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Discovering La Dolce Vita: Why a Luxury Villa in Puglia is Your Ultimate Getaway
by Guest Author
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Discovering La Dolce Vita: Why a Luxury Villa in Puglia is Your Ultimate Getaway

Discovering La Dolce Vita: Why a Luxury Villa in Puglia is Your Ultimate Getaway
Jillian McComiskey is a luxury family travel writer for the website Compass Roam. In this guest article, Jillian explores Italy's hidden gem, Puglia, and why it's perfect for the ultimate luxury getaway.
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By: Jillian McComiskey

Jillian McComiskey is a luxury family travel writer for the website Compass Roam. If you’re interested in learning about her specific villa experience, you can read more about her stay at Thinking Traveller’s L’Argentiera villa.

Selecting the perfect villa can feel like hitting the jackpot, especially when it's set against the backdrop of Puglia -- Italy's rising star of travel destinations.

These luxurious high-end homes offer far more than lavish amenities; they serve as your private enclave in a region celebrated for its authenticity, natural beauty, and growing popularity.

Even if you've ventured to Italy many times, I can promise you, you have more to see.


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Set aside any preconceptions about what Italy looks like, and leave your mind open to something new. Unlike the romantic canals of Venice or the art-filled streets of Florence, Puglia exudes a distinct allure. In Gallipoli you'll think you've landed in Greece, with its labyrinth of streets that reflect its Hellenistic past. At times, walking the streets of Otranto will feel like the historic alleys of Jerusalem. A few days later you'll be strolling the streets of Alberobello, questioning if you're in a fairytale. And when you hit the beach, you'll swear water is only this clear in the Maldives.

Puglia's location in the heel of Italy's "boot" has led to a layered past of Greek, Roman, Byzantine, Middle Eastern, and even some African influences. But, here, you're not a tourist—you're an explorer rediscovering 'la dolce vita' in an unspoiled haven, with layers of history reflecting all around.

In recent years, the travel world has seen a surge in luxury villa rentals, particularly those that offer the perfect blend of home-like comfort and high-end opulence. For globetrotters with a taste for the extraordinary, nothing comes close to the curated experiences provided by The Thinking Traveller. This is not merely a rental company; it's a gateway to personalized luxury, offering villas that are architectural masterpieces equipped with five-star amenities. Imagine lounging in your private infinity pool overlooking olive groves, or sipping local fine wines in a centuries-old farmhouse, updated with every modern convenience you can imagine.

Staying at a Thinking Traveller villa guarantees the luxury and comfort akin to a 5 star hotel, coupled with the privacy you can usually only find at an exclusive resort. Their seasoned team curates a list of select villas tailored to align seamlessly with your family’s specific vacation aspirations, leaving you wishing you could extend your trip just to experience them all. Let's delve into what a vacation looks like when you hand over the reins to The Thinking Traveller's "Puglian Pros."


Discovering Italy's Hidden Gem: Puglia

Imagine an Italian landscape that defies any preconceived images of Italy —this is Puglia, a region that seems to dwell in its own universe despite being deeply rooted in a seductive slice of Italian peninsula. While Tuscany is celebrated for its rolling hills and vineyards, and Rome is revered for its historical grandeur, Puglia offers a different, but equally intoxicating flavor of "la dolce vita." Here, you’ll drive through the countryside where tens of millions of olive trees surround you – some dating back 3,000 years to Roman times! The ancient groves stretch as far as the eye can see. Unlike the well-trodden tourist paths of Venice or the bustling streets of Milan, Puglia's allure lies in its quiet majesty of small towns with maze-like streets, surrounded by rolling hills. The region is a kaleidoscope of contrasts: from the mysterious, conical-roofed trulli houses of Alberobello to the pine forests that border beaches reminiscent of the Maldives.

Puglia is also refreshingly authentic. You can see it in the centuries-old "masserias," traditional Puglian farmhouses that have been preserved and sometimes converted into charming guesthouses or lavish villas. The local cuisine, too, is unapologetically genuine; orecchiette, or handmade pasta resembling "little ears" is made fresh on the streets of Bari every morning by the nonnas who have lived there their entire lives. Puglia is in fact where the Italians have vacationed themselves for years, knowing that it's Italy's best kept secret.


Why a Luxury Villa in Puglia is Your Perfect Vacation Home

A luxury villa in Puglia is not merely an accommodation -- it's an immersive experience that offers comfort and exclusivity. You'll be staying in your own oasis, while having access to bespoke concierge services, and amenities thoughtfully selected for multigenerational enjoyment.

Your Own Slice of Paradise

Picture this: waking up to the sounds of the Adriatic Sea where you begin each morning with a quick dip. At L'Argentiera, a villa in Castro, Puglia -- you can do just that. You can go from "bed to beach” in 60-seconds, or curl up on a lounge chair on a deck that overlooks the sea. When you're ready, you'll return to find homemade pastries, fresh fruit, coffee and tea spread out on a table before you. You even have a personal chef waiting to whip up any orders!

Multigenerational-Friendly Villas with World Class Amenities

The age of multigenerational sojourns has taken root. Not only do travelers have their sights set on renting luxury villas, but they want to experience all the adventures with their entire family -- as many grandparents, uncles, aunts and cousins who'll say yes!

Perhaps you're traveling with a large group, ages ranging from 2-72. You know that the kids will yearn to splash in a pool all day, and that the adults will want to begin each morning with a swim in the sea. The grandparents will want to enjoy a book in a comfortable chair, while the teenagers check out the game room. You also may have a few foodies along for the ride, who are set on trying a culinary experience or dining in some of the best local restaurants.


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With layouts ranging from cozy retreats for couples to expansive estates for large family get-togethers, The Thinking Traveller's Puglia villas cater to everyone's needs. Young children will find endless amusement, while older family members can have a moment of solitude. The gardens at Masseria Belvedere double as kids' playgrounds, while athletic teenagers can play a friendly tennis match Villa Elia – perhaps taking on Mom and Dad. Grandparents can savor the tranquility of L'Argentiera's open-air terrace. And let's not forget—the private pool is a crowd-pleaser for all ages. In this home away from home, there's something to delight every family member.

Uncompromising Value

For the discerning traveler, value is measured not in numbers but in experiences and quality. When you opt for a luxury villa in Puglia, you are investing in an unparalleled experience that offers more than just a place to stay -- it’s truly unforgettable.

Each villa is a work of art, often blending historic architecture with modern amenities, providing an experience that is as enriching as it is luxurious. Furthermore, the personalized services—from private chefs to bespoke excursions—amplify the value of your stay, allowing you to explore Puglia's authentic culture without compromising on comfort. It's not about spending less; it's about gaining more—more exclusivity, more customization, and more meaningful experiences.


The Thinking Traveller – Your Key to Unlocking Puglia

When it comes to tailoring a vacation that transcends the ordinary, The Thinking Traveller stands in a league of its own. Recognized for its unparalleled commitment to luxury and exclusivity, this distinguished company takes the Puglian villa experience to unprecedented heights. It's not merely about finding a place to stay; it's about crafting an entire journey that caters to your discerning tastes. With The Thinking Traveller, you gain access to a handpicked collection of the region's most lavish villas.

But what truly sets this company apart are the layers of customized service—be it an exceptional Local Specialist team available round the clock, a cadre of local chefs who turn each meal into a gastronomic event, or an array of one-of-a-kind experiences designed to bring Puglia's authenticity right to your doorstep. You'll return telling your friends about something they've never quite heard of – it’s mysterious and magical all at the same time.

Curated Collection of Villas

Each luxury villa has its own unique history -- its own unique amenities that secured them a spot in the exclusive Thinking Traveller collection. In fact, their standards are so discerning that only 1% of villas which apply to be a part of the collection receive a stamp of approval. Once a villa appears in their collection, you won't turf it up on any other rental website out there. Here's a small preview of some of the unforgettable properties in Puglia:


Castello Caprarica

Imagine stepping into a world where history meets modern luxury, as you make your grand entrance into Castello Caprarica - a castle from the 1600's. This opulent villa offers an enchanting blend of antiquity and contemporary amenities. Stone walls of the past surround the villa, but cutting-edge technology guarantees modern day comfort. Relax in the inviting pool, while the little ones run through the gardens reenacting their favorite fairytale movies. As a night chill descends, you can curl up next to the giant fireplaces, which used to be located in the castle chapel. At any point, you can step outside the castle walls and you're already in the town of Tricase, which has plenty of shops and delicious restaurants.

Book Castello Caprarica


Trulli Andrea

Nestled amidst rolling hills and ancient olive groves, Trulli Andrea offers a unique blend of traditional architecture and ultra-modern comfort. The iconic Trulli cones of this property stand as a testament to Puglian heritage, offering a surreal, almost fairy-tale-like escape. It’s also one of the best properties for multigenerational trips too, accommodating up to 12 guests with plenty of outdoor lounging areas, including two pools with panoramic views of the countryside. Guests can also explore the spacious grounds before heading into town. You’re only 10-15 minutes from some of the cutest storybook towns – Martina Franca, Ostuni, Ceglie Messapica, and Locorotondo.

Book Trulli Andrea


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With its seaside location overlooking the rocky coastline and azure waters of the Adriatic Sea, L'Argentiera offers an unparalleled experience. This sleek, modern villa comes with expansive terraces, an infinity pool that seems to blend into the sea, and floor-to-ceiling windows that invite the outside in. The interior is equally stunning, with white washed walls mirroring that Santorini look from across the sea. At night you can enjoy homemade pizzas made in the authentic stone oven by a local pizza master, while watching the sun dip below the horizon, casting orange glows all around.

Book L'Argentiera

Your Personalised Local Specialist services

Beyond the exceptional villas in The Thinking Traveller's portfolio, what truly distinguishes this company is its personalised concierge service and dedicated local teams.

Your journey with The Thinking Traveller begins with a phone call, where you can describe the “wish list” of everyone coming along – perhaps a pool is a must-have, or proximity to town. This information will help your Villa Specialist curate a list of villas for you to choose from.

The Thinking Traveller’s team intimately knows every villa and its staff. They’ve stayed as overnight guests. They’ve tasted the meals you’ll enjoy in your al fresco seat by the sea, and they’ve embarked on the very same private boat tours along the coast. They have first hand knowledge of where you're staying and the experiences that exist nearby.

If you're searching for the perfect property to host a multigenerational gathering, they may recommend Masseria Canali or Villa Elia. Masseria Canali has spacious courtyards and gardens, a lavish pool, and a bunk bed suite that will make you wish you were 8 years old again. Villa Elia's massive property includes tennis courts, steam/sauna complex, billiards table, and an outdoor gym. If you're planning a getaway with friends and looking for a property that is more modern and sleek, they'd instead introduce you to Villa Eterea - a stylish villa that has sweeping panoramic views of the coastline, stunning infinity pool, and home gym.

Once you've chosen a property, your dedicated Experience Specialist will assume responsibility for orchestrating a flawless itinerary. From coordinating airport transfers to arranging car rentals to be delivered directly to your villa, they'll manage all the logistics. They will also secure exclusive restaurant reservations and curate unforgettable experiences for you and your loved ones. Acting as your liaison for all pre-arrival planning, your Specialist ensures that every detail is meticulously taken care of. Upon your arrival, a local team steps in to elevate your stay further. They will organize daily housekeeping and enlist local culinary masters to craft bespoke meals within the comfort of your villa—be it freshly baked bread adorned with homemade marmalade or artisanal pizzas tailored to your taste from your villa's own pizza oven. While the younger family members delight in the freedom to explore, adults can relish the opportunity to reconnect and unwind."


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Exceptional Experiences for the Whole Family

The Thinking Traveller doesn't merely curate an extraordinary portfolio of luxury villas in Puglia -- they also carefully handpick exclusive experiences that are made available solely to their discerning clientele. If Puglia is on your travel radar, you simply cannot overlook their bespoke offerings.

The castle-based cooking class stands as an unmatched experience that transcends the typical culinary workshop. Get ready for a meal and a mystery all wrapped together in one unimaginably awesome night. As you step into the historic 15th-century estate, the world beyond its grand walls vanishes, replaced by the intoxicating aroma of jasmine and roses. Orange trees and ancient fortifications envelop you, making it feel as if you’ve landed right in the middle of a movie set - part Downton Abbey, part Game of Thrones (the scenic parts, that is).

Guided through the estate’s architecturally stunning interiors, adorned with intricate tapestries and vaulted ceilings, you'll eventually ascend to the rooftop kitchen. Here, a gourmet chef instructs you in crafting seasonal gourmet dishes—a summertime feast might feature creamy pasta sauce with fried zucchini, a succulent roasted eggplant caponata, and a decadent homemade chocolate mousse. You'll dine under a canopy of stars while the younger family members are immersed in a living fairy tale, casting themselves as valiant princesses and dragon-slayers in their imaginations.

The adventure continues the following day as you embark on a private yacht, where you'll jump into crystalline waters, explore towering sea caves, and even take the SeaScooter for an underwater spin. The dads may have a little too much fun pretending they’re James Bond. Back on deck, you can relax on plush chaises and enjoy a fresh pasta lunch and refreshing drink.

Yet, these are merely the tip of the iceberg when it comes to the “Think Experiences” collection. Additional curated activities range from serene bike rides along Puglia’s azure coastlines to off-the-beaten-path hiking adventures, and even a behind-the-scenes look at artisanal cheese-making in Alberobello.

When to Reserve Your Villa in Puglia

Contemplating the ideal moment to reserve your idyllic villa in Puglia through The Thinking Traveller? Several key considerations will guide your decision-making process.


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1. The Season Matters

Are you envisioning sunny beaches of summertime? Or are you captivated by the idea of autumnal harvest festivals, celebrating the region's olives and grapes? Perhaps the serenity of a winter visit, benefiting from Puglia's mild climate and reduced tourist flux, aligns more closely with your aspirations. The first step is to pinpoint the season that resonates with your family's desired Puglian experience, a task in which your Villa Specialist at The Thinking Traveller excels.

2. Start Early, Score Big.

If you're eyeing a particular villa, and your preference is to visit during the high season (May-September), then it's recommended to reserve the property 6-9 months in advance. Puglia may not be as popular as Amalfi or Tuscany just yet, but it’s becoming one of the hottest destinations in Europe – everyone wants to go! As we transition into autumn, don't let your summer planning zeal wane; this month is, in fact, the optimal time to reserve your Puglian summer haven, often with the added enticement of an exclusive discount.

3. Off-Peak Perks.

If your dates are flexible, an off-peak retreat holds its own unique appeal, offering diminished competition for the most sought-after properties—sometimes even at preferential rates. A Thinking Traveller Specialist can provide expert recommendations for villas situated near vibrant towns that maintain their commercial and culinary liveliness even in the shoulder season. Properties such as Masseria Palmieri, Palombara Piccola, and Trulli Andrea are strategically located, offering convenient access to enchanting towns like Alberobello, Polignano a Mare, Monopoli, and Locorotondo.