TWO WEEKS IN THE GREEK ISLANDS - Our itinerary you can totally steal (Free Download)

Greek Island Itinerary planning - free download

No matter what trip you’re planning we always recommend one thing - An Itinerary Planner Spreadsheet! We use different versions of this excel document to plan every. single. trip. Download it free below, then check out our Greek Island itinerary in this article. Feel free to completely replicate the same adventure if you like. We loved the pace and balance of relaxing and adventure. You can probably move a tiny bit faster if you are not filming like we were.

Day 1-2: Fly Direct to Mykonos or Santorini

If you’ve never seen the Acropolis or visited Athens, I’m not necessarily recommending that you skip it. BUT did you know it is incredibly easy to fly to one of these two Greek Islands?

Most of our followers are coming from the States, and Athens is really just that much farther from the USA. You could book direct and likely wind-up with a layover in Frankfurt or London, but if the Greek Islands are what you’re traveling all this way for, here’s what I’d recommend:

Look for and book the cheapest round trip flight to anywhere in Europe. Then, separately, book another round trip ticket between that European airport and Mykonos or Santorini. This could potentially reduce your flight cost by up to $1500 USD

This flight hacking strategy could also grant you some time to get over your jet lag while you spend a night or two gazing at the Eiffel Tower.

Ok, now that you’re on the islands, take this trip forward or backwards—

2-4 nights in mykonos

Despite our silly thumbnail, in this video we share how we recommend spending your time and money in Mykonos. If you haven’t yet accounted for jet lag, add an extra night here if you can.

Highlights in Mykonos included

Nissaki Hotel (for so many reasons but mostly the breakfast)
180’ Sunset Bar (table 45)

2-4 nights - NAXOS and/or PAROS

Welcome to the reason you’re here … island hopping! It’s time to use the Greek Ferry system. Book tickets in advance. You can do this on an aggregate website like Ferryhopper.com or Greekferries.com or one the ferry company website themselves like SeaJet or Blue Star. We decided to complete the entire itinerary on Sea Jet just so each day wasn’t a new learning curve for us.

It is required to check-in online and receive a QR code in order to board. The time limit cuts off a few hours before boarding so remember to do this the night before, and not while you’re sitting at the ferry port!

VLOG - TAKING THE SEAJET FERRIES FROM MYKONOS - NAXOS - PAROS

Naxos and Paros Highlights:

Naxos - Evening cocktails at 520 Cocktail Bar
Naxos - Temple of Apollo
Paros - Town of Naousa to stay overnight
Paros - Hotel Senia, starlight infinity pool
Paros - Souvlakia Kargas, best Gyros in Greece!

3-5 nights on milos

“Ay Milos, you are going to Milos? Ay, ay I love Milos” - Every Greek person we talked to.

Milos is a fairly large island. (Naxos is actually one of the largest). But why I bring up its size here is how it will affect your itinerary. Most of the “top things to do in Milos” are very spread out and you’ll want to organize your days based on island location. Having your own transportation is a must here.

Milos Highlights

The Family renting scooters (only scooters available, and international drivers license required)
The family running this Airbnb
Cliff Jumping at Sarakiniko Beach
Sunset drinks in Klima
Hiding out on Tsigrado Beach (ladder)
Wasting the day away at Fyriplaka Beach
Overrated Food (but great ambiance): Nostos Seafood Experience

3-4 nights in santorini

There’s so much more to this island than just a sunset in Oia. We even returned after 5 years of full-time travel to continue to enjoy what Santorini has to offer. Santorini can get extremely expensive so you’ll want to check out our video below to learn how to create a plan based around your budget. For even more information check out our article all about Santorini in under $50 USD/day from our trip in 2015.