The Greek Sampler – Best 1st time visitor’s itinerary!
Experience the vast history of Athens, enjoy amazing Greek wine overlooking the caldera in romantic Santorini, and let your hair down in legendary Mykonos town with this epic ten day itinerary that I call the Greek Sampler. This best 1st time visitor’s itinerary will give you a great intro and feel for what this exciting and historic country has to offer. So let’s get right into it!
Planning your trip
Greece is a pretty big country that includes thousands of islands across 3 seas, so you have to put in a little work upfront to make your trip a success. You’ve got to decide when to go, what cities to visit, and how to get to there? And that’s what I’m going to breakdown for you in this post. That way, by the time your trip rolls around, you’ve made the best plans, booked the perfect excursions, and hopefully saved some money too.
When to visit
You want to catch the 2 shoulder seasons. Those are in late spring (April through the 1st week of June) and the shorter one in the fall (September – mid-October). These are the absolute best times to visit where you will beat the summer crowds, have pleasant weather, and not break the bank! Now you can certainly go during summer peak season but you will easily be paying double and sometimes triple for air and lodging. Visiting from late October – March is not recommended as most island businesses shut down and you will find a lot of closed shops/restaurants/etc.
Our trip began over the Memorial Day weekend and ended right before the Summer season kicked into gear. It was the perfect sweet spot as my wife is a teacher and we had to wait for her last day before departing. It just so happened to be the Friday before the holiday weekend. A much needed vacation after a long school year and it all started with an airfare alert text from July of the previous year!
Getting to Greece and Airfare Cost
You will fly into Athens. Unless you are flying from a neighboring country, most international visitors will land and depart from Athens when visiting Greece. From Houston, airfare ranges from $700 to $2,100 per person so it is critical that you get this part right. You need to monitor prices and set alerts using any number of apps or websites. Kayak, Google flights, and Skyscanner are your best bets to keep tabs on those weeks you have in mind for travel.
The alert for our airfare came from Going.com and if you’ve read any of my other posts, then you know I vouch for this company every day of the week and twice on Sundays! I’ve received and booked so many deals through them the last few years and I highly recommend you sign up for their alerts and give them a try yourself.
$700 per person to fly to Greece during Memorial Day weekend! I had been watching prices to Athens for over a year, so I knew a good deal when I seen it. I called my wife to double check with her that she would be out of school for the summer and booked immediately. It just so happened I was drinking with my cousin and told her what I just did and she’s like, “we’re down to go too, let me see if we can get the same price”. After closing my tab, I started driving home and within 30 minutes got a screenshot text from her, “Booking Confirmed!”
The Greek Sampler 10 day Itinerary
When one thinks of Greece, several things come immediately to mind. The cradle of civilization, the culture/history, the Acropolis, mythology, and Olympics to name a few. You also remember all the travel advertising showing the blue domed churches overlooking cliffs and a caldera. You start imagining yourself walking through all those beautiful white alleyways and staying up all night at their epic beach parties. Well we were no different. And that is why we chose Athens, Mykonos, and Santorini for our 10 day vacation!
Those 3 cities have everything I just mentioned and then some. They provided us with the perfect Greek experience we were looking for and will do the same for you. The highlight reel of Greece if you will. But now that the cities have been chosen, we had to figure out several things.
- In what order to visit them?
- How much time to spend at each?
- The logistics of getting to each city.
- What hotels to stay at?
That took some trabajo. And part of that work involves putting what you want to see and do down on paper (or in our case, a PowerPoint presentation, lol). I put together the 10-day itinerary for us and had mock itineraries on slides. I also added links to hotels we liked in each city and then called an in-person meeting to review and book over wine and beers 😆. We had to have 2 of these meetings (one to book the hotels and another to book excursions/day trips). Below is what our final draft looked like.
Day 1 – Arrive in Athens & head straight to Mykonos. Relax by hotel pool then party at 180 Sunset Bar!
The reason I recommend that you take a short flight to Mykonos as soon as you land instead of immediately exploring Athens are twofold. The first is because you inevitably have to return to Athens to fly back home, so it makes sense to spend the last few days there. That way on the last day you are already in the city. And the second is that you want to catch Mykonos when you are the most hype and have the most energy and that is always at the very beginning of any vacation.
Use Greek airline Sky Express for the 30 minute flight (it didn’t even seem that long). It’s relatively cheap and it’s much better than taking the ferry. Trust me on this. I’ll have more on the ferry experience later. Just clear customs in Athens, grab your checked bags (if any), and head to your new gate. We landed in Athens at 10:30 am and were in Mykonos at 1:30 pm. It worked out perfectly.
Vencia Boutique Hotel
What can I say about this Vencia Boutique hotel other than it was damn near perfect for the price. The hotel grounds, the staff, the view, the pool, and rooms were as advertised. As soon as we checked in they sat down with us, provided welcome drinks and a map, and went over key attractions of the island. They answered all of our questions and really went out of there way to make us feel at home.
Relax by the pool
After checking in and showering, you’ll want to enjoy a nice drink by the infinity pool overlooking the town and Aegean Sea. You’ve earned it. After a long day of travel, you are finally in Mykonos! Enjoy a local beer or indulge in your favorite cocktail and take it all in. We got online and booked our table at the 180 Sunset Bar for the evening and took the rest of the afternoon off. Once the battery is recharged, it’s time to catch your 1st Greek sunset.
180 Sunset Bar
Book your table in advance and for as soon as they open (7 pm). Arriving a little after 6 pm is cool because the grounds are pretty neat outside the main area and you’ll meet people from all around the world while in line. We met some very chill peeps from Wales and had some good laughs while waiting to get inside. And once you do get inside, get ready for some fantastic views of Mykonos! This bar sits on a high hill and in the most perfect spot to watch the sun dip below the horizon.
When we arrived we got right to business, We ordered delicious Greek wine and cold Greek beer with some appetizer plates as soon as we sat down. I employed the same strategy we used in Cartagena at the Cafe del Mar bar. Both bars had the same good rating but complaints (that service got steadily slower as the night went on) so we ordered quickly and a lot, lol. But to be honest, we didn’t have to. The service was excellent and our waitress was funny, witty, and a ball to be around. Here she is striking a pose with us 😆.
As the sun starts to go down, so do the temperatures. Add a coastal breeze to temps in the mid 60’s and it can feel nippy for sure. But staff at 180 Sunset bar got you covered and offer light blankets to everyone. They were definitely welcomed by my small crew. And speaking of the sun, you can’t name yourself the 180 Sunset bar unless you can deliver on some amazing sunsets and let me tell y’all, this place comes all the way through!
As for the vibe, well it’s probably better to show you with these short video clips.
DAY 2 – Mykonos town tour, exploring the city, Little Venice, and the Happiness sign!
I setup a guided walking tour of Mykonos town for 9 am, so after breakfast we made the 10 minute walk into town to the meeting location by the water. I highly recommend walking tours in new cities because you gain so much knowledge about where you’re at & get to familiarize yourself with your surroundings. Plus, tour guides offer up some great insider advice on places to eat, drink, and shop!
Like all guided walking tours you will learn about the history of the area, hear great tales/stories from the past, and learn quirky facts as you stroll through all those bright white alleyways. It’s pretty easy to get lost in all the zig zagging as there doesn’t appear to be any rhyme or reason why the small streets were setup the way they were, lol. The only thing that made sense was the tale of the first inhabitants laying out the town in this manner to confuse pirates.
Our tour guide took us along the waters edge and through the town. We made several stops including at a museum, some churches, a bakery, the windmills, little Venice, and by special request (from me!) at the Happiness sign! #happiness😊
Exploring the town
Once the tour is over with, you’re free to explore on your own. So off we went exploring and battled the dreaded cruise ship people in the narrow streets. The cruise ship people remind me of the World War Z zombies swarming. Once you see the ships drop anchor and the hordes get off on the boardwalk, as we say in spanish, “ya valio madre”, lol.
We walked a good amount more through various streets and did some souvenir shopping. We also got in a light lunch and spent the rest of the early afternoon day drinking and people watching at an outdoor café/bar. The sky started to further clear and temperatures were perfect. After a great buzz took over, it was time to get back to our hotel for a swim before dinner.
Back to the Pool
From our walking tour we all decided where we would be having our sunset dinner. It would have to be the picturesque Little Venice part of Mykonos Town. But first we wanted to cool off and relax at our hotel pool. This would become our daily routine while in Mykonos during the late afternoon hours (from 3’ish to 6 pm). I mean, can you blame us? Look at these views.
Little Venice
This is one of the most photographed coastlines in Mykonos and for good reason. When the sunlight hits the water at just the right angle and you have clear blue skies for a background, all the colors just come to life. There are several restaurants along this stretch and seaside tables are hard to get so try and make reservations ahead of time. Our tour guide had earlier mentioned the “Nice n Easy Seafood” restaurant so we headed there at 7 pm. We got lucky as a family had just got up to leave when we arrived and we got the perfect table.
We had an array of drinks and appetizers before the main dishes were served and it was all delicious. I definitely recommend this place to have a sunset dinner. It was all enhanced and made that much more delightful as the sun hovered just about the water. Made for some beautiful memories and very cool sunset pics.
Later in the evening we somehow ended up back at the happiness sign while looking for a particular spot. So of course I had to have a pic taken of us four. Mexicans in Greece! (that was the name of our group chat). #happiness of course.
Day 3 – Mykonos Beach Day
Mykonos has several beaches to choose from and it really does depend on what type of experience you are looking for. There is literally a beach for everyone here. From quiet and isolated so you can read and relax to raucous and rambunctious for the wild and uninhibited. We went with the most popular which was the world famous Paradise Beach. Not to be confused with Super Paradise Beach which is more of a gay party scene. There is also a Super Duper Paradise Beach that, nah I’m just kidding 😂. Now that would be a silly name.
Paradise Beach
You have 2 ways to get to Paradise Beach. The public buses that run every hour and stop at the major beaches along the way. This will cost about $5 Euros a person and the pick up location is at Fabrika in Mykonos Town. We witnessed 1st hand how it was a little hassle and crowded at that location the day before for so we opted for private car and had the Vencia hotel arrange it for us. We paid about $40 euros each way but it was 4 of us so $20 per couple.
So there is no entrance fee to visit Paradise Beach. You pay only if you want to rent a pair of layout chairs and umbrella. It’s a modest amount too and cheaper than South Padre Island for those of you that are familiar with that Texas beach. All the front row spots were taken so we settled for 2nd row. We arrived around noon and the atmosphere was still very chill with some people playing music from their wireless speakers and there was also some more music being played at the bar areas.
This would all change when the daytime beach party started (more on that later). There is a waitress that comes by and checks in on you but we found it faster to just head to the bar ourselves and get our drinks. It was a short walk and the service was fast. There are also several food places on the premises so when you get the munchies. All in all the place is laid out nicely.
Day Beach Party Event
Paradise Beach has 2 main party events, a daytime party that starts at 4pm and a wilder one that begins at 10 pm. Both are free entry. We definitely knew upfront we weren’t going to keep up with them youngsters at night (nor did we want to) so we stayed in our lane and partied during the day time event. And holy shit did we make the most of it. It was such a great fun time had by all and out of respect for all, I’m only posting a few pics and family friendly video to give you an idea of the vibe once the party starts.
Granted these pics and video were taken right around the start of the day event. People kept steadily showing up and it progressively got more hype from there.
While the party area started to get more packed, we took advantage as we had the water almost to ourselves. Me and my cousin’s husband decided to swim to the rocks that lined a sandbar and started posing and dancing. No I’m not going to post those videos. Vegas isn’t the only place things should stay, lol. Paradise Beach is the real deal! Make sure you visit.
Greek Sampler – End of Mykonos part of trip
We left Paradise Beach feeling real good and I’ll leave it at that. Somehow our crew jumped into the wrong ride back to our hotel and that was an adventure into on itself, lol. We wanted to keep it going so we went to Vencia to shower and change to go out. That’s where we lost my cousin 😂. She knocked out, so the 3 of us left and went across the street for dinner and a night cap.
Our hotel pool bartenders were there with some “dates” and bought us shots. Perfect ending to our last night in Mykonos. We had to catch a ferry in the morning to head to Santorini so we wrapped it up by 11 pm. The first 3rd of the Greek Sampler was in the books and it was off to an epic start. Continue reading Part 2 on this link, On to Santorini! Thanks for your support!