Destinations / Greece

6 Tips From a Travel Addict to Plan the Perfect Holiday to Greece

September 5, 2018

Yes. A “travel addict”. That’s what I’ll call myself because it sounds better (and less incriminating) than “serial killer” organized in regards to trip planning. I can totally envision a lawyer quoting this blog post in my conviction if I ever end up a murder suspect or if my future husband goes missing which becomes headline-grabbing news that will inevitably inspire the plot of an Affleck-directed movie tentatively entitled “Gone Guy”. I will be famous. For horrible reasons but famous nonetheless.

On one of the first trips that I took abroad, the extent of my preparation was briefly scanning Wikipedia but in anticipation of my upcoming Greece trip, I have reached new heights of terrifying having arranged my “Eating” list into several specific, hyper-focused sublists. It’s my precious. I’d show you but then I’d have to kill you and then I’d definitely go to jail.

Trip planning is hard work but have no fear if you are not naturally serial killer organized as I am, I have put together tips, tricks, and questions you should ask yourself to plan the perfect holiday to Greece! So as to not alarm the authorities, instead of calling it “Tips from a Serial Killer” we’ll call it “Tips from a Travel Addict”. Less of a life sentence and more of an overnight stay in the bullpen.

You are ripe for choice when it comes to Greek islands because they are all so jaw-droppingly gorgeous. You can’t really go wrong whichever ones you choose!

Decision makers:
+ How long are you in Greece? This will determine how many and which islands to visit (3 nights per spot for a comfortable pace). Islands like Crete and Zakynthos are little more out of the way so it’s not ideal if you’re short on time.

+ What sights MUST you see? For example, the moon-like volcanic rock beach, Sarakiniko, on Milos island looks otherworldly and is definitely a bucketlist spot for me, so that’s one island already selected!

+ What kind of holiday you’re looking to have? If you’re on your honeymoon, romantic and laidback Oia in Santorini is ideal while Mykonos is the destination to don your designer finery and shimmy the night away at glam beach clubs.

+ Scope out itineraries listed on the sites of established travel companies like Contiki , Topdeck, and MedSail, as well as boutique ones such as For The Love Of Travel. Not only will you see which islands they consider essential but you can gather ideas for activities to do at each destination.

Now that you’ve chosen the islands you’re going to visit, it’s time to determine what order you are going to visit them in and how are you going to get to each island.

Decision makers:
+ What’s their proximity to each other? Look at where each chosen location is on Google maps and determine what the most logical and direct route is.

+ Time or Money? You want to try and get the best bang for your buck but time is of the essence. A domestic flight within Greece (i.e. from Athens to Mykonos) has slightly higher pricetag than a budget-friendly ferry but it’ll cut your travel time in half.

+ What pace do you want to set? If you prefer to kick your trip off with a festive bang by partying the night away and end it by relaxing, that may affect which island you start and end with.

+ Rome2Rio is a great resource to see all of the transportation options – flights, ferries, catamarans, buses, etc.. – available between destinations. While Santorini may look further away from Paros than Milos, Rome2Rio shows that the route is actually twice as long and more costly as you have to switch boats at island stopovers in between.

+ If you want more time to frolic on the beach and are opting for domestic flights, scour Skiplagged for deals on flights for as low as $50 for Athens to Mykonos!

Armed with your island selections and how long you’re going to spend at each, you can create a schedule outline and begin to book where you’re going to lay your head at night that satisfies your budget as well as your aesthetic preference that’s in the middle of all the action.

Decision makers:
+ What do you want to be near? If you’re looking to immerse yourself in bustling nightlife in Satorini, Fira is the best choice. If you’re on a romantic vacation then you may want to seclude yourself in idyllic Oia. Would you rather be a hop, skip, and a jump away from all the most drool-worthy restaurants or within walking distance of the most picturesque beach?

+ What’s the group vibe? Luxury boutique hotels are best if you’re looking for some pampering by attentive staff whereas renting an entire apartment/home if you’re travelling with a crew will afford you more independence. Solo? There are even nice hostels in Greece where you can meet people!

+ Hostelworld has always been my go-to for finding aesthetically pleasing hostels, like City Circus, to meet fellow vagabonds. is also a great site to hunker down to search for deals.

+ From stylish villas to bachelor pads in the middle of all the action, AirBnB has something at every price point but don’t forget to read the reviews to help make your final selection.

This is where I start to get a bit scary-organized, like watch-you-while-you-sleep-but-I-swear-I-was-I-was-having-an-asthma-attack-and-that’s-why-I-was-breathing-heavily scary. But that’s because eating is one of the most important things to me when I travel, especially somewhere that has such an stellar reputation for fresh cuisine like Greece.

Decision makers:
+ When in Greece….? Do as the Greeks do and eat your fill of creamy Greek yogurt (do you think they just call it “yogurt” there?), souvlaki, gyros, the freshest seafood, and smother it all in tzatziki sauce! Don’t waste any prime real estate in your belly on anything that isn’t Greek.

+ Where is the restaurant located in relation to your accommodations and the day’s activities? If you’re already going to the other end of the island, you might as well check out that taverna with the octopus carpaccio nearby for lunch!

+ When I’m compiling my restaurant list, I will just go on a rampage of blogs and online “top ten” lists until a pattern emerges. I’ll cross reference the restaurants that keep popping up and check the reviews on TripAdvisor before it makes it to the must-eat list.

+I further abuse Google maps to see where each restaurant is in relation to where I’m staying and what I plan on doing that day for maximum efficiency!

There’s nothing like busting out a new bikini or dress that you purchased specially for a trip! Whether you’re hiking the caldera in Santorini and sweating like a beast or chilling at a fancy beach club in Mykonos, you want to make sure you’re appropriately attired for the day to not only be comfortable but look MF fantastic.

Decision makers:
+ What are the main activities you’ll be doing? A trip to the Greek Islands means you’ll likely live in a bathing suit but what about post-swim? Think about light, flowy clothes that won’t stick to your skin and comfy shoes to wander around the cobblestone alleys.

+ What’s going to stand out? If you’re doing it for the ‘gram in Greece, consider what will stand out against the stark whites and complement the vivid blues.

+ Either invest in classic bathing suits that you can wear for longer than a hot minute or go for inexpensive trendy pieces. NA-KD Fashion has a great selection, quick delivery, and topnotch customer service. I bought 2 bathing suits for $50!

+ If you fancy, treat yourself to breezy, boho-chic outfits by brands like Tularosa and Faithfull the Brand at Revolve.

Chase lifelong memories to treasure in one of the most idyllic destinations in the world. If you’re not motivated to do more than chill poolside then at least consider doing otherwise to work up an appetite in between meals!

Decision makers:
+ What are the things you can only do in Greece? Sailing languidly around Milos and exploring the Kleftiko caves and old pirate-lairs, a 3-hours hike from Fira to Oia in Santorini, devouring seafood so fresh you can taste the salty sea at trendy beach clubs in Mykonos…distinctly Greek experiences.

+ Pinterest is a great place for my inner visual hoarder to collect destination porn for trip experience inspiration.

+ Scan geotags on Instagram for picture-perfect activities to add to your Greece bucket list.