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
Wander the gorgeous streets of Baroque Lecce
Explore the cave dwellings of Matera
Learn to make fresh mozzarella by hand
Visit and taste high-quality olive oil in a centuries old family-run olive mill
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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You'll Be Staying Here
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
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
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, 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.
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.
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
What's Not Included
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
FAQs
When should I arrive?
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.
What airport should I fly into?
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.
What should I pack?
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.
What is the weather like in late May and early June?
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.
What are the new travel requirements for Europe?
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!
What is the activity level of this trip?
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.
Is there anything else I need to know?
Visit our Frequently Asked Questions (FAQ) page to see answers to most other questions about traveling with Girls' Guide to the World.







