The Cyclades are the most popular of the Greek islands, and for good reason. In this trip we take a luxurious 11 day journey to explore all that Santorini and Mykonos have to offer. Join us as we wander the charming streets of Oia and Mykonos Town, indulge in wine, discover ancient sites, relax on pristine beaches, and sample some of the finest hotels the Aegean has to offer!
We are very fortunate to live in such a beautiful world. Why not make it a point to see the very best of what our planet has to offer? When we think of the very best, the Greek islands are what come to mind. The culture, the food, shopping, and scenery are all second to none. Having only briefly stopped in the Greek Islands before, we decided to do a deeper dive this trip. There are many Greek islands on our bucket list, but we decided to focus on the most popular islands of Santorini and Mykonos.
The Greek Islands have an abundance of luxury hotels to choose from. We were looking for the best hotels in Santorini with the nicest suites. Incredible views and convenience were paramount to our decision. In Mykonos, we capitalized on the opportunity to burn Marriott Bonvoy points on a luxurious stay. Below are the hotels we called home on this trip.
We are about to embark on an 11 day adventure of these incredible islands and will be doing so in style! Now, the Greek Islands are notoriously among the most expensive places in the world to visit, so we had to be smart to offset the cost. We decided to unload our Chase Ultimate Reward points and Marriott Bonvoy points on this trip.
We used the Chase Ultimate Rewards points to book business class on United Polaris to Athens. We would take local flights between the islands on separate bookings. Flying Polaris was a good choice because it also gave us access to the Aegean Business Class Lounge at Athens International airport.
First up was Santorini. We spent 7 nights here and split our time between Imerovigli and Oia and we recommend both. Imerovigli sits at the highest point on the island, faces west, and has spectacular sunset views. Oia is one of the most charming villages you will ever visit, has amazing views, and delivers on every thought you ever had about the Greek Islands. We spent 4 nights in Imerovigli and 3 nights in Oia and that time felt about right. We headed over to Mykonos next for a 3 night stay. 3 nights is definitely not enough time, so plan on another day or two. We opted to fly between islands, which requires a connection in Athens. It makes for a long day. You could opt to take the ferries to save time if you don't get sea sick.
We had been saving Chase Ultimate Rewards points for a good use and splurging on business class for this trip seemed like a good time to unleash them. We booked round trip flights from Washington D.C. Dulles to Athens on United Polaris Business Class onboard the 787-8. Click below to read our full review of the experience.
We were able to utilize the brand new Aegean business class lounge in Athens International Airport since United and Aegean airlines are both Star Alliance partners. This lounge was contemporary and clean and provided a nice refuge from the busy terminal below. Click below to get more information about this lounge in our blog.
We decided to focus heavily on Santorini for 8 of the 11 days of our trip and we are glad we did. Santorini has so much to offer and an abundance of beauty to absorb.
Santorini was formed 3600 years ago from a volcanic eruption at the height of the Minoan civilization. The sheer power of the eruption caused the volcano to collapse into itself forming the incredible crescent moon shaped caldera. Santorini is located in the Aegean sea and is part of the Cyclades islands.
Located in the middle of the Aegean Sea, Santorini enjoys a semi-arid climate. The summer months experience average high temperatures of 84℉ (29℃) with the shoulder months averaging highs of 73℉ (23℃). Rain is virtually non-existent from April through October.
Santorini is a seasonal island with most hotels, restaurants and businesses operating from April to October. The island is packed with tourists during the summer months of June, July, and August, so planning your trip in May or September is ideal to avoid the huge crowds and enjoy summer-like, but not blistering hot weather.
Santorini is a very relaxed island and caters to travelers who want to relax in luxury, dine, and take in the spectacular views. While there are some bars and clubs, mainly in Fira, Santorini is not the place for party goers. Try Mykonos if legendary nightlife is what you are after.
Santorini is a romantic island and draws a lot of couples celebrating honeymoons and anniversaries. However, there is room for families and there is plenty for kids to enjoy on the island. Just be sure to verify your hotel accepts children as many are adults only. Additionally, Santorini is a popular cruise port and can become inundated with tourists in the main towns of Fira and Oia.
We split our time between two hotels. First, we stayed 4 nights at Cavo Tagoo in Imerovigli. Imerovigli is centrally located on the island and sits at the highest point offering spectacular views of the caldera. After Cavo Tagoo, we spent the next 3 nights at Andronis Luxury Suites in the heart of Oia.
Stunning views and a legendary infinity pool crown this property as one of the most instagrammable hotels in the world. Top notch food, spacious suites and impeccable service make Cavo Tagoo an obvious choice for your Santorini holiday!
Andronis hosts several properties on Santorini and the flagship hotel is Andronis Luxury Suites. This property boasts some of the best suites on the island, one of the top restaurants (Lycabettus), and an on-site spa, all within the heart of Oia.
Santorini has an abundance of activities including exploring its’ charming towns, visiting wineries, discovering ancient sites, and taking a break on the beach.
You certainly know by now that Oia is the most popular spot in Santorini, but for good reason. This town is the very essence of Santorini. The luxury hotels, fine dining, killer views, and jaw dropping sunsets are some of the reasons you need pay this place a visit.
Skaros Rock is a hiker / climbers dream. It is a perfect mesa jutting out from the very center of Santorini’s crescent moon in front of Imerovigli. The hike is easy about 90% of the way up, with the last 10% presenting a bit of a climbing challenge. However, anyone in decent physical shape should be able to climb it. The photos below show the most difficult part. Those who brave the final 10% are rewarded with incredible 360 degree views of Santorini. Don’t forget to hike down the backside of Skaros Rock as there is a cliffside church allowing for perfect Instagram shots!
Allocate 1.5 to 2 hours for the round trip hike from any of the hotels in the vicinity of Imerovigli. Do this hike in the morning to avoid the heat and the crowds. Be sure to bring bottled water with you.
The charming town of Imerovigli contains numerous high-end hotels, especially 15 minutes north on the Fira-Oia trail. The main town is small with a few shops and restaurants. However, you will certainly want to pay this town a visit as it enjoys views of the caldera from the center point of the crescent, at the highest point on the island. Imerovigli also faces west and, in my opinion, provides even better sunset views than Oia.
The Fira-Oia trail hugs the cliffs of the caldera and provides a walking path from Fira to Oia. The entire one-way trip takes about two hours with numerous stopping points along the way with killer views.
Santorini is famous for its’ sunsets. The perfect summer weather and westward facing geography will provide all the eye-candy you could ask for each evening.
The most popular place to catch a sunset is on the far west flank of Oia, but this is hardly the best spot. If you want to get a good view, you will need to camp out hours before sunset as this is easily the most popular viewing spot in all of Santorini. The crowds are insane and detract from the experience. I recommend heading over to Imerovigli, getting a table at one the amazing restaurants, and taking in the perfect views.
Wine is a big business in Santorini and Wineries dot the map all over the island. The island is famous for its’ unique grape varietes, Assyrtiko, Athiri, and Aidani, thanks to the volcanic soil and cool evening Aegean breeze.
The concierge at Cavo Tagoo, as well as our Greek friends, recommended Domaine Sigalas, which is right down the hill from Oia. We are not wine snobs by any stretch, but the winery provided excellent tasting menus with an assortment of snacks. Of course, all were available for purchase.
Santorini provides some of the most unique beaches in the world thanks to the active volcano. Here you can find red, black, and white sand beaches.
The most popular, by far is Red Beach and can be found in the southwest corner of the island, just a 10 minute walk from the Akrotiri archeological site. There is plenty of parking on either end of the beach with small restaurants and food vendors.
Entrance to the beach is easy from the west side. However, if you park on the east side, you will encounter a small hike over rocks to get to the beach. It is an easy hike, but watch your step since you will probably be wearing sandals.
Ancient Akrotiri was a thriving settlement 3600 years ago until it was completely obliterated by the Minoan eruption circa 1600 BCE. The town was completely covered in ash, preserving the frescos and other works of art.
The site is completely enclosed and is open to the public. The town is not large and will take only an hour to 1.5 hours to walk through. This archeological site is a perfect stop before hitting nearby Red Beach. Click the button below for the official website.
There are plenty of companies in Santorini that can charter a boat or arrange a dinner cruise on the caldera. If you are staying at a fancy hotel, the concierge should be able to arrange this for you. Be aware that the Aegean is a windy place and the boat ride may be rough. You may want to reconsider if you easily get sea sick.
Take Santorini’s insane views to another level, literally. There are numerous companies running helicopter tours of the island. Utilize the concierge if available at your hotel as this will make coordination much easier.
After Santorini, we headed to Mykonos for a 3 night stay. In retrospect, 3 nights was too short and another one to two nights would be better.
Mykonos served as a popular trading port through the centuries as part of the Roman, Byzantine, and Ottoman empires. The island became part of Greece after the Greek Revolution against the Ottoman empire and lost its status as a trading powerhouse with the creation of the Corinth Canal. Mykonos later emerged as a travel powerhouse in the 20th century and is now one of the most visited islands in the Cyclades.
Located in the middle of the Aegean Sea, Mykonos enjoys a semi-arid climate. The summer months experience average high temperatures of 83℉ (28℃) with the shoulder months averaging highs of 79℉ (26℃). Rain is virtually non-existent from May through September.
Mykonos is a seasonal island with most hotels, restaurants and businesses operating from April to October. The island is packed with tourists during the summer months of June, July, and August, so planning your trip in May or September is ideal to avoid the huge crowds and enjoy summer-like, but not blistering hot weather.
You will find a lot more action in Mykonos than other islands in the Cyclades. Mykonos is famous for over the top parties that run well into the night. You will feel this Vibe in Mykonos town in the evenings. Restaurants and bars are packed while the music blasts from clubs in Little Venice. The vibe is calmer away from the town and families will find an excellent selections of resorts to enjoy a relaxing holiday.
Mykonos is a party island and will draw large crowds of people in their 20's and 30's. Resorts here will cater to families and there are plenty of family friendly activities available outside the party scene. Additionally, Mykonos is a popular cruise port and Mykonos Town can become flooded with tourists. Don't expect to get a crowd-free shot of the windmills.
We decided to stay at Santa Marina, which is part of Marriotts’ Luxury Collection to use points to save on cost. This hotel is located in Ornos Bay, which is a 10 minute drive from Mykonos Town. If you want to explore the town more thoroughly, you should consider staying at a hotel directly in town because the traffic and parking is terrible.
There are a lot of resorts to choose from in Mykonos, but what makes Santa Marina an easy choice is that it is part of Marriotts’ Luxury Collection. Luxury hotels in Mykonos are not cheap and the ability to use points to book Santa Marina is a huge draw.
The hotel itself has a large selection of rooms and multi-room suites, making it the perfect choice for families. The private beach on Ornos Bay is the highlight of this hotel. The pool and spa are also awesome!
Mykonos is famous for its’ nightlife, but there is so much more the island has to offer. Mykonos town is one of the most charming in the Aegean, there is an abundance of shopping, beautiful beaches, and of course, the windmills!
The main town is the most popular attraction of course. This Labyrinth of stone streets and whitewashed buildings oozes with Greek Island charm. Enjoy the vast selection of restaurants and go shopping at the many boutiques. Just wandering around this town is eventful on its own.
Nestled right in town are the world famous flour windmills. Do your best to get the perfect shot, you won’t be alone!
Also located along the waterfront of Mykonos town is an area known as Little Venice. This is a small area with restaurants and bars and certainly not much space. However, it is another spot to get some great photos.
With nearly two dozen beaches, Mykonos is a sun worshippers paradise. Unlike many other Greek islands that feature rocky beaches, granular tan and white sand graces many of Mykonos’ finest shorelines. Some of the most popular beaches include Ornos Beach, Platis Gialos Beach, and Agios Ioannis Beach.
Mykonos is world famous for its’ over the top nightlife. Bars and clubs can be found all over Mykonos town. There are also many beach clubs. One of the most famous is Scorpios and is the place to see, be seen, and dance the night away.
Sunsets in Mykonos are incredible and one of the best ways to take them in is by cruising the local bays. Lots of operators provide sunset cruise tours. Book early!
A helicopter tour is usually one of the most unique and special ways to see the world and Mykonos is no different. There are plenty of operators in Mykonos and your hotel concierge can assist with arranging this for you. I recommend coordinating with either the operator or your concierge well in advance of your visit.
The island of Delos and its’ ancient town is only a 45 minute boat ride west from Mykonos. If you like to explore, taking in the sights at Delos is a must.
Mykonos may be known as the party island, but this place has plenty of beauty to share with couples and families alike. Explore the town, take selfies with the windmills, shop the fine boutiques, and eat at one fine restaurant after another. Get off the beaten path and enjoy the many fine beaches on tap. Mykonos has so much to offer and our 4 days wasn’t nearly enough. We will definitely be back to sample more of what this island has to offer. See you out there!
