What I’d Do Differently: Greece Edition

Updated April 2026 | 3 min read

Greece in October was shoulder season perfection — warm weather, fewer crowds, lower prices. But we still made mistakes worth sharing.

Do Not Try to Do Athens, Santorini, and Mykonos in One Week

We crammed all three and felt rushed everywhere. Athens alone deserves three days. The islands each need at least two nights. Pick Athens plus one island, or skip Athens and do two islands slowly.

Rent a Car in Santorini

We relied on buses and they were infrequent and crowded. A rental car in Santorini costs about 35 euros per day and gives you access to the beaches and villages that the buses barely serve. Parking is manageable outside Oia and Fira.

Watch the Oia Sunset from Somewhere Else

The famous Oia sunset viewpoint is so crowded that you cannot see the sunset — you see the backs of heads. The castle ruins in Oia are better, or watch from a restaurant terrace in Imerovigli with a glass of Assyrtiko.

Eat Away from the Caldera Edge

Caldera-view restaurants charge double for average food. Walk to the back streets of any village and the food improves while the price drops. The view restaurants are worth one splurge dinner, not every meal.

Ferry Schedules Change with the Season

We booked October ferries based on August schedules and they did not exist. Ferry frequency drops significantly after September. Check FerryHopper for real-time October schedules and book in advance.

What We Got Right

October timing. The weather was perfect, the water was still warm enough to swim, and we never waited in a line.

Travel Tools We Actually Use

• eSIM Data: Airalo eSIM for Greece — Buy before you land. You need data the moment you arrive for navigation and translation apps.
• Car Rental: Compare rental prices for Greece — We compare across all major companies here. Book early for best rates.

Book Tours and Activities

• Greece Tours and Activities on Viator

Gear We Recommend

• Osprey Farpoint 40 Travel Backpack — Carry-on sized, opens like a suitcase.
• Anker Nano Power Bank — Essential for long days of navigating with your phone.
• Packing Cubes (6-Pack) — We bring these on every trip now.
• Universal Travel Adapter — One adapter for every country.
• Reef-Safe Sunscreen — The Greek sun is intense even in October.

Book on GetYourGuide:

• Acropolis and Parthenon Guided Tour
• Santorini Caldera Cruise

Find Flights to Greece

Plan Your Trip to Greece

Ready to book? Search flights to Greece to compare prices across airlines. And compare hotel rates in Greece to find the best deals for your dates.

Affiliate disclosure: This post contains affiliate links at no extra cost to you. SafetyWing, Skyscanner, Airalo, Booking.com, Viator, GetYourGuide.

Plan your own trip: guides I actually use

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• Europe’s Best Shoulder-Season Itineraries: Iceland, Greece, Portugal, and Scandinavia Compared
• Greek Islands Guide: Santorini, Mykonos, and the Underrated Ones I’d Add

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Staying connected abroad:

• Best VPN for Travel 2026 — NordVPN vs Surfshark and Why You Need One
• Best eSIM for Travel 2026 — Holafly vs Airalo vs Nomad

Travel gear I actually use:

• Best Portable Chargers for Travel in 2026: Which Size You Actually Need
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• Best Noise-Canceling Headphones for Travel in 2026: Tested on 40+ Flights
• Best Travel Backpacks for 2026: The 5 I Have Actually Used
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