A Romantic Guide to Santorini

The cynics do not stand a chance in Santorini. I should know, I married one (well, an externally cynical one anyway – deep down, he is the warmest of the warm fuzzy sorts but fuzzy sorts rarely admit such things.) On the surface, Pumpkin can assume the role of grumpy old grump in almost any situation – not in Santorini though, not on the volcanic Greek island that absorbed him as much as it did me, not in Santorini, the island that melted every last pretend-icicle in his armoury. When he could no longer beat the romantic wave engulfing us in the Cyclades, he joined it, music to the ears of the silliest hopeless romantic of them all – me.

romantic break ideas Santorini

Santorini is equally picturesque whether you are flying solo, travelling with children (though do have a read of my Santorini travel tips prior) or living it up with friends but this soil calls out to lovers across the globe so whichever kind of party you arrive with, you soon learn to expect and accept smooching couples, wispy wedding gowns and paired adults walking in tandem, glued at the palms.

best viewpoints Santorini

Conversely, though, if you happen to be travelling within your own besotted bubble, you will be very much in your element in Santorini and a skim through this romantic Santorini checklist may just help towards building your most romantic break of all.

romantic activities Santorini

The Santorini Sunsets

No visit to Santorini is complete without taking in one of the world-renowned Santorini sunsets. We had an opportunity to view it from both Firostefani and Oia but the two experiences were at polar ends of the romantic spectrum. Undoubtedly, there is a captivating spell cast by the Oia sunset, as its amber glow glazes the tiered platter of whitewashed windmills, churches and homes that comprise Oia. This is the Santorini sunset you have seen plastered accross the press and it delivers.

But it delivers in the way that a music festival does – it might be epic but you’ll still be competing with the crowds to reap the rewards, struggling to find a good spot, fighting for entry and exit and SO MANY selfie sticks.

Add to this the sunset tour groups that descend upon Oia en masse and it becomes a standing room only kind of situation. Despite arriving 45 minutes before sunset in Oia, we only just managed to find space to perch – and this was shoulder season.

Firostefani sunset

If you have enough for both, my suggestion for a more serene sunset is Firostefani, where the sunsets blaze just as potently without any of the large tour groups wading through. In Firostefani, especially off season, only a handful of people join you in that dusky spell of day, although you may find yourself in the company of some furrier, feline friends, also in search of a suitable sunset-viewing spot.

cats Santorini

And if hunger pangs kick in after all that golden hour photography and all the steps you climbed to reach the viewpoints, then dinner spots don’t get much more beautiful than Remvi, where you can tuck into fresh seafood to views like this. Luckiest of all, we booked our sunset table at only a few hours notice (nigh on impossible for any decent sunset facing-restaurant in Oia.)

Santorini for couples

A Romantic Photo Shoot

Ordinarily, cheesy couple pics wouldn’t be my go-to thing on a holiday, even a romantic holiday but in Santorini, if you can’t beat ’em… And you won’t – because they are everywhere, sporting bridal couture, shooting Instagram updates, with their professional photographer-come-doting-boyfriends in tow and their drones circling above. And even the regular tourist folk spend just as long framing themselves in those classic Santorini scenes.

Localgrapher Photo Shoot Blog Review

No judgement because ultimately, it is one of the most photogenic islands in the world so why the heck wouldn’t you?! With that in mind, we threw caution to the wind & participated in our first ever vacation shoot but if, like me, you feel utterly self-conscious about such antics, Santorini is the place to conquer that, since photo shoots are so commonplace that you’ll soon let go of your inhibitions.

Vacation Photography Santorini Localgrapher

Movie Night under the stars at the Open Air Cinema

Date nights don’t get much more classic than dinner and a movie and timeless trends remain timeless for a reason. Cosying up together at the back of a cinema, sneaking in cuddles and sharing a large candy-striped box of popcorn has been part of the American teenage dream since (at least) as long as Saved by the Bell!😁(Who else is going to admit to being old enough to remember that?!)

romantic experiences Santorini

Imagine though, if dry air con was replaced by balmy, autumnal Greek island air with a basket of fleece blankets on standby for the win. Imagine if, alongside the popcorn, you dabbled in gourmet snacks and desserts & imagine if you swapped tanks of corporate soda for lovingly hand shaken frozen strawberry daiquiris, served by charming bar tenders with beaming hospitable smiles.

Santorini highlights

Over at the Kamari open air cinema, the dark cinema has no walls and no roof, aside from the star-studded charcoal sky above it. Have a romantic meal on the shores of Kamari beach first or save your appetite for the tasty bites on offer at Kamari but of all the romantic moments we had in Santorini, this was our favourite and if it’s piqued your interest, there’s a full lowdown of it in my previous post.

best cinemas around the world

Fine Dining with a View

Fine dining on an island with such worldwide acclaim was never going to be a cheap affair but a meal with a view may just be worth the splurge with a backdrop of panoramic sunsets and the geological majesty of the caldera views.

romantic restaurants Oia Santorini
Romantic Dining at Lauda Restaurant, Oia

Aside from the aforementioned Remvi in Firostefani, my other recommendation is Lauda in Oia, which we had already set our sights on, when we realised it happened to be based in our hotel! October evenings in Santorini can rapidly turn nippy so dress in anticipation, although as a lovely touch a Lauda, we were given blankets during our meal, as we dined by candlelight after the sun went snoozing for the night.

photogenic stunning Greek islands

Foodies, Santorini is home to Vinsanto (it’s kind of in the name right?) For the wine drinkers among you, a romantic wine-tasting experience to indulge in it is a must. As for me, however, there wasn’t really much place for a teetotaler on a wine tour….but then again, we are talking about the same teetotaler who found herself in a beer house in Munich and a Port tour in Porto

Red Beach & Black Beach Kamari

Once you’re all cultured out and have had your fill of fine food, a laid back, romantic day is in order and for that, I pescribe the sound of the waves, beaches you virtually have all to yourself and a cocktail in a swinging hammock (wouldn’t it be nice if I could actually prescribe these things?)

black beach Santorini

For these therapeutic interventions, the Santorini beaches have got you covered. Those of you more inclined towards yellow/white powdery sands may be left disappointed but as someone who had never previously seen either black or brick red beaches, these shores had a truly mesmerising and in some ways, eerie charm.

We may have had to clamber up some rocks in our flip flops to reach the viewpoint at the red beach but that only served to add to the comedy value of our day out.

Oia – Fira hike

If, however, you are one of those outdoorsy couples, for whom the very mention of the word lazy is sacrilege, then fear not. How’s about 5 hours of walking together to switch off from reality, soak up the breadth of the island and ogle at the jaw dropping vistas.

romantic walks Santorini

The renowned Oia to Fira hike, (which we actually did the other way around) is an absolute must-do activity for those who can manage it and was one of our slowest but most liberating and uplifting moments of the trip. During much of the hike, we could easily have deluded ourselves into believing we were the only ones on the island, such was the extent of the vast volcanic formations around us .

Oia Fira hike

We weren’t on a mission to race through the walk and instead hiked at our own leisurely pace, slowed down only by my desire to take photos of the caldera almost every 3 minutes. I am not a regular hiker and wouldn’t describe myself as particularly active (I doubt flitting between different cupcake and cookie shops counts) but even I found the hike easily doable so rest assured, you don’t need to have climbed Kilmanjaro to complete the Oia to Fira route.

Caldera View Santorini

Magical Megalochori

Years ago, on this very blog, I wrote about Piran a dreamy coastal town in Slovenia that proved to be one of the highlights of my trip, despite me never having heard of it till the day of our visit. Megalochori was my Santorini equivalent; an artistic canvas splattered with bougainvillea, baby blue doors & baklavas that blow the mind.

baklava Santorini
Bitesized Baklava

We indulged in the fanciful daydream of one day eloping into these pocket-sized streets, painting the semilunar front door to our own Aegean pod, our new homes shaded by olive branches and our leaping hearts shielded by the flawless still of our surrounds.

pretty houses Santorini

I knew nothing of Megalochori till the afternoon we arrived there, nor can I label it a happy accident. Instead, I owe my Megalochori diamond discovery to Pumpkin, who, with his boundless travel planning abilities, stumbled upon it during his research and asked me if I wanted to take a chance on a lesser known village. For me, the impromptu gambles in travel really do pay off.

romantic Santorini

Crazy Golf at Perivolos Beach

Now, you might think of crazy golf as something to do with the little people in your life rather than a date activity but for us, it conjures up all sorts of romantic nostalgia, as one of our earliest dates was a crazy golf day that Pumpkin organised and to this day, he recalls me describing it on Facebook as the “bestest day ever,” my intentionally appalling grammar only marginally offset by the saccharine sentiment that underpinned it.

During our afternoon on Perissa and Perivolos beaches, we found a crazy golf course and because we were a wide berth away from school holidays, we had the golf course to ourselves. As has become custom for us during crazy golf, I wound up reminding myself that “it’s the taking part that counts” and when all the intense golfing left us in dire need of rehydration, we certainly weren’t going to decline the offer to slurp our cocktails in the comfort of our own vertical hammocks.

romantic guide Santorini

Caldera View Hotels with Private Hot Tubs

After scrambling back through the crowd that departed the sunset viewpoint in a mass exodus, the decision to have forked out for a boutique Oia hotel for a couple of nights paid off, when we were back at our hotel within moments. We felt frauds referring to it as a hotel “room” when really, it was more a suite with a spacious living area, private outdoor patio and outdoor lounging area and most pampering of all, a private outdoor hot tub on the terrace, concealed behind the front door to our abode. Pumpkin used the moment to crack open the bottle of sparkling wine left for us by the hotel. Whilst he embraced the drinkable bubbles, I had long since retired to the warm, soakable bubbles of the jacuzzi.

Oia is a goldmine of luxury hotels and properties with attached astronomical fares. We chose to go in October rather than summer holiday season, in part to avoid crowds but also because it represents much better value for money with hotels.

luxury hotel Oia Santorini

Was it out of this world romantic? Yes? Was it worth it? Yes (if only for a just a few days.) Was it still one of the most expensive places we have stayed, even off peak? Yes. Romantic bliss but not without hefty cost so Oia hotels may not appeal to all Santorini visitors but we adored our time there and I hope to write a full blog review of both our Santorini hotels in due course.

cave hotels Santorini

Have you been to Santorini? Do you have any additional romantic Santorini activities to add to this list?

13 thoughts on “A Romantic Guide to Santorini

  1. Wonderful blog about a wonderful place. Imerovigli is another lesser known village peering over the caldera without the crowds. The walk down to the caldera takes you to a pretty church.

    1. Shikha (whywasteannualleave) April 24, 2019 — 7:27 am

      Thanks so much for the kind words Alex. So glad you think the blog post has done it justice – very hard to find words that truly convey the magic of the island. I think we may have walked through Imerovigli (though not stopped there) when we were doing the Oia to Fira hike but it looked absolutely charming & I definitely recall, as you say, the views over the caldera from there being absolutely magnificent. It’s a village I would want to look at staying in next time – and I really hope there will be a next time!😊

  2. Aww it looks lovely there Shikha, and you two – so cute! (shh, don’t tell Pumpkin lol!). I’ve wanted to visit here for a while but worried that the hills would be too much, is it manageable for someone like me?

    1. Shikha (whywasteannualleave) April 24, 2019 — 7:31 am

      Lol, won’t tell him – might make him either vom or run away 🀣🀣 To be honest, it was very hilly and lots of lots of steps. There are a few parts of the island, which are flatter like some of the coastal and beachy corners and that bit should be fine but for all the classic postcard and brochure style photos you’ll see of Sabtorini, most of those vantage points are from uphill and even both our hotels involved going up and down lots of steps daily. I do think you could manage it but it’s just that it could start to get quite uncomfortable or tiring but then again, you never cease to amaze me with all the travels you damage so for all I know, it could be that I’m being massively over cautious with my advice Keri😊

  3. Truly one of the most beautiful places I’ve been!

    1. Shikha (whywasteannualleave) April 24, 2019 — 7:35 am

      Isn’t it just Angie?! I wasn’t sure if it could really live up to all that hype before I went but now I know how justified the hype is!

  4. like that cat photo:) and the rest:)

    1. Shikha (whywasteannualleave) April 24, 2019 — 7:36 am

      Haha! So many cats on this island – it would be a cat lover’s dream and I loved how this one was just happily looking out at the sunset in the perfect Insta pose πŸ˜‚

  5. How I miss the Greek Islands – it’s been so long since my last visit. Your post brought it all back, even though I’ve yet to visit Santorini. That has to be remedied ASAP – especially after seeing your photos!

    1. Shikha (whywasteannualleave) April 24, 2019 — 7:38 am

      Well this visit to Santorini was actually my first return to the Greek islands or Greece in general in about 12 years, Aaron & I felt the same but was reminded how utterly dreamy they are! Which island/s did you visit in the past? Thanks so much for reading 😊

      1. Have been to Cephalonia and Ikaria – both were amazing..

  6. it looks too good to be true! The whole place is a postcard!

    1. Shikha (whywasteannualleave) April 24, 2019 — 7:38 am

      I didn’t think it would live up to all those postcard images Andy but it proved to be genuinely that picturesque (if a little crowded at times!)

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