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Originally from Toronto but now living in Italy, I’ve always been a traveler at heart. When I’m not planning your luxury European trip, you’ll find me hiking the Italian Alps or enjoying a lemon Spritz in Amalfi.


Italy Specialist

+1 844 879 7838


  • from $2,855 PP
  • 9 Nights
  • Private
  • Apr - Oct
  • Easy
  • 2hrs from London / 9hrs from NYC


While Puglia may be one of Italy’s lesser-known regions, it boasts many spectacular sights and one of the country’s best gastronomic scenes. On this nine-nights adventure you’ll explore everything from the famous cave city of Matera, the whitewashed hilltop town of Ostuni and the stunning baroque city of Lecce to the world-famous conical trulli buildings in Alberobello and beautiful Polignano a Mare with its spellbinding coastline and sea caves. Along the way, learn to make bread, experience wine and olive oil tastings, savour lots of mouthwatering Italian fare, and gaze up at magnificent architecture on fascinating private sightseeing tours.

Our Flexi - Promise

  • 10% deposit to book

    Book your trip with us and pay a reduced deposit with the rest 90 days before your departure

  • Full Flexibility

    If you are not comfortable travelling, you have the right to cancel and get a refund up to 45 days before your departure

  • ATOL & ABTOT Protected

    Your trip with us is fully financially protected by our travel insurers. Peace of mind guaranteed.

  • No Change Fees

    We will not charge you any admin fees if you would like to change your travel dates or destination with us

What's Included

Matera, Italy
  • 9 nights 4 or 5 star hotel accommodation, staying on a bed and breakfast basis.
  • Private airport departure and arrival transfers
  • All domestic transfers
  • Private walking tour of Matera
  • Breadmaking class
  • Puglia villages tour with wine tasting
  • Monopoli and Polignano day trip
  • Private guided walking tour of Lecce
  • Half-day tour of Otranto
  • Ostuni walking tour and Cisternino olive oil tasting
  • Private guided tour of Gallipoli
  • Expert trip planning advice
  • 24/7 support from our dedicated staff

Day by Day Itinerary

Day 1 Matera: Arrival into Bari, Italy

Matera, Italy

Welcome to Puglia! While it may not be on many tourists’ radar, that’s all the better as you’ll be able to explore the sights without having to worry about long lines and crowds. After landing at Bari Airport, you’ll be met by your private driver for transfer to Matera, one of the world’s most amazing cave cities. Set atop a ridge with deep canyons on either side, many people here live and work in caves that have been transformed into homes, hotels, restaurants, bars and more. After checking into your hotel, enjoy wandering through, stopping for dinner in one of the unique cave-style eateries.

Day 2 Matera: Private Guided Walk & Breadmaking Class

Matera, Italy

A private guided walking tour will bring you though the unique Sassi di Matera which originates from what’s believed to be one of Italy’s very first human settlements. You’ll be able to enter the Casa Grotta, one of the homes dug into the calcareous rock to see how the early settlers once lived along with one of the cave churches. Afterwards you’ll visit one of the most popular local bakeries to take a breadmaking class, learning the traditions and secrets to making bread here while kneading the dough. You’ll be able to savour the results and leave with your own bread too.

Day 3 Savelletri: Transfer from Matera via Alberobello


This morning your private driver/guide will meet you at your hotel for the transfer to Savelltri. Along the way you’ll make two very interesting stops, first the Castellana Caves, considered Puglia’s most impressive natural highlight with the network of caves featuring majestic stalagmites and stalactites. Afterwards you’ll visit Alberobello, one of the most unique towns with its Trulli structures, homes and other buildings with whitewashed walls, stone roofs and a conical shape. Enjoy a four-course lunch and wine tasting inside a Trulli home/restaurant before a walking tour to watch artisans at work in the workshops, and then continue to your final destination.

Day 4 Savelletri: Villages Tour and Wine Tasting

Locorotondo, Italy

Travel to Locorotondo, one of Italy’s most beautiful villages, with your private driver/guide. It’s known for both its beauty and wine production, with its historic center perched atop a hill, filled with narrow lanes lined with centuries-old buildings that range from magnificent structures with grand baroque archways to faded gems with lots of character. Enjoy exploring before heading to a winery nearby for a guided visit that includes a wine tasting and local light bites. You’ll stop in Cisternino too, a lovely village with whitewashed streets, with time to dine on your own before returning to Savelletri.

Day 5 Savelletri: Monopoli and Polignano Day Trip

Polignano Italy

Another exciting day awaits with a day trip on the agenda. Your private driver/guide will pick you up this morning, stopping in seaside Monopoli, a baroque town first settled in 500 BC. You’ll begin at the old port, strolling the historic ramparts and then enter through the main gate to see the castle of Charles V and enjoy a view of the town’s 15th-century cathedral and baroque bell tower. Continue to lovely Polignano, built atop cliffs that overlook the glistening blue of the Adriatic Sea. A leisurely stroll brings a panorama of gorgeous terraces, limestone houses and sea caves.

Day 6 Lecce: Private Guided Walking Tour

Lecce, Italy

Continuing to your next destination, your private driver/guide will bring you to Lecce, a beautiful city that’s like an open-air museum with its Baroque and Rococo monuments, impressive palaces and churches. A two-hour walking tour will bring you to its 2nd-century Roman amphitheatre that once held as many as 20,000 spectators, as well as the spectacular Santa Croce Basilica built over various periods between the 14th– and 17th-centuries. It boasts an elaborately decorated façade and large rose window. Nearby, marvel at the Government Palace, once used by Celestine monks as a convent and then enjoy time on your own to explore Piazza del Duomo.

Day 7 Lecce: Half-Day Otranto Tour

Otranto, Italy

Venture outside of Lecce for a half-day tour of Otranto with your private driver/guide. This historic seaside town boasts an outstanding mix of architecture, history, waterfront restaurants and white sandy beaches. Visit one of its highlights, the Otranto Cathedral, which dates back to 1088 featuring a synthesis of various architectural styles, including Byzantine, early Christian and Romanesque elements. Inside is the Chapel of the Day which holds 800 skulls that belonged to the city’s martyred citizens who were beheaded by Turkish pirates in the 15th-century for refusing to renounce Christianity. You’ll have another 90 minutes of free time to explore on your own.

Day 8 Lecce: Ostuni Walking Tour and Cisternino Olive Oil Tasting

Ostuni, Italy

Enjoy a visit to the whitewashed hilltop village of Ostuni which overlooks a landscape dotted with olive trees and the Adriatic Sea. Within the medieval walls are a maze of narrow streets where you’ll start your tour and enjoy the postcard-perfect photo-op. Following the walls to Piazza della Liberta in the historic center, you’ll see the Town Hall and column dedicated to Sant’ Oronzo. Marvel at the 15th-century Romanesque-Gothic Cathedral of Assunta and then continue your journey by driving towards Cisternino. Where you’ll learn how olive oil is produced, see a modern oil press and enjoy an olive oil tasting with bruschetta.

Day 9 Bari: Tour of Gallipoli

Bari, Italy

Your private driver/guide will bring you to Bali, stopping to tour Gallipoli along the way. Meet a local guide for a private tour to stroll the winding streets in the Old Town that’s connected to the modern part of the city by a 16th-century bridge. There are many historic buildings and gorgeous churches waiting to be discovered, and you’ll get a great view of the 13th-century Byzantine castle along with the 14th-century fortifications. Stop at the mysterious “Greek” Fountain, a relic that’s age continues to be debated – some say it’s from the 3rd-century BC, while experts believe it dates to the 16th-century.

Day 10 Departure

Bari, Italy

After enjoying breakfast in Bari, your ‘Pearls of Italy’ tour comes to an end. While it’s always hard to say goodbye, you’ll have plenty of memories, and probably lots of photos, of this unforgettable region of the world. After checking out of your hotel, private transfer will bring you to Bari’s airport for your return flight home, or to continue your travels elsewhere.

What's not Included

  • As we have clients from all over the world. Our itineraries do not include flights. If you would like us to include flights in your trip, we are happy to do so. Please speak to your travel specialist at the planning stage to include them.
  • Gratuities for local guides
  • We strongly advise all guests purchase comprehensive travel insurance
  • Visas if required

Let’s get started making this itinerary yours.

Speak to experienced Destinations Experts about designing this itinerary around your budget and trip preferences

Why book with Unforgettable Travel Co.

  • 100% Financial Protection

    We are a licensed and fully bonded tour operator financially protected by both the Civil Aviation Authority (ATOL) and the Association of Bonded Travel Organisers Trust (ABTOT). All clients that travel with us are fully financially protected.

  • Destination Experts

    Our travel experts live and breathe the destinations they specialise in. This shows in their passionate to create hand crafted trips for our clients. We don’t offer cookie cutter trips, just truly unforgettable journeys unlike any other.

  • The Best Guides

    What makes our trips extraordinary is the unique immersive experiences we include. We pride ourselves in our black book of sought after expert guides, game rangers and local contacts who believe in our philosophy, unforgettable.

  • We Care

    From the moment you book your trip, we are on hand 24/7 to assist you throughout your journey. With regional offices around the world, we have ground logistics teams on hand to help you every step of the way.

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