Santorini | What to Pack for a Two Week Holiday in the Greek Sun

At the end of the month I’ll be jetting off to the island of Santorini – a long-awaited two week holiday in the Greek sun and I cannot wait! Not wanting to make a mess of my packing, I thought I should prep what I’m wearing well in advance. I’m never normally this organised but I thought that sharing it with you would give me the best reason to make sure I’m fully prepared (and don’t over-pack). This is the first relaxing holiday in the sun (one where I can relax by the pool and not follow a strict itinerary of visits to historical and cultural hotspots) we’ve had in 12 years… so planning my holiday wardrobe is a huge deal for me!

We booked our holiday to Santorini earlier this year through Expedia – I first used them four years ago when we did a big US road trip and booked everything for that holiday through their website. That holiday went like a dream: Six different hotels, four different airports, two hotel transfers, one hire car – and not a single hiccup along the way. That’s just the kind of service I want from my travel operator, so when it came to booking two weeks on a Greek island there was no question about who I was going to book it with.

Like San Francisco and the Grand Canyon, Santorini was one of our bucket list destinations. Even if you don’t think you know it, you may well recognise pictures of the famous sunsets and blue-domed churches set into the cliff face (especially if you’re on Pinterest a lot) – it’s visually stunning and I’ve heard nothing but great things about it:

Photo credits: Above left – karol m | Above right – Mike Atkinson | Main photo: Lacy (all via Wikimedia Commons)

It should still be about 25-27°C by the time we get there, so it’s bikinis, kaftans, t-shirts, shorts and summer dresses all the way. Here’s a quick round up of what I’m taking with me – if you follow me on Instagram you’re bound to see many of these pieces pop up on my feed, and I’ll do proper outfit posts on my return in October.

Have you been anywhere on your holiday destinations bucket list yet? If so, do share where you’ve been – or where you’d LIKE to go – in the comments!

1. Bikini top / bottoms | 2. Bikini top / bottoms | 3. Kaftan | 4. Bikini top / bottoms | 5. Kaftan (sold out but I love this one)
– The essentials for lounging by the pool: Kaftans and bikinis (how great is that yellow one going to look with a tan?). Late summer is a great time to buy them because they’re often massively reduced in the sales – I got some amazing bargains at Asos.

1. Dress | 2. Dress (this is similar to mine but mine is blue and white-striped) | 3. Dress
– I’ll probably take at least couple more, but dresses are the easiest, throw-them-on pieces to take on holiday with you. I’m taking the white Grecian-style dress to wear in the evenings, and the striped and floral dresses for day. Dress them up with jewellery and they’re perfect for the evening, too.

1. Shorts (almost identical to mine) | 2. T-shirt | 3. Top | 4. Top (sold out but this one’s similar) | 5. Shorts | 6. Trousers
– You always need a selection of shorts and t-shirts for sightseeing. Again, I’ll take a few more but these are the basics: I love the fact that I got such a pretty embroidered kaftan top in the sale at Dorothy Perkins (how perfect for Greece is it?) and the tropical print trousers will be a great alternative to a dress in the evenings.

1. Earrings | 2. Beach bag (sold out but I like this one) | 3. Sunglasses | 4. Sandals | 5. Bag (sold out but I love this one) | 6. Sandals
– I’m going to try and keep my shoes and accessories to a minimum as I usually take far too many of both on holiday with me. Earrings that’ll go with everything, the all-essential beach bag, sunnies, and sandals (flats for day, heels for night).

Santorini skirt by Chicwish
– This could be the ultimate in resort wear… I’ll be wearing the resort! Wearing a skirt with a photo of the actual destination itself on it might be the cheesiest thing ever, but then it might just be the coolest – I just haven’t decided which yet. Either way, this is the pièce de résistance in my holiday wardrobe: I’ve had it for months and have been saving it for my holiday. I’m already thinking photo opportunity…!


P.S. You’ve got till the end of the weekend to add what you’ve been wearing to my #iwillwearwhatilike link up – there’s a theme but as always it’s optional!

Linking up to: iwillwearwhatilike, Visible Monday, Let It Shine, Monday Mingle, Style Sessions, Turning Heads Tuesday, Trend Spin Link-Up, What I Wore Wednesday, Brilliant Blog Posts, Throwback Thursday, Passion for Fashion Friday, Friday’s Fab Favourites

Disclosure: Thank you to Expedia for collaborating with me on this post (click here for my full disclosure). All content is original and opinions are my own and 100% honest – the collaboration had no influence whatsoever on my decision to book my holiday either in Santorini or through them.