, usually about 10 minutes, with the kind of views that make you stop every few steps anyway.
At Giardini di Augusto, give yourself time to linger along the terraced paths and look down over the Faraglioni and the curve of Via Krupp. The gardens are small but perfectly placed, and they’re typically open daily from around 9:00 AM to 7:30 PM in season, with a modest entrance fee of roughly €2–€3. Afterward, continue toward the Faraglioni Viewpoint in the Via Krupp / Marina Piccola area — this is the classic Capri photo stop, and it’s worth doing slowly rather than rushing through. If Via Krupp is open, the walk itself is unforgettable; if it’s closed, just follow the signed paths and viewpoints above Marina Piccola. The light is nicest here before noon, and the sea-stack view is one of those island moments that actually lives up to the postcard.
By midday, head to La Fontelina, tucked below the cliffs at Marina Piccola, for one of Capri’s most memorable lunches. This is very much a splurge stop — expect about €50–90 per person depending on what you order, and in high season you really should reserve ahead. The whole point is the setting: striped umbrellas, turquoise water, and those direct views back toward the Faraglioni while you linger over seafood, chilled wine, and maybe a plate of pasta with clams. If you’re walking, allow extra time getting down to the beach area; if you’d rather save your energy, a taxi or local boat transfer in season can be worth it. Don’t try to “do” too much here — this is the meal to stretch out and let the island slow you down.
After lunch, keep the pace loose and make your way to Marina Grande, Capri’s port and a good reset after the polished feel of the upper island. The harbor promenade is a different mood entirely: ferries arriving and leaving, little fishing boats, and a more everyday side of island life. It’s an easy 10–15 minute ride or a longer downhill walk depending on where you are starting from, and it’s a nice place for one last gelato, a quick espresso, or just to sit and watch the water before heading on. If you have energy left, wander the edge of the marina rather than trying to over-plan the rest of the day — Capri is best when you leave a little room for chance.