Our Greek Island Itinerary You Can Totally Steal (and Free Download)
Relax
You’re off to greece.
And we have the guide for you! Whether you’re visual, map-based or just want to watch some beautiful video for inspiration on an upcoming trip, we’ve got you covered.
After falling in love with what we thought was going to be “too touristy” Santorini in 2015 we made a plan to head back to the Cyclades the minute they re-opened in July 2021.
If you’d like to sit back and relax and join this 2 week adventure around 5 Greek Islands, I invite you to grab some popcorn and watch this video on your largest screen.
Already seen it? Let’s Dive In.
Save This Map
Save thESE greek island favorites
Love maps? I love maps. My first step in trip planning always starts with browsing the internet for interesting sights, top recommended restaurants and most popular things to do. From there I research accommodation and transportation to determine “what type of trip this will be”… hiring a car? Taking public transportation? Moving hotels night to night or using a home base and exploring new locations each day.
First step for you? Save our Tim and Fin Favs to your own Google Maps. Not only will this help get you started, but when you’re in Greece, just pull up your phone when you need a quick recommendation!
Our Greek Island Itinerary
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 in 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 cut’s off a few hours before boarding so remember to do this the night before, and not sitting at the ferry port!
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!
(These are all on the map above, did you save it yet?)
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 it’s 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)
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.
1-3 TRAVEL DAYS
If this is your time to check out Athens, do it! You can easily take an overnight ferry, enjoy some historic sights, then fly home.
Free Download
PLAN YOUR GREEK ITINERARY
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.
…but what are we wearing?
GREECE PACKING LIST for women
Heading on your trip soon? I have you covered! here’s everything I brought to Greece.
GREECE PACKING LIST for men
Dude, I know you’re worried about your Instagram shots - I’ve got you covered. -Tim