By Drea

Where I go: Santorini, Greece.

Without getting caught up in the clichéd trappings of an enamored tourist, I’m going to stop short and say that there’s a good reason why Santorini is overrun by tourists. The landscape is beautiful, the weather is crisp, and on a clear day the sunsets look like watercolour paintings. I wouldn’t go so far as to say there’s something for everyone in Santorini. If you’re looking for a shopping adventure or buzzing nightlife (to Mykonos you must go!), or if you hate Greek food (shame on you) then only disappointment is in store. But if you’re set on a chill island holiday replete with little adventures, then believe me, there’s no better place. 

Take a trip down in May, right before the sweltering sun and the swarms of tourists catch up. The waters may be a little chilly but a shot of ouzo will warm you right up.

Wearing: There’s no denying I’m terrible at packing, but when left with no option (on a 3 week long trip with fairly limited luggage room and a modest carry-on), I will make it work, Tim Gunn style.

Breezy pieces in an eclectic range of brights are my island holiday go-to. A chartreuse jersey dress, cobalt chiffon top, coral skirt, some neutral basics and a whole she-bang of turquoise hued accessories! Basically all the summer pieces I neglect for snooty corporate wear.

Oh, not to forget a floppy straw hat (which one may purchase for 20 euros and immediately regret as one would later find it impossible to pack into luggage), my trusty marc jacobs shades, printed h&m scarves to throw over when it gets nippy at night, and some strappy sandals to prevent any flip-flopping when exploring them black and red sand beaches.

Toting: It’s still somewhat of a beach holiday so I bring a tote that withstands weather abuse but still transitions nicely from café chic to beach bum. Bring something that won’t make you scream if you find remnants of sunblock or sand in it. I carry my well-used navy longchamp, canvas country road duffel or my round brown zara tote.

Reading: Some Peter Mayle and Stephen Clarke – anything lighthearted and tongue-in-cheek. And with the technology I have now, every interior décor, lifestyle and home & garden magazine uploaded in my iBooks! Magic at my fingertips.

Eating: Being openly referred to as a “sex bomb” may be considered sexual harrassment in some places, but not at Mama’s House in Fira. The same bubbly hostess who doles out ego boosts serves up the heartiest breakfast, amazing Greek coffee and yogurt drizzled with honey. Then you look around, and there she is calling the guy at the next table a sex bomb too! You immediately feel unspecial and sort of just shut up and eat. The food is good anyway.

If you can tear yourself away from the wonders of Mama’s House, head to Taverna Nikolas for a carafe of wine and some Imam (eggplant and tomato stew, not the spiritual leader), some grilled calamari at Naoussa, giant slabs of feta cheese on the Greek Salad anywhere (it’s Greece), and the glorious plates of slightly charred meat at any Gyros stand.

For a little bit of a tipple, have some mid-morning ouzo (it turns from clear to cloudy with ice like magic!) to do as the locals do, or head over to Highlander where you can have the tastiest flaming B-52’s with a dash of cinnamon and a singed eyebrow, if you’re not careful. They even encourage you to dance on their tables. To get quite buzzed, make a trip to Santo Wines in the afternoon, sit there with good friends and finish all the tasting wines. I guarantee you will be better friends after.

Watching: The stunning Santorini sunset.

Get yourself up to the Akrotiri lighthouse in Faros and take a seat at the very edge of the cliff. The experience is like being in the most incredible omnimax theatre you will ever imagine. As you sit there, it almost feels like the cerulean sea is merging with a palette of dusty pinks, purples and blues and extending to envelop you on all sides. It’s the kind of place I’d go to recover from a mid-life crisis. It’s like instant inner peace.

Alternatively, one-up the crowds in Oia to catch the famed sunset. Find yourself a pretty perch by climbing on to low level roofs and just wait. “Watching sunsets” may now be listed as one of your Facebook interests.

Bringing: My reliable Fuji Finepix F20, my Sony Nex-5 and a giant SD card. Avoid the unpleasant scenario where you’re about to catch an amazing picture only to be notified that you’re out of space. Buzzkill.

In my bag to save me from looking like a hobo are my John Frieda Frizz-Ease serum to detangle salty hair, Pacifica tuberose lip salve and L’occitane green tea “solid perfume” to rub behind my ears. The latter smells better than it sounds.

Also, a callous attitude towards sanitary hygiene. The plumbing system on the island is so sensitive it can’t withstand paper flowing through its pipes. That means, throw your dirty-doos in the wastepaper basket! Something you should definitely brace yourself for.

Loving: While I loved everything about Greece, I have to say the moments I remember most are the ones spent in good company – playing ridiculous games on the rooftops in Oia, driving an ATV uphill after lunch and pointing fingers at why it was rolling backwards, and dancing on the bartops at Highlander. The best backdrop in the world is only made perfect if you have somebody to share it with. So really, my only noteworthy advice for a great summer holiday is: bring good company ;)