Italy

Perfect Puglia, An Exclusive Escape into Italy’s Hidden Heart

Discover the heel of the boot of Italy. Puglia boasts golden beaches with crystal-clear waters, intense flavors, and charming villages.

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Overview

Join us for a historical, cultural, and culinary adventure to “the heel of the boot,” one of Italy’s quieter tourist destinations. The Salento Peninsula has hosted many ancient civilizations, including Byzantine Greeks, Romans, Arabs, and Bourbons. Puglia features golden beaches, whitewashed hilltop villages, and Baroque cities such as Lecce and Bari. It is a captivating destination rich in history. This region is also the heart of traditional Italian cuisine and offers many lesser-known delights. From Pane di Altamura, a bread dating back to 1420, to orecchiette with greens, focaccia, and cartellate, we'll enjoy a variety of flavors while taking part in cooking classes and tastings. Wine also plays a vital role, with renowned wines like Nero di Troia, a flavorful red. The scenery competes with the food for enjoyment. We're surrounded by water from the Adriatic and Ionian seas, often with dramatic views. On this trip, we'll visit UNESCO's Alberobello, sail the coast of Salento, and even dine in a cave restaurant in Matera, an experience unique to this region. Are you ready for this journey of complete indulgence?

Highlights

Taste the famed bread of Altamura

Taste the famed bread of Altamura

Wander the gorgeous streets of Baroque Lecce

Wander the gorgeous streets of Baroque Lecce

Explore the cave dwellings of Matera

Explore the cave dwellings of Matera

Learn to make fresh mozzarella by hand

Learn to make fresh mozzarella by hand

Visit and taste high-quality olive oil in a centuries old family-run olive mill

Visit and taste high-quality olive oil in a centuries old family-run olive mill

Sail the Salento Coast on a private boat

Sail the Salento Coast on a private boat

Itinerary

Here's a day-by-day itinerary of the trip. Press the "<" and ">" buttons below to scroll through each day.

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LadiesdressedfordinnerPuglia

Welcome to Puglia

Day 1: Monday, May 31, 2027

Plan to fly into Brindisi Airport (BDS) by 3 pm, jump into a taxi and meet at the pre-trip night hotel, we'll be whisked away to the charming Trulli region to start our trip. There are plenty of daily flights into Brindisi from major European hubs such as London, Zurich, Rome, and Munich. 

Our home for the next few nights is Masseria Calderisi, a historic farmhouse nestled amidst acres of centuries-old olive trees, citrus groves, and herb gardens. 

Unpack and settle in before we gather in the evening for our first of many apertivos. Apertivo is an Italian tradition enjoyed before dinner, consisting of light snacks and wine. It's meant to open up our appetites for the meal ahead, while offering space for conversation and laughter. 

We'll seamlessly transition into a lovely dinner prepared for us at the on-site restaurant, La Corte, made with fresh, local ingredients. It's the perfect introduction to all of the outstanding Italian cuisine we'll enjoy on this trip. 

Included

Welcome Drink & Dinner

Not Included

Flight to Brindisi

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Itria Valley

Day 2: Tuesday, June 1, 2027

Wake up and soak in the views while we have our first breakfast together at the hotel. Our driver will pick us up mid-morning to begin our adventure through the Itria Valley, famous for its rolling countryside, ancient olive groves, and picturesque whitewashed villages.

Our first stop is Alberobello, a UNESCO World Heritage Site, renowned for its iconic trulli, unique conical-roofed houses. After walking through the village and learning about its significance and history, we'll stop to enjoy lunch at a local taverna. 

We'll continue to explore Locorotondo, with its circular historic center, and Cisternino, known for its narrow alleys and traditional butchers grilling meat in the streets, a gem of authenticity.

We're in for a real treat as we head to visit an olive grove to learn about the process of making olive oil. Our good friend Luigi will introduce us to the wonderful plant that is the olive tree and explain the principles of sustainable farming.

He'll lead us through an olive oil tasting experience, teaching us how to appreciate the health benefits and flavor profiles of high-quality EVOO.

Dinner will be at Serri Bistro, a cozy restaurant that makes you feel like a true local with its authentic Val d'Itria cuisine.

After a long and wonderful day, we'll return to Masseria Camarda for dinner and a restful night's sleep.

Included

All meals

All activities & tours

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Martina Franca & Ostuni

Day 3: Wednesday, June 2, 2027

After indulging in breakfast at our hotel, we'll spend the morning with a local cheesemaker, before continuing on to Martina Franca and Ostuni, two must-see towns in Puglia.

We'll have the pleasure of meeting Sara, a local cheesemaker who will explain the steps involved in transforming fresh milk into delicious mozzarella, ricotta, caciocavallo, and many other cheeses.

Sara will expertly create "pasta filata", which we'll take and shape into our own fresh balls of mozzarella. Can you think of anything more delicious? She'll then guide us through a tasting of the cheeses she produces at her farm, both new and aged. 

Once we're done with that delicious endeavor, we'll explore Martina Franca's historic center with its winding alleys and grand piazzas, including the UNESCO-recognized Basilica di San Martino. Then, we'll visit Ostuni, 'The White City,' known for its whitewashed buildings, hidden cafes, artisan shops, and views of the Adriatic Sea.

We'll round out the day back at the hotel with a private dinner, specially prepared for our group. As the sun dips below the horizon, we'll toast to another gorgeous day in Puglia.

Included

All meals

All activities & tours

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Matera - Pizza Making & Walking tour

Day 4: Thursday, June 3, 2027

We absolutely must put the mozzerella we made yesterday to good use! Before we leave for our next destination, we'll meet up with Gigi, a local pizzaiolo who will teach us how to prepare the perfect Italian pizza. 

Gigi will impart the tricks of the trade for preparing and stretching the dough, dressing it with the best toppings, and baking it to perfection. We'll enjoy the fruits of our labors for lunch. Yum!

Then, we're off about two hours west to Matera, one of the most distinctive cities in Italy. 

Once we arrive, we'll check in and settle into our rooms at Sant'Angelo for the next couple of nights, a stunning 5-star cave hotel comprising 33 historic residences spread throughout the historic center of Sassi di Matera and connected by a maze of caves, stairways, courtyards, and alleys. Please note: Due to the nature of the property, most rooms are accessed via historic staircases that might be steep and narrow.

After some time to get situated, we'll step out to explore the town on foot with an experienced local guide. As one of the world’s oldest continuously inhabited cities, it's famous for its ancient cave dwellings, known as the Sassi di Matera

We'll stroll through the picturesque streets of this UNESCO World Heritage Site, visit the stunning rock-hewn churches, and enjoy breathtaking views from the Belvedere before wrapping up at one of the local cave restaurants, Oi Mari, a unique experience that's an essential part of any visit to Matera.

Included

All meals

All activities & tours

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Altamura - Bread Workshop

Day 5: Friday, June 4, 2027

After choosing a sweet or savory breakfast spread at the hotel, we'll continue our Italian culinary adventure. 

A 20 drive brings us to Altamura, a hillside town known for its traditional pane di Altamura, a durum wheat bread. Here, we'll visit a legendary local bakery to discover how the local bread is made and savor fresh creations. Bread produced here is a designated protected designation of origin (PDO), similar to Champagne, halloumi, and kalamata olives, to name a few.

We'll sit down for a hearty brunch before returning to Matera to enjoy the rest of the day at our leisure.

Make sure to take some time and explore the iconic caves around Matera, many of which have been preserved and are open to the public. Enjoy dinner on your own or with new friends. Your guide has plenty of recommendations for local spots if you need inspiration. 

Included

Brunch

Altamura bread workshop

Not Included

Dinner

Activities on your own

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Lecce

Day 6: Saturday, June 5, 2027

We'll have breakfast and check out of the hotel before beginning our journey to Lecce with a scenic drive through the region's sun-drenched countryside, where centuries-old olive groves and whitewashed villages.

Along the way, we'll stop at the renowned Cantina di Manduria to explore its fascinating wine museum and discover the history of one of Puglia's most celebrated wine-producing regions. We'll then settle in for a relaxed tasting lunch, pairing exceptional local wines with a selection of regional specialties.

By early afternoon, we'll arrive in Lecce, a city celebrated for its ornate Baroque architecture and lively piazzas. During a guided walking tour, we'll stroll through its streets, admiring intricately carved limestone churches, elegant palaces, and hidden courtyards while getting a feel for the city's unique character. 

Then, we'll check into our home for the next few nights, the charming Palazzo de Noha, an intimate boutique hotel tucked within the heart of Lecce's historic center.

This evening, we'll be welcomed into the home of Alessandra De Mauro for an unforgettable cooking experience that feels more like gathering with old friends than attending a class. Guided by conversation, local traditions, and the flavors we love, we'll prepare a menu of authentic Salento dishes, from fresh fish appetizers and handmade pasta to a beloved regional dessert. 

As the evening comes to a close, we'll gather around the table to enjoy the meal we've created together, sharing wonderful food and warm conversation.

Included

All meals

All activities & tours

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Salento Coast

Day 7: Sunday, June 6, 2027

After breakfast at the hotel, we'll depart for a morning boat ride along the stunning Salento coastline, where crystal-clear waters and breathtaking cliffs create a truly unforgettable experience.

After taking in the beauty of the coast, we'll dock for lunch at Lo Scalo di Novaglie, a charming seaside restaurant offering freshly caught seafood-based dishes. 

This afternoon, we'll head off for some free time to stroll through the gorgeous town of Otranto, known for its stunning beaches, historic old town, and rich cultural heritage. 

While we're there, don't miss the iconic Aragonese Castle and the Cathedral, with its famous mosaic floor that reflects centuries of history. Stroll along the picturesque seafront, explore the medieval alleys, and admire the breathtaking views of the Adriatic.

Returning to Lecce, take the rest of the evening to explore, relax, and socialize at your leisure.

Included

Breakfast & Lunch

All activities & tours

Not Included

Dinner

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Galatina & Gallipoli

Day 8: Monday, June 7, 2027

This morning we'll set off southwest towards the little town of Galatina and the once-fortified village of Gallipoli, perched on the Ionian Sea, stopping to visit the colorful fish market and to stroll its narrow, whitewashed streets.

We'll enjoy a late lunch and wine tasting at Masserie Le Stanzie. This agricultural farm is a diverse operation featuring orchards, olive groves, vineyards, a garden that produces seasonal vegetables, and livestock, including cattle and sheep. 

Take this evening to wander Lecce one last time, indulge in an Italian sweet treat, or sip on local wines while you watch the world go by. We'll toast to our last night in Puglia and the beautiful journey we've been on this week with a wonderful farewell dinner at Alex Ristorante

Included

All meals

All activities & tours

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Departure Day

Day 9: Tuesday, June 8, 2027

Sadly, our time in Italy together has come to an end. After breakfast, we'll transfer to the Brindisi airport for your onward travels. 

We'll exchange pictures and phone numbers and promise to stay in touch with all the new friends we've made along the way. Until next time...

Included

Breakfast

Group transfer to Brindisi Airport

You'll Be Staying Here

Masseria Calderis

Masseria Calderis

Surrounded by centuries-old olive groves and just moments from the sparkling Adriatic Sea, Masseria Calderisi is a beautifully restored 17th-century estate that captures the understated elegance of Puglia. Whitewashed stone buildings housing thoughtfully designed rooms create a tranquil, historic retreat. 

Sant'Angelo

Sant'Angelo

Carved into the ancient limestone cliffs of Matera's remarkable Sassi district, Sant'Angelo is an unforgettable stay in one of Italy's most extraordinary settings. Carefully renovated cave dwellings and historic stone structures have been turned into stylish guest rooms that perfectly combine centuries-old charm with modern comfort. 

Please note: Due to the nature of the property, most rooms are accessed via historic staircases that might be steep and narrow.

Palazzo de Noha

Palazzo de Noha

Hidden within the winding lanes of Lecce's enchanting Baroque old town, Palazzo de Noha is an intimate boutique hotel where history and modern Italian design exist in perfect harmony. Meticulously restored, the historic palazzo features elegant suites, original stone architecture, curated artwork, and inviting spaces. A rooftop terrace with a plunge pool offers sweeping views across the city's honey-colored rooftops, while the Duomo, lively piazzas, artisan shops, and celebrated restaurants are all just a short stroll away.

Hosts

Cheri Kendrick

Cheri Kendrick

Cheri, who lives on the idyllic island of Utila, Honduras, finds her peace amidst serene waters and lush tropical gardens, cultivating a profound connection with nature. She thrives on immersive travel experiences that explore diverse cultures, gastronomy, and horticulture, with safaris being her ultimate favorite getaway. 


As the Operations Manager at Girls' Guide to the World, she leverages her extensive background in tourism and hospitality to expertly plan wellness retreats, transform chaos into harmony, and lead teams with finesse. Cheri's passion for enriching experiences and her commitment to well-being make her a driving force in creating unforgettable journeys.

Price

Private Room

Private Room

Everyone gets their own fabulous room!

$11,955

Shared Room

Shared Room

Share a room with a friend or family member.

$10,995

The Heel of the Boot of Italy

Puglia

Dreamlike bays, stone villages, olive groves, wilderness, unique architecture, and four UNESCO sites, each one more fascinating than the next. Puglia has been named the "most beautiful region in the world" and for good reason. Scattered across the seashore and hilltop villages lie cathedrals, castles, whitewashed houses, and flowered balconies. Puglia's captivating charm and delicious rustic food should not be missed. 

Puglia

What's Included

What's Included

All meals (except where indicated), including beer, wine, or cocktails with dinner

Visit to a legendary bakery to discover how local bread is made

Guided tour of the historical center in Lecce

Pizza making experience with a pizzaiolo

Tour and tasting at Cantina di Manduria

Private boat cruise on the Salento coast

All guides, experts and entry fees

Tour and tasting of Masserie Le Stanzie

Local cheese-making experience

Tour and tasting at an olive oil farm

Walking tour of Alberobello

Group departure airport transfer

Lodging at unique hotels

A small group experience

All in-country transport

Local cooking class

Wine tastings

Walking tour of Matera

Additional wine, beer, or spirits beyond what is offered at meals.

Travel and Medical Insurance (required)

All personal souvenir purchases

International Airfare to Italy (and Brindisi)

Arrival airport transfer

Reviews

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Puglia was more than I imagined. Beyond beautiful! The friendships and memories that were made will last a lifetime. I can't wait to do another trip.

Rebecca W-Houston Texas,USA

FAQs

The trip officially starts on May 31, 2027. If you’re traveling across an ocean to reach Italy, consider arriving a day or two early to allow time to relax and adjust to the local time zone. 


If you would like to arrive early or stay an extra day at the end of the trip, you can purchase these options in the Add Ons section.

Fly into Brindisi Airport (BDS). If you plan to see more of Italy, you can fly to any other major airport and take a short flight to Brindisi. Many major European hubs also fly here, so you should have plenty of options when planning your travel. If you need assistance, let us know what we can do to help. 


Other nearby airports include Bari (BRI, 120 km) and Dubrovnik (DBV, 196.4 km). We'll only provide transfers to and from our accommodation on the first and last day from Brindisi airport, so if you fly into a different city or on a different day, you will be responsible for arranging transport into town.

We'll have a Zoom call about 8 weeks before the trip starts to discuss important logistics and give you packing guidance. In the meantime, here is a great website that we love that will help you with packing and travel trips. 

Late May to early June is one of the best times to visit Puglia, with warm, sunny days and comfortable evenings. Daytime temperatures typically range from 73–79°F (23–26°C), while evenings are pleasantly mild. The Adriatic Sea begins to warm, making it suitable for swimming, and rainfall is generally light and infrequent, with only a few rainy days throughout the period.

Beginning in late 2026, travelers from visa-exempt countries—including the U.S., Canada, and Australia—will need an ETIAS permit to visit most of Europe.


No action is needed just yet. As we get closer to the launch date, likely several months in advance, we’ll share all the details on how to apply. Feel free to reach out with any questions!

We require that everyone traveling with Girls' Guide be able to walk 3–5 miles per day unassisted comfortably, and without difficulty, can navigate stairs, uneven streets or paths, and occasional steep terrain. Most of our trips require this level of physical mobility and fitness, especially when visiting historic towns and landmarks where vehicle access is limited and walking often offers the best experience. 


Additionally, some of the 4 and 5-star boutique or historic hotels we stay in do not have elevators and may require climbing stairs to get to your room or access other facilities in the hotel.

Visit our Frequently Asked Questions (FAQ) page to see answers to most other questions about traveling with Girls' Guide to the World.

Inquire about this trip

Perfect Puglia, An Exclusive Escape into Italy’s Hidden Heart

Italy· Departs on May 31, 2027 · 8 nights

$11,955/pp