A Curated Greek Journey: Athens, Mykonos & Santorini
A luxury 8 day itinerary for the discerning traveler
Day 1-2 Athens: Four Seasons Astir Palace
There is something almost magical about arriving at the Four Seasons Astir Palace. The moment you pass through the gates, the energy of Athens melts away and you find yourself surrounded by one of the most stunning private resort settings in all of Greece. With three private beaches and multiple pools, you’ll feel as though you’ve escaped to a private island without ever boarding a ferry.
Getting There:The resort sits about 45 minutes from the city center (plan accordingly to avoid going back and forth too often) -, but it’s only about 30 minutes from the airport, making it an effortless arrival or departure. I love positioning this property as your first night in Greece or, even better, as your final one or two nights before flying home.
Choosing Your Room Category: This is a property where I love to get extra involved in your booking. The resort is made up of two distinct buildings, each with its own personality and vibe, plus standalone bungalows. The experience can feel quite different depending on where you’re placed, and I’ll make sure we find the right fit for you. Regardless of your building, all guests have full access to every facility on the property.
Who This Property Is Perfect For: This is one I tend to recommend for guests who have already experienced Greece and are ready to slow down and truly savor it. If you want just one day of exploring Athens followed by complete relaxation in a world-class resort setting, this is your place. It’s also ideal at the end of a Greek island itinerary so you can decompress and depart feeling restored.
Don’t Miss: The resort recently added a stunning marina and an exceptional high-end shopping complex right on the grounds, featuring some of the world’s most coveted designers. It’s a lovely way to spend an afternoon. And most importantly: the cabanas. Situated right on the water’s edge, they are absolutely dreamy and among the most sought-after spots on the property. They book up well in advance, so this is one of the first things we’ll reserve once your trip is confirmed.
Day 2-5 Mykonos: Kalesma
If your idea of Mykonos is non-stop parties and crowded beaches, Kalesma will completely reframe the island for you in the best possible way. Sleek, sophisticated, and carrying the most beautiful thread of Asian influence throughout its design, Kalesma feels like a world apart. You’ll be tucked away in complete serenity, yet just ten minutes from the energy of Mykonos town whenever you want it. The balance is genuinely perfect.
Who This Property Is Perfect For: Kalesma speaks most loudly to couples. It has a romantic, intimate quality that makes it ideal for milestone celebrations (think: a 50th birthday, anniversary, or honeymoon). The on-site villa takes that privacy even further: it’s your own sanctuary with every amenity of the hotel at your fingertips. That said, the villa also works beautifully for a multi-generational group that wants togetherness without sacrificing privacy.
What Makes It Special: The details here are what set it apart. A chapel on the grounds. A weaving loom. These are the kinds of touches that make a property feel genuinely unique. You’ll find yourself lingering and noticing things all week long.
While You’re on Mykonos: A visit to Mykonos town is non-negotiable. You will wander the whitewashed lanes, discover the hidden corners, and soak in that iconic Cycladic beauty. I can even hire a photographer to capture iconic vacay photos of you and your travel companions. From there, Scorpios beach club is a must, as is an afternoon at Nammos Village for world-class dining, shopping, and people-watching at its most glamorous.
And here’s what I always arrange for my clients: private yacht charters to get between it all. I work with the very best on the island, and there is simply no better way to experience Mykonos than from the water.
Day 5-8 Mykonos to Santorini: The Crossing
Rather than a quick flight, I strongly encourage an all-day private yacht charter from Mykonos to Santorini. This is one of those travel experiences that becomes the memory of the whole trip. Expect picturesque stops to swim in the crystal-clear Aegean, water toys (think paddle boards, kayaks, etc), a spread of fresh mezze, cold rosé, and the dramatic arrival into Santorini by sea. There is nothing quite like it, and it is absolutely worth building into your itinerary.
Santorini: Canaves Epitome
I want to be upfront with you before we go any further: Canaves Epitome is not on the Caldera. For some guests, the iconic Caldera-edge view is the non-negotiable heart of Santorini, and if that’s you, we’ll look at other options. But if you’re open to hearing me out (and I hope you are) this property may just surprise you.
The sunset views at Canaves Epitome are, without exaggeration, among the very best on the entire island. And being just five minutes from Oia means you can slip into that magical village world whenever you wish, then return to a quiet, lush sanctuary that feels entirely removed from the crowds.
What Sets It Apart: Santorini is known for its dramatic, spare beauty with stark white and volcanic stone being iconic. Canaves Epitome feels like a lush counterpoint. The property is filled with an abundance of trees and greenery that is genuinely rare on this island, and it creates an atmosphere that feels both opulent and deeply peaceful.
Room Recommendations: My top pick for families or a pair of guests is the Aqua Suite, which is a two-bedroom option that is simply stunning. For multi-generational travel, the on-site villa is extraordinary, featuring the full privacy and atmosphere of a private villa, with everything the hotel offers right there when you want it.
Experiences Not to Miss:
Private Catamaran on the Caldera
Even if you’re not staying on the Caldera’s edge, you should absolutely experience it from the water. A private catamaran charter around the Caldera and past the volcanic islands is one of Santorini’s true highlights. There are dramatic cliffs rising above you, the chance to swim in volcanic hot springs, and some of the most otherworldly scenery in the Mediterranean. I’ll arrange everything privately so you aren’t sharing the experience with a crowd.
Curated Wine Tasting at the Vineyards
Santorini’s wine culture is far more serious and fascinating than most visitors expect. The island’s volcanic soil produces Assyrtiko grapes unlike anything grown anywhere else in the world, and a private, curated tasting at one of the estate vineyards is a wonderful way to understand the island on a deeper level. We’ll put together an experience that goes well beyond a standard tasting. Think: intimate, behind-the-scenes, and paired with the right setting as the afternoon light falls over the vines.
Private Guided Hike: Fira to Oia
This is one of the great walks in all of Greece, and doing it with a private guide transforms it completely. The path winds along the Caldera rim for roughly 10 kilometers, passing through whitewashed villages, ancient ruins, and offering views that photographs don’t do justice. Your guide will bring the history, geology, and culture of the island to life along the way, and we’ll time it so you arrive in Oia perfectly positioned for sunset with a table waiting for you.
This itinerary is built for guests who want Greece done beautifully – not rushed, not generic. Every booking, transfer, yacht charter, and cabana reservation will be handled personally.
