Skipping Santorini

Summer is the classic season for group getaways, a time when families, couples and groups of friends traditionally decamp to a relaxing destination for some QT and R&R. And as more travelers are discovering, for the ultimate, private space in which to gather your crew, few options beat renting a villa.

“Villas are the ideal accommodations for group vacations, as they provide the intimacy of a home, with shared spaces for gathering and private areas for everyone in your party,” says Dimitris Giannakopoulos, cofounder of White Key Villas, an Athens-based company specializing in luxury villa rentals. “Plus, everything from the transportation and experiences to the chef-prepared meals are personalized to the guests’ needs and lifestyle, and the service is high-end. Even at the best hotels in the world, you still have to operate on their schedules, but a villa is all yours, so the experience can be as flexible and low-key as you want—whether that means enjoying your private beach or just lounging around in your pajamas.”

Giannakopoulos says that Greece is a particularly standout choice for a villa vacation, even for travelers who feel like they’ve “done” the destination. “There are still plenty of beautiful, sophisticated Greek islands where there is no mass tourism yet, but where the hotel options or quality of service may be limited—so private villas are the best bet for luxury travelers wanting to experience those places. In these stunning locations, sometimes the villa itself is the main destination.”

Of course renting a whole home comes at a price—most White Key properties cost between €10,000 and €30,000 per week, though some come in at over €100,000 per week. The villas typically have a one-week minimum stay (some a two-week minimum during July and August, the high season months), and that cost includes services listed in property descriptions, fees and taxes.

In addition to diving deep into a client’s travel requirements (so they can do everything from plan for gluten-free meals to add more sand to a beach—which they’ve been asked to do), the White Key Villas team helps match guests to the best Greek island for their style and needs. Read on for their Worth picks for the best islands—and top villa picks—for three types of group travel.

For Families/ Multi-Generational Travel

The Islands: Paros and Antiparos

This easy-to-access combo in the Cyclades island group affords the opportunity to enjoy two destinations in one go. Just a 30-minute flight from Athens, larger Paros has got everything from notable Crusader-era Byzantine churches to ancient marbles quarries (it’s said the marble used to make the Venus de Milo came from the island), along with charming port towns lined with cafes and boutiques. The nearly 76-square-mile spot is also full of beachfront homes, making it ideal for families. Many of the larger beaches offer an array of watersports (including surfing), horseback riding and places to enjoy a relaxing stroll, ice cream in hand. If you’re feeling more active, there are historic villages to explore (like the cobblestoned, hilltop Lefkes), excellent restaurants to enjoy (particularly around the port in Naoussa), and even wineries to tour (stop into Moraitis for a tasting.) But overall, the vibe is relaxed. “This is not the Mykonos mayhem,” says Giannakopoulos.

About a five-minute ferry ride away, Antiparos—population about 900—may have its celebrity fans (Tom Hanks and Rita Wilson have a home here), and the one main town its fair share of chic shops and breezy eateries along the pedestrian lanes, but the feel is decidedly “old-fashioned summertime,” making this another family favorite. In between beach time, hop a private boat to visit the archeological site of Despotiko, once home to an ancient sanctuary dedicated to Apollo and Artemis. On the way back, your skipper can regale little ones with stories of the pirates who used the surrounding caves before depositing you at Pipinos Taverna for some of the freshest seafood around.

Villa Picks

On Paros, the five-bedroom Villa Jasmine sits on a protected natural preserve on the island’s secluded south coast, surrounded by olive and fruit trees and blooming gardens. While grand and gracious, the décor is uncluttered and spartan—so there’s no worrying about kids knocking over precious objects. There’s also a well-stocked chef’s kitchen where both home cooks and private chefs will feel comfortable, a new pool just off the cushy main living room and direct access to a nearly private cove.

On Antiparos, the impeccably-designed Villa Melissa is a Mediterranean-style estate with 11 bedrooms spread out over a main house, master suite and guest cottages (including quirky kids and nanny quarters.) There are both indoor and outdoor lounging and dining areas, but you’ll never want to be far from the sweeping sea and island views best enjoyed from the cushy loungers around the emerald-tiled pool. Access to a semi-private beach and an attentive house staff rounds out the perks.

For a Group of Friends

The Island: Hydra

For generations, this island in the Saronic group has been the favorite getaway of artists, musicians and prominent Athenian families—as evidenced by the beautiful 18th- and 19th-century mansions that frame its harbor and the cosmopolitan flair in its main town. The island has remained blissfully suspended in time, thanks to preservation laws that limit new building and car-free streets traversed only by donkeys. A group of friends traveling together will find plenty to please any interest or speed, from lots of dining, shopping and nightlife options to annual sailing and yacht regattas and a lengthy roster of international-caliber art shows (Hydra is also known as “the Art Island.”)

Villa Pick

Perched on a cliff about 130 feet above the coast and enjoying the endless sea and forest views that position affords, Villa Mirkella is an ideal choice for groups that want to hang out together, but also value independence. (It’s also housed kings and prime ministers, so the privacy levels are top-notch.) The gray marble main house holds four bedrooms, gathering spaces, a lounger-ringed pool and a stand-alone kitchen convenient for al fresco dining, while a guest house, built in traditional Greek style, has two more bedrooms with separate entrances. A short walk brings you to a quiet beach, while the town of Hydra is a quick sea taxi ride away.

For Romance

The Island: Patmos

This remote spot in the Dodecanese chain is known as “the Holy Island” for its significant religious sites, which include the ancient Cave of the Apocalypse and the UNESCO-listed 11th-century Monastery of Saint John the Theologian. Perhaps it’s thanks to the mystical feeling that pervades the island, but Patmos has also become a favorite with an international sophisticated set, who come for the scenic beaches (including Lámpi, lined with colorful pebbles), yacht-lined harbor and the picturesque capital of Chora, with its cobblestoned streets and traditional whitewashed houses.

Villa Picks

While most of White Key’s villas have multiple bedrooms, couples visiting Patmos can snuggle up in The Honeymoon Suite, a charming one-bedroom apartment set in the center of Chora. Behind an 18th-century exterior lies a private courtyard, vintage romantic interiors, a second-level mezzanine bedroom and a roof terrace with views of the monastery and the Aegean Sea.

If you’re planning to host friends during your vacation, upgrade to  Villa Elli, a five-bedroom spread (also in Chora) that melds traditional Patmian architecture with contemporary décor and a modern art collection. The highlight: a spacious rooftop terrace with cushy seating, candles and postcard views.

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