Step-by-Step Guide to Planning a Greek Island Holiday

The Greece Cyclades are on the top of everyone’s bucket list every year! We booked our flights last minute and my only regret is that we had to leave. 10 days in the islands was perfect but I could’ve stayed a month to soak it all in. 

I’m not going to sugar coat it, this trip was a bit overwhelming to plan. Through this blog I’m hoping to break down the steps into an easy, comprehensive guide for planning your bucket list Greek islands vacation. The best way to utilize it is to do one step a week (or a day if you are trying to go to Greece next week!) 

Things to Know 

The Greek Islands have a high and low season. The high season is from late June to early September. The mainlanders live on the islands during summer to work and they go back home towards the end of September. 

If you’re looking to save money on your trip, avoid traveling to Greece during August and book your flights and accommodations 3 to 6 months ahead of time. Put it in your calendar to book in April! Enjoy less crowds and better prices for accommodations in June and September. 

A unique surprise about the Cyclade Greek islands is that your accommodations typically provide concierge services like booking shuttles to and from the airport or to your ferry (highly recommend), booking dinner reservations, and activities, and more. I was blown away by the hospitality of all our Airbnb hosts! 

Step 1: The Big Decision of What Islands to Visit

There are nearly 300 Greek islands to choose from and they all have a different vibe. Every islands is in full operation from late June to early September. If you visit outside of this small window be prepared for most of the restaurants, shops, and activities to be closed.

We chose to go to Santorini to experience the cliff side archectiure, Paros for the fresh food and sandy beaches, and Milos for off-the-beaten-path adventure. Athens was a fun stop for our flight to and from Greece to see the Acropolis and experience the city culture! 

Step 2: Find Your Flights

After you figure out what islands you want to visit then you should book flights for the long distance journey to Greece and then hopper flights between the islands. To save money, book a flight to Athens as tickets are typically cheaper into the mainland and then book a separate hopper flight or ferry to the islands. 

You can also take hopper flights (typically 30€-60€ per flight) between the islands instead of the ferry. Flights will be a bit more expensive, but you’ll save time. We took a Volotea flight from Santorini to Athens because they had the cheapest prices. 

Pro tip: Learn from our mistake and be sure to check in online 24-hours before your flight. If you forget to check in online the smaller airlines like Air Ryan, WizAir and Volotea will charge you 30€ per traveler to check in at the airport! 

Step 3: Plan Your Ferries 

We booked our ferries through FerryHopper and tried to select SeaJet ferries whenever possible because they are the fastest option. Ferries are typically delayed by an hour or more. The good news is, they you can download the ferry hopper app to track the ferries in real time and plan ahead. We were thankful to have a little extra time to grab cocktails when our ferries were delayed.

Step 4: Where to Stay 

If you know me, you know I like to travel like a local. Airbnb‘s are my favorite place to stay because you are usually hosted by a local who will give you the best dining, drinking, and activity suggestions. 

In Greece, Airbnb‘s tend to run on the more expensive side. If you’re looking for a cheaper option search for hotels through Google Maps. During high season, hotels and Airbnb sell out quickly and are extremely expensive. Book well in advance to get the best rates. 

If you are coming during the summer months grab a hotel with a pool so you have somewhere to cool off during the day.

Step 4: Book Your Wheels

Most Airbnbs and hotels will help you book shuttles to and from the airport. If you aren’t renting a car or ATV, I highly recommend this option because taxis are hard to find on the islands. 

You will need to book ATVs and car rentals in advance if you are coming during high season. These are the best options for getting around the islands. We ran into a few travelers who were struggling without a ride in Santorini and Milos.

ATV rentals don’t require an international drivers license, but cars do! You can get your international drivers license easily online through AAA for $20. Be sure to print your international drivers license at home before arriving in Greece because you will need it on you at all times while driving. 

Surprisingly, some islands have great public transportation systems so be sure to look into this if you are comfortable traveling on buses. Paros had a great bus system and we didn’t find a need for a car. 

Step 5: Activity and Dinner Reservations 

Most of the restaurants and bars run on European time and are open from noon to about 3am. Thankfully, mostly all Airbnb’s and hotels provide breakfast so you don’t have to worry about finding a cafe in the morning. 

All of the islands are busy from July through September. Catamaran tours, cooking classes, and dinner reservations can sell out a month or more in advance. 

I found Google Maps, TripAdvisor, and Viator the best places to look for activities and dining options. Make sure to book your activities like Catamarans and tours directly through the company’s website. Activities like catamaran tours should be booked through the boating company and not with TripAdvisor or Viator. These referral companies can charge nearly triple the price compared to the company’s actual website prices. 

For dining options you can book directly through Google Maps or Open Table. Europeans dine later in the evening so no matter what time you are looking to book, make reservations. For sunset views book your table an hour before sunset so you can get the best seat in the house.

As I mentioned earlier, your Airbnb or hotel host may act as a concierge to book you last minute experiences, dinner reservations, ATV rentals, and more. However I wouldn’t solely rely on this service being available and try to book as much as possible in advance on your own. 

Step 6: What to Pack

Light weight garments are key for summers in Greece. I wore, and re-wore, my lightest pieces the most throughout the trip. 

Water shoes like Tevas are also necessary for the hot, pebbly beaches, cliff jumping, and general water sports. I’m assuming if you are reading this blog you will be partaking in cliff jumping and other activities meant for adventurous souls.  

Hats are a must and we also brought some reef safe sunscreen with us because sunscreen can get expensive after you arrive. 

Quick drying swimwear is key for beach days that turn into late nights in the town. It’s typical to see people dancing the night away or sitting at dinner still wearing still sporting their swimwear under a coverup. 

Pack some dark colored swimwear options if you plan on visiting any volcanic hot springs. The sulfur water will stain any light colored suits! 

These are the special packing needs for traveling to the Greek islands, but read this blog for some more tips for packing lightly.

Step 7: Soak it All In 

I hope this step-by-step guide helps you relax while planning your Greek Island vacation! Whether you plan to visit the Cyclades Islands, Dodecanese Islands, Sporades Islands, Crete or Ionian Islands, this guide will take some weight off your shoulders knowing you didn’t forget a step.

As always, reach out to me on Instagram if you have any questions. Stay safe on your journey and cheers! 

Seeing the islands from a boat is a MUST do
Airbnbs can be pricey in the Greek Islands so look for cheaper hotel alternatives.
Pack light and breezy clothes to stay cool in the hot weather.
Cheers to this view and your Greek holiday!


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