Itinerary Summary
The trip flies into Athens, then straight to Santorini for three days of Oia sunsets, blue-dome photos and a volcano-and-Thirassia cruise. A two-hour high-speed ferry crosses to Mykonos for Paradise B…
Day-by-Day Itinerary
Day 1
Athens connection and a caldera cave suite in Oia
10:00
3h
Athens to Santorini domestic flight
Clear immigration at Athens, then take the short domestic flight to Santorini. Baggage is normally through-checked, but confirm at the first check-in desk so you are not caught at the connection.
📍 Athens to Santorini
15:00
1.5h
Check-in at a caldera cave suite
Settle into a cave-style suite carved into the cliff, with a plunge pool or terrace over the caldera. Porters carry bags down the steps; tip a few euros per bag.
📍 Oia or Fira, Santorini
20:00
2h
Sunset dinner on an Oia terrace
Book a west-facing terrace table for a first dinner of grilled seafood and Santorini white wine. Tables on the caldera edge go weeks ahead, so reserve before you fly.
📍 Oia, Santorini
💡 Pro Tip: Fly into Athens and connect to Santorini; the domestic hop takes about 45 minutes and baggage is usually checked through. Greece is UTC+2 (UTC+3 from late March to late October). Entry rules depend on your passport, so check the Greece visa section. Book caldera cave suites four to six months ahead, and expect steep stairs and unrailed terraces at cliff hotels, so pack soft luggage that porters can carry.
Days 2-8 are member-only
Members get the complete day-by-day plan with timing, transport and on-the-ground tips.
Budget Breakdown
AccommodationUS$1,15035%
Cave hotels and boutique resorts, 7 nights
Food & DiningUS$66020%
Waterfront seafood and taverna dinners
Remaining cost categories are member-only
Members see the full breakdown for flights, hotels, food, tickets and more.
Frequently Asked Questions
Which month is best for an 8-day luxury island-hopping holiday in Greece?+
June to September gives the warmest sea at 24-26°C and long evenings. May and early September are quieter and better value while still warm enough for beaches. July and August are hottest and busiest, with Santorini and Mykonos at peak rates, so decide whether you want atmosphere or calm.
How much does a luxury Santorini, Mykonos and Crete holiday cost?+
Expect roughly $2,690-3,890 (about €2,340-3,380) per person excluding international flights. That covers caldera-view suites, beach clubs, private transfers and ferry or flight connections. Peak July-August rates can be 50-80% above shoulder season, so May, June and September stretch the same budget further.
Are fast ferries between Santorini and Mykonos reliable in high summer?+
The high-speed crossing takes around two hours and runs frequently in summer, but the meltemi wind can cancel or delay sailings, especially in July and August. Book morning departures where possible, keep a spare half-day, and check the operator's app on the day before heading to the port.
How far ahead should I reserve a caldera cave hotel in Oia or Imerovigli?+
For June to September, book six months ahead or more, since cliffside cave suites with plunge pools sell out first. May and October are easier but still warrant several months' notice. Ask about steps and luggage handling, as many caldera properties are car-free and reached on foot.
Attractions in This Guide
Guide at a Glance
- Duration: 8 days
- Budget: Luxury · approx. $2,690–3,890 (≈ €2,340–3,380), excl. int'l flights
- Difficulty: easy
- Best for: Beach Getaway
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