We’ve all seen those quintessential Greece vacay photos. You know the ones I’m speaking of: bright blue church domes topping white washed buildings, perched high on the edge of a cliff among a Tetris-like formation of other sun bleached buildings overlooking the cobalt blue Aegean sea that appears as if it’s miles beneath. It’s these picturesque photos that grace nearly every travel book, magazine, blog etc. that feature Greece as a travel destination. And these are the photos that draw us in and place Greece at the top of all our bucket lists. At least that was my experience.
If you haven’t had a chance to research Greece for a potential holiday stay yet, these breathtaking images we’re always seeing are taken on the island of Santorini in the Cyclades, but more specifically in the tiny village of Oia.
Santorini was once a much larger island (like thousands of years ago), but after a volcanic eruption, the volcano actually sank into the sea and formed a caldera (volcanic crater), which is why the island is now shaped more like a crescent. It also provides a very unique and dramatic backdrop for vacay photos, or for simply enjoying what many say is the most beautiful sunset on earth.
If you’ve been around for any length of time and follow along on our travel adventures, you may be finding it difficult to pinpoint our likes and dislikes, and our overall travel philosophy. So let me just say this to try to clarify: we have nothing against touristy destinations when the pay-off is so great. You can’t expect to go to London, Paris or Rome and do ‘allll the things’ and not be surrounded by hoards and hoards of other tourists, but the sites are so spectacular in these places you just deal with it, or better yet….try your best to embrace it.
On the other side of the spectrum, when we’re looking for a more relaxing destination (eg. an island hopping getaway), where we’re not really trying to see all the ancient wonders of the world, or the best museums, I generally don’t want to be surrounded by oodles of selfie stick wielding tourists.
So when it came time to plan this trip, and having zero previous experience in Greece under my belt, I poured over loads of blog posts covering Greek Island hopping, and ordered every travel guide that seemed worthwhile. In hindsight, none of the guides were really worthwhile. I figured Mykonos wasn’t our scene, but I also didn’t want to veer too far off the beaten path so I added Santorini to our itinerary. And it was without much hesitation, as everything I was reading about Santorini was resoundingly positive. Plus, who wouldn’t want the opportunity to snap their own pic in what’s probably the most photographed spot in Greece?
You may remember that prior to our arrival in Santorini, we had been staying on the rather quaint island of Milos (you can read about our three days in Milos here, here, and here). Our peaceful stay on Milos proved to be poor preparation for our arrival in Santorini. But honestly, I don’t think anything could have prepared me for the Disney land level of tourism we encountered as soon as we stepped off the ferry at the port in Fira.
I don’t think I’m exaggerating when I say it was sheer pandemonium, and we were there on the cusp of the shoulder season in September. But to be fair, the chaos disperses along with the tourists, once everyone is shuttled off to their hotels or villas.
I’m not high maintenance or a diva when it comes to traveling, so I didn’t really mind the cattle call that ensued when we arrived. The local tourism pros have it down to a science, so they’re able to swiftly herd the hundreds of passengers arriving on the ferry into taxis or transport shuttles in a relatively quick manner.
We were planning to hire a taxi to get to our hotel in Oia, but a driver of one of the many nicely air conditioned transport shuttles must’ve recognized the classic look of ‘slightly overwhelmed tourists without pre-arranged transportation’ we were sporting on our faces, and quickly shuffled us into his van, along with a handful of other travelers going to different hotels. It probably took a good 45 minutes to get to our hotel in Oia. I couldn’t tell you a thing about the ride there bc I was keeled over with a bout of motion sickness from sitting in the last row of the large transport van, combined with hairpin turns, and some pretty erratic driving. We learned erratic driving is basically standard practice on this busy island that has very few traffic signals, and poorly marked stop signs that seem to be ‘optional’ for locals.
When we arrived in Oia, I was initially very excited. Our hotel villa was fabulous with incredible sea views, a beautiful pool, and the host was extremely kind and helpful with advice on how to spend our time. She was also happy to help us make dinner and tour reservations if needed.
If you’re looking for a great budget friendly option in Oia located just before the pedestrian zone begins (which makes it easier to access by taxi or shuttle), I would highly recommend Maria’s Place to get a lot of bang for your buck.
But once we got settled and stepped out to explore the pedestrian zone of Oia, I grew annoyed with the type and amount of tourist activity taking place. It was just too much for this tiny, beautiful village, and definitely put a damper on our experience.
One of the seemingly popular, yet extremely irritating tourist activities you immediately notice upon arrival on the island is the rental of four wheelers. I’m sure there’s little to no screening done, so they’ll basically rent them out to anyone with money, regardless of ability. The end result being packs of extremely loud, disruptive ATVs, operated by many clueless drivers running amok all over the island in places where they probably shouldn’t be (eg. pedestrian only zones). I’m sure I sound like I’m an 80 year old grouch complaining about this, but seriously….when you’re trying to enjoy lunch, or a relaxing glass of wine in what is, quite literally, one of the most beautiful places on the planet, the last thing you expect to see are a half dozen four wheelers roaring through a tiny village. But that’s the reality here.
The other thing that kinda puts a damper on the experience is the large volume of cruise ship guests visiting for the day. I mean, I totally get the appeal of a cruise for some, but I can’t imagine doing a Mediterranean type route and only having only a handful of hours to explore some of the most incredible destinations. These travelers are missing out on the very best aspects of experiencing any given location because they don’t really get to experience the true culture and vibe. They have no choice but to rush to pack as much as they can into a 5-6 hour port call, or they can choose to chill out and see not much of anything at all. Neither are great options. Many of these travelers are comin’ in hot with their selfie sticks and jam packed agendas, so they’re not on island time, which only adds to the chaos.
Have you ever traveled to a cruise-ship destination and experienced the calm after the cruise ship leaves the port? It reminds me of the end of a trade show when all the vendors stop pitching and start packing up, except in this case it’s all the tour operators, shop owners, and drivers, and it’s honestly kind of incredible to witness the calm before and after the storm of cruise ship guests. It always strikes me as a big shame that cruisers don’t get to experience the more low key, less hustling vibe. Or the joy of a leisurely three hour dinner in some of the most magical settings on earth.
We usually try to avoid traveling to islands or small coastal cities that host cruise ships because we’ve also found that the tours offered in these locations are generally poorer quality, as most companies are strictly catering to the short timeline of a cruise port call, so the tours are usually rushed, and the substance and value are often lacking. I’m experiencing this now trying to book tours for our upcoming trip to Corfu. Most of them reference accommodating the cruise ship timeline, and reviews indicate the tours are rushed.
But I digress…
Verdict on Santorini
Now with all that being said, if you were to ask me if you should visit Santorini, you may be surprised to learn that I would tell you YES, you should absolutely visit Santorini. There truly is no other place on earth like it, but just be prepared that everyone and their mother, brother, sister, aunt, uncle, and cousin twice removed has the same exact idea as you.
Now for the top three can’t-miss activities while visiting…
I need to preface this recommendation with the reality of trying to view the sunset in Oia the old fashioned way…from the ground, along with everyone else.
As we set out to view the sunset on our first evening, we quickly learned that watching the sunset from the tip of Oia is one of the most popular things to do on the island. So much so, there are several tour operators who haul visitors into the tiny village by the giant commercial bus load just to watch it, unbeknownst to us.
It didn’t take long for us to realize that this activity is best done from the comfort of a restaurant with prime views, as the experience on the ground was honestly one of the worst experiences ever. Below you can see a closeup of what our view was for most of the evening, and we actually got there super early. At least I had a good view of the Frenchie tattoo though.;) There were people flying drones that were noisy and annoying and getting in the way of everyone’s camera shots (and there are signs everywhere saying ‘no drones allowed’), people climbing onto the rooftops of businesses and residences (ignoring signs advising not to), selfie sticks everywhere, and just all around unpleasantness from people jockeying to get into a decent position.
Michael and I couldn’t figure out where the hoards and hoards of people were coming from that were filing into every possible vacant nook and cranny since Oia is so tiny with limited lodging, but we finally figured it out when we made our way off the pedestrian zone to avoid the herd on our way back toward our villa, which is when we discovered the parking area just outside of the village with allllll the giant tour buses (like at least a dozen…and they’re literally the size of a city bus). And then we almost got taken out by the mirrors on a couple of them as they went barreling down the one lane road exiting Oia. There’s no sidewalk after the pedestrian stretch ends, so Michael and I literally have to wedge ourselves into any recess we could find along the walls lining the streets whenever a bus whizzed by us on the dark road.
(see below pic of said stretch of road during daylight)
So having learned our lesson, on our second evening in Oia we asked our host to make reservations for us at whichever rooftop restaurant had availability. We ended up at Pelekanos, and needless to say our sunset experience was exponentially better not having to fight the crowds. So take our advice and get yourself some reservations if you’re planning to view the Oia sunset.:)
I’ve seen plenty of amazing sunsets in my life, but the view of the Aegean sunset from Oia is truly something special. The crowd actually erupts in applause when the sun finally sinks beneath the horizon, which is pretty cool to witness. See little vid here of the tail end of the applause on our first night. The joyful crowd reaction was basically the only positive aspect of our experience viewing the sunset from the ground on night one.
Of course if you’re staying in a villa that has front row seats to the sunset show, then by all means stay in and enjoy it privately.:) We weren’t willing to shell out $500+ dollars a night for the luxury of a caldera view. No matter how nice the places we book are, we’ve learned over the years that we basically don’t spend any time there except to shower, change clothes, and sleep.¯\_(ツ)_/¯
After our incredible sailing experience on Milos Island, we knew we wanted to try to book another sailing trip in Santorini. Since Santorini is significantly more touristy than Milos, excursion prices were also significantly higher, and unfortunately they seemed to include less perks.
We didn’t plan this ahead of time, so obviously we had fewer options available and were unable to find an all day sailing trip similar to the one we did on Milos. Basically everything offered seemed to be half day tours, which were all only three to five hours, and either ran in the morning, or in the late afternoon to catch the sunset. Three to five hours may sound like a long time, but time truly flies when you’re on the water. The longer tours seemed to run during the day, but we also liked the idea of a sunset sail and ultimately couldn’t make up our minds because we wanted both.
We decided to talk to our helpful host at our little villa for some insight, and we’re glad we did because she immediately said we needed to do one of the sunset tours and helped us book one. We ended up booking with Sunset Oia, and we really enjoyed the experience despite it being a bit different than what we were expecting. By “different” I guess I mean I wasn’t expecting a beautiful catamaran to be retrofitted with several rows of bench seating to accommodate more tourists. Thankfully we were able to grab a spot up front on the trampoline (the netting between the hulls), so it still felt like a somewhat luxurious experience as long as we didn’t turn around and see the ferry boat looking seating behind us;).
The crew was absolutely incredible though. There was a full bar in the back with attentive (and handsome;)) Greek men eager to pour drinks, and another small crew that made an amazing greek meal for us. It was one guest’s birthday, and I don’t know who supplied the cake, but her husband had arranged for a crew member to surprise her with it, lit candles and all, and then everyone somewhat spontaneously sang Happy Birthday to her.
We also stopped at a couple swimming and snorkeling spots (so I was able to get my mermaid fix in) before we headed back toward the tip of Oia to get positioned for the magical sunset. By the time the sunset rolled around, everyone was pretty settled and merry with a few drinks down the hatch, so it really was a magical experience. They played great music too, which added to the good vibes. This song is permanently engrained in my brain from hearing it during the sunset. I literally get chills whenever I hear it now and it will forever be one of my favorites.
(here’s a link to an iphone vid I took while my fave song from the trip was playing as all the sail boats were getting into position for the sunset, so you can get an idea of the vibe. Not the best quality as we were basically just laying on the trampoline and taking it all it:)).
While we had a wonderful time and I would certainly do this tour again, it may not be for everyone if you’re looking for a more intimate experience, so I definitely recommend researching all the sunset sailing excursions to find one that suits your schedule and needs.
I’m definitely thankful we were able to experience the sunset from the water, as that was, by far, the best sunset experience of the three we had during our stay.
We love taking in a wine tasting whenever possible while traveling, and Santorini is honestly one of the most fascinating places to learn some history of wine production. There’s evidence of wine production on the island since the Bronze Age, and some of the existing vines are said to be approximately 400 years old. What’s also impressive is that the island averages something like 2 inches of rainfall a year, yet the Assyrtiko grape, which is indigenous to Santorini, somehow thrives here with the help of porous pumice stone in the earth that absorbs moisture from the sea fog and humid climate. The way they cultivate the grapes by forming the vines into baskets that protect the harvest from the harsh sea breeze was another interesting little fact we learned.
We chose this tour, which includes tastings at three very different wineries, and a tour of the ancient Akrotiri ruins, and I highly, highly recommend it. I wish I remembered the name of our sommelier because he was fantastic. All I remember is he was actually from Crete, but he works and lives in Santorini during the high season.
Michael had accidentally left his phone at the second winery, so we were planning to just go back in a taxi and get it after the tour, but when our sommelier overheard us talking about it he quickly arranged to have someone drive the phone to our next stop. He was not bothered at all by the inconvenience (or at least he didn’t let on that he was), and was so reassuring that it was no trouble. This is the sort of attentive service that keeps them at the top of the TripAdvisor rankings.
There were three other couples who did the tour with us, and by the end we were all basically bffs;) They keep the groups small, so it’s a pretty intimate experience.
As far as the Akrotiri Ruins go, if you’re not into wine tours, but even slightly into history, then I highly suggest making an effort to see these ruins. For some perspective, Akrotiri, which was a sophisticated Minoan era civilization, pre-dates Pompeii by 4000 years. Pompeii is basically modern compared to Akrotiri; and like Pompeii, Akrotiri is very well preserved from being smothered by the erupting volcano it was built upon.
If you visit as part of the wine excursion, they arrange for a guided tour with one of the experts who works at this archaeological site. I’m not sure if this is offered if you arrive on your own, but there are employees around to answer any questions. They’ve done a great job modernizing the experience of visiting Akrotiri, as they’ve essentially built a museum around the ruins, so it’s shaded and pleasant to visit.
Closing Thoughts on Santorini
We stayed on Santorini for three nights, which I actually felt was decent amount of time (at least by American standards) considering how long our vacay was altogether, and how many different places we visited in a little over two weeks (Athens, Milos, Santorini, Naxos, and Crete).
When we’d talk with European travelers and they’d ask how long we were staying, we quickly learned three days is basically a layover for them, as most were there for much, much longer. Meanwhile, whenever I see my fellow Americans visiting Santorini it’s usually either for a cruise ship stop, or for one or two nights, so I think most Americans will feel that three nights is sufficient based on our travel styles and comparatively short vacations.
My only regret is that we didn’t get around to visiting the beaches in the (supposedly) less touristy part of the island. I wish I could’ve seen these areas because I’m curious if I would’ve enjoyed staying there, vs. the super touristy Oia. We could have squeezed it in if we tried, but we didn’t want to run ourselves ragged since we were only halfway through our trip.
I know this post is lengthy, and I apologize for that, but I hope you all find my opinions somewhat helpful to get a better understanding of what to expect when visiting Santorini. I see so many “Santorini Travel Guides” that sugar coat everything and most are merely an opportunity to share sponsored content, or pretty vacation photos, but otherwise there’s just a few lines of fluff that don’t offer valuable insight to help with planning decisions. My ultimate goal is to help others that are looking for some kind of guidance.
Please understand that we all have different travel styles and philosophies, so things that may drive me bonkers, some of you may find rather endearing. Simply put, different strokes for different folks, so I know many won’t agree with my assessment, and that’s to be expected:)
You may wonder if I’d ever want to return to Santorini, and the answer to that is I absolutely would, but I’m definitely not in a hurry to with so many other unique Greek islands to explore.:)
A large chunk of Greece’s economy relies on tourism, so I encourage everyone to visit if it’s on your bucket list. We truly don’t know why we waited so long! We ended up loving it so much that we hope to buy a second home there one day:)
Have any of you visited Santorini? How did you feel about your visit? Please tell me in the comments!
And if you think this post might help other travelers, please share or pin the graphic below:)
Until next time, guys!….
Great tips! Another tip would be as a person from the UK – we would never ever travel to the Mediterranean islands & even some coastal places like St Tropez/Dubrovnik /Amalfi etc in late June to 1st week Sept, especially popular islands like Mykonos, Ibiza, Mallorca, SANTORINI Hvar ETC unless you like huge crowds & high prices.
Yes! Such an excellent point! We had to travel in July on trip after this bc we were traveling with good friends and it was the only time everyone could get a couple weeks off and I was completely overwhelmed! Corfu was actually pleasant, but everywhere else we went was total madness. Never again! We were back in greece in 2021 and probably went just a little too late (end of September to early October) so weather was a bit cooler than we’d like and things were starting to shut down for the off season, but we were in less touristy spots so we knew it’d be kind of hit or miss. We still had a wonderful time….can’t ever go wrong with Greece:)