Hotel 1: Borgo Egnazia (Nights 1–5)

Borgo Egnazia (Savelletri, Itria Valley) is the gold-standard property in southern Italy. A purpose-built village across 250+ acres of olive groves, constructed entirely from local honey-colored stone, it functions as a true resort with multiple pools, a private beach club, the Vair spa (one of the best in Europe), Michelin-starred dining, and a service culture that’s almost unsettlingly attentive.

Past guests include the Beckhams, Madonna, Justin Timberlake, and Jessica Biel (her wedding was here). It’s where to go for the grand, full-resort experience and for exploring the Itria Valley, Polignano a Mare, and Monopoli.

Hotel 2: Masseria Trapanà (Nights 6–9)

Masseria Trapanà, just outside Lecce, is widely considered the most romantic hotel in Puglia. A meticulously restored 16th-century fortified farmhouse, it was transformed into a 12-suite boutique property by Australian creative Rob Potter-Sanders, who lived in the masseria during the renovation and curated every detail himself. The result is a hotel that feels less like a resort and more like staying at the gorgeous country estate of an impossibly stylish friend.

The grounds are arguably the most beautiful in southern Italy — citrus orchards, century-old olive trees, lavender, prickly pear, an Italian-tiled swimming pool, and quiet stone courtyards. The interiors blend antique Italian pieces with contemporary art, and the food program — built around the estate’s own gardens and small Salento producers — is exceptional. Service is intimate, warm, and deeply personal, the kind where the team remembers your morning coffee order by day two.

Most flights into Puglia route through Rome or Milan and land at Brindisi airport, which is small, easy, and only about 45 minutes from Borgo Egnazia. The most luxurious arrival is a helicopter transfer arranged through the hotel — it cuts the trip to about 15 minutes and gives a stunning aerial view of the olive groves and the Adriatic.

By car or helicopter, guests arrive at a property that looks less like a hotel and more like a real Puglian village built from the same honey-colored stone as the surrounding countryside.

Don’t try to sightsee on arrival day. Check in, get oriented, and let the staff walk you through the property. Spend the afternoon by La Piscina (the main pool), have an early aperitivo on the terrace as the sun sets behind the olive trees, and book a casual dinner at Trattoria Mia Cucina, Borgo’s most relaxed restaurant. Bed early.

Italians call it il dolce far niente — the sweetness of doing nothing — and Borgo Egnazia is purpose-built for it. Spend the morning at the Vair spa, which is rated one of the best in Europe. The signature ritual is called Pasolibero, a slow, sensory journey through warm pools, herbal steam, and a long massage. Book it at least a few days ahead.

Light lunch at La Frasca, the casual outdoor restaurant tucked into the olive grove. Afternoon by the pool with a book.

Around 5pm, drive 20 minutes inland to Ostuni, known as la città bianca — the white city — because every building in the old town is whitewashed in lime, making it glow at sunset. Wander the maze of alleys, climb up to the cathedral at the top, and have aperitivo at Cielo, the rooftop bar at La Sommità hotel, where you can see the white rooftops cascade down toward the Adriatic. Stay for dinner at Osteria del Tempo Perso, a beloved cave restaurant carved into the rock — book ahead, it fills up.

This is the day to see what makes inland Puglia so unique. Leave the hotel by 8:30am to drive 45 minutes to Alberobello, a UNESCO World Heritage town entirely built from trulli — small conical stone houses with peaked roofs that look straight out of a storybook. Get there early because by 11am the tour buses arrive. An hour wandering the Rione Monti district is plenty.

From Alberobello, drive 15 minutes to Locorotondo, a perfectly circular hilltop town with quiet streets and panoramic views over the Valle d’Itria — much less touristed, very photogenic, perfect for a cappuccino.

Midday, the hotel will arrange a private truffle hunt in the oak forests near Cisternino. A local hunter and his trained dog take you walking through the woods to find fresh truffles, then you sit down at the farmhouse for a long, multi-course truffle lunch — handmade pasta with shaved truffle, truffle frittata, local cheeses, wine. One of the most memorable experiences in the region.

Back to Borgo Egnazia for the afternoon. Dinner tonight at Due Camini, the hotel’s Michelin-starred restaurant — a refined tasting menu showcasing modern Pugliese cuisine. Dress up a little.

The day everyone remembers. Through the hotel, charter a private gozzo (traditional wooden boat) or a Riva-style yacht for a captained day on the water. The standard route heads up the coast to Polignano a Mare, one of the most dramatic towns in southern Italy — built directly on cliffs over a tiny cove, with sea caves carved underneath the old town.

Guests swim into the grottos (including Grotta Palazzese, the famous cave that houses a restaurant on a cliff above it), anchor in turquoise coves like Cala Paura, and either eat lunch onboard from a curated picnic or pull into a beach club for a long seafood meal. Expect 8 to 10 hours total, with prosecco, espresso, fresh fruit, and music playing softly the whole time.

End the day on land in Polignano a Mare itself — walk the cliff-top old town as the sun sets, peer down at Lama Monachile, the famous tiny beach tucked between two cliffs, and have a final aperitivo at Il Bastione looking out over the sea. Drive back to Borgo for a late, casual dinner or eat in your room.

A purposefully slow day after the boat — and the last full day at Borgo. Spend the morning and early afternoon at La Cala, Borgo Egnazia’s private beach club. A complimentary shuttle runs from the hotel down to the coast, and once you’re there you book a daybed, swim in the Adriatic, and eat a long, unhurried lunch right on the water — grilled fish, crudi (Italian sashimi-style raw fish), and chilled white wine.

Late afternoon, drive 15 minutes north to Monopoli, the more authentic and less touristy coastal town. It’s still a working fishing port, with brightly painted boats in the harbor, a beautiful cathedral, and a tangle of medieval streets. Walk through the old town, stop in a few independent shops, and have dinner at Osteria Perricci — family-run, white tablecloths, exceptional crudo and pasta

A leisurely morning at Borgo — final breakfast, one last walk through the olive groves, maybe a quick spa visit. Check out late morning and drive about 90 minutes south to Lecce, the most architecturally stunning city in the region. It’s known for barocco leccese — a wildly ornate baroque style carved from a soft, golden local limestone that glows in the sunlight. The whole centro storico looks like wedding-cake architecture.

Park in the centro and spend the afternoon walking Piazza del Duomo, one of the most beautiful enclosed squares in Italy, then through to the Basilica di Santa Croce, the masterpiece of Lecce baroque, and the partially excavated Roman amphitheater in Piazza Sant’Oronzo. Lunch at Alex Ristorante, a long-standing favorite for refined Salento classics. Before leaving, buy a pasticciotto from Pasticceria Natale — the iconic warm custard pastry of Lecce.

After a leisurely afternoon in Lecce, drive 15 minutes out to Masseria Trapanà. Check in slowly — there’s no rush. Wander the citrus orchard, swim in the Italian-tiled pool before sunset, and have a quiet first dinner on the masseria terrace, where the kitchen serves estate-grown produce and Salento wines by candlelight.

Drive about 45 minutes east to Otranto, a historic walled town with one of the most extraordinary cathedrals in Italy. The Otranto Cathedral has a 12th-century mosaic floor that runs the entire length of the church — a massive Tree of Life made of millions of tiny stones. The town also has a Norman castle and a charming harbor.

Wander the old town, stop at Caffè L’Approdo by the harbor for gelato, and have lunch at Peccato di Vino for an upscale Salento seafood meal.

Spend the afternoon swimming at Baia dei Turchi or Porto Badisco — both have impossibly clear water and a wild, undeveloped feel. Drive back to Masseria Trapanà for sunset cocktails by the pool. Dinner at Bros’ in Lecce if guests want the most-talked-about Michelin meal in Puglia (book months ahead — polarizing but a real experience), or stay closer to home for a relaxed seafood dinner at La Locanda in Castro.

Drive about an hour south to Pescoluse, the long stretch of white-sand beach nicknamed the Maldives of Salento, with shallow turquoise water that feels more Caribbean than European. Book a daybed at one of the upscale lidos — Lido Maldive del Salento or Samana Beach — and have a long, unhurried lunch on the sand.

Late afternoon, drive 30 minutes north to Gallipoli. The old town sits on a tiny island connected to the mainland by a bridge, and its position on the Ionian Sea makes for one of the most spectacular sunsets in Italy. Walk the cobblestone streets, peek into the baroque Cathedral of Sant’Agata, and watch the sun drop into the sea from the western walls.

Dinner at La Puritate, a famous family-run restaurant on the old town walls — the place to try gambero rosso (the raw red prawns Puglia is known for) and perfectly grilled fish.

A relaxed final full day. Morning visit to a Primitivo or Negroamaro wine estate — Tenute Rubino, Cantine Menhir, or Masseria Li Veli are the standouts. Primitivo is the bold red grape Puglia is famous for (genetically the same as California Zinfandel, though Italians will tell you their version is better). A tasting and tour at a working estate is a beautiful way to spend a morning, typically followed by a long lunch among the vineyards.

Afternoon back at Masseria Trapanà — a final swim, a last walk through the citrus orchard, time on the terrace. Final dinner somewhere memorable: Bros’ in Lecce if not done earlier, or — what most guests choose — a romantic farewell dinner at the masseria itself, candlelit on the terrace with estate produce and Salento wines.

A leisurely breakfast at the masseria, one last espresso under the olive trees, and a transfer to Brindisi airport (about 45 minutes from Trapanà). If there’s an afternoon flight, stop in Lecce one more time for a final pasticciotto and an espresso before heading home.

Best windows: late May through mid-June, or September into early October.

July and August are gorgeous but hot and crowded with Italian vacationers. May has perfect weather and quieter beaches. September has warm sea temperatures and harvest energy.

Fly into: Brindisi (BDS) is best for this itinerary — central for both Borgo Egnazia and the Salento. Bari (BRI) is a backup if flights are limited.

On the ground: Rent a car or hire a driver for the duration. A car is essential for hill-town day trips; a private driver is the more elevated option if guests prefer not to navigate. Both hotels can arrange transfers between properties on Day 6.