2 Weeks in Greece: A Greece Itinerary for Island Lovers

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Greece truly is a bucket list destination. With so much to see and do, an incredible history, and some of the best food I’ve ever had, Greece quickly became one of my favourite destinations and somewhere I plan to return to again soon. However, planning your Greece itinerary can be tricky because it has so much to offer. From ruins and museums to beaches and islands, it can be hard to pick and choose if you only have 2 weeks in Greece.

I’ve been to Greece 5 times now and spent a total of nearly 3 months exploring this country. Based on my experience, I’ve picked my favourites to create this Greece itinerary perfect for first-timers. The main focus is the Cyclades islands, but I have also included some great sites for ruins and history as well. So, if you are a first time visitor, here’s my suggested itinerary for 2 weeks in Greece. 

How to Get To Greece

Getting to Greece is really easy and can be done by pretty much every method of transportation: plane, train, bus, and boat.

Chances are you’ll be flying into Greece. The easiest airport to get to is in Athens, which is where I’m going to start this itinerary. The Athens airport is located about 45 minutes outside of the city centre, but you can easily take a train from the airport into downtown Athens. Keep in mind, this train does not run 24/7 so if you are arriving into Athens late at night or really early in the morning it may not be running. If this is the case you can take a taxi, however, since taxis in Athens have a reputation for overcharging tourists (it’s true, I fell victim to this) I recommend arranging a private transfer ahead of time. It will probably be cheaper and definitely less stressful. You can book an airport transfer here.

2 Weeks in Greece: Getting Around

Greek Ferry

Since you are spending a couple of weeks in Greece, you’ll be moving around. This Greece itinerary is focused more in the islands which means you can either fly or take the ferry. There are pros and cons to both.

Getting around Greece by Ferry

The ferry is a popular way to get around the Greek islands. There are several ferry companies offering both fast and slow options (fast is best), however, they aren’t always as cheap as you would think. 

The ferries are nice in that you can get up and move around, but they can also be insanely crowded and they do take a while. Depending on the island you are travelling to, however, it may be easier to find a ferry than a flight. If you are travelling during high season (June-end of September) its best to book your ferry tickets in advance. They fill up quickly and get more expensive closer to travel dates. 

Book your Greek Ferries here.

Getting around Greece by Air

Depending on how early you book your flight, what island you are going to, and if you are checking luggage or not, flying may actually end up being cheaper than taking a ferry. Not to mention, it’s a much faster way to travel. For example, a flight from Santorini to Athens is 45 minutes but the ferry ride is 9 hours. That being said, flight schedules can be limited which may not work with your travel schedule. Again, its best to book in advance to save on your airfare.

Transportation on the Greek Islands

car rental in Greece

Once you have actually got to the islands, you’ll need to figure out how you want to explore them. For some people, you may just want to pick one spot and stay in the village for the duration of your trip. If that’s what sounds best to you, go for it! However, exploring the islands is part of the fun and even the small ones have some cool things to see and do. 

Renting an ATV or Motorbike in Greece

The most obvious way to get around is to rent a vehicle. On the islands you can either rent a car or rent an ATV or motorbike. Now, renting an ATV or motorbike might sound like a lot of fun, but it’s actually not encouraged. In fact, many agencies will not rent to you unless you have a motorbike license and have experience. Even then, they will try to encourage you to get a car instead. This is because the roads on the islands aren’t necessarily in the best condition and they can be very twisty. There are lots of tourist accidents so really think about it before you decide to rent an ATV or motorbike.

Renting a Car in Greece 

As for renting a car, you can get one for about 30 euros a day; a pretty good deal, especially if you have some friends to split the price with. You will need to show your license and it’s a good idea to know how to drive standard. Automatic cars are a rare find in Greece (well, in most of Europe). 

You won’t want to rent a car for the duration of your 2 weeks in Greece, but maybe for a couple of day trips. Dependent on the island and where you want to go, you may need a 4×4 type vehicle. Have that conversation at the rental company. 

Public Transit on the Greek Islands

Another option is to use the public transit on the islands. Keep in mind, not all islands will have buses and the schedule will depend on the season, but, if you are visiting one of the bigger islands in summer time you won’t have a problem.

Bus tickets usually cost between 1.50 euros and 3 euros depending on the island and the destination. They go to the main places and run on a reliable and fairly regular schedule during peak season. That being said, sometimes they do stop for a couple hours every day in the afternoon as a sort of ‘siesta’ so make sure to keep that in mind and plan around it or you might end up stuck (it happened to me).

Buses also mean you’ll need to deal with more crowds. In less popular places and route that’s not a big deal, but in Santorini the bus between Fira and Oia was always overcrowded with people being left behind having to wait for the next bus. If you plan on using the bus, get to the station early.

How to Spend 2 Weeks in Greece: My Greece Itinerary

Days 1-2: Athens

Athens, which is the capital of Greece, is one of those destinations that people seem to either love or hate. Personally, I loved it. Granted, I only spent one day here and definitely stuck to the safe and touristic spots but I thought it was a lot of fun to explore and, as an ancient history nerd, I found the ruins and archeological sites fascinating.

If you are up for a busy day, you can absolutely see the highlights of Athens in a single day (check out my 1 day in Athens guide for my suggestions). I do however suggest staying on the mainland for a second day to go to Delphi for a day trip. It will be a long day (Delphi is a 3 hour drive from Athens) however, it’s pretty incredible and if you are into ancient Greek history then it really is a must-see! Book a day trip to Delphi here.

Need a place to stay in Athens? Try:

Hostel: City Circus Athens (I stayed here, cool hostel with awesome rooftop views)

Midrange hotel: Adrian Hotel Athens or Central Hotel

Luxury hotel: Grecotel Pallas Athena or Electra Metropolis

Days 3-7: Paros

Naousa, Paros

Paros was the first island I visited in Greece and it ended up being my favourite. I went towards the end of May and, based on my experience, it felt like one of the more authentic islands considering its size. It wasn’t overrun with tourists (especially not big groups) and it had plenty to see and do. I stayed for 6 days and loved it so much I came back for another week a couple of years later. For that reason, it’s my first recommendation for those looking to spend 2 weeks in Greece.

I based myself in Naousa, an adorable village on the north end of the island. I spend my days exploring the different beaches (Naousa has its own small beach and there are a few in the bay you can take the boat too). The village itself is also full of great tavernas and cute boutique type shops where you can find anything from local soaps to jewellery to artwork. There’s also a winery within walking distance, Moraitis Winery, which is worth a visit for a wine tasting. I definitely recommend staying in Paros if you are looking for somewhere fun to explore that’s not too loud or crazy in the evenings.

Naousa, Paros

Need some suggestions? Try:

Hotel Senia

Katerina Mare

Paros is a pretty big island, so you can rent a car or hop the bus and explore different parts. The port area, Parikia, is fun to explore for a bit and I really enjoyed Lefkes and Marpissa. I definitely recommend doing a day trip to Anti Paros- the small island which is just a short ferry ride away. Find my full Paros Guide here.

Days 7-10: Naxos OR Milos

I love both of these islands and think they are great picks, especially for first time visitors. I’d say Naxos is better if you are interested more in history and mythology while Milos is better for those who love beaches. Here’s a bit more on both to help you decide. 



Naxos is the biggest island in the Cyclades and definitely worth taking a few days to explore. If you are able, I definitely recommend renting a car for at least one of your days here and doing a little roadtrip. I did one with 3 other girls from my sailing tour and we had SO much fun. Make sure to check out the temple of Demeter and the village Apiranthos which is cute, historic, and famous for its food and secret family recipes. Definitely plan to stop here for lunch. Depending on your timing, there are also a couple of distilleries and an olive press that you might enjoy visiting.

Naxos town can be explored in one day as well. Lots of great shops for those looking for souvenirs. A favourite include Pagonis Greek Sandals where you can get customizable leather sandals. As for food and drink, there are endless options. However, ice cream fans HAVE to try Waffle House, it’s amazing. Also, for sunset drinks check out 520 Cocktail bar; delicious drinks and a great view or, head to Apollo’s Arch (it gets pretty crowded though!)

sunset in Naxos

As for beaches, there’s one about a 10-minute walk from the old town. You can pay (or buy drinks) at one of the beachside tavernas to use their beach chairs and umbrellas. There’s also a beautiful beach a little further away called Agios Prokopios. If you have a car, you can drive here. Or, you can take the local bus which runs frequently during the high season. It’s one of the best beaches on the island.

Need a spot to stay in Naxos? I recommend using the old town as your base so try:

Chateau Zevgoli

Alkyoni Beach Hotel

Nastasia Village Hotel























Milos is known for it’s beautiful beaches, and as a beach lover, this is one of my favourite islands. Milos is home to the famous Sarakiniko Beach. It’s considered to be one of the best beaches in Greece and is known for its lunar landscape. It’s best to come in the morning since it faces east, but it’s also a good spot to spend a few hours. 

Milos isn’t the best to get around by public transit. There are bus routes but they don’t go everywhere so if you can, consider renting a car. You will likely need a 4×4 to get to some places. I also highly recommend taking a boat trip for a day around the island. It was a highlight for me. 

Hannah wearing a yellow dress sitting on a beach with a backdrop of colourful houses in Klima, Milos Island






















The larger towns themselves aren’t quite as exciting. Adamantas is the main city by the port, there is also  Plaka which is a bit more atmospheric on the hill. However, what is really special about Milos are the tiny little fishing villages, many of which have boathouses that have been converted into accommodation. I stayed in one in Klima. It’s so colourful and right on the water- its absolutely magical and I highly recommend. You can find my full guide to Milos here with accommodation options for these very cool boathouses here. 

Days 10-14: Santorini

No trip to the Greek islands is complete without a visit to Santorini. Is it expensive? Yes. Is it crowded? Yes. But, is it worth it? Absolutely. Santorini is stunning so I definitely recommend that you spend 3-5 days in Santorini to see what the hype is all about.

Santorini is a big enough island that you’ll want to make sure you have a few days to see and do things. The biggest attractions are usually the villages themselves, specifically Oia, but there are beaches, ruins, museums, and outdoor and foodie adventures to be had as well. Check out my list of unmissable things to do in Santorini for some ideas.

The biggest question, however, when it comes to Santorini is usually deciding where to stay. I also have a post on that, depending on what you are looking for in terms of your stay and accommodation; check out my where to stay in Santorini post for more tips. I will also point out that splurging on a luxury hotel in Santorini is definitely worth it for the true Santorini experience. I’m a self-labelled cheapskate when it comes to travel, but spending a few hundred dollars on a private cave hotel for a couple of nights in Oia was amazing. 

Want to See More Islands in a Short Amount of Time? Consider Sailing

Three islands not enough? Don’t worry, I feel you. Greece has hundreds of islands and it’s hard not to want to see them all. Though with only 2 weeks in Greece, you’ll need be selective. While I do think the islands above are worth spending a few days, if you are really keen on seeing more or, if you have more time and can add another week or so to your itinerary, then consider doing a sailing tour.

I did a 10 day Cyclades sailing tour with Intrepid Travel for the first time in 2019 and it was honestly one of the best travel experiences of my life. In fact, I loved it so much that I’ve run this same tour as one of my ESBT group trips twice now. We spend a few hours every day on the boat sailing from one island to another, often with really cool swim stops in-between such as caves and a WWII plane wreck (weather permitting). During our 10 days (which start and end in Santorini) we visit 8 other islands; popular ones like Mykonos and ones I’d never think to go to on my own such as Irakleia. The value is fantastic and the sailing itself was a ton of fun (especially when dolphins decided to swim along beside us).

While 2 weeks in Greece may not be enough time to see it all, but this Greece itinerary will give you a good taste of what this country has to offer and probably convince you to come back!

Ready to Book Your Trip?

Don’t forget travel insurance!

Please do not travel without travel insurance! I’ve had to use it multiple times throughout my travels and it has saved me thousands of dollars. You can learn more about travel insurance here. If you are looking for a provider I love and recommend SafetyWing. For Canadian readers, take a look at SoNomad.

Book your accommodation

I love and recommend booking.com for accommodation. They have a range of hostels, guesthouses, hotels, and resorts. Plus, the platform has a great loyalty program that means the more you book, the more you can save. 

Book your tours

My go-to tour provider that I love to recommend is GetYourGuide. They have options all over the world and partner with local companies for everything from day trips to food experiences and even airport transfers. 

Get connected

If you want to have data while travelling for online maps or any other needs, an esim is one of the easiest solutions. I’m a big fan of Airalo and have used their sim cards around the world from Brazil to Uzbekistan, Greece to the USA. It’s really easy- you download the app, pick what country you want an esim for, and after you purchase it follow the installation instructions. You can use promo code HANNAH3326 to save $3USD on your next esim purchase. 

Not sure what to pack?

I have destination-specific guides for some countries but you can also check my travel essentials and camera gear if you are looking for some ideas. 

Looking for a travel buddy?

Check out my group trips!

Two Weeks in Greece


  1. travel4fun on September 10, 2019 at 3:18 pm

    I am really impressed by the way you have organised the itenerally for Greece, It is the most beautiful place to travel but mostly if you don’t plan it well you realize that you have less time to see all the good places, so for me i will say is start with your first priority. For myself i love santorini i have never been there but iam planning to visit during my next vacation which is coming in December, so i will absolutely consider all your other suggestions. Thanks for sharing

    • Hannah Logan on September 10, 2019 at 6:45 pm

      So true! Greece has so much to see so you really do need to do a bit of planning. I hope you love Santorini!

  2. Frances Michaels on May 27, 2021 at 1:34 am

    €140 Santorini-Athens (1 bag) w/2 weeks in advance in May !??? Is there a typo somewhere here !?? Clarify if you can !?

    • Hannah Logan on May 30, 2021 at 4:39 pm

      As I said in the article that price is in Canadian dollars, not GBP. And no, that’s what I paid. Inter-island travel is not cheap! You might get lucky and find better deals but I suggest booking as early as possible to try to save. Leaving it until 2 weeks before was pretty late.

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