Italy

Off the Beaten Path in Italy

Trulli houses, sea caves and a wine estate in Puglia ; the Italy most first-timers never reach.

12 Nights / 13 DaysDuration
5Cities

Rome, Florence and Venice cover the north and centre of a first Italy trip, and Puglia rarely makes the cut ; it's a different flight, a different pace, and a region most travellers only hear about after their first trip is already booked. This one goes there directly: Bari, Alberobello, Polignano a Mare and Lecce, before Milan closes.

This is one of the Italy itineraries we've planned for a group of friends before ; 12 nights, 13 days through Puglia and on to Milan, built for 3 adults travelling together. It's shared here to show what an off-the-beaten-path route through Italy could look like. A version built around your own group's size, pace and dates would look a little different ; and that's the point.

Why This Trip

Why Go South to Puglia

Why Go South to Puglia

Alberobello's trulli ; the conical-roofed stone houses unique to this part of Italy ; and Matera's cave dwellings sit nowhere near a standard Rome-Florence-Venice route, which is exactly why they hold up as a genuine detour rather than a rebranded highlight.

The coastal towns do double duty here: Polignano a Mare's cave-boat tour and Otranto's sea stacks give the trip a beach-holiday texture that the north of Italy doesn't really offer.

If you asked us: the Negroamaro winery visit near Lecce, with its Gaudi-style hermitage on the grounds, is the stop most groups don't expect and remember longest ; better than another cathedral at this point in the trip.

Holiday Overview

Cities Covered
Bari, Alberobello, Polignano a Mare, Lecce, Milan
Starting Price
₹4,84,895

per adult, based on 3 adults travelling together, excluding international airfare

Best Time to Travel
June, for warm coastal swims before the peak summer crowds
Experiences Covered
Bari street food walking tour, Castel del Monte & Matera private tour, pizza & tiramisu cooking class, Alberobello trulli walking tour, Polignano a Mare cave boat tour, Negroamaro winery tour, Otranto sea cave boat tour, Lake Como & Bellagio

Tap a pin to preview each stop

Trace Your Path

An itinerary designed
for every moment.

Bari Day 1–2

An evening walking tour through the old town's street food scene, and a private day trip to Castel del Monte and Matera's Sassi district.

Alberobello Day 3–4

The town of conical-roofed trulli houses, with a private pizza and tiramisu class and a walking tour of the Rione Monti and Rione Aia Piccola districts.

Polignano a Mare Day 5–6

A boat tour along the rocky coast, visiting sea caves including Grotta Palazzese, with a swim stop and a Prosecco toast on board.

Lecce Day 7–8

A winery tour near Guagnano with a guided tasting of Negroamaro and Primitivo wines, paired with a traditional Apulian spread.

Milan Day 9–13

A private day trip to Lake Como taking in Bellagio and the lakeside villages, and a day trip to Serravalle, one of Italy's largest designer outlet villages.

Day By Day

Italy Trip Itinerary

  1. Day 1

    Bari Arrival ; Street Food Walking Tour

    Land in Bari and check in, then a guided evening walking tour through the old town's street food scene ; orecchiette pasta, focaccia baked in a 13th-century chapel oven, and gelato to close.

  2. Day 2

    Castel del Monte & Matera

    A private day trip to the octagonal, UNESCO-listed Castel del Monte, then on to Matera's Sassi district ; ancient rock-hewn homes and churches carved into the hillside.

  3. Day 3

    Alberobello Arrival

    A transfer to Alberobello, the town of conical-roofed trulli houses, with the evening free.

  4. Day 4

    Pizza & Tiramisu Class ; Trulli Walking Tour

    A private cooking class making pizza and tiramisu from scratch, followed by an evening walking tour through Alberobello's Rione Monti and Rione Aia Piccola trulli districts.

  5. Day 5

    Polignano a Mare Arrival

    A transfer to the clifftop town of Polignano a Mare, with the afternoon free.

  6. Day 6

    Polignano a Mare Cave Boat Tour

    A boat tour along the rocky coast, visiting sea caves including Grotta Palazzese, with a swim stop and a Prosecco toast on board.

  7. Day 7

    Lecce Arrival ; Winery Visit

    A transfer to Lecce, then a winery tour near Guagnano with a guided tasting of Negroamaro and Primitivo wines, paired with a traditional Apulian spread.

  8. Day 8

    Otranto Sea Caves Boat Tour

    A three-hour boat tour from Otranto past Baia dei Turchi and Grotta Sfondata, with swim stops in clear water.

  9. Day 9

    Flight to Milan

    A transfer to Brindisi Airport for the short flight north to Milan.

  10. Day 10

    Lake Como & Bellagio

    A private day trip to Lake Como, taking in Bellagio and the lakeside villages.

  11. Day 11

    Serravalle Outlet

    A day trip to Serravalle, one of Italy's largest designer outlet villages.

  12. Day 12

    Milan, at Leisure

    A free day in Milan at the group's own pace.

  13. Day 13

    Departure

    Transfer to Milan Airport for the flight home.

What's Included

Experiences Included.

Where You'll Stay

Hotel Stays.

Movenpick Hotel Bari and Grand Hotel Olimpo in Alberobello, followed by Cala Ponte, a Tribute Portfolio Hotel, in Polignano a Mare.

Grand Hotel di Lecce for the wine country stretch, and a four-night close at Unahotels Century Milano.

The Fine Print, Handled

What Travenza Holidays
Will Arrange.

Itinerary planning, hotel reservations, private transfers and tours, internal flight from Brindisi to Milan, travel support for the whole group.

Customised by group size and pace ; this is the deeper, southern alternative to a standard Italy route, for a group that wants to see past Rome, Florence and Venice.

Ready When You Are

Plan Your Off the Beaten Path Holiday to Italy

Trulli houses, sea caves, and a wine estate most first Italy trips never get near ; this route trades the standard north-and-centre loop for a slower run through the south.

This is one of the itineraries we've built for a group travelling together before, shared here to show what the trip could look like. A version built for your own group's size, pace and dates would look a little different.

Estimated from ₹4,84,895 per adult · All inclusive

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