A Practical Guide to Romantic Travel in Santorini
Updated: Mar 24, 2021
Santorini is perhaps the crown gem among jewels of the Greek Islands. It’s a classic travel destination because it consistently lives up to the image it’s etched into the minds of countless travelers.
And don’t get me started on the island being picturesque, if I were to list the destinations I’ve been to which truly live up to the term picture postcard perfect – popular spots such as Thailand or Mexico are definitely beautiful and offer a lot for couples. But with an average of only 45-50 days of rainfall throughout the year it's difficult to compete with just how dry Santorini remains throughout the year.
It’s really hard to picture a more idyllic destination for a couple to celebrate their romance, with or without the honeymoon or anniversary. You may find cruise passengers and families with the kids in tow, but Santorini feels like it was made for love.
We send a fair number of our clients to Greece and Santorini has always been the top request for any itinerary.
Here are some of my top tips for planning a more relaxing romance and less stress during your vacation. That way you and your partner can focus on being in the moment together rather than worrying about missed connections or spoiled sunsets.
Part of what I love about Santorini for couples is because it offers fewer recreational activities, the pace of life and variety of experiences are geared toward relaxing together and doing laid back activities focused on great drinks, delicious food, and spectacular views.
You can hike, go scuba diving, ride horses, sail a boat... but you can also blissfully neglect all those activities and enjoy a guilt-free week of doing nothing together.
Before I get carried away with recommendations for experiences and where to stay, it’s important to set the expectation for arrival onto the island. This is a practical guide after all.
Unless you’re visiting Santorini as part of a cruise or yachting itinerary you’re likely going to need to fly or ferry from Athens.
I recommend against the ferry
The ferry might be reasonable for a shorter journey onto Milos or Naxos, but Santorini is far enough from Athens and mainland Greece to consume the bulk of your day – if you’ve only got a week to enjoy your vacation and you’ve already flown across the Atlantic and most of Europe, do you really want to spend another day on (mediocre) transportation?
Greece and the waters around the islands can also be breezy, to say the least. This can result in delays to the ferry, meaning you’ll have no choice but to wait for the seas to calm and spend even more of your valuable vacation time at the most boring place you could possibly be during your honeymoon or romantic trip.
You should instead plan to fly as directly as possible onto the island
I have further recommendation for the final scheduled arrival time into JTR. Flying overnight from North America will mean a morning arrival into Europe, depending on where you connect or which airlines you trust to get you there, you may find that you’re scheduled to arrive mid-afternoon. Basically any time about 2-3pm local time in Santorini.
This is not comfortable, this is a visit from the ghost of future vacations past. This screams future stress to me.
Even where we don’t expect your flight to be delayed, anything such as lost luggage, a delayed taxi or a bit of traffic (it happens, keep reading) can consume your afternoon.
Part of Greece’s appeal as a relaxing destination is the laidback lifestyle enjoyed by locals.
That includes your villa staff and resort reception, they might very well be packed up and home by 5 or 6pm. Your trip will not be off to a good start if an unscheduled hour on the tarmac means no keys to your luxury suite and a panic stay at the last available hostel-standard room on the island…
There are only about 16,000 actual residents on Santorini. That number fluctuates during the summer season and throughout the year. But with more local residents and visitors during peak months, you might actually find a bit of traffic around dinner time – at least around the capital, Fira.
Solve this whole problem by planning to spend a night in Athens on your arrival into Greece and then arrange professional transfers in advance, have someone meet you at the airport and don’t mess around getting to your accommodation.
Do the same in reverse on your way home, but you shouldn’t feel obliged to charter a driver for the whole of your stay in paradise.
If you’d like to rent a car or even rent a motorized scooter or quad bike, you’re going to need an international driver’s permit. Be sure that all your vehicle classes are translated onto the document.
My last visit to Greece was a surprising lesson in futility when it came to driving permissions. I hold an EU license, however my family doesn’t enjoy the same privilege.
We tried picking up a pair of vehicles for a spontaneous day trip on Milos for the 8 of us, and although the rental clerk begrudgingly offered me a 4-seater, he gleefully offered us the only thing available for the license category held by my companions - electric assisted bicycles!
Is a week enough for couples in Santorini? What is there to do?
Many visitors spend a long weekend or up to about a week on the island, that’s plenty of time to see most attractions and still relax a fair bit. Think 3-5 days for most people, a full week for the professional relaxers!
The most obvious activity is to simply enjoy the sunset, Santorini’s main attraction.
Views from anywhere on the western slopes/cliffs of the island will do but you’re probably going to enjoy it more from your private pool deck or at least with a glass of local vintage in your hand somewhere comfy.
Get yourself some elbow room and avoid some of the crowds by heading down to Megalochori and enjoying some of the quieter wineries such as Venetsanos. You’ll need to arrange a table in advance to pair with the sunset, but it’s a wonderful way to explore the island together while remaining in the lap of luxury.
You might also enjoy viewing the sunset from a yacht charter or a boat cruise.
This is my recommendation for getting around the island conveniently too, I might add, and just about the only way to really enjoy the limited beaches comfortably.
Reality check – if you’re like me and your wife (or husband/partner) is obsessed with the sea you need to have a real heart to heart about the beaches in Santorini.
As a dormant volcano where almost everything is built up on clifftops, Santorini is not really a beach destination.
There are a few dotted around the island, but in my opinion the nicest aren’t actually maintained and access is safest and most comfortable by sea.
Red Beach on Santorini’s southern edge, near Akrotiri, sports clear waters you can swim and some beautiful red rock and stone. But it isn’t so easy to get to if you have any sort of mobility issues or if you plainly don’t feel comfortable shimmying up & down a rock face with just a rope to guide your hand.
You'll also need to bring your own snacks and water, along with shade and sunscreen.
Again, if your partner needs a daily beach infusion during your vacation, you might consider Crete, Mykonos, Milos, Naxos, Zakynthos… you get the picture.
Back to the pool/taverna/café/wherever: Local food is delicious and plentiful, you should really try the local wines.
Two things I couldn’t quite figure out when I was in Santorini, did the myth of Atlantis come about with the cataclysmic eruption of the volcano and collapse of the caldera – wiping out the Minoans about 90 miles south in Crete? Do the farmers really neglect to water their grapes throughout the summer?
The first part is absolutely true or at least makes for a great story! There was an incredible eruption about 3,600 years ago and which may have been the beginning of the end for Europe’s first civilization, the Minoans.
The second part, I could believe it but it’s tough to swallow. Good thing the tiny grapes make for great wine, right?
I’m told the crop is not watered throughout the summer as water is so scarce and precious on the island - the economics just don't add up. Instead the plants take in moisture through humidity in the air and wick down dew to the roots during the cooler period of the morning,
before the sun rises.
It’s quite evident that the resulting scrub is short and doesn’t really resemble the grape vines we think of elsewhere. It also means tiny grapes with a particularly concentrated flavor!
Some people liken it to ice wine, many of the vintages on Santorini are sweet and better suited as dessert wines. But there are a few interesting flavors which truly resemble caramelized sugars or burnt fruit, said to be as a result of being partially cooked under the heat of the island sun!
Day trips to explore the dormant volcano on foot are popular if you’d like to escape local village life. Following the sunsets, the main attraction in Santorini for couples is probably as simple as going for a stroll and dining together between dips in your private pool.
When you’re shopping or walking, most people head to either Fira or Oia. Thira has a little more nightlife and they both offer dining and great views - although Oia's just the littlest bit prettier in my mind.
You might also see Fira spelled out as Thira or Thera, the names and spellings can be a bit confusing for visitors and those who don't speak Greek. Oia is frustratingly pronounced Ia, as in “ee-ya”.
They’re the larger villages of the island and host the postcard views of white walls, blue domes, sea & sky. They’re also fairly busy during the peak months. Don’t be surprised if you have to wait your turn to get a photo in certain spots.
Despite the crowds, maybe because of them, there are countless tiny pathways to lose yourselves down and just pop out the other side, spilling into some great little artist’s gallery.
Be mindful of your belongings, but definitely have fun getting lost!
You might also visit the Castle of Oia, the Kasteli of Agios Nikolaos. If you're intent on viewing the sunset from the Kasteli, or really from any scenic spot in Oia really, you might have to stake your claim on a spot an hour in advance. Don't feel bad just heading to a rooftop taverna or retiring to your sunset suite.
If you’re finding the crush of visitors to be too much or you’re not into sharing the view, consider a hike between the two villages via an old goat walk. You might best enjoy a change of location to nearby Imerovigli.
The village is about a mile north from Thira and for all intents and purposes looks very similar. You won’t have nearly as many options for food & drink, but you also won’t have nearly as many fellow travelers to contend with for the best views and fewer stranger faces to edit out of your best holiday pictures together!
Lastly, where are you going to stay during your romantic escape?
Most people stay in Oia or Thira, occasionally Firastefani or Imerovigli, finding their own slice of paradise in a villa or luxury boutique perched on the cliffside.
This is probably a perfect place for most couples celebrating, but I can’t help but feel that the prying eyes of others elsewhere above or along the hillside will have view onto what is supposed to be your romantic hideaway!
You could head to Megalochori if you’re OK with village views instead of caldera views. Imerovigli is again a very amenable option.
However, I might suggest something in the up and coming area just to the north of Oia, such as the Santo Maris Oia Luxury Suites & Spa.
Great proximity to Oia, which despite my alternative suggestions above is the place to see when you’re in Santorini. You’re only about a 600-800 foot walk onto the nearest cafes and gelaterias of the village, but the lane looks quiet and unassuming enough that only fellow guests and some local workers should be using the paths and roadways. You’ll be about 1,000-1,100 feet from the village center Orthodox church, Panagia Platsani.
I suggest this property for a romantic couples’ vacation because it's the tiniest bit larger than other properties in the area, offering some of the amenities you'd only find at a larger resort. At the same time it's split into several “neighborhoods” to help keep the secluded, romantic feel and maintains the unique atmosphere of an exclusive Santorini vacation.
The on-site spa is the largest spa on the whole island and you won’t have to walk anywhere for al fresco dining. You can also just hide away in your own villa or luxury suite.
Choose from among a variety of room categories, mostly named for their romantic value or exclusivity. Think Honeymoon Suites, sure, but you can be excited with luxury private pool villas or even cave suites!
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