Villas in Puglia are Serving Up the Sweet Life

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Move over Tuscany -- there's a new star on Italy's travel map, and it comes complete with sun-soaked villas set amid Puglia's captivating landscape.


It doesn't matter how many times you’ve been to Italy, if you haven’t laid eyes on Puglia, I can promise you, you have more to see. 


Throw away all your preconceptions about what Italy is, and what it looks like.  Make room for something new.  Puglia feels Greek one moment, then a little Middle Eastern the next.  Or, it’s reminiscent of a fairytale when strolling the streets of Alberobello, only to abruptly transport you to the Maldives when swimming in completely crystal clear waters.  And, what’s that off in the distance on the horizon?  Oh, hi Albania.   


It’s almost as if all the historical eras of Roman, Byzantine, and Medieval times converged on this one spot, diffusing with the architecture, food and fashion.  It’s where Italians have vacationed for eons, and every fiber feels fully authentic.  And now this seductive slice of the Italian peninsula is on your radar too.


How can you travel here with your family, in an age where multigenerational sojourns has taken root?  Here's how I did it.


As I was trying to coordinate the logistics of a multigenerational vacation spanning ages 2 to 72, I discovered a company who seemed to be my Fairy God Mother.  You see, I’d invited 11 people — proud members of “The Finer Things Club” — to Puglia, Italy, and I needed to scout a villa that both elderly in-laws would consider relaxing, and thunderous toddlers could find endlessly entertaining.   As a luxury traveller, I was searching for an accommodation with exquisite amenities, excellent service, delectable food, and spacious accommodations.  I’d entertained the idea of looking for a 5 star hotel, but it would require cramming into multiple rooms.  Also, the villa offered gathering spaces for our group to be together, instead of siloed hotel rooms that made it challenging to convene post kid bedtime.  


So, I turned my research radar on full blast and searched for a villa instead.  I’m going to save you a lot of time and skip to the good part. 


I found The Thinking Traveller.  


The Thinking Traveller holds the keys to the most exquisite villas in Puglia, Greece, Sicily, and Corsica.  They’re like a mini “villa version” of the Roman Empire — they have a highly curated collection of high-end homes for you to choose from, and they’ll provide all the conveinances of a 5-star hotel too.  I'm going to warn you, it won't be easy to choose just one. 


Let me show you around. 

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Photo Courtesy: The Thinking Traveller
Photo Courtesy: The Thinking Traveller
girls jumping into pool at l'argentiera - the thinking traveller villas in puglia
Photo Courtesy: The Thinking Traveller
Photo Courtesy: The Thinking Traveller

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    Need Help Planning Your Trips?

    What are the Benefits of a Luxury Villa in Puglia?

    little boy jumping into pool at l'argentiera- villas in puglia

    On my first call with The Thinking Traveller  I admitted something I didn’t think I would reveal so quickly. “I’m a hotel girl,” I confessed. “Hotels are easy, they’re reliable at the luxury level, and they just take all the legwork out of family travel”, I explained over the phone.


    “So do we,” Kerry, from The Thinking Traveller, countered intriguingly.


    Was this for real?  I hadn’t found rentals to be reliable in the U.S.  Even the luxury properties – while granting a guest more space and privacy – weren’t akin to a pampered experience at a five-star Four Seasons.


    The Thinking Traveller seemed to check every box.  But, was it a mirage or a miracle that they were offering?


    Three months later, I can now declare that I’ve been converted from Rental Rookie to full blown Villa Visionary. Their team of specialists will help you both find a vacation house of your dreams, and craft an unforgettable itinerary that you simply can’t turf up on TripAdvisor.


    Each luxury villa has its own unique history -- its own “special something” that landed them on the exclusive Thinking Traveller list.  In fact, only 1% of the villas that apply to be included receive a stamp of approval.  You might be staying in a castle from the 1400’s, or waking up each morning steps from the Adriatic Sea, or experiencing unique living in a trullo.  Once on the list, you’ll never find that property on another company’s website.  Welcome to the club.


    The Thinking Traveller’s team intimately knows each villa and its staff, and because of that, they can recommend the best property for your group.  They’ve stayed as an overnight guest themselves.  They’ve tasted the meals you’ll enjoy in your al fresco seat by the sea, and they’ve embarked on the very same excursions. They have first hand knowledge of what you're signing up to experience.

    Photo Courtesy: The Thinking Traveller
    Photo Courtesy: The Thinking Traveller

    Some of the 5-star features included in their villas are:   

    • Personalized concierge planning services - An Experience Specialist will help plan your itinerary, including activities and car rentals.   
    • Local support- Have your dinner plans changed?  Need a local recommendation?  You'll have a team available to help 24/7. 
    • Hotel-level amenities - Jump into your infinity pool!  Relax in your personal hamam.  Run through the gate to your private beach.  Your villa may even have a gym or tennis court, so keep working on that top spin.  
    • Home cooked meals - Moms!  Enjoy a break from meal planning and prepping!  Each villa has a team of local chefs to take care groceries, cooking, and cleanup.
    • Daily cleaning - There is daily cleaning of the entire villa included in your stay.
    • Spacious accommodations -  Every villa has a space for your group to spread out, relax, and spend time together.  It may be dinner al fresco overlooking the sea, soaking in the warmth by the pool, or lounging in a home-cinema together at night.
    • Clean and updated accommodations - While many of the villas are historic, they have been beautifully restored to include modern amenities.  Yes, you'll have AC in the summer!
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    l'argentiera the thinking traveller - villas in puglia
    Photo Courtesy: The Thinking Traveller
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    pool floatie at l'argentiera

    L 'Argentiera: One of the Best Luxury Villas in Puglia

    Villas have names in Italy, and ours was L'Argentiera.  

    Let's take a peek inside one of the most exquisite properties in the collection, so that you can see from beginning to end what a holiday with The Thinking Traveller looks like. 

    Thinking Traveller L'argentiera - villas in puglia
    Photo Credit: The Thinking Traveller


    Step 1 will be an initial call.  The Thinking Traveller's team will learn more about your family, your vacation goals, and any accommodation preferences.  As I spoke with Kerry Berry, our villa specialist, I communicated my “Multigenerational Mediterranean Mission:” 

    My Multigenerational Mediterranean Mission

    I  wanted to discover a luxurious accommodation that could comfortably fit 11 people, ages 2-72, along the southern coast of Italy.  I knew the kids would yearn for a pool to play in all day.  I knew the adults would love to start each morning with a swim in the refreshing Adriatic waters.  I knew the grandparents would search for a little solitude, and enjoy a book in a comfortable chair by the sea.  I knew quite a few foodies would be along for the ride.  And I knew proximity to charming towns was paramount too.  

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    Kerry used this information to curate a specific list of villas that would be a mission-go.  She had personally stayed at many these properties, allowing her to easily answer my discriminating questions.  When my eyes landed on  L’Argentiera, I knew it was “the one."  Booking complete!


    Step 2 was to start crafting the itinerary with my Experience Specialist, Federica.  As a travel planner, I'm not accustomed to handing over the reigns, but this service was invaluable.  Federica coordinated car rentals, airport transfers, restaurant reservations, and special experiences.  She was my liaison until we arrived in sunny Castro, Puglia.

    Welcome / Arrival

    When we arrived at our villa in Puglia, our host Luigi cheerily greeted us, and provided a full tour of the property.  We learned the “lay of the land,” and enjoyed a welcome drink and snack.  Each villa has a host who lives near the property, and stops by to answer any questions.  He even saved the day with a few grocery store diaper runs!  


    At L’Argentiera the star of the show was the infinity pool and private sea access.  The massive square pool overlooked the rocky shoreline.  We had a private gate to the sea, where there were areas to lay down with a towel, and jump easily into the cool, refreshing waters.  There were also kid-friendly coves to explore and walking paths along the shore. 


    At the villa, there was also an authentic pizza oven, multiple al fresco dining areas, a private deck overlooking the ocean, and an outdoor shower – a true lifesaver with little kids!  

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    Photo Credit: The Thinking Traveller
    Photo Credit: The Thinking Traveller
    Thinking Traveller L'argentiera - villas in puglia
    Photo Credit: The Thinking Traveller


    If you’re that reader out there who’s questioning if a family holiday with that many people under one roof is a good idea….well…L’Argentiera has you covered.  There's plenty of room for everyone to spread out comfortably.


    L’Argentiera consists of two separate wings - it's literally split into 2 sections, so two families with kids can be entirely contained in their own wing.  There are 9 bedrooms, each with its own en suite bathroom, so there is plenty of space to bring additional guests, like grandparents, aunts or your favorite uncle.  

    Photo Credit: The Thinking Traveller
    Photo Credit: The Thinking Traveller
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    kids room at l'argentiera
    Photo Courtesy: The Thinking Traveller
    Photo courtesy: The Thinking Traveller
    Photo courtesy: The Thinking Traveller

    Looking To Book This Exact Villa?

    Mention code COMPASSROAM when booking for 2024 (before the end of October 2023), and you'll receive a 5% reduction on the week's cost. You’ll also receive a 6-bottle case of wine at your villa. Contact a Thinking Traveller Villa Specialist today - this offer is not valid for online bookings.

    Dining in a Luxurious Villa in Puglia

    At your villa in Puglia, you'll have access to a full service kitchen, and you can have a private chef prepare meals at the house.  


    We chose to leave the Italian cooking to the Italian chefs. 


    Every morning we bounced downstairs to find a table already filled with homemade pastries baked before dawn, fresh fruit, coffee and tea brewing, and a chef ready to whip up egg orders.  While the food was being prepared, we jumped into the sea for a quick swim and leisurely started the day relaxing on the outdoor sofas with panoramic views of the sea.  


    We also opted to have a few dinners in the villa as well.  The kids had the flexibility to roam freely between courses, while the adults were able to catch up and connect.  We feasted on massive platters of grilled vegetables, local bruschetta, fresh fish caught just that morning, and a light ricotta cheesecake.  As always, there was some gelato too. 


    On another occasion, Federica arranged for a professional pizza chef to craft artisan pies in our villa’s wood burning oven by the sea.  We watched him heat it to a whopping 900 degrees, learning about his passion for pizza, while he prepared the dough and toppings.  Once the oven was fired up, he magically spun 14 pies over the next hour!  We devoured traditional options, like Margherita with fresh mozzerella oozing all over, but also tried a local specialty – "tuna pizza," and for dessert...nutella pizza!

    Photo Credit: The Thinking Traveller
    Photo Credit: The Thinking Traveller
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    Curated Experiences in Puglia

    Just as The Thinking Traveller has invested ample time into curating only the best villas featured in their collection, they’ve applied the same level of scrutiny to the "Think Experiences" available exclusively to their clients.   Here were two unforgettable experiences we added to our itinerary. 

    Cooking Class in a 15th Century Palace

    I’ve been to Italy many times — I’ve done the tours, I’ve done the cooking classes, and I’ve had fun with all of them — but none of those incredible experiences compare to this magical night, cooking Italian food together in a 15th century castle.  This was a meal and a mystery all wrapped together in one unimaginably awesome night.  


    Driving from our villa to the estate, through small towns and quiet streets, it was difficult to imagine that something akin to a castle would be waiting for us at the end of road.  We parked our car in the town square, and walked a few minutes to our location.  Our guide stopped in front of two massive doors, which he unlocked and swung open for us.  


    I don’t think anyone in our group was prepared to walk into, what felt like The Garden of Eden. 


    Immediately the town outside the palace walls disappeared and the smells of jasmine and roses filled the air.  Orange trees and the castle walls surrounded us. It felt as if we had landed in the middle of movie — part Downton Abbey, part Game of Thrones (the scenic settings, that is).  


    We were led inside to tour the beautiful interiors - there were double valuted ceilings, timeless tapestries decorating the walls, and a great fireplace that almost made me yearn for winter, just so I could hear the wood crackling away under the great mantle. Outside, we stood on the towers where archers used to take their place!  

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    castello albergo the thinking traveller
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    We followed our gourmet chef into the rooftop kitchen, where she led us through a demonstration of some her favorite Italian recipes.  We fried summer zucchini and folded it into a creamy pasta sauce for our spaghetti.  We roasted summer vegetables to create a melody of flavors in an eggplant caponata.  We breaded and baked freshly caught Swordfish.  Then, we indulged in a decadent homemade chocolate mouse.  

    And the kids…? 


    They were in imagination heaven!  This was after all a real life castle where envisioned themselves as princesses fighting off dragons.  Cousins chased one another through the gardens, lounged on the hammocks, and explored every corner.  


    When dinner was ready, we dined outside on the rooftop verandah under the stars.  It wasn't just the little girls who felt like princesses anymore.  As the clock struck a metaphorical midnight, we yearned for our Cinderella-spirited Apuglian fairytale to continue forever.  It was everyone’s favorite night of our vacation in Puglia.  

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    Sailing Along the Salento Coast

    A vacation in Puglia is simply not complete until you’ve sailed along the rocky coastline, peering into its gargantuan caves and stopping to swim along the most beautiful beaches.  


    We opted to embark on a private boat tour, whose friendly and gregarious crew made it an unforgettable day.  


    They welcomed us on board - a sleek 76 ft vessal equipped with a kitchen, 3 bedrooms, 2 bathrooms, and a living room.   We sailed along the "heel" of the Italian boot, past Santa Maria de Leuca, and stopped to jump into the azure waters.  The kids climbed onto the inflatable raft, and the dads immediately lived out their “James Bond” dreams by using the underwater SeaScooters to dive deep below the surface.  Later, after we'd had plenty of time to swim, we sailed past the looming caves, learning about some of Puglia's fascinating history.  While some of of us stayed on board to enjoy the fresh orchhiette served for lunch, others swam into the caves to see the blue light dancing off the walls.  

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    sea luxury yachts

    Location of This villa in puglia

    L'Argentiera is a perfect villa for families keen on exploring the various treasures of Puglia. Located conveniently in the Salento area, it's the perfect balance between existing as its' own slice of luxury, while still being close to a few idyllic seaside towns and "pinch-me" beaches.  


    • A short drive away is Otranto -- a fortress coastal city, renowned for its storied castle and the mesmerizing Cathedral.  Don't miss seeing the masterpiece mosaic floor from Medieval times.
    • Beach lovers will appreciate the proximity to some of Puglia’s most beautiful coastlines, where the Ionian and Adriatic seas meet in a splash of turquoise and emerald.  Torre dell'Orso, Baia dei Tuchi, and I Faraglioni di Sant'Andrea are some of the most stunning beaches along this coastline.
    • Then, there's Santa Maria di Leuca, sitting at the southernmost tip of the Salentine Peninsula.  You can marvel at its iconic lighthouse and take a boat trip to explore mysterious sea caves.
    • Take a day trip to the "Florence of the South" -- Lecce.  Known for its ornate buildings made from local Lecce stone, it's a beautiful town where you can roam the streets and see a theater from Roman times still in tact.  Lecce is also famous for its papier-mâché artisans.



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    While L'Argentiera offers you a getaway to the most beautiful cities in Puglia, it's also just steps away from the small marina of Castro.  This town is where local Italians spend their summer nights. .   


    There are two sections of Castro – the historic center at the top of the hill, and the marina.   The historic center is surrounded by old castle walls, with a few shops and restaurants lining the streets.  Da Amedo is a delicious restaurant tucked in between orange gardens, serving seafood focused cuisine.  The marina is further down the cliffside, with a few restaurants, gelaterias, and even mini rides for kids to hop on. From L’Argentiera you can walk to the marina to grab some dinner at 37 nodi - another seafood based restaurant, which also serves gourmet pizzas.  Grab a slice and enjoy the sunset views.

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    Need Help Planning Your Trips?

    5 More Exquisite Villas in Puglia

    Our only regret with booking L’Argentiera was that we should’ve stayed for 14 days!  Although we never wanted to leave this corner of Castro, I know Puglia is a destination we'll revisit many times.  Here are a few villas in Puglia I have on my own wishlist for a return visit.  

    Villas in Puglia Near The Sea

    Masseria Palmieri has it all - stunning historic architecture, spacious accommodations for large groups, a fantastic pool, and a prime location!   Situated in the Valle d’Itria region of Puglia, you’re not far from popular towns such as Pogliano a Mare, Alberobello, and Monopoli.  These seaside and hilltop towns are frequented year round, so if you're visiting in the shoulder season it's wise to pick a villa closest to these cities, like Palmieri.  When you're not exploring the towns, there's plenty to do on the villa's grounds.  Guests can enjoy walks through the gardens, a yoga session or even a tennis lesson.  At night, during the cooler months, cozy up by the wood burning fireplace.  

    Photo Courtesy of: The Thinking Traveller
    Photo Courtesy of: The Thinking Traveller

    Villas in Puglia Close to Town

    You simply can not go to Puglia and skip sleeping in a trullo!  Trulli (plural of trullo in Italian) are cone shaped structures that are typical to this region.  The limestone provides a cooling escape to the heat, and the structure looks straight out of a fairytale.  Trulli Andrea is an exquisite property that is perfectly positioned in the Valle D’Itria.  You’re only 10-15 minutes from some of the cutest storybook towns – Martina Franca, Ostuni, Ceglie Messapica, and Locorotondo.  It’s also one of the best properties for multigeneratoinal trips too, accommodating up to 12 guests.  There are two pools with panoramic views of the countryside, and guests can explore the spacious grounds before heading into town.

    Photo Credit: 
The Thinking Traveller
    Photo Credit: The Thinking Traveller

    Villas in Puglia with Private Pools

    Most of the villas in The Thinking Traveller’s collection have private pools, but Palombara Piccola is at the top of my “villa wish list.”  This property looks like it bounced straight out of a magazine (and in fact has been in one).  Situated within olive groves along the Adriatic coast, guests can enjoy the gorgeous 16m long heated pool, strolls through the rose gardens, relaxing at night in the private movie room, and meals under the shady loggia.  It’s also perfectly located, only 10 minutes from Ostuni, down the road from plenty of beaches, and nestled within the rolling hills of the Valle D’Itria. 

    Photo Courtesy of: The Thinking Traveller
    Photo Courtesy of: The Thinking Traveller

    Unique Villas in Puglia

    Castello di Capririca is a 16th century castle that has everything families are looking for on a holiday away together.  The grounds include a massive swimming pool and green spaces for kids to run around.  The castle can accommodate up to 18 people!  It is a castle afterall...

    As an added benefit, you can walk right into the town of Tricase, or hop in the car and it’s a short drive to the Salento coast. 

    Photo Courtesy of: the Thinking Traveller
    Photo Courtesy of: the Thinking Traveller

    Villas in Puglia For the Off-Season

    Masseria Belvedere is an impeccably restored farmhouse, that has panoramic sea views of the Adriatic Coast.  You're just a few minutes from stunning beaches, and the Torre Guaceto Nature Reserve.  The villa includes an infinity pool, steam room, and a hot tub!  It's one of the best properties for families too, as it can accommodate up to 16 people, with 8 bedrooms and plenty of al fresco areas for spending time together.  You're also conveniently located close to the town of Ostuni - one of the most beautiful hilltop cities in Puglia.

    Photo Courtesy: The Thinking Traveller
    Photo Courtesy: The Thinking Traveller

    When should you book your villa in Puglia?

    If you're looking to experience Puglia at its warmest, I'd recommend planning your trip between May and September.  We traveled in June when it wasn't too hot, but the water was still warm enough to swim. Summer is when the region truly comes alive, from its beaches and open-air markets to late-night piazzas buzzing with local festivals.  That being said, the shoulder season months of September and October are also pleasant in this region -- the temperatures have cooled down, the tourists have returned home, and the ocean water is still warm enough to swim.


    I'd recommend making your villa reservation 6-9 months in advance, if you plan to travel in peak season.  Puglia is quickly becoming the rising star of European destinations, and so it's a good idea to secure accommodations early.  However, The Thinking Traveller has over 50 luxury villas just in Puglia -- so if you're searching for a "spontaneous stay" then they can still help secure the perfect place.  

    Photo Courtsey: The Thinking Traveller
    Photo Courtsey: The Thinking Traveller

    Need Help Planning Your Trips?

    How much does it cost to stay at a luxury villa in Puglia?

     While the bottom line dollars of a luxury rental villa are comparable to a luxury hotel, you'll experience a multigenerational family holiday where you can comfortably spread out, connect over delectable diners, and have a personal concerige team plan all the logistics of your stay.  You'll have private use of your villa's 5-star amenities, and access to their "Think Experiences" incredibly unique excursions. 


    The cost of the villas vary based on size and amenities offered.  They include options that range from accommodating a family of 4 to 24. The website includes real time up to date pricing, so you can compare which villa of your dreams is the most financially friendly for your group. 


    There are even a few ways enjoy reduced rates!

    Looking for a discount on a luxury villa in Puglia?

    • Mention COMPASSROAM when you call and book a villa for 2024 (before the end of October 2023), you'll receive a 5% reduction. You’ll also receive a 6-bottle case of wine at your villa. Contact a Thinking Traveller Villa Specialist today - this offer is not valid for online bookings.
    • Travel during the shoulder season (October-March) for reduced rates.  Many of the villas in The Thinking Traveller's collection would be perfect for a vacation away in the fall, and even during the holidays.
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    grandmother and son at l'argentiera the thinking traveller

    That's a Wrap

    In 7 beautiful, sun soaked Puglian days, The Thinking Traveller converted me from “hotel girl” into Villa Visionary.  The imaccuately appointed villas, impeccable amenities, gourmet meals, curated experiences, and personal conceirge services made us feel like we were staying at our own personal 5-star hotel.


    While The Thinking Traveller offers villas throughout the Mediterranean, Puglia was unlike any region of Italy I've experienced.  The idyllic fairytale towns each have their own feel and flair -- you may be lost in a maze at Locorotondo, walking the sea walls overlooking turquoise waters in Otranto, or laying next to a beach next to a cliffside town in Pogliano a Mare.  Millions of olive trees cover the countryside, and pine forests border the crystal clear coastal waters.  It's the perfect destination for a multigenerational holiday that everyone will remember for a lifetime.

    I hope this article has inspired your own family getaway to a Thinking Traveller villa in Puglia, Italy.  If you have any questions, or your own travel tips, please leave them in the comments below.  Also, don't forget to sign up for the monthly newsletter, packed with travel tips, upcoming news, and access to FREE destination itineraries.

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