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

Santorini, Greece | What to wear 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:

Santorini, Greece
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!

What to pack for a two-week holiday in the sun
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.

What to pack for a two-week holiday in the sun
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.

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What to pack for a two-week holiday in the sun
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.

What to pack for a two-week holiday in the sun
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).

What to pack for a two-week holiday in the sun
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…!
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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: iwillwearwhatilikeVisible MondayLet It ShineMonday MingleStyle Sessions, Turning Heads TuesdayTrend Spin Link-UpWhat I Wore WednesdayBrilliant Blog PostsThrowback ThursdayPassion for Fashion FridayFriday’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.


  1. 26 September 2015 / 11:57 am

    Santorini looks stunning, have a wonderful time! Def wear the skirt my vote is for coolest not cheesey
    livinginaboxx | bloglovin

  2. 26 September 2015 / 6:54 am

    Santorini is divine and loving your holiday style. That sold out Grecian top (4) took me right back to my childhood too, I reckon you will find some stunning pieces while there too x

  3. 23 September 2015 / 10:44 pm

    Frankly I'd wear anything to have a visit to Greece! Hoping to get there next year after kids exams. #BriliantBlogPosts

  4. 21 September 2015 / 1:40 pm

    Catherine the photos from your trip will be incredible and I can't wait to see the outfits!

    Santorini is one spot I've always wanted to visit and I can't wait to visit it vicariously through your travels!

    Ashley || Sed Bona

    • 23 September 2015 / 1:19 pm

      Ashley thank you – I can't wait either (only three sleeps to go)!!! My mind is buzzing right now at the thought of all those photo opportunities =eeeeeek=

  5. 20 September 2015 / 6:06 pm

    Woman I cannot think about holidays…. I work like mad, no holidays in sight, only rain and cold.
    Sorry you are on your own.

    • 23 September 2015 / 1:17 pm

      Ohhh Greetje that's such a sorry tale…!! I'm so sorry to rub it in :(( Never mind, I'm sure you'll have some lovely Christmassy stuff to look forward to soon xx

  6. 20 September 2015 / 2:53 pm

    Great Post Catherine – Have always wanted to go to Santorini – still on the list 😉
    Will you be going to any of the Fashion Weeks in Europe?

    Yvonne from

    • 20 September 2015 / 5:20 pm

      Thank you, Yvonne!

      I'm afraid not… I'm not even doing LFW – I've done it twice and I feel a bit "been there, done that" about it! Just not worth the painful feet and expense for me, unfortunately! x

  7. 19 September 2015 / 8:12 am

    I hope you have s superb time and leave you wanting for more and come to Málaga, even for a long weekend.
    I am off to New York with Rebecca, my oldest daughter on the 4th October. I can´t hardly wait.

    • 19 September 2015 / 8:58 am

      Oh Sacramento that would be lovely to come out and see you, we'll add it to our list!! I hope you have a fabulous time in New York – we've been there once but would love to go again! Thank you so much sweetie x

  8. 19 September 2015 / 7:59 am

    Santorini is definitely on my 'to do' list! We recently visited Hawaii and Las Vegas, both of which were bucket list places for us!

    • 19 September 2015 / 8:56 am

      Oh gosh both of those places were on our bucket list, Claire – we did Vegas a few years ago and so Hawaii have moved up the list a bit! It's so nice to tick off dream destinations, isn't it :)))

  9. 19 September 2015 / 5:44 am

    As a girl from Santorini and owner of the Serenity Suites & Villa in Fira in Santorini I was very pleased and surprised to see this post. Should I suggest a cardigan or jacket for the evenings? It gets really chilly and dining al fresco is an experience not to be missed. You did very well to include low heels. Have in mind that you will walk on cobbled streets and it is better to wear some sturdy shoes. Have a wonderful time in my Santorini.

    • 19 September 2015 / 8:54 am

      Mary thank you – how envious am I that you actually live there…?! I can't imagine what it's like to live somewhere so beautiful!!

      Thank you for the advice, I definitely plan to take some warmer cover ups as well as a pair of Adidas or something for walking… the post was getting a bit long so I stuck to the fun stuff! Can't wait xx

  10. 19 September 2015 / 1:51 am

    Can I please come!? Pleeeeese!?

    I cannot wait for this trip and plan to swoon over your pics. Catherine, my husband said he loved me for the first time through a kazoo in Greece. Wow! Memories…. we fell in love so fast, and about a month in we were in Greece on a rooftop, too tipsy from Retsina, and he told me that. Awww, memories.

    So, have a wonderful time. Everything you've chosen is perfect! And I've had my eye on that Chicwish skirt. Time for me to just purchase one of those great ones.

    Safe travels!



    • 19 September 2015 / 8:49 am

      Oh wow what a gorgeous story, Ann!!!!!!!!!! No wonder you fell in love if you were in Greece…!

      I think we're going to be spoiled for choice when it comes to photo opportunities. The Chicwish skirt will be a winner methinks :)) Thank you sweetie x

  11. 18 September 2015 / 8:25 pm

    Like Suzy, I immediately thought of Mamma Mia! and Sisterhood of the Traveling Pants! Oh, I will admit I'm envious! Wearing the Santorini skirt in Santorini is definitely cheesy, but THAT is exactly what will make it the most FANTASTIC photo opportunity EVER! I can't wait to see how choose to photograph you and your skirt in this beautiful setting.

    My bucket list destinations are Wales, Ireland, and Sweden…but I fear these vacations will not happen until my children are a bit older (driving 4 hours to get home for holidays is hard enough with the little beasts!)

    Have a fabulous holiday!


    • 19 September 2015 / 8:45 am

      Would you believe I've not seen either of those two films, Shelbee…!! Thank you, I can't wait to go. The skirt was an absolute MUST HAVE when I first saw it ;))

      It's frustrating having so many places to want to see isn't it…?!! And to my shame, despite being English, I've never been to Ireland or Scotland (though I've been to Wales many times). That really should change seeing as I live in the UK! x

  12. 18 September 2015 / 6:28 pm

    Beautiful place and great ideas 🙂

    • 18 September 2015 / 8:02 pm

      I reckon it will be, Ivana…! Thank you x

  13. 18 September 2015 / 6:28 pm

    Great choices Catherine, hope you have an amazing holiday xx

    • 18 September 2015 / 7:57 pm

      Aww Gail thank you so much my lovely!! x

  14. 18 September 2015 / 3:53 pm

    Gorgeous items! What a lovely place too!

    • 18 September 2015 / 4:09 pm

      Thanks Caramella – I absolutely can't wait…! x

  15. 18 September 2015 / 2:57 pm

    That yellow bikini is stunning… as is the Santorini skirt! Don't forget to pack a couple of cardigans too coz, if it's anything like where I live in the Algarve, the evenings can get chilly now we're well into September. I'd love to go there one day… it reminds me of Mamma Mia and The Sisterhood of the Travelling Pants!
    I love Canada and the US which is where we tend to holiday at the moment. Although our next trip is all booked – Wales……. in January! I know, we're nuts lol. But we do love the cool, wet weather 😉
    Suzy x

    • 18 September 2015 / 4:08 pm

      Thanks so much, Suzy…! Yes I do have plans to take a cardigan and a few other bits – like a couple of sun hats! – but I thought of so many other things after I'd written the post, and it was already getting a bit long! 😉

      I can totally get you holidaying in the US – there's so much to see there, but Wales in January?! Not sure about that one!! hehe xx

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