Wander with us as we get lost in the beauty of narrow stone streets, hilltops overlooking the Adriatic and seaside towns that make up the Puglia region of Southern Italy. Then head to Sicily where you will explore wineries and ruins, eating fabulous food in the shadow of Mount Etna.
5 days, 5 nights in Puglia | 4 days, 4 nights in Sicily
Welcome to this beautiful region of Italy - Puglia! The heel of a fashionable, beautiful boot! It’s known for it’s whitewashed hill towns, centuries old farmland and hundreds of miles of Adriatic coastline.
You will start out near the town of Locorotondo which will be your home base for most of your time in this region. Each day you’ll be visiting all the amazing towns. Some are whitewashed, some are rounded on hilltops, and some are beautifully situated on the seaside. Amazing views and food and wine are the essence of this area. And don’t forget the ruins and buildings, brimming with history. You will visit all the amazing places you’ve seen or read about - Cisterno, Alberobello, Ostumi, Monopoli, Polignano, Lecce and more!
Our next stop is the seaside town of Pizzo, in the Calabri region. I guess you could say this is toward the toe of the boot! Here you’ll see the Aspromonte area and enjoy more wonderful food and the freshest seafood.
Onward we travel by ferry to the magnificent island of Sicily with it’s towering volcano - Mount Etna! Here we’ll discover the largest island in the Mediterranean, dotted with Greek temples and adorned with Byzantine mosaics. We’ll be staying at the base of the volcano, in Zafferana Etnea. We will see the towns of Taormina, Syracuse and the island of Ortigia. We’ll even have a cooking class on the volcano! How memorable!
Italy preserves a culture that is rich, diverse and a joy to discover. Fishermen still tend their nets, sheep and cattle dot the beautiful landscape and the charming towns are filled with history and surrounded by vineyards! These tiny towns can be traced back 1000 years and their culture is still vibrant, delicious and thriving.
In all these areas, you will encounter friendly locals, a rich culture, seaside towns, historic architecture and amazing cathedrals surrounded by hills and views of the water. Don’t miss this opportunity to delve into a gorgeous, slow-paced world surrounded by sparkling waters.
Day 1 | Private transfer to hotel in Martina Franca, welcome aperitifs & dinner at hotel
Day 2 | Towns of Locorontondo, Cisternino & Alberbello
Day 3 | Towns of Ostuni, Monopoli & Polignano
Day 4 | Towns of Lecce & Otranto
Day 5 | Towns of Matera & Pizzo
Day 6 | Aspromonte’s Shepherds & Ferry to Sicily
Day 7 | Morning cooking class & afternoon in Taormina
Day 8 | Cooking class on Mount Etna & wine tasting
Day 9 | Town of Syracuse & Island of Ortigia with wine tasting
Day 10 | Departure to airport & home
*Pricing to be confirmed.
Credit Card payments are accepted with an additional 4% fee.
Arrival date is September 16 and departure date is September 26.
Minimum of 6 travelers and maximum of 12.
There are many pre- or post-trip options to extend your stay. Extra days in Sicily are easy to arrange - you can visit Palermo, or head over to Malta!
All breakfasts provided beginning on Day 2; Includes 6 lunches, 7 dinners and a few wine tastings. Wine, beer and cocktails are not included unless stated.
Some walking through villages with uneven footing. Clients must be able to walk at least three miles without assistance.
*NOTE! If there is significant exchange rate change between the time of deposit and balance due, we may adjust final fees.
We design our excursions with a degree of flexibility to provide our clients with the best possible opportunity for exploring a particular destination. Therefore, our itineraries may change due to any factor, at our discretion. We will do our best to keep any changes to a minimum. Many times, they are the final pieces of the puzzle, and they would only be made to enhance your trip!
Independent arrival with private group transportation provided from airport to our home in the heel of the boot, near the town of Locorotondo. Welcome to Puglia! We will make our way to the hotel, drop off our luggage and freshen up. We are staying at the Ottolire Resort (or similar), which stands on a small hill in the green hills of the heart of the Itria Valley.
Upon our arrival, we’ll have a welcome aperitif and a delightful dinner paired with wines, at the gorgeous restaurant on site.
Lodging for our first night: Ottollire Resort (or similar)
Dinner Included
After breakfast at the hotel, we will meet our driver and guide in the lobby and set off for Locorotondo, for a stroll in the city center. This picturesque town has spectacular valley views, and is formed in the shape of a perfect circle on top of a hill. The buildings are white with steep gabled roofs. Every corner is a pretty image, and it’s named one of Italy’s prettiest villages. We’ll be having lunch here, and tasting the local wines.
We will then head for the town of Cisternino. Another beautiful village with white washed buildings on a hill. The charming center has a kasbah-like knot of streets and there are charming gardens with lovely rural views. Before we leave, we’ll be learning how to prepare and taste burrata.
After stopping at these famous “white towns of Puglia” we’ll stop at Alberobello. This town has been a Unesco Heritage Site since 1996, and has the most “trulli” in any one town. These are white-washed huts with conical roofs. Such a magical place to see. Here, we’ll be tasting the famous “tarallini pugliesi” in a local bakery. These are little snacks that come in many flavors and are popular in the region.
After our day, we’ll head back to the town of Martina Franca for dinner.
Lodging for tonight: Ottolire Resort (or similar)
Breakfast and lunch included
Today you’ll be experiencing the rich history and stunning beauty of the Puglia region of southern Italy. You will head northeast along the coast of the Adriatic Sea, and your first stop is Ostuni, known as the “White City”. This one is also on a hill but overlooks the sea. You will explore the historic center of town and the cathedral which dates back to the 15th century. A whitewashed fairytale place with stunning views.
Next on your agenda is the town of Monopoli, a picturesque seaside town with beautiful beaches and a historic center. The town is surrounded by a wall that dates back to the 16th century and is home to many ancient landmarks.
Your last stop today is to Polignano, a stunning coastal town perched on a cliff overlooking the Adriatic. The town is known for it’s crystal clear waters, and lovely beaches. You’ll be having lunch here and, no doubt, sampling the fresh seafood, homemade pasta and delicious wine.
Dinner tonight is in the nearby town of Cisternino.
Lodging for tonight: Ottolire Resort (or similar)
Breakfast, lunch and dinner included
Your driver meets you at the hotel this morning and whisks you away to the southeast along the Adriatic Coast. You are visiting the town of Lecce, known as the “Florence of the South”. There are plenty of Roman ruins, including a huge ampitheater, and 17th century Baroque buildings built of limestone. You’ll enjoy a guided tour of the town, stopping to see the cathedral there and the old city, and here you’ll have lunch.
After lunch, your driver will take you to the town of Otranto, where you can explore at your leisure. It’s a charming town with it’s own castle and a small port. The beautiful floor mosaics from the 12th century, in the cathedral should not be missed. Enjoy.
Dinner tonight will be at a local farmhouse in Martina Franca, where you’ll enjoy a true “Apulian” dinner. We will pack up for our next stop tomorrow night.
Lodging tonight: Ottolire Resort (or similar)
Breakfast and dinner included
Today we’re heading toward the Tyrrhenian Sea and the towns of Matera and Pizzo. Our first stop is Matera, another beautiful city on a hill, known for its’ “sassi” - prehistoric settlements. These houses are excavated in the rock and are characteristic of the region. Some of them are only caverns and in some parts the streets go through the roofs of houses. It is similar to ancient towns near Jerusalem. Lunch is on your own here, but we will be tasting the bread of the region “Pane di Matera”.
We leave Matera and head east for the town of Pizzo, which is on the water and is in the “toe of the boot.” This is a picturesque town along the stunning coastline. This will be our home tonight and we’ll have a wonderful seaside dinner, followed by a delicious gelato dessert “Tartufo di Pizzo”.
Tonight finds us staying at the Piccolo Grand Hotel on a cliff by the sea in Pizzo. This is a small, luxurious boutique hotel designed by two German architects and opened in 2011. We can’t wait!
Lodging tonight: Piccolo Grand Hotel (or similar)
Breakfast and dinner included
Aspromonte is a mountain range located in the southern region of Calambria. It’s a rugged landscape that’s steeped in culture and history. One of the best ways to experience the area is to take a day trip from Pizzo, and that’s what you’ll be doing today. Your day starts out with a light hike, led by an experienced guide, pointing out the flora and fauna and sharing the area’s history. Along the way, you might meet some local shepherds. What an experience.
After your hike, you’ll head to a typical farmhouse for a hearty lunch, featuring locally sourced meats, cheeses and vegetables. Your hosts will share the wine of the region and share stories and legends passed down through the generations.
At the end of this glorious day, you’ll take the ferry to the famed and wondrous island of Sicily. You will cross through the strait between the island and the mainland. You will see towering mountains on either side, and shimmering blue waters of the Mediterranean as far as the eye can see.
You’ll arrive in early evening and have dinner at your hotel, the Monaci delle Terre Nere (or similar), which is in Zafferana Etnea. This will be your home while in Sicily. This hotel is an gorgeous 18th century villa on a terraced hill, where you’ll have views of Mount Etna, the vineyards and the sea.
Lodging Tonight: Monaci delle Terre Nere (or similar)
Breakfast, lunch and dinner included
Your first day on Sicily starts after breakfast, where you’ll have a relaxing morning, with a cooking class and a late lunch, when you arrive in the town of Taormina.
After your relaxing lunch, you’ll have a guided tour of the town - such a magical experience. The charming streets are lined with colorful buildings and historic architecture, and the ancient Greek Theater offers breathtaking views. You can enjoy the shops, delicious local cuisine, or soak up the sun. You might even spy locations where The White Lotus was filmed. Taormina is a must-see for any traveler to Sicily.
Dinner is on your own tonight, with a plethora of spots from which to choose!
Lodging Tonight: Monaci delle Terre Nere (or similar)
Breakfast and lunch included
A food and wine experience on the volcano is a unique experience and that’s what you’ll be doing today! The local wines are deeply rooted in the volcanic soil that surrounds the landmark. The fertile slopes are covered in vineyards, and today you’ll be learning about these local wines and preparing “arancini” - fried rice balls stuffed with meats, cheeses and/or veggies and “pasta alla norma” - a simple pasta dish made with ricotta, eggplant and tomatoes! Sounds delish!
After your class and lunch, the rest of the day is on your own. Such an array of things to see and do!
Lodging Tonight: Monaci delle Terre Nere (or similar)
Breakfast and lunch included
Rise and shine! We are heading out for the island of Ortigia, located in the heart of Syracuse. As you explore the narrow streets, you’ll be captivated by the ancient ruins and buildings, including fountains, cathedrals and the Temple of Apollo. One of the most impressive sites is the Piazza del Duomo, such a stunning town square. We’ll have a guided visit of the area, and no doubt will find treasures in this home to many artisan shops, boutiques and galleries. Lunch is on your own today.
Following our tour, we’ll head to a winery near our hotel, and tonights farewell dinner will be at the wonderful hotel restaurant.
Lodging tonight: Monaci delle Terre Nere (or similar)
Breakfast and dinner included
After checking out, you will have your driver take you to the airport for your flight home.
Fees are non-refundable so we encourage you to purchase trip insurance at the time of your deposit. Allianz quotes will be provided to you at that time.
We encourage you to arrive a day early, before your trip starts...Please note that this tour assumes arrival in Bari on April 23, and departure from Catania on May 2. Those who require alternative options please request and provide specific information. Airport arrival and departure transportation fees can vary. We are happy to help with transportation advice and information. Private transportation services will be determined once your flights are finalized.
Air travel is not included. Suggested flights will be suggested once they are available.
There are additional options to extend your tour, for anyone wanting to spend a few more days in Sicily or travel to any other regions in Italy or nearby. Please inquire about other “add-on” options if interested. (Additional itinerary planning at no extra cost.)
Watch “The White Lotus-Season 2” on HBO Max
Read “Eating & Drinking in Italy - Menu Translator & Restaurant Guide” by Andy Herbach
Watch “Stanley Tucci - Searching For Italy” on Amazon Prime
Read “How to Order an Italian Coffee in Italy” by Sara Rosso
Read “One Italian Summer” by Rebecca Serle
Read “Extra Virginity” about olive oil in Italy, by Tom Mueller
Watch “Ben Hur” filmed in Puglia
Read “The Italian Wine Guide” by Touring Club of Italy
Watch “The Godfather” on almost any channel
Read Andrea Camilleri’s “Inspector Montalbano” Series, set in Sicily
Read “Mezza Italiana” by Zoe Boccabella
Read “Beautiful Ruins” by Jess Walters
Watch “No Time To Die” filmed in Southern Italy
Read “The Sicilian” by Mario Puzo
Review Travel Tips from Galavant in your trip information
