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Santorini and Mykonos Travel Guide

Santorini/ Mykonos Travel Guide

This is a long overdue post on our dream honeymoon to Greece! I wrote a post on planning a trip to Santorini and Mykonos here and it was a hit. So now I am going to share with you how we broke up our time, our favorite places, and must do/see at these breathtaking places.

We surprisingly stuck to our rough itinerary pretty well! I am going to break this post up into a few different sections to make it easier to follow because this is going to be a long one!!

Getting There
Thankfully everything went as planned on our flight there (that is always such a stressful part of traveling out of the country for me because if one thing is delayed it can mess up your entire trip!).

We flew from Boston to JFK because it was cheaper to get a direct flight to Athens out of JFK. Our BOS-JFK flight was on a separate reservation and was super cheap. When we got to JFK we had about 4 hours to waste. My husband has a Delta credit card and status on Delta which is given to a spouse when you book their ticket so we both got into the Sky Club for free. They have free drinks, free food (like buffets), outdoor deck, leather couches and chairs, etc. so it was a nice area to let the time go by. We then took an overnight flight to Athens which I don't think I slept at all, I couldn't get comfy but oh well, we were going to Greece! Delta is great to fly internationally because you get like 3 free meals! I have to say when we went to Italy my husband got our seats upgraded to first class so for that flight we slept the whole flight because your'e legit in a bed lying down- we deff missed that this flight, haha!!

Once you land in Athens you have to go through immigration/ passport control which was pretty quick.  I originally left 2 hours before we boarded our next flight to Santorini and we definitely could have taken a flight that was an hour after we landed. You wait for your gate and then go through security. Our flight was on Olympic Air and was a 45 minute flight on a little puddle jumper (scary!!) it was a little delayed to take off. I did watch the monitor for the other airlines that people claimed to be always delayed or canceled and they took off on time. We probably could have spent less money on tickets and just booked on one of the flights but I wanted to be safe. I am SO glad we paid for the flight option because the 6 hour ferry after our long flight would have been terrible. (You have to take a taxi to the ferry port from the airport too).

When we finally landed in Santorini we were so exhausted we just wanted to sleep! Our hotel, The Vedema, offered free shuttle pick up from the airport and was about a 25 minute ride to the hotel which was in a little village with locals that are literally neighbors to the resort!

Santorini - 5 nights @ The Vedema (a Marriott hotel)
The hotel really felt like you were staying in a Greek village and was in the area of the Island called Megalochori. You have an old fashion key to enter your room and your room/suite really had the Greek feel to it (lots of white and blue and an older feel). This hotel hands down was the best breakfast I have EVER had a hotel. We got free breakfast with our stay and man, the buffet had a ton of traditional Greek items (Greek yogurt bar, Greek pancakes, cheese bar, etc) and was so incredibly good. Our hotel was south of the island and offered shuttle services to the following at set times throughout the day (you could pay to have a private shuttle at another time if needed):
  • To and from Thira (mid island)
  • To and from the sister hotel/restaurant if you have a reservation in Oia (top of the island)
  • To and from another sister hotel on the beach south of the island 
When we got to our room we needed to eat something before we went to bed so we went to this little local restaurant in our village that was walking distance called Geromanolis and OMG, wow so good. We got the calamari (best we had the whole trip) and 2 entrees, and you get free dessert! 

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Day 1- Santorini 
After sleeping the rest of the day/night when we got there we decided to do our hike while we were well rested. We took the shuttle bus from the hotel to Thira (mid island) which dropped us at the bus station in the main part of the town and started the trail there. It is pretty well marked once we asked some shop owners how to get to the start of the trail. Most of the trail at the beginning is on paved walk ways and there is deff a lot of steps and elevation change (and stray cats!!). There were a few times we ended up wandering down the paths (stairs) into hotels/ villages but the staff always pointed us in the right direction. It took us about 4 hour to complete and I would say it was challenging but doable, it is definitely a trail not really a hike. The last hour is the hardest and is on dirt and up and down steep hills- BRING LOTS OF WATER! I think we went through like 6 water bottles between the 2 of us. We stopped a lot for pictures because wow, the most incredible views of the entire trip and I would do it again just to see those views. The end of the trail brings you right into Oia (top of the island) which is a totally different vibe- very classy, lots of white, marble walkways, etc. We ate at Roka which had signs and was easy to get to from the end of the trail, it was so nice to sit. Not a great view but its good food- I had the fresh dorotto fillet and it was SO good. 

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That night we had dinner at Metaxi Mas which we got a shuttle to. It is kind of out of the way but holy cow, the best meal we both had the whole trip! A must go to! I made reservations about 3 months in advance. It is not a Caldera/ ocean view but you can see the sky change color during sunset. You can go before or after sunset here, no need to plan around a sunset. Mike had the lamb and still talks about it, I had grilled octopus.

Day 2- Santorini 
We took the hotel shuttle to the sister resort which is located on the famous black sand beach. You got to use there free comfy beach beds and umbrellas and they have waiters. Wow, what a cool experience the black sand beach is surrounded by mountains. We live 50 minutes from beaches but this was like nothing else. The sand is like mini black pebbles and you just sink into it in the water and man it is HOT when you are walking on it. I would add this to your list if you can find some time to go! We spent about 4 hours there just relaxing and swimming. 

We hung by the hotel pool and then walked to a local gyro place and got 2 gyros for $6 and then to the 24 hour bakery called The Family by our hotel for baklava.

I made reservation at Venesanos Winery 3 months in advance for a tour, tasting, and sunset table. There was a path that we could walk to from our hotel which was awesome because they drive crazy on the main road! The winery is so cool, the wine was delish, and the view here is unreal, very windy though! The tasting view of over the Caldera (ocean) and the sunset table is near the vineyard/ Caldera. We started at 4 and sunset was at 7 so we chilled at our table and had apps and some wine until the gorgeous sunset. Make sure you call ahead and reserve a sunset table, its free as long as they have openings!

Day 3- Santorini 
We used this day to just explore. We took the shuttle to Thira and just walked around and explored for a few hours and took a ton of pics! We walked down a ton of stairs and just got lost in the villages and it was so beautiful. Everywhere you turn there is beauty. If you take one thing out of this post- go to Lucky's Souvlakis and get a Gyro. The best on the entire island and cost about 3 Euros. It is located right near where all the busses drop off. We probably ate there 4 times and still drool thinking about it.

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The other half of the day we hopped on a bus from Thira to go to Oia (top of the island) and spent the day exploring there popping into places and having drinks, apps, sweets just to see all the gorgeous views.  Oia was really busy because there was like 6 cruise ships docked but it was still easy to walk around. A fav spot with a pretty view for a sweet and beer/wine was called Skiza Pizzeria Cafe. We watched the sunset in Oia just standing around- you can catch a view anywhere! I know this is frowned upon but we did ride the donkeys down the 500+ flight of stairs to the fish village at sunset and WE WOULD NEVER DO THAT AGAIN. It was so scary and we felt so bad after. There is not much down there and the only way back up is the donkeys or the cable cars so we took the cable cars, haha.

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We ended up back in Thira having dinner at another GREAT place called Louis Family Restaurant  which is locally owned and the food was soo good. We didn't need a reservation and went after sunset so were lucky to get a seat!

Day 4- Santorini 
Another day exploring Thira because there is so much to see! Seriously, just wander around and get lost. 

We took advantage of the free hotel shuttle to Oia with a reservation at the sister hotel, Mystique (the only other option would be to pay for a shuttle which would be about 100 Euros or take 2 buses so this was a good deal!!). The view was incredible and the food was pricey but SO SO good. I wish that we could have stayed at this hotel for a night or two because it is so incredible. There are a lot of stairs to get down to the hotel but so beautiful and breathtaking.  The restaurant was called Charisma and has a gorgeous Caldera / sunset view. Reservation recommended for sunset- ask for an edge table!

Image may contain: Mike Simao and Haley Simao, people smiling, people sitting, ocean, sky, table, outdoor, water and nature

We spent the rest of the night walking around Oia at night and admiring its beauty. 

Day 5- Santorini / Mykonos
This was our travel day so we took a shuttle to the ferry port (which is a zoo!!) to hop on a 2 hour ferry ride to Mykonos. I bought tickets in advance on Ferry Hopper just to make sure we had tickets. Our ferry was called Sea Jet. When you get to the ferry port 2 hours in advance you go to the Sea Jet booth and have them print your ticket. They board the ferries SO fast- its crazy how fast they get people on and off and out of the water!! The seating is like an airplane, you are given a seat number and have to find it. You store your luggage underneath the ferry when you walk on but we were nervous we would loose it so we just put our carry on luggage on our laps. I never, ever get seasick but wow that ferry ride was soooo bumpy I really had to coach myself not to puke! They have snacks and a bar on board too.

When we got to Mykonos our hotel shuttle was waiting for us and we went to the hotel. We were staying 2 nights at the Santa Marina hotel in Mykonos which is a luxury resort. This is another hotel where we could use Marriott points. We were lucky to be upgraded to a suite with a private pool out front, it was amazing! We settled in, hung out at our pool, and then took the ferry shuttle into town to explore and find a spot for dinner. We just grabbed a gyro somewhere and watched the sunset at the famous windmills in Mykonos (where are my bachelorette fans at?!?!).

Image may contain: sky, outdoor and nature

Day 6- Mykonos 
The Santa Marina hotel is the only hotel in Mykonos that has its own private beach. We spent the morning at the beach and then the afternoon at their amazing infinity pool. It was probably the nicest pool I have ever been too!! We bought a bottle of wine at the pool and just chilled there for awhile. The food at the hotel is reallly expensive but its not that far of a walk into a small town area with bakeries and little places to eat.

I made dinner reservations at Karavaki restaurant which is located inside of Vencia Boutique Hotel in Mykonos. I called about 4 months in advance and requested a sunset edge table and we got it! The food and service was great and oh my gosh.. the view!!! The sunset was blocked by clouds but the view with the color changing sky was incredible.

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Day 7- Travel Day/London
Our flight did not leave Mykonos until 7pm so we were able to get late check out and hung out at the pool until about 3:00 which was awesome. We took a shuttle to the airport and checked into our flight on British Airways to London. The flight was 3 hours and I have to say I have never flown an airline that charges you for every single thing - water, chips, cookies, etc.

We landed in London at about 7pm but with the time change all we did was go to our room and head to bed! I kind of wish we had some time to explore but oh well, next time!

 Day 8- Travel Day
Our flight out of London was booked to leave at 8am. We had a shuttle pick us up at 6:00am and when we were in the lobby waiting we got a message our direct flight was canceled and they booked us on one for the next day. We panicked and decided to just go to the airport anyways and figure it out. We ended up being able to get onto a direct flight to Boston on the airline we booked and had to hangout at the London airport for like 6 hours. We totally could have left and explored but they gave us free access to the lounge which had comfy seats, buffets, free drinks, etc. so we just chilled.

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SO that was our trip to Greece! I still can't believe that we were able to make this trip happen!! A very long, detailed post but I hope you find this helpful if you are planning a trip to Santorini or Mykonos. My tip is to take the amount of days your there and break up what you want to do- make sure to take some time to just RELAX. I am so glad I drafted out a rough plan of what we wanted to do each day to make sure that could see/do everything we wanted to with our time there. It was an equal amount of relaxation and exploring!