Essential Dos and Don’ts for Planning Your Dream Greek Island Getaway

Embarking on a two-week getaway to the Cyclades, Editor Britney Eschelman shares her firsthand experience and insights on planning your island-hopping expedition efficiently and effectively. Read on for her essential dos and don’ts for your dream Greek Island vacation. 

Sifnos, Monastery, Greek islands

Do: Visit an Unexpected Island Other Than the Tourist Hotspots

Listen, Mykonos and Santorini deserve all the hype they get. The views in Santorini will take your breath away, and Mykonos is the ultimate party island. Ibiza, you’re great, too, but Mykonos has more of an upscale flair.

However, if you’re traveling all this way to see the islands, the most expensive part is the flight to get there anyway, so you should take advantage of being halfway across the globe. While these destinations aren’t totally off anyone’s radar, consider these options as itinerary add-ons: Ios, Milos, Paros, Sifnos, and our under-the-radar favorite, Folegandros. (Don’t sleep on Folegandros; it’s incredible and feels like you’re on a Greek Island from 50 years ago. It’s a total hidden gem!)

Enough of this rant; read our guide to seven Cycladic islands you must visit if you want to know more.

Don’t: Overcomplicate Your Island Hopping—Opt for Flying Instead of Ferry for Certain Routes

When it comes to island hopping, keep it simple. If flying from Mykonos to Athens, consider skipping the four-hour ferry and opting for the zippy 40-minute flight. It’s a quicker and more comfortable option, especially for specific routes. Flying not only saves you time but also allows you to enjoy the journey in a more relaxed and comfortable manner.

It’s essential to consult a map and understand where you’re traveling, as some flights may be more complex than taking the ferry. To prevent this issue entirely, we recommend focusing on one island group, such as the Aegean, Cyclades, Dodecanese, or Ionian.

Do: Include Athens in Your Itinerary as More Than Just a Layover

While many may treat Athens as merely a layover on their Greek Island getaway, it’s a significant oversight not to include it in your itinerary. Athens shouldn’t be the main event of your trip, but staying one or two nights is enough to explore one of the world’s oldest cities. If you’re too eager to make it to the islands, tack this on at the end rather than the beginning of your trip. (Pro tip: Book a hotel in the Plaka neighborhood for incredible views of the Acropolis and a lively atmosphere that will make you fall in love with this ancient city.)

Don’t: Pack Any Suitcase Larger than Carry-on Size Luggage

Honestly, you never need to check a suitcase that’s the size of a small house. Take it from me—I’ve overpacked countless times for long trips, only to realize halfway through that I wouldn’t wear half of what I brought. (And to be quite frank, people with massive luggage on the ferries look pretty ridiculous with their enormous bags. Sorry, not sorry.) Additionally, the rugged—yet beautiful—terrain means you’ll often be dragging your suitcase over rocky walkways and inclines. Spare yourself the hassle and pack light.

Do: Rent a Moped or ATV for Island Explorations

Uber isn’t readily available at the touch of a button in many Greek Islands. Moreover, the taxi services can be quite expensive for short distances, with a minimum charge of 35 euros by law in islands like Mykonos, no matter what the distance. Therefore, renting a car is best, or if you’re comfortable driving an ATV, we highly recommend it. If you want to explore all the secret beaches and coves, this is the way to go. (Ladies, plan your outfits accordingly here.)

Don’t: Miss Out on Trying Traditional Greek Food Dishes

We know your tastebuds are accustomed to commercialized American foods like pizza, sushi, and avocado toast for breakfast. But we can assure you that it’s such a missed opportunity if you don’t step outside your comfort zone and try the local food, especially in Greece, as Mediterranean cuisine and traditional Greek food are mouthwatering and delicious. 

Of course, there’s Greek yogurt, which is tart and fresh to another level—it would be a sin not to have some. Plus, it’s a healthy option paired with rich Greek coffee, making it a delightful combo. If available, try the local goat and rabbit dishes with potatoes and an assortment of vegetables. For dessert, savor the sweet, tangy flavors of portokalopita or the delicate pastry of baklava.

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