Last Updated on February 19, 2024 by AMANDA CASTILLO
Santorini and Crete! The best itinerary and details of a magical adventure!
Visiting Greece was such a magical experience and such a special trip! I really awakened to my own capacity as someone who can thrive and live a life full of joy and appreciation like never before. Having practiced Buddhism since I was 13 this is saying a lot. Any trip I have ever taken I have always felt so fortunate to be on, but this was different. I was fresh off of a very hard breakup and determined to still go on this Greece getaway that was meant for he and I! Thankfully my best friend stepped up and was able to come and experience this amazing adventure together instead! Did someone say single in Santorini?! Whaaat !!! We visited Santorini and Crete for 8 days and really came up with the best itinerary! Shout out to my friend, Alma! She thoroughly trusted and supported my research and all my crazy ideas. In this blog you’re going to hear a real life account of our trip and the best Greece itinerary! We pretty much lived on the Mediterranean Diet which consisted of a lot of Wine, Greek Salad, Feta and Vine Leaves! Aka grape leaves or dolmas.
Arrival: Santorini
Our first stop was Santorini! Visiting Santorini was just next level, chef’s kiss! I mean it was incredible. From the views and unreal sunsets to the amazing food and wonderful people, I couldn’t take it in enough! I definitely see myself returning to Santorini one day!
Being that we are from Los Angeles we flew out of LAX with a layover in Germany. We had our hotel transfer booked in advance with Welcome Pickups. I highly recommend using them if you prefer to have a driver pick you up as I do. It was very easy to locate our driver once we landed. We were welcomed warmly with a cute tote and map of Santorini. It wasn’t until I was back in LA that I realized it was a tote but it’s fine, I use it as a market bag now. Moving on, our hotel was about twenty minutes away from the airport in Santorini and with all of our excitement it felt like five minutes. Santorini is mainly built on a cliff and a lot of cool hotels are built right into the mountains. Most cars can’t pull right in front of a hotel to drop you off either. Our driver was so kind, he helped bring our luggage all the way to check in, down what looked like a secret corridor to get there.
Ramida Villas, Santorini
Our hotel was the cutest! Again this really was the best Greece Itinerary. We stayed at the Rimida Villas in Oia located right on the Caldera. Literally the perfect location! The room had a built-in cave style private jacuzzi and a fresh breakfast included in our stay served to us on our private lanai every morning. Did I mention our room and patio was overlooking the beautiful Aegean Sea and a gorgeous volcano right in the middle of it?! Dimitri, the Villa Manager brought us breakfast as soon as we called to tell him we were awake and ready to eat. Fresh juice, an assortment of breakfast sandwiches, pastries, fruit, yummy coffee, the most delicious yogurt, granola and local fresh honey I’ve ever tasted. Our morning spread was literally spilling off the side of the table.
It was everything we needed to start our day off right and to keep us nourished while wondering all over Santorini until we found more yummy food! Seriously, the food in Santorini was by far my favorite of the entire trip. Cretes food was good but for whatever reason it was great in Santorini.
The Villa itself could use a little updating but didn’t take away from its homey charm at all. I did however want to start moving furniture and changing things in the room to flow better but for two single ladies in Santorini it was everything we needed. My only minor disappointment was being under the impression that there was a pool. Having a private built-in jacuzzi was a close second and really made our stay feel so special. [See more about this in Greece Fails.]
After indulging in our morning breakfast, a little bit of meditation and yoga. Off we went! Rimida was close to a cute market, the local and easy to use bus station and only a 10-minute walk along the Caldera to Ammoudi Beach. This is where the best view of the sunset can be found near Oia Castle.
Day 1: Sunset Taverna at Ammoudi
We spent the day exploring our new stomping grounds. We had no set plans except for dinner reservations that night. I planned it purposely this way so we could have time to decompress after our travels. We hit the market to stock our room with snacks and beverages then spent the majority of the day relaxing and lounging on our private lanai, basking in the Mediterranean Sun and dying over the killer view. After such a relaxing day and realizing this was real life it was time to get ready for the most amazing dinner of my entire life! Seriously the most amazing dinner of my life!!
Sunset Taverna in Ammoudi is not to be missed. I came across this restaurant on Instagram and made reservations almost immediately after booking our flights. Not only did we have reservations at the perfect time of day to see the incredible Mediterranean Sunset but our table was practically over the water! Our rafraichissoir, or table’s wine cooler, was literally hanging over the water!
If the view and ambiance wasn’t enough to excite the senses, the food was absolutely mouthwatering, every bite was delicious!
We started with fresh squid that was fried, calamari style like we are used to in the states and continued our feast with a fresh local white Fish and the Orzo Risotto with Shrimp. Talk about Fresh…I was literally taken over to pick the fish out myself!! It was so soft and practically melted in your mouth when you took a bite. Everything blew me and my taste buds away! Even the Wine, the volcanic soils of Santorini add a rich taste to the white wine they are known for.
Day 2: Catamaran Tour
We went on a Sunset Catamaran Tour that was literally all day and one of the best days! I had done a lot of research prior to going so I had a couple ideas of tour companies to book with. I am so happy I decided to go with Spiridakos Sailing Tours.
The crew was fantastic and well-spoken in English. There were towels and snorkeling equipment provided to us upon boarding, and I really felt like I was on the TV show Below Deck. It was so much fun. Food and Beverages were included and of course there was a very yummy Mediterranean style spread. We sailed to 8 different locations and were able to swim in the natural hot springs near the volcanoes! I love to snorkel, so I packed my own and was out in the ocean living my best life.
After a long day on the water and in the sun, we were beat and went back to the Villa to refresh and rally for the night ahead. After having a nice dinner we hung out with our new friends that we made on the sailing yacht earlier that day and enjoyed the rest of the night into the wee hours.
Day 3: Kamari Beach & Atlantis Books
Another incredible day in Santorini. We didn’t have anything officially planned and thank goodness because the night before was a late one. Nights like that you can’t plan or put in an itinerary. I love the organic connections and memories you make with people while traveling. They last a lifetime and make some of the best stories to come home with.
Some of the people we met while in Greece we are still in touch with today, even people we met on our flights! Back to the third day though…We decided on taking the local bus to Kalamati Beach…which was not on my Google Doc but recommended to us by Dimitri! (The best recommendations come from locals so don’t be shy to ask.)
The bus was very easy to use and very inexpensive compared to a taxi or private driver. Kalamati Beach was beautiful with rows of bean bag loungers and umbrellas, beachside service and yummy food. We were in absolute heaven! Throughout the entire trip we literally just kept looking at each other in awe, like is this real life?!
After spending most of the day beachside we took the bus back to Oia to rally for the night ahead of us. Famished, ready for dinner and more adventures we were back on the Caldera. We enjoyed a couple bottles of the famously local crisp white wine and dined at a cute restaurant near the Castle of Oia. This was a low key but great night. 
Wondering around we came across cute shops and the most wonderful bookstore called Atlantis Books E.E. It is the only bookshop in Santorini filled with books in all languages and some great first editions! It was really cool.
Day 4: Fast Ferry to Crete
On our 4th and final day in Santorini we had to catch the fast ferry in the afternoon to head over to Crete! Of course, we couldn’t miss our breakfast, proudly served by Dimitri, meditation and yoga routine. After checking out of the Villa we still had plenty of time before we needed to head to the ferry port, so we had Dimitri hang on to our luggage while we went out for one last adventure on the Caldera. 
I had to have one more look at the Castle and the best view in Santorini. We also grabbed some last-minute souvenirs, and I came across my first spinach pie!!!! It was the only time I was upset our whole time in Santorini because I would have had a spinach pie everyday had I known where they were and how insane they tasted. They were next level mouth explosions!
Our ferry tickets were pre booked so all we had to do was walk onto the ferry!
It was actually very easy and kind of cool. I had never taken a fast ferry or been on one that carried cars. On to another adventure excited and laughing the whole time I really had so much fun on that ferry! It flew by! maybe because we had our own dance party just us two on the outside top deck somewhere in the middle of the Aegean Sea, truly living our best life!!! I couldn’t have had a better travel companion.
Alma was such a great sport and fully trusted me, my research and all my crazy ideas. We never stopped smiling or laughing!!! The ferry ride itself was under 2 hours and from Santorini we arrived at the Heraklion port in Crete. We quickly departed the ferry and found our rental car company representative waiting for us with a name sign. My favorite kind of welcoming.
Our car was on sight, and we were on the road in no time! It was super easy and I would definitely recommend them to use if in Crete. Shortly after starting our drive we had to pull over to take in the incredible sunset. Having our own transportation was a game changer. Mediterranean Sunsets just hit differently and I’ve never met a sunset I didn’t like.
Crete & Rental Car Info
Having just come from the oh so romantic and wonderful Santorini to Crete you get two totally different trips. Being in Crete felt more like I was in Europe wondering the cobblestone streets and driving around the countryside. After much research I knew Chanias Old Venetian Harbour was where we would stay!
You can feel the history and energy when you arrive. The history is part of the reason I wanted to visit Crete. The other part was to be able to check out the many amazing Cretian beaches, churches and monasteries Crete is known for. I also had some locations in mind to see along with a few secret beaches I had come across on instagram that I wanted to check out too. Most tours don’t go to those kinds of off the beaten path places, plus I’m really only into tours or hiring a guide when it’s on a boat so having a car was wonderful. I must admit I like the control and being able to stay or go at my leisure which helps with my anxiety too. The amazing thing about having a car is you get a whole other kind of experience and adventure. You feel more at one with the land and the culture and less like a tourist.
We stayed at The Amphora Hotel, which was super cute and right inside the Old Venetian Harbor. It had a great view of the harbor and lighthouse complete with a private balcony to take it all in on..
The room was huge and right above all of the action, restaurants and shops. We got to the hotel well after the check in window, around 9pm, [See more about this in Greece Fails] and were starving so we quickly settled in and went down to check out the scene. The Amphora also has a restaurant below that is so yummy and for the guests that are staying in the hotel you receive a discount when dining… I’ll take it!!!
Day 5: Seitan Beach & Taman Restaurant
Our first day in Crete we went to Seitan Beach as soon as we got up. I had seen it on Instagram and was determined to visit it. This was definitely part of the itinerary and I so happy we made time for it.
Our first day in Crete we went to Seitan Beach as soon as we got up. I had seen it on Instagram and was determined to visit it. This was definitely part of the itinerary and I so happy we made time for it. The Seitan Beach is a secluded, out of a movie one of a kind beach! It’s unreal so you’ll want to get there early for a good spot because it is not a very large beach. Something I wish I had known and that I want you to know before adding this to your itinerary is that you have to be ready for hiking, heat and goats. As you get closer to the “parking lot” you are on this ultra-winding and super small road. It literally feels like you could fall off of the cliff when coming around these crazy tight turns.
It was insanity, but not as insane as it was getting down to the beach itself. I joke when talking about the beach now referring to it as Billy Goat Beach! There were only two goats that we actually saw but that wasn’t the reason dubbing it the name. WE were the billy goats!!!… Climbing up and down the side of this mountain!! When I think of hiking I’m thinking of a dusty trail in between mountains and maybe some trees. Not the case here. It’s a mountain, yes but with no flat surface or trees. You are literally rock climbing, better yet scaling up and down these rocks that make up this mountain. The whole time you’re thinking what did I get myself into and that there is only one way back up after you get down. I tend to be a wee bit dramatic but still…all of my research referred to it as a hike, with no emphasis on describing the reality that you’ll be rock climbing to get to the beach and back to your car. Had we known and been more prepared we would have brought more water, adult beverages, food, towels instead of sarongs to lay on and extra shoes for the rocky beach. Keep in mind most beaches are rocky, not sandy in Greece so water shoes are where it’s at.
When we finally reached the water and looked up at our accomplishment I was dying to jump off of the rocks into the beautiful blue water! Unfortunately, my fear of heights got the best of me. I did jump off of a little baby rock 
but I wanted to hang with the cool kids that were actually cliff jumping into the water. It looked like so much fun. Be sure to secure your belongings from the ever curious Billy goats while you’re taking a dip. They like snacks too.
Another thing you’ll want to prepare for is no shade at all while you’re hiking or when you get there. The sun is fierce, so sunblock it up!! (ocean safe sunblock of course) It sounds like a lot but again had we been better prepared it would have made the experience complete. I’ve never experienced anything like its beauty before. I would totally recommend visiting this beach if a little adventure doesn’t scare you. It is so worth it and I would do it again given the chance.
After the whirlwind of an adventure we had, we were on our way back to the hotel to refresh and rally for the rest of the day. We probably got back around 1 or 2pm from the beach so we had plenty of time to enjoy a glass of wine and vine leaves in the harbor just people watching. We stayed local the rest of the day wondering about the harbor and all its beauty and history. That evening we enjoyed the best food in Crete. Stopping at a couple of places, we had wine and more vine leaves at a random quaint restaurant we happened to stumble upon while looking for another restaurant. It was such a vibe especially with the guitarist playing soft traditional Greek music. We actually went back to that place twice just to enjoy the music and have a glass of wine. I wish I knew I was going to blog about all of this at the time, I would have gotten the name of the restaurant!
I highly recommend Tamam for dinner!
Make reservations if you plan on it or at least try to be understanding if there is a wait. It is so worth it to eat here! It’s also walkable from the harbor and easily found if you put it in the GPS on your phone. We both had the Lamb Kabobs, and I was not disappointed, it was the best lamb I’ve ever tasted.
We also checked out a bar I came across during my research called Synagogi.
Literally it was in an old synagogue and was so cool. It had a slower pace than expected so we only stayed for a couple of drinks. Later that night we found ourselves at DNA nightclub tucked away above some other restaurants. Talk about fun! We met great people and danced the night away making memories to last a lifetime. I’d be lying if I said the next day wasn’t a little rough and we had to get a very early start.
Day 6: Elafonisi Beach
On our second day in Crete we went to Elafonisi Beach. It was a destination I had researched prior and it was also at the top of my list! We jumped in the car and were on the road early! I really wish we had a better experience there. All the posts I came across recommended arriving early because it can get crowded, which I thought was crazy because it is huge. What they really should have shared is that it’s not so much crowded as it is running out of loungers with umbrellas. The heat was so strong at the end of June when we went that it was unbearable to be in it directly for too long. Not even long enough to wait for an umbrella with shade to become available. We were already burnt from being in Santorini so the heat was sizzling on our skin by the time we were in Crete. The salt water plus no shade was not comfortable to stay in for too long. There was also a wind tunnel that the beach seemed to be right in so the hot air was also smacking into your already sunburnt skin and it just wasn’t pleasant. We arrived before 10am and still weren’t able to score an umbrella and loungers so we were on our way back around 1pm. I think with shade and less wind we could have made it work and really enjoyed ourselves!
Getting back to our hotel early wasn’t the worst thing either. It gave us plenty of time to refresh and rally as I like to say aka nap and shower. We were back out in the harbor for a late dinner in true Euro style and to see where else the night went. Another unforgettable late night filled with so much fun and 2am Gyros! It was truly an epic way to spend our last night in Chania.
Day 7: Lake Kournas & Heraklion Hotel
We ate at a family owned restaurant right on the lake where we were able to take it all in. I could almost cry now thinking back to it. If we had more time that day we would have taken a dip and stayed longer than we did because it was absolutely serene there. We felt so lucky to have come across it. Moments like those, a look was all we needed to pass between us to know we were both feeling so fortunate and present in that moment.
After leaving the lake we continued on our journey to Heraklion making several more small stops because why not and because we could! We couldn’t miss our last Mediterranean Sunset either so our final stop was at a random beautiful beach that we pulled over to. The beach was full of umbrella loungers, music and beachside food and drink service… It was perfect! After the sunset we finally checked into our hotel for the night. Since we had been in Heraklion twice now we felt it right to at least walk around and have dinner for a last round of vine leaves and wine. It didn’t disappoint.
The morning of our departure we loaded up the car and drove ourselves to the airport. I had made prior arrangements to drop off the rental car at the airport even though we picked it up at the ferry port and it couldn’t have been easier. And just like that we were on our way back to reality. With more highs than lows this trip was absolutely incredible. I still smile thinking about it and looking at pictures. Being able to write about it and share my adventures with you really is so gratifying. Thank you for reading . Let me know your thoughts…drop a comment below.
