Salento Beach Life: Ostuni, Alberobello's Trulli & Beaches of Italy's Heel




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Itinerary
Puglia is a state of mind! On this road trip we discover the wonders of Italy’s heel, from Brindisi to Ostuni and Gallipoli: a full immersion in incredible flavors, spectacular landscapes, crystal-clear waters and dream beaches. Sometimes you don't need to travel to the other side of the world to be left speechless.
We 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. We hang out on some of the region's most beautiful beaches, cliffs or sandy shores, sunsets and aperitifs included. And of course the various culinary specialties of Puglia, famous for its variety and delicious food, plus the locals, whose genuine warmth and unique hospitality make us feel right at home. Flavors and scents we won't forget easily… Ready to go dancing in Puglia?


Welcome to Puglia!
Meeting in Brindisi
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 get going right away.
Picking up the cars: we head straight to the car rental to pick up our rides.
Off to Ostuni: then we set off for Ostuni: we're finally in Puglia!
First aperitivo: first things first, an Italian "aperitivo" together to toast to our first sunset in Puglia and dive into some of the local culinary delights.

The Castellana Caves and Monopoli
100 million years underground
After our first breakfast in Puglia, we hop in our cars to visit an enchanted place that's over 100 million years old: the Castellana Caves, a unique underground karst complex.
Through the caves: winding through corridors and tunnels, you reach 122 meters below the surface, and the caves stretch for over 3km.
At la Grave: the natural entrance is a massive 60-meter deep sinkhole called "la Grave".
An immersive visit to enjoy with the awareness of an adult and the 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, a city that radiates good vibes. If you're a beach lover, you can take your pick:
Cala Paradiso: lovely, with its two small sandy spots and sports facilities.
Purple Beach: stylish and flashy.
Porto Ghiacciolo: enchanting (and admittedly popular), and the food is a total win.
Craving proper sand? If so, it's Lido Le Macchie or Lido Bellifreschi.
Monopoli's old town
The city center is just as impressive, and you can't miss the cathedral.
Inside the cathedral: the Chiesa della Madonna della Madia is massive and majestic, and the interior will blow you away.
The icon above the altar: look out for the Madonna della Madia: legend has it, it arrived by sea on a raft, and the wood from that raft was used to build the roof.

The Itria Valley: Locorotondo and Alberobello
The round place and the trulli
Today we explore the bucolic Valle d'Itria, between historic centers and trulli.
Around Locorotondo: Locorotondo literally means round place, thanks to the walls that have encircled the town since its origins: its historic center is a gem you can explore in a couple of hours.
Among the trulli of Alberobello: next stop, Alberobello, where we can see around a thousand trulli, protected as a national monument since 1930 and recently added to the UNESCO World Heritage list. The trullo, a timeless rural construction, has always been one of the most typical expressions of Puglia's farming soul.
A dip in Savelletri: in the afternoon we head to the Savelletri area for a refreshing dip, then it's back to Ostuni.
Dinner at a masseria: we don't want to be late, tonight there's a traditional dinner at a masseria waiting for us!

Porto Cesareo: a day fully dedicated to the sea
Salento: the sun, the sea, the wind.
Along the Ionian coast of Puglia, less than 30 kilometers from Lecce, Porto Cesareo is a must on any Salento bucket list. The town has ancient roots, and you can spot traces of its past in the historic center.
Sun, sea and wind: along its coastline are some of the most stunning beaches in all of Salento, and today's plan is crystal clear!
On to Gallipoli: in the evening we head to our new home for the next few days, Gallipoli!

Boat trip in Santa Maria di Leuca
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 together how to carry on:
By boat to Santa Maria di Leuca: the boat trip starts our day.
Trek to the Grotta della Poesia? We soak in the crystal-clear water of one of Salento's most iconic spots.
Too hot for a trek? If the heat feels too intense, we head to the Torre San Giovanni area to enjoy its wonderful sea instead.
We're back in Gallipoli by the evening, more than ready for bed after such an action-packed day!

Gallipoli and its beaches
Relax and more sea
The last two days of the trip are dedicated to sea and relaxation: we wake up fresh, rested and ready to dive into the crystal-clear waters of the Ionian coast! We stay around Gallipoli, so we can pick the beaches that call to us most:
Punta della Suina: just a few kilometres from the centre, golden sand and turquoise water that'll leave us breathless.
After a calmer vibe? If so, we can head to Lido Conchiglie.
Rivabella beach: and we can't forget Rivabella beach... officially spoilt for choice!
Farewell feast: we wrap up this final day together with a feast of the best Puglian dishes, the perfect way to end our adventure.
Goodbye Puglia
Back to Brindisi and cheers
Early start today: from Gallipoli we head back to Brindisi, where it all began and where we say our goodbyes.
What we take home: a trip packed with amazing food, nature, relaxation and parties... not to mention new friendships! See you on the next WeRoad!
What's included
7 nights in a shared room with a private bathroom for participants' exclusive use
Car rental from Day 1 to Day 8
A relaxing boat trip to soak up the sea of Santa Maria di Leuca
Dinner at a traditional Salento masseria
Group Leader's assistance
Medical and baggage insurance - (coverage limits by destination country/region - €10,000 Italy, €20,000 Europe, €30,000 World, €50,000 USA/Canada)
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
- Accommodation
Hotels, typical accommodation, and apartments.
- Transport
Rental cars.
- Info on private roomsShow all details
Reviews
based on 109 verified reviews
Rating breakdown
- 5 stars48%
- 4 stars32%
- 3 stars14%
- 2 stars5%
- 1 star2%
TommyFirst WeRoad
5August 2026
My first trip with WeRoad was fantastic. It was much more than I expected. The group, the people, the shared adventure with strangers who then became friends. I'm coming home with much more than I left with. Thanks WeRoad (and thanks to our Travel Coordinator Benni❤️)
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Giuseppe3 WeRoad trips done
5August 2026
The close-knit group, the beaches of Salento that looked like the Maldives, the activity of kneading orecchiette...
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Francesco4 WeRoad trips done
5August 2026
The group was truly exceptional. The Travel Coordinator was also veeery, very nice and versatile in planning even off-schedule activities.
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LorenzoFirst WeRoad
5August 2026
It was a fantastic experience. An unforgettable holiday with a fantastic group of people, I think one of the most fun of my life. In my opinion, the programme was well balanced, between days of absolute relaxation at the beach and days for sightseeing. There was a lot of flexibility from the Travel Coordinator who actively involved us in the organisation. This allowed us to manage our time better and make small changes to the programme by mutual agreement, allowing us to experience some places even more deeply without rushing.
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AlessiaFirst WeRoad
5August 2026
It's an experience I recommend, because it allows you to meet new people and have a lot of fun!
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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
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