The picturesque island of Santorini, Greece – home of blue-domed churches, dramatic cliffs, picturesque villages, and magnificent sunsets – makes for an incredible luxury vacation. Though it is one of the most popular of the Greek islands, there are ways to explore this gorgeous island without the crowds, if you know the secrets of Santorini’s luxury travel options. I planned a luxury Santorini vacation and experienced all these activities first-hand; read on for how you can plan your own vacation in style.
Why Santorini and When to Visit
Athens and Santorini was one of the best trips I’ve planned yet; it was the perfect balance of activity and downtime, convenience and privacy. I thought I would love Santorini for its picturesque views and killer food. I ended up loving it for all that and more – its surprisingly complex local wines, friendly hospitality, small towns, and safety.
The closest comparison I can make for the type of trip I was able to plan in Santorini is Lake Garda in Italy. Though Italy holds my heart, I actually felt like Oia in Santorini was an upgrade in many respects from Gargnano, the town I stayed at on Lake Garda.
Who Will Love Santorini
Santorini is the ideal location for foodies who appreciate wine, people who love a birds-eye view of the water as opposed to laying on the beach, and people in good physical fitness.
You could easily plan your trip to Santorini around food alone, which is one of the best things about travel anywhere, I suppose. We did not have a bad meal in Santorini, though I would steer you away from the hotel restaurant at Mystique (overpriced and mediocre, as hotel restaurants so often are). Whether you’re looking for a romantic private dining multi-course experience (try Panorama at Canaves Oia) or rock-solid street food (try Pito Gyro), Santorini is not going to disappoint. The wine scene is also surprisingly robust, with luxury wine tasting experiences featuring unique, high-quality wines you can’t find outside Santorini.
Santorini is a large island, but most of the population and amenities are clustered in a few towns. Luxury travelers are likely to migrate toward Oia, where most of the 5-star luxury hotels are located. In these towns, you will see stunning views of the water and nearby islands, making them perfect for relaxing poolside with a book. Visitors looking to recharge, soak in the views, and who are willing to hop in a car and drive to excursions and activities will find Santorini to be a great fit. I was surprised at how much time we spent in a car, touring the island, moving from one hotel to another, and driving to the activities I booked. It was well worth it, however, to be able to stay in Oia with its world-famous views.
Who Might Want to Skip Santorini
Santorini is a rocky, volcanic island, with its towns perched on cliff tops. That means that its beaches, which are more pebbly than sandy, are out of the way from where you will likely be staying. For this reason, I don’t recommend it as a beach vacation, especially for families. Some beaches are accessible only after a walk/hike over rocks, and others are only accessible by boat. Santorini is more for looking at the water than being in it.
Santorini’s main towns of Oia, Fira, Firostani, and Imerovigli cling to the cliffs at the top of the island. There are narrow roads that connect the towns, but once you arrive, it’s a different story. Most hotels and holiday rentals are located on pedestrian-only cobblestone paths. These paths are narrow and feature frequent elevation changes, with uneven stairs and no concessions for visitors with mobility challenges. Visitors with limited mobility would be able to navigate some of the towns in the south of the island like Megalochori, but would have to miss the quintessential Santorini experience.
How Many Days to Spend on Santorini
The short answer is 2-3 days to see the major sights and 5-7 days to relax and recharge.
In 2-3 days, you can walk around the major towns on Santorini, see a famous Santorini sunset, try some local wine, and maybe even get out on the water. In 5-7 days, you can pace your trip more slowly, experiencing all that and still enjoying long stretches of unplanned time just looking at the insane view or lingering over a good meal. You can stay in 2 different towns, allowing you a fuller experience of the island and providing a respite from the cruise ship hoards that won’t have time to visit the smaller spots in their one day on shore.
Where to Stay
Though there are several options for luxury travelers, one of the best luxury hotels (and where I stayed) is Mystique, a Luxury Collection hotel in Oia. This is one of my favorite Marriott hotels worldwide, because it is perfectly located a 5-minute walk from the pedestrian area of Oia, and yet it was completely secluded from the cruise ship crowds visiting the Cycladic village. Mystique offers the perfect combination of space, privacy, convenience, and service. Mystique checks all the boxes for a luxury cave hotel – simple, beautiful design, some rooms with their own swimming pool (we loved room 19), private hot tubs, and unobstructed caldera views.
Canaves is a family-owned group of several luxury properties on Oia, including the hotel next door to Mystique. Its service is purported to be better than Mystique, and I could believe it, as the service at Mystique is adequate but not exceptional. I was able to peek at the patio of a room at Canaves from Mystique and it is similar quality with the same view.
Where to Eat
Try a New Take on Moussaka at Alisachni (Megalochori)
Alisachni in the town of Megalochori was a food highlight for me. Everything we tried was delicious and inventive, with the moussaka being a particular winner. It was deconstructed and not like a traditional moussaka, and it was delicious nonetheless. Alisachni has a solid wine list, and you can enjoy a glass while looking over the cobblestone streets of Megalochori, or inside one of the many inner courtyard or covered seating areas. Alisachni also serves as an art gallery, with fine art displayed for sale throughout the restaurant. It was the perfect lunch spot for a two-dollar-sign meal that punched above its price class.
Dive into the Classics at PitoGyros (Oia)
You can’t visit Greece without digging into classics like gyros, souvlaki, Greek salad, and tzatziki. I found PitoGyros in Oia to be the perfect mix of casual street dining, good value, and excellent food. It’s not fancy, and it doesn’t need to be. Sometimes luxury means quality without pretense, and that’s what you get at PitoGyros. There are no online reservations, so be prepared to walk up and put your name down. You may have a wait, but it’s worth it. Visit here for dinner when you want good food without any fuss.
Dine with a View at Aegean Restaurant (Imerovigli)
Dine on fresh seafood with a view of white-washed buildings and the sparkling blue sea at Aegean Restaurant in Imerovigli. This open-air cafe serves seafood, pasta, and light bites perfect for a leisurely lunch. The grilled octopus was delicious; the fava bean dip was good but not particularly memorable. Sadly, they could not accommodate my husband’s gluten allergy with the dip by serving raw vegetables in place of bread, nor did they have gluten free bread. Overall, Aegean is a great place for lunch or an afternoon coffee break.
Take in the Sunset on the Water at Sunset Tavern Ammoudi (Ammoudi Bay)
Santorini is known for breathtaking sunsets, but to see them, most people crowd the tiny streets and alleyways of Oia, staking out their spot hours in advance and waiting in the hot sun. Skip this and book a table at Sunset Tavern Ammoudi, where you will dine directly on the water (tables are inches from Ammoudi Bay!) with an unobstructed view of the sunset.
This is a different view of the sunset than you will get at the top of the cliffs, but a much more pleasant way to enjoy this ritual than packing in to the tiny walkways of Oia.
Sunset Tavern Ammoudi is known for its lobster pasta, and it did not disappoint – they even made it with gluten-free pasta for my husband! We loved everything we tried, from the dips to the drinks to the Greek salad.
One thing to note about this restaurant is that it is seaside, meaning that you have a long and somewhat slippery walk down a road that zig-zags from Oia to the water. It was doable in daylight, in flat sandals with heel straps, but I would recommend sneakers if possible, and I would be extra careful about returning to the top after dark. We opted to have a car come pick us up (there is a parking lot right down at the waterfront – who knew) and drive back to our hotel. Mystique charged us $25 for this, and though it was a bit overpriced, it was worth it to us.
Sunset Tavern Ammoudi is popular, which means prices are high. This was one of our most expensive dinners on the island, and it was good, but recognize that you are paying for the uncrowded sunset views and the ambience more than the food itself. If you have the right expectations of what you’re getting, you will have a great evening.
Dig Into Small Plates at Melitini (Oia)
Melitini is a few blocks back from the cliff edge in Oia, but its rooftop dining area still sports a peekaboo view of the water. What it lacks in view, it makes up for in variety and quality of food. Made for sharing, the small plates at Melitini let you try lots of options. Our favorites were the lamb shank, the dip trio, and the chicken skewer with grilled vegetables. Melitini is great for lunch or an afternoon snack / happy hour. It is open for dinner, though I think I would reserve nights for somewhere with a view of the Cycladic architecture all lit up against the dark sky.
What to Do – Best Luxury Activities in Santorini
Santorini can be cookie cutter, crowded, and overdone. It can also be private, customized, and unique. I’m constantly seeking out ways to dig beneath the surface when I visit a new place. That usually means turning left when the tour groups turn right, visiting a location in off hours, and working with locals to get a fuller sense of what I’m seeing. If you want the best with no compromises, read on for the best luxury activities on Santorini.
Take a Private Sunset Boat Trip
A private boat excursion is an amazing way to see Santorini from a new angle. Join one of the popular sunset cruises, which can take you around the island to places like Red Beach, White Beach, and Thirassia (one of the islands ringing the caldera that was connected to Santorini before the volcanic eruptions), with a stop to swim in the warm springs heated by the volcano. Enjoy secluded luxury against the backdrop of the turquoise waters of the Aegean Sea and get spoiled by a dinner feast that is truly eye-popping.
There are many luxury boat tour options, but I recommend Spiridakos.
Double Down on Glam with a Flying Dress Photo Shoot
Looking for an unforgettable experience on Santorini with a souvenir you can’t get anywhere else? Book a professional flying dress photoshoot, where you’ll transform into a Greek goddess in a long, flowing dress and spend an hour taking photos with a variety of backdrops, including the iconic blue domes and traditional architecture clinging to the high cliffs overlooking the caldera. Read my review of my photo shoot with Flying Dress, who I enthusiastically recommend.
Get Off the Beaten Track with a Private Tour of the Island
An efficient way to see a lot of Santorini is to book one of the private tours offered on the island. Your driver can take you wherever you like, and the beauty of a private excursion is that you can control the pace, staying as long or as short as you like in each place. On my 6-hour private tour with Omega Travel, we started in the town of Megalochori, did a leisurely wine tasting at Estate Argyros before a quick visit through Art Space. We then visited one of Santorini’s black sand beaches, detoured up to see some windmills, and stopped at numerous points for panoramic views of the island. These were places our driver, a Santorini local, recommended, and ones I likely wouldn’t have known about myself. It gave us a chance to peek into towns like Imerovigli Village and Firostani. We had enough time for a coffee break with a view before our driver dropped us off in Oia (where we were moving hotels).
If we hadn’t spent so much time at the wineries, we could have also visited the ancient ruins in the village of Akrotiri, one of the most popular destinations on the island for its history.
Go Wine Tasting in a Secret Cave
The wine on Santorini was a surprising highlight of my trip. I have taken wine-focused vacations to Italy and Portugal before, but I wasn’t expecting to love Santorini wines as much as I did. Perhaps my favorite wine tasting experience on the island was in the secret cave at Vedema, a Luxury Collection hotel in Megalochori. We were spoiled to have the food and beverage director lead us through a private tasting in a 400-year-old cave, introducing us to all the quirks of Santorini wines. We learned everything from why Santorini grapes don’t have to worry about grapevine-killing phylloxera (the volcanic ash in the soil is inhospitable to the bugs) and how they keep the plants watered without irrigation in a place that rarely rains (the unique basket-shaped vines collect and preserve the dew for the grapes to absorb).
If Megalochori isn’t in your plans, I also loved the tour and tasting at Estate Argyros, the private cave tasting at Mystique, another Luxury Collection hotel, and, to a lesser extent, Art Space.
Top Rated Private Tours
What to Bring Back
I struggled a bit with what kind of souvenirs to bring back from Santorini. I am a proud member of Team Carry On, which meant that olive oil (one of my first ideas) was out. It didn’t feel particularly authentic, as Santorini doesn’t produce olive oil. There are some olive trees on the island but it’s not a crop. Similarly, the liquids limit meant that we weren’t bringing wine back. So, what is authentic to Santorini and avoids the kitsch?
There are several wonderful art galleries on Santorini, with works for sale that capture the essence of Santorini’s warren of pedestrian streets and blockbuster views. Additionally, street artists are happy to produce a custom piece of art for you while you wait. Check out Art Space in Exo Gonia for original works or the streets of Oia for street artists.
If you aren’t limited by your liquids, bring back a bottle or three of Santorini wine. The main grape on the island is a native white varietal called assyrtiko, and their only native red varietal is the light, drinkable mavrotragano. I was surprised and impressed at how high-quality the wines on the island were, and I will happily hunt for Santorini wines at speciality wine shops at home.
Looking for a specific bottle? I loved the NV brut from Santo Wines, the only sparkling wine made on the island, the 2002 vinsanto dessert wine from Estate Argyros, and the 2021 mavrotragano from Hatzidakis Winery.
Photos from a Professional Photo Shoot
Santorini is ridiculously photogenic, and the island abounds with photographers who know just where to go for the perfect backdrop. I did a flying dress photo shoot in Imerovigli and consider the photos one of the best souvenirs I’ve ever gotten on a trip, but if you want to keep it a bit more casual, there are many photo services that offer more traditional photoshoots for couples, families, and solo travelers alike.
What to Wear in Santorini
Think chic, breezy, and colorful – and practical. Take a look at our full guide on outfit inspiration for Santorini.
I’m still dreaming of Santorini. From private tours to exceptional wine to turquoise waters, the island offered surprise after surprise. It was what I dreamed of and more, and with this guide, you too should be able to easily plan your perfect luxury Santorini vacation. Yamas!