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Puglia isn’t visited, it’s lived! Between crystal-clear seas, trulli, and white villages, every day is a mix of flavors and traditions. From Brindisi to Gallipoli, from Alberobello to Santa Maria di Leuca, get ready to dance with your heart in the heel of Italy.

Is this trip for me?

Party and nightlife
Relax
Nature and adventure
City and cultures
Monuments and history
Physical effort
Trip type
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Itinerary

Puglia is a state of mind! On this group trip, we’re heading out to discover the wonders of Italy’s heel, from Brindisi to Ostuni and Gallipoli! Get ready for a full immersion into a land packed with incredible flavors and spectacular landscapes, not to mention crystal-clear waters and dream beaches—as we always say, sometimes you don’t need to travel to the other side of the world to be left speechless.

After Brindisi, Ostuni, and Gallipoli, we’ll wander through villages perched above the sea, explore the trulli of Locorotondo and Alberobello, and visit charming spots like Santa Maria di Leuca and Monopoli. During our road trip, we’ll have plenty of time to hang out on some of the region’s most beautiful beaches—whether you prefer cliffs or sandy shores, we’ve got you covered, sunsets and aperitifs included. And of course, we’ll dive into the various culinary specialties of Puglia, a region famous for its variety and delicious food, and meet the locals, who with their genuine warmth and unique hospitality will make us feel right at home. The flavors and scents of this land are something you won’t forget easily… Ready to go dancing in Puglia?

A stylized map showing a travel itinerary with multiple stops, starting and ending in Brindisi, Italy.
A panoramic view of a whitewashed town on a green hill overlooking the sea under a clear blue sky.

Start your journey

Transfers to the destination aren't included in the package, so you're free to choose where you want to depart from, what time, and how you want to get there. We want to give you maximum freedom! You can reach Brindisi by plane and train or bus.

Find out more about the meeting point here! We’ll meet at the airport and head straight to the car rental to pick up our rides and set off for Ostuni: we’re finally in Puglia! First things first: we’ll grab an Italian "aperitivo" together to toast to our first sunset in Puglia and dive into some of the local culinary delights.

The interior of a large cave with numerous stalactites and stalagmites illuminated by warm, artificial lights.

The Castellana Caves

After our first breakfast in Puglia, we'll hop in our cars to visit an enchanted place that's over 100 million years old. Yes, 100 MILLION. We're talking about the Castellana Caves, a unique underground karst complex: just think, winding through corridors and tunnels, you'll reach 122 meters below the surface! The caves stretch for over 3km, and the natural entrance is a massive 60-meter deep sinkhole called "la Grave".

Visiting the Castellana Caves is an immersive experience that lets you appreciate them with the awareness of an adult, but also with the curiosity and wonder of a child: an absolute must-see during a trip to Puglia!

A dip in Monopoli

Still wide-eyed with wonder, we’re off to our second stop: Monopoli. This city just radiates good vibes—it’s the kind of place that instantly calms you down and recharges your soul. If you're a beach lover, Monopoli is going to spoil you for choice. You've got the lovely Cala Paradiso (with its two small sandy spots and sports facilities), the stylish and flashy Purple Beach, the enchanting (and admittedly popular) Porto Ghiacciolo—where the food is a total win—or, if you're craving proper sand, Lido Le Macchie or Lido Bellifreschi.

The city center is just as impressive. You can't miss the cathedral, the Chiesa della Madonna della Madia. It’s massive, majestic, and honestly, the interior will blow you away. Keep an eye out for the icon of the Madonna della Madia above the altar. Legend has it, it arrived by sea on a raft, and the wood from that very raft was used to build the cathedral's roof.

Map point

A vintage bicycle with baskets of purple flowers is parked on a stone alley between whitewashed houses with conical roofs under a blue sky.

Locorotondo and Alberobello

Locorotondo  is one of those unmissable spots: nestled in the bucolic Valle d'Itria, its name literally means round place, thanks to the walls that have encircled the town since its origins. Its historic center is an absolute gem and you can easily explore it in a couple of hours!

Next stop? Alberobello. We can't talk about this little town without mentioning the trulli: today, there are around a thousand of them, protected as a national monument since 1930 and recently added to the UNESCO World Heritage list. The image of the trullo—a timeless rural construction—has always been associated with Puglia as one of the most typical expressions of its farming soul.

In the afternoon, we'll head to the Savelletri area for a refreshing dip, then it's back to Ostuni: we've got a traditional dinner at a masseria waiting for us tonight, and we don't want to be late!

An aerial view of a long, curving coastline with a sandy beach, turquoise water, and lush green vegetation under a clear blue sky.

Salento: the sun, the sea, the wind.

Along the Ionian coast of Puglia, less than 30 kilometers from Lecce, Porto Cesareo is a must-see spot on your Salento bucket list. The town has ancient roots, and you can spot traces of its past just by wandering through the historic center. But that’s not all—along its coastline, you’ll find some of the most stunning beaches in all of Salento. Today’s plan is crystal clear: sun, sea, and wind!

In the evening, we’ll head to our new home for the next few days: Gallipoli!

A tall white lighthouse on a grassy cliffside overlooking the deep blue sea, with a dirt path in the foreground.

The southernmost point of Puglia!

Today is a jam-packed one: we've got a fantastic boat trip to Santa Maria di Leuca lined up! After that, we can decide whether to tackle a trek to the Grotta della Poesia—where we'll soak in the crystal-clear water of one of Salento's most iconic spots—or, if the heat starts to feel a bit too intense, we'll head over to the Torre San Giovanni area to enjoy its wonderful sea instead.

We'll be back in Gallipoli by the evening, and we're pretty sure we'll be more than ready to dive straight into bed after such an action-packed day.

An aerial top-down view of a rugged, light-colored rocky shoreline meeting a clear, turquoise sea.

Relax and more sea

The last two days of the trip are dedicated to sea and relaxation: we'll wake up fresh, rested, and ready to dive straight into the crystal-clear waters of the Ionian coast! We're staying around Gallipoli, so we can pick the beaches that call to us most: Punta della Suina, just a few kilometres from the centre, boasts golden sand and turquoise water that’ll leave us breathless. If we're after a calmer vibe, we can head to Lido Conchiglie. And we can't forget Rivabella beach... we are officially spoilt for choice!

We'll wrap up this final day together with a feast of the best Puglian dishes: the perfect way to end our adventure!

Check-out and cheers

Early start today, let's get moving: from Gallipoli we head back to Brindisi, where it all began and where we'll say our goodbyes!

Our adventure has come to an end, time to say goodbye: we've shared a trip packed with amazing food, nature, relaxation, and parties... not to mention new friendships! See you on the next WeRoad!

What's included

What's not included

Round-trip flights to the destination

  • Food and beverages when not specified
  • Petrol, and any parking fees and tolls

  • City tax - approx. USD 18

  • All the extras you'll be able to fit in your backpack :)
  • All that is not mentioned in "what's included"

Optional activities

Please see below extra optional activities that you can experience during your trip. Your Group Leader will be happy to assist with organizing these activities for the group. Availability may vary depending on location and group preferences.
Please note these activities are provided by third party suppliers and liability rests exclusively with these third party suppliers.

  • Castellana Caves - approx. USD26

  • Beach Clubs access - approx. USD47

Additional info

Learn more about accommodation, transport, and other useful travel information.
  • Accommodation

    Hotels, typical accommodation, and apartments.

  • Transport

    Rental cars.

  • Info on private roomsShow all details

Why WeRoad

  • Small groups, on average 11 people

  • Move or change your trip for free up to 31 days before departure

  • Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed

The Group Leaders

Our Group Leaders are chosen because they’re people just like you: passionate travelers who share the experience authentically, while having the skills to take care of the organisation, and help you get the most out of every moment of the trip.

Find your flight

For this trip, we recommend arriving and departing from these airports.

ArrivalBrindisi (BDS)
ReturnBrindisi (BDS)
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FAQs – Frequently Asked Questions

About this trip

About WeRoad

About Puglia