Luxury Greece Vacations & Tailor-Made Trips

Why choose Black Tomato for Greece luxury travel

It took Odysseus ten years to cross the islands of the Aegean. But he made it.

There is a small, twisted olive tree in the grounds of the Temple of Poseidon. Here, on the cliffs of Sounion, you can watch the setting sun like nowhere else on earth: burnt orange, the sea singing with myth. Since 2005, we’ve been crafting luxury Greece vacations that return to places like this – getting to know each lump and rivet in the landscape. We want you to feel the same pull that made 18th-century travellers like Lord Byron yearn for this country: its poetry, its food, its warmth. Whether you’re sailing the Cyclades or dining on the island of Spetses, our private tours of Greece are shaped entirely around you. This is Greece luxury travel on your terms.

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What to see and do in Greece

If there’s more you want to add, just ask. Our Greece specialists can plan it for you.

EXPERIENCE GREEK CULTURE

Explore the home of the gods and delve deep into the mythology that underpins this Mediterranean paradise’s welcoming cities, white-stone ruins, and secluded isles. Fall in love with Greece whether you’re café-hopping in Athens, enjoying the stunning sunsets of Insta-perfect Santorini, or seeking seclusion away from the tourists on Paros island.

TOUR SANTORINI BY HELICOPTER

Care to make a glamorous entrance on Santorini? Embark on a private helicopter transfer from Mykonos across the sapphire water to sunny Santorini. Circling over the impressive white and blue landscape, you’ll catch the sun rising over the sloping mountains before admiring the feast of colour that spills over the iconic architecture below. This is how you visit Greece in style.

A LUXURY STAY IN MYKONOS

Mykonos is an island destination that never fails to remind us of what we love about Greek culture. It’s an irresistible combination of al-fresco tavernas, atmospheric beach clubs, and bright blue waters. A care-free, bohemian vibe has penetrated the island’s luxury scene, placing Mykonos as the reigning destination for experiencing Greece in style and sophistication on your VIP vacation.

SECLUSION IN PAROS

Straight out of an Aegean fairytale, this remote isle offers intriguing history, enchanting beaches, and awe-inspiring landscapes, complemented by the scent of native jasmine and bougainvillea. Whether you explore the maze of intricate side streets of Parikia, the whitewashed, marble town of Lefkes, or charming marinas of Naoussa, we’ll make sure there’s room to sit with the locals and enjoy fresh, local dishes. Next, visit one of the remarkable golden beaches dotted along the island’s coast, from Santa Maria to Kalogeros, and try your hand at kitesurfing in the pristine bay.

ISLAND HOP TO GREECE’S HIDDEN GEMS

Part of our attraction to Greece comes from the idea that some islands – and by some, we mean many of the 6,000 islands that Greece is comprised of – are still free of crowds and untainted by mass tourism. Of course, the traditional Greek vacation destinations are favorites for a reason: Crete, Corfu and Rhodes offer sun-drenched family fun, but islands like Folegandros and Sifnos feel like a couple of our best-kept secrets. You don’t want to miss out on these smaller, authentic Greek islands, known for their ancient villages, freshly-caught seafood, and rustic boutique hotels. Want to charter a private yacht to see them all? Just ask.

EXPLORE THE ANCIENT RUINS OF THE ACROPOLIS

Buried in culture, the Acropolis of Athens, the Temple of Parthenon, and Erechtheum are goldmines of history. Join a local archaeologist and explore the ancient ruins, immersing yourself in the magnificence of the structures on a private tour. You’ll also be guided through the old town towards Lycabettus Hill where you can spend as long as you need looking at the modern city landscape and the ruined remains of the ancient civilization.

GASTRONOMIC EXCELLENCE IN SIFNOS

Discover the art of traditional Sifnos gastronomy and become a culinary genius with the guidance of Elies Resort’s master chefs. Create your own version of the local lamb mastelo dish and master the art of clay cooking, learning how each ingredient offers something different to the dish and your palate. This is a cooking class you’ll never forget: a Mediterranean education you can serve up at dinner parties for decades.

Luxury Travel in Greece

On your luxury bespoke trip to Greece, you’ll be shown around by some of the warmest and most knowledgeable guides this mesmerising country has to offer. Whether that’s uncovering the historic secrets of the mighty Acropolis on a private tour led by an expert archaeologist or learning the art of Sifnian cuisine with a local chef in their own home. If you wish, we’ll even arrange for private helicopter transfers between the dazzling array of Greek islands before you embark on your very own odyssey; gliding over tranquil waters in search of tucked-away bays on a luxury yacht. Between relaxing in your own ‘cave pool’ in Santorini and admiring the Parthenon from the balcony of your suite in an Athenian neoclassical mansion, you’ll enjoy gourmet picnics, private wine tastings, and world-class spa treatments.

The best of Greece

FAQs

Everything you need to know about visiting Greece with Black Tomato

When is the best time to visit Greece?

Greece rewards visitors in almost every season, but May to June and September are the sweet spots — warm enough for swimming, calm enough to actually enjoy it, and far more breathable than the peak-summer rush. July and August bring the energy, the heat, and the crowds; with private villa access and tailor-made experiences they’re entirely manageable, but it’s worth knowing what you’re signing up for. October is quietly one of the best months of all – the sea holds its warmth, the light turns golden, and the historical sites feel almost entirely your own. Winter suits the culturally curious: Athens and the mainland stay open and atmospheric year-round, stripped of the tourist noise. For hikers and slow travelers, March and April offer wildflowers, mild temperatures, and near-total solitude.

What are the best Greek islands for a luxury vacation?

Santorini and Mykonos are just the beginning. Folegandros delivers dramatic clifftop villages with a fraction of the foot traffic. Milos offers volcanic beaches unlike anything else in the Aegean. Spetses carries an old-money Athenian elegance that feels entirely its own. For genuine seclusion, the smaller Dodecanese islands are hard to beat. Patmos in particular pairs world-class hotels with the kind of privacy that’s increasingly rare in the Mediterranean.

Can you combine Athens with the Greek islands?

Absolutely, and it’s one of the most rewarding ways to experience Greece. A well-designed itinerary might open with two nights in Athens, taking in the Acropolis and the city’s quietly excellent food and design scenes, before moving on to the islands by ferry, helicopter, or private yacht. Whether you’re visiting two islands or five, every transition is handled seamlessly.

What's included in a private tour of Greece?

Our private Greece itineraries can include accommodation, private transfers, and tailor-made experiences — skip-the-line archaeological access, private sailing days, chef-led cooking classes. You’ll have a dedicated travel expert from the start and 24/7 support on the ground. Flights are typically excluded but can be arranged if you’d prefer everything in one place.

Why book a luxury Greece vacation with a travel specialist?

A specialist like Black Tomato unlocks access you won’t find online: private after-hours Acropolis tours, tables at restaurants with no website, the right captain for a Cyclades sailing day. If anything changes — flights, weather, plans — there’s someone ready to pivot instantly. You spend your trip experiencing Greece, not planning it.

Is Greece a good honeymoon destination?

Greece is one of the most naturally romantic honeymoon destinations in the Mediterranean — and not just for the obvious reasons. Santorini’s cave hotels with infinity pools above the caldera. Private sailing days through the Cyclades with lunch in a hidden cove. A candlelit dinner at a restaurant nobody else knows about on Spetses. An after-hours tour of the Acropolis, just the two of you and a guide who’s spent years learning the stories. Greece does romance with a particular depth that the more obvious honeymoon destinations often can’t match. For a dedicated guide to planning your Greece honeymoon, see our Greece honeymoon guide.

How much does a luxury vacation in Greece cost?

The cost of a luxury Greece vacation with Black Tomato ranges in cost based on your travel preferences since all trips are customized. Pricing varies based on location(s), time of year, hotels, transfers, experiences and more. For an accurate quote built around your specific travel dates and preferences, submit an enquiry and we’ll connect you with one of our Greece Travel experts.

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