What I’d Do Differently: Greece Edition
Updated April 2026 | 3 min read
- Do Not Try to Do Athens, Santorini, and Mykonos in One Week
- Rent a Car in Santorini
- Watch the Oia Sunset from Somewhere Else
- Eat Away from the Caldera Edge
- Ferry Schedules Change with the Season
- What We Got Right
- Travel Tools We Actually Use
- Book Tours and Activities
- Gear We Recommend
- Find Flights to Greece
- Plan Your Trip to Greece
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
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:
Find Flights to Greece
Cheapest Flights to Greece
| Departure at | Return at | Stops | Airline | Find tickets |
|---|---|---|---|---|
| 28 April 2026 | 2 May 2026 | Direct |  |
Tickets from 411 |
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.
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Plan your own trip: guides I actually use
More from this region:
- Greece Road Trip: The 7-Day Athens-to-Delphi Route I’d Book in October
- 4 Best Beach Destinations Ranked: Bali vs Thailand vs Greek Islands vs Amalfi Coast
- 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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- Best Travel Credit Cards for 2026: The Cards I Actually Use and Why
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Finding cheap flights:
- Going vs Dollar Flight Club vs Thrifty Traveler: Which Flight Deal Service Is Worth It in 2026?
- When to Book Flights by Region — The Booking Windows That Actually Save Money
- How to Find Error Fares and Flight Deals — The Services I Actually Use
- Google Flights vs Skyscanner vs Momondo — Which Actually Finds the Cheapest Flights
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
- My Exact Travel Tech Setup After 15 International Trips
- Best Noise-Canceling Headphones for Travel in 2026: Tested on 40+ Flights
- Best Travel Backpacks for 2026: The 5 I Have Actually Used
- Phone Photography Tips for Travel: How to Take Great Photos With Just Your iPhone
Written by Jenna Fattah
I have visited 25+ countries across 6 continents, attended 7 Formula 1 races, and spent 4 years writing about what actually works and what I would do differently. Every recommendation on this site comes from trips I planned and paid for myself. Read more about me
