Greek Travel Itinerary

This is another itinerary that spans over a two week period. If you have got limited time, however, I have highlighted some of my favourite islands and must-see spots to take advantage of your time in this glorious sun-filled country.

With soft sandy beaches, absolutely clear blue waters, and as much Greek salad as you can manage, Greece is a prime destination for a relaxing vacation. Throw in loads of history and it becomes a rich adventure that leaves you appreciating Greek culture even more.


Recommended stay: 3-5 days

Easy to get to by plane, Crete is an excellent island to visit on the beginning or end of your journey. The easiest option is to fly into Heraklion and use it as your base for a few days. Now, Heraklion isn’t the loveliest of towns, but it did have some excellent food and was nearby to some of the best rated beaches in the world. If you’re looking for more of a popular destination, and perhaps more beautiful, I would recommend checking out Chania, which you can visit by renting a car or taking a city bus. I would highly recommend visiting Crete on a trip to Greece and note that it is much less expensive when compared to some of the other Greek islands.

Stay: For our time in Heraklion, we stayed at the Galaxy Hotel, a 5 star gem on the town’s main road. The rooms were spacious, quiet, and most importantly, comfortable. Plus, the hotel has a hidden pool which gets loads of warm sun throughout the day. Location wise, we took a taxi from the airport, but were able to walk to all the main sights from our hotel.

Do: Make your way to the harbour and tour the old stone walls and docks, built back in the 900s. You can walk all the way along the river, and back up into the main hubbub of the town, where there are lots of shops and small restaurants.

The town itself only takes a day to explore, but it is an excellent location for a number of other day trips. A visit to Knossos should not be missed – the oldest city in Europe, the palace was used from about 7000-1000 BC. The old ruins have been carefully restored and some of the original frescos have been repainted to aid in authenticity. The bus to/from Heraklion comes quite regularly and the entrance fees are modest.

As mentioned above, Crete is home to some of the best beaches. If you choose to stay in Heraklion, Matala beach is one of the closest. Again, you can take a city bus out there (or drive if you rent a vehicle) and the trip is about an hour long. If you choose to make a day of it, there are a number of shops and restaurants located steps from the beach. In addition, if you are up for a bit of a hike, you can make your way up the hill behind Matala beach and across and over to Red Beach (a nude beach) for additional views and relaxation.

If you choose to stay in Chania, Elafonissi beach is highly recommended, with soft white and pink sand and cedar trees along the coast.

Eat: Along the riverfront is a number of large patio-style restaurants, perfect for taking in the sea breeze. My favourite of the bunch was Paralia, which used really fresh ingredients to make classic Greek dishes. If you manage to stop by in tourist or shoulder season, make sure you get the Loukoumades – a local Crete dessert. Some restaurants will gift them to you as a finale to your meal, and it’s basically a dish of little fried dough balls, drizzled in honey and syrup, and paired with ice cream.

You can also head into the downtown core of Heraklion, where you will find a number of boutique restaurants, loud music, and vibrant dishes. If you’re feeling overwhelmed, Veranda is a good choice. With a massive patio overlooking the town square, it’s got a trendy atmosphere and great food.

If you’re craving pizza, Silfio has an excellent selection of Italian style thin crusts, all at an exceptionally reasonable price. (Heads up, if you decide to stay at the Galaxy, Silfio is right next door).

And finally, if you’re looking for a more up-scale meal, leave the main road and walk into Merastri, where you can order some of the best baked feta and other authentic Cretan cuisine.






Recommended stay: 2 days

Athens has a bit of a poor reputation for being less than desirable when compared to other metropolises such as London or Paris. With that being said, Athens is beyond rich in history and many of the sights are worth the visit. You can easily fly into Athens from around the world (or from Crete if you take my advice above), and once you arrive, the majority of sights are within walking distance.

Stay: When I visited Athens, we rented an Airbnb in Metaxourgeio. It was close to the subway, but a little bit of a walk from the Plaka district. To save time, however,  I would recommend staying in the district that is bordered by Pireos, P. Tsaldari, Stadiou, and Highway 91 (west of the acropolis). Some hotels in this area are the Plaka Hotel, Hotel Grande Bretagne, and the King George (but there is a wide variety for each price point). Although more expensive and touristy, this area is prime for touring the main sights of Athens.

Do: A visit to the Acropolis is a must, and you can see it perched atop the hill from most locations in Athens. Walking down any street will lead you to a number of other historical sights, and in particular Panepistimiou road. Other sights of note are the Panathenaic Stadium and the Temple of Olympian Zeus. Neighbourhoods of note are the Plaka, mentioned above, which has narrow clustered roads and a lively amount of activity.

Eat: For general eats, the plaka (again) has a wide variety of restaurants with large patios onto the boulevards. It is likely that you’ll want to eat here if you’re only visiting for a short time. There are a number of streets in this area with large tented patios, and you can stop into any of them for a pita or gyro meal.

For upscale cooking, a visit to Aleria is highly recommended (reservations necessary). With a rustic interior and a secluded patio, Aleria represents fine Greek dining and offers one of the best steaks I’ve had in my life.





Recommended stay: 3-4 days

You may be thinking to yourself, I’ve never heard of Naxos. But, this is where I set my guide apart from all of those basic Greek travel guides. While lots of people rant and rave about Mykonos & Santorini – they’re basically just fancy, over-priced, tourist havens. And, quite frankly, a lot of the time people rave about these islands because they haven’t been to any of the smaller ones. In my opinion, it is locations like Naxos that really enlighten you about Greek culture and island living.

Easy to get to by ferry from Athens, Naxos is an excellent island to relax. Prices are not as expensive, the beaches are just as lovely, and the town is full of real charm. After talking to a number of people who visited Naxos, it seems like those who visit, love it. I highly recommend adding it to your list of island hopping – even at the expense of missing somewhere like Mykonos.

Stay: There are a number of hotels in Naxos which are located along the main beach line and are all ideal spots to stay. Although the island has a number of little towns, you want to stay in the heart of Naxos itself.

Do: The best part about Naxos is its beaches. All along the coast, there are a number of stellar locations to set up your town or beach chair and bask in the sun rays. The location near Paradise Restaurant & Café is quite popular and easy to walk to from town.

I would also highly recommend exploring a bit of what the island has to offer. Rent an ATV, Vespa, or Car at any of the rental vehicle locations for the day and take it to discover hidden coves or other popular sun-worshipper destinations. In particular, a drive to Aliko beach (approximately one hour) is highly worth it, where you can discover the site of an abandoned hotel. Below it, are nooks of clear turquoise waters and virtually private beaches.

From there, you can shoot back down through Naxos and over to the Eggares Olive Press. This is a must-visit, where you can taste (and purchase) a number of olive based products from skin care to cooking. There are bottles of high-quality olive oil, jars of olive pastes, and some of the best lemon cake you will ever eat, ever.

And finally, the highest recommendation of all, goes to the Captain Panos sailing tour. At 80E a person, it’s every bit worth the price. The tour lasts all day and will take you to a number of islands, where you will swim in the clearest of blue waters, duck under caves, and jump of cliffs. If you do nothing else that I’ve recommended when you visit Greece, at least do this.

Eat: At night, you can find a number of restaurants located along the beach in the heart of downtown Naxos. Any of these offer a selection of Greek cuisine – and a lot of fresh fish.

And, because I haven’t made a recommendation on chocolates yet – visit Aktaion, which is a quaint boutique offering a selection of elaborate mini-cakes, mousses, ice creams, and macarons.





Recommended stay: 2-3 days

Last, but not least, comes Santorini. Although it is truly beautiful at the sunset, I was a little disappointed by how over-crowded the town gets, even at the end of shoulder season (late September). There were at least six massive cruise ships visiting per day, pouring their guests into the tiny and narrow streets, and filling up every restaurant and hotel around. Now that I’ve seen and done it, I don’t see myself heading back. You can get to Santorini by ferry from most of the other Greek islands, and there are speed overnight ferries that will bring you back to Athens for your flight home.

Stay: Two things you need in a Santorini hotel: a pool and a caldera view. Without it, you’ll be left quite disappointed, and likely envious of each neighbouring hotel. The temperatures are hot, and as Santorini doesn’t have waters to wade in, a pool is really the only way to cool down. I would recommend staying in either Thera or Imerovigli, both of which are only about 10 minutes apart.  Some hotel suggestions are White, Pegasus, Keti, and Katikies Hotel.

Do: Thira is the main town in Santorini, and you can spend hours walking through and up and down each winding road. Be prepared for it to be exceptionally busy, but the colourful doors and views of the coast are what makes it special. You may also want to spend an evening visiting Oia, which has a number of local artisan shops and some excellent restaurants.

If you are in dire need of a beach, take a city bus to the Black Beach, which is exactly how it sounds. Loaded with red and black volcanic pebbles, it’s not like the rest of the beaches on the Greek islands and the waters are much less welcoming for a swim.

And finally, if you fancy yourself a wine connoisseur, I would recommend a wine tour of some of the popular Santorini wineries. It’s a good way to learn about the trials and tribulations of wine making in Santorini, while tasting a bit of local flavour.

Eat: Be prepared for a bit of sticker shock when you visit Santorini. As it’s a popular destination, the prices of food really reflect that. I, however, have a number recommendations if you’re in search of upscale, quality meals.

The first, is La Maison, which is nestled in Imerovigli and offers high quality French cuisine with an incredible view of the sunset. And the second, is Ambrosia, which is on the ridge of Oia and offers Italian inspired dishes. This restaurant offers a rare view of Fira as the sun sets upon it and is quite romantic. Reservations are highly recommended at both. For breakfast or lunch (or brunch), take yourself into the heart of Thira, and stop in at Galini café for a bright and cheerful start to your day.


Hopefully you will find this guide helpful in planning that dream Greece vacation. In reality, all of the islands are lovely, but you must limit yourself to a few in order to avoid spending your entire trip on the ferry.

Please comment below if you have any questions and I’ll try to answer them the best I can.

As always, if you refer to my travel section on Greece you can find detailed posts about each of these towns and the activities mentioned.

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