Most people already have a picture of Greece in their heads, and it's usually the wrong one. The Greece they imagine (overcrowded Santorini, party-hard Mykonos, backpacker hostels) is only the surface of one of the most sophisticated places to travel in the Mediterranean.
How should you plan a luxury trip to Greece? Give Athens at least two days, then pick two islands that match your energy: Santorini for romance and volcanic wine, Mykonos for beach clubs and great dining, Crete for food and history. Go in May, June, September or October, and fly between islands instead of taking slow ferries.
Key facts
- Best months: May to June and September to October. September is our favorite.
- Getting around: island flights run about €50 to €150 (as of October 2026). Athens to Mykonos or Santorini takes under an hour by air.
- Where to stay: Hotel Grande Bretagne in Athens, Cavo Tagoo or Kalesma on Mykonos, Blue Palace or Domes of Elounda on Crete.
- Caviar trip:The Greece Experience, 9 days across Athens, Santorini and Mykonos, planned privately around your dates.
As a 6X Condé Nast Travel Specialist who has organized luxury group experiences across 7 continents, I can tell you that Greece done right is one of the most rewarding trips you'll ever take. "Done right" means knowing which islands match your energy, which hotels actually deliver, and which experiences are worth the money. This guide covers all of it.
Why Should Greece Be on Your Travel List in 2027?
Greece has poured money into high-end hotels over the last decade. The country that used to mean budget Mediterranean holidays now has a deep bench of five-star resorts, from the Athens Riviera to Crete.
Where Should You Go in Greece?
Photo: Caviar in the Air
Athens: Where It All Began
Don't skip Athens. So many travelers treat it as a layover city: fly in, see the Acropolis, catch a ferry. That's a mistake. Athens has become one of Europe's most exciting food cities, with a contemporary art scene to match.
Stay at the Hotel Grande Bretagne for old-world elegance with Acropolis views from the rooftop, or Four Seasons Astir Palace on the Athens Riviera for a beach-resort feel close to the city.
Photo: Courtesy of Four Seasons Astir Palace Hotel Athens
Photo: Courtesy of Four Seasons Astir Palace Hotel Athens
Santorini: Beyond the Postcards
Yes, the caldera views are real. But Santorini's real luxury is in its volcanic wine, its cave suites with private plunge pools, and its small, personal experiences. Avoid July and August unless you enjoy crowds. I wrote a whole piece on whether Santorini sunsets live up to the hype.
Photo: Caviar in the Air
Mykonos: Glamour with Substance
Mykonos has grown beyond its party reputation. Properties like Cavo Tagoo and Kalesma are calm retreats with great dining, beach access and art-forward design. Today's Mykonos works if you want a late dinner and an early swim on the same trip.
Photo: Caviar in the Air
Crete: Greece's Best-Kept Secret
The largest Greek island has Venetian harbors, Minoan palaces, mountain gorges and some of the best food in the Mediterranean. Blue Palace and Domes of Elounda give you luxury without pretension.
When Is the Best Time to Visit Greece?
| Season | Months | Weather | Crowds | Price Level |
|---|---|---|---|---|
| Peak | July-August | Hot, often 85-95°F, little rain | Very high | $$$$ |
| Shoulder (Best) | May-June, Sept-Oct | Warm and mild | Moderate | $$$ |
| Off-Season | Nov-March | Cool, some rain | Very low | $$ |
September is our favorite. The light softens, the sea stays warm, and the islands start to feel like yours again.
Is Greece Safe for Black Travelers?
Yes. Greece is a safe country for travelers, and the Greek idea of philoxenia (literally "friendship to the stranger") runs deep in the culture.
In our experience organizing group trips, our Black travelers consistently rate Greece as one of the most welcoming European destinations. Hotel staff go above and beyond, restaurant owners treat you like family, and people are warm and curious in the best way.
Photo: Caviar in the Air
What Should You Budget for Luxury Greece?
At the top end, Greece is good value compared with the South of France or the Amalfi Coast. Rough ranges as of October 2026:
- 5-Star Hotels: €350-€1,200/night depending on island and season
- Fine Dining: €60-€150 per person with wine
- Full-Day Private Yacht Charter: €2,000-€5,000
- Flights Between Islands: €50-€150
Top 5 Luxury Experiences in Greece
- Private Sailing Through the Cyclades: Charter a yacht from Mykonos through Paros, Naxos and Santorini with a private chef
- The Acropolis Without the Crowds: Go at opening time, or ask us about private after-hours visits when they're available
- Wine Tour of Santorini's Volcanic Vineyards: Taste Assyrtiko grown in volcanic soil with an expert guide
- Spa at Amanzoe: Aman's Greek outpost in the Peloponnese, with treatments built around local olive oil and herbs
- Cooking Class in a Cretan Village: Learn traditional dishes from a Greek grandmother
Want to see how it all fits together? Here's our exact 8-day Greece itinerary, and what nobody tells you about Greek island hopping. Our Greece Experience covers Athens, Santorini and Mykonos in nine days, with the ferries, hotels and tours arranged for you.
Destination Guide
Destination Guide
Destination Guide