Flirting with Greece: Where to Start (and Why You’ll Stay)
We’ve all seen the gorgeous photos of Greece: whitewashed Cycladic houses and blue domes spilling down volcanic cliffs, the startlingly azure Aegean stretching endlessly beyond. The scent of grilled octopus hangs in the air, ferry horns echo across the water, and suddenly you’re living inside a dream.
But here’s the truth: not all Greek islands are created equal, and the order in which you visit them can make or break your trip.
After exploring Athens, Mykonos, Santorini, Naxos, Paros and Crete this year, I’ve learned what I’d tweak, what I’d repeat, and how I’d plan it differently if I were designing your dream Greece itinerary.
If it’s your first time in Greece, plan on no fewer than 10 days. Anything shorter is doing yourself a disservice. I typically recommend starting in Athens, then hopping to Mykonos, Santorini, Naxos, and finishing in Crete. Each island has a distinct personality, and there truly is a perfect fit for every travel style. We of course plan your tour based on the best flow for ferries and transport, so when you are ready, we can chat through that.
Below is what I love about each stop, where to stay, and what’s worth prioritizing. And remember—this is just a taste. Thanks to my extensive travels and close relationships with hoteliers, local guides, and restaurateurs, I create elevated itineraries that often include upgrades when available, complimentary breakfast, exclusive experiences, and behind-the-scenes access.
ATHENS: ANCIENT MEETS EFFORTLESS
Spend two nights here to fully appreciate the city’s history and energy. Short on time? One night still works—we’ll make sure you hit the essentials, namely the Acropolis and a guided food tour.
Where to stay:
- The King George or The Dolli for a central location near Syntagma Square and the Acropolis
- One&Only Aesthesis on the Athenian Riviera for a more relaxed, seaside experience
The One&Only feels like a Mediterranean hideaway, with private gardens and plunge pools in every bungalow. It’s a bit of a drive from the main sites, but it strikes a beautiful balance between city buzz and coastal calm. I could have moved in.
SANTORINI: THE ISLAND OF POSTCARDS
Those iconic Greece photos you’ve seen everywhere? Most were taken here.
Santorini is romantic, dramatic, and carved from lava rock—perfect for couples and dreamers, but not ideal for strollers or small children.
Where to stay:
- Canaves Oia Suites or Andronis Luxury Suites for the classic cave-hotel experience in Oia
- Andronis Arcadia or Canaves Epitome for more space, easier access, and private pools
A quick heads-up: many cave hotels involve 100+ steps, often without railings, and most don’t allow children.
Don’t miss: A private catamaran cruise around the caldera. Swim near the White Beach, soak in volcanic hot springs, and watch the island glow pink at sunset. It’s unforgettable—and yes, I’ll arrange it for you.
NAXOS & PAROS: THE SOUL OF THE CYCLADES
If Santorini is romance, Naxos is heart.
Authentic, warm, and unpretentious, Naxos offers some of the best food in the Cyclades and a truly welcoming spirit.
Where to stay:
- Sundunes on Plaka Beach, steps from beach bars and tavernas
- Laguna Coast Resort for families or travelers who want extra space and kitchens
I loved everything about Naxos and will absolutely return.
How to spend your time:
- Explore mountain villages
- Taste olive oil in Kaloxylos
- Sip citron liqueur at Promponas Estate
- Ferry to Paros for the day to wander chic Naousa or charming Lefkes
If Paros steals your heart, it’s easy to base yourself there next time. When you’re ready, I can arrange stays at Andronis Minois, Cosme Cove, Parilio, or Avanti Mare on Piperi Beach.
CRETE: DEPTH AND PERSONALITY
Crete feels different—bigger, wilder, and layered with history. I recommend ending your trip here to slow down and savor it.
Important to know: Crete is large, and travel times between regions can be longer than expected. While Heraklion and Chania may look close on a map, the drive between them takes several hours. It’s far more rewarding to focus on one region rather than trying to do both.
Heraklion
- Energetic and urban
- Easy access to the Palace of Knossos and major museums
Chania
- Atmospheric and scenic
- Venetian harbor, pastel Old Town, beaches, and gorges
Where to stay:
- Daios Cove for families (saltwater plunge pools, multiple restaurants, and a standout kids’ water program)
- Minos Beach Art Hotel for couples or families with older children who appreciate design
- Rosewood Elounda (opening 2026), already on my radar
Pro tip: Don’t skip the olive oil experience at a family-run press. You’ll roll up your sleeves and press oil the traditional way—it’s harder than it looks and completely worth it.
Important to know: Crete is large, and travel times between regions can be longer than expected. While Heraklion and Chania may look close on a map, the drive between them takes several hours. It’s far more rewarding to focus on one region rather than trying to do both.
MYKONOS: BENEATH THE BUZZ
Sure, Mykonos has a reputation for late nights and legendary beach clubs, but there's so much more to savor here. I love wandering along sun-faded lanes, past iconic windmills, into Mykonos Town for boutique shopping (one can always use more linen vacation wear in the islands!). Yes, the beach clubs are fabulous, but the island also surprises with refined stays like Bill & Coo Coast (perfect for beach lovers), Mykonos Grand Hotel & Resort, which is an excellent option for families thanks to spacious suites and a calmer vibe, and the very on-trend, but elegantly understated Kalesma Mykonos. A private cruise to Delos Island for history and contrast to the island's glamour is a must. And for those who like to plan ahead: A Four Seasons opening mid-2026 makes this island one to watch.
GETTING AROUND THE ISLANDS
A few things to keep in mind when island hopping:
- Ferries are scenic but fast-paced—be ready to board quickly
- Flights between islands use small planes, so pack light
LET’S PLAN GREECE YOUR WAY
Whether this is your first visit or a pre- or post-cruise escape, Greece has a rhythm that’s impossible to resist. While planning a multi-island itinerary can feel overwhelming, that’s where I come in.
Every transfer, ferry, hotel check-in, dining reservation, and special experience is handled seamlessly, so you can actually relax and enjoy the journey.
All itineraries are fully customized to your interests and travel personality. What you’ve read here is just a sampling of the destinations, hotels, and experiences I recommend.