REAL ITINERARY: 10 Days in Greece – Island Guide

Mykonos, Santorini, Greece, Greek Islands, Cyclades Islands… words you’ve surely Googled if a Greek adventure is what you have been planning.

Though I don’t have all the answers, the least I can do is share precisely what my husband and I did when we took off to the Greek islands in May 2019 for 10 days.


  • Arrival in Mykonos by plane
  • 3 nights in Mykonos
  • Ferry ride Mykonos – Ios
  • 2 nights in Ios
  • Ferry ride Ios – Santorini
  • 3 nights in Santorini
  • Flight Santorini – Athens
  • 2 nights in Athens


Before I go into detail, I want to share the websites and services I used to make this trip the success that it was. All my accommodations were booked through ($25 cash back if you book with this link), which I have been using for a few years now. Because I have been making bookings through there consistently, I started to get discounted offers on hotels and “secret deals”, making travel a lot more affordable. I found and booked all my hotels and BnBs on These are the places I booked:

  • Mykonos: Hermes Mykonos Hotel
  • Ios: Kritikakis Hotel
  • Santorini: Astir Thira Hotel
  • Athens: Athens Luxury Suites


When a transfer wasn’t included with our hotel, I made a request for transfers on in advance, where drivers could bid to give me a ride. Kind of like Uber, but has to be arranged in advance. This helped save A LOT of money in Athens, where we ended up spending a fraction of what a taxi would cost. Alternatively, hotels are often able to arrange a discounted transfer, or island ports often have mini-busses that stop at all main hotels.

Mykonos and Santorini being two of the most popular islands, both have a tiny airport onsite with some domestic (and even some European) flights. All islands have a ferry port, and for the most part it is quite easy to book and find ferries. One thing to keep in mind is that you may run into a ferry cancellation or rescheduling – one that may happen the day of, with no warning. For this reason, I don’t recommend taking a ferry the same day as a flight in your arrival port, as you may just add unnecessary stress to your travels.

Given the distances between all the islands, I strategically planned our itinerary so we have minimal travel times. This resulted in taking a ferry from Mykonos to Ios (1 hour) and from Ios to Santorini (30-50 minutes). To get from Santorini to Athens by ferry would have taken 5 hours, and cost about 50 euros per person. By opting for an “inconvenient” 11:55pm flight, we were able to get to Athens in 45 minutes for 30 euros per person (no luggage included).



Upon early arrival in Mykonos by air (from Tel Aviv with a connection in Athens), we took a pre-arranged transfer to our hotel, Hermes Mykonos Hotel, and much to our pleasure, checked into our room bright and early. Our hotel was set up the hill/mountain overlooking Mykonos main town, just a short 10-minute downhill walk. Though great in theory, coming back at night after partying was a little sketchy as it involved choosing between a hike on a pitch black trail, or walking along the winding roads meant for vehicles. The hotel itself was incredible, with an amazing pool and bar, incredible breakfast buffet and menu, and gorgeous accommodations.


Our biggest mistake in Mykonos was not booking an ATV right away. We ended up having one for 24 hours during our 3-night stay, and I think it hindered our experience on the island. Mykonos is an island meant to be explored, and unfortunately it’s impossible by foot, and not very comfortable by public transportation.

Beach clubs are a big thing in Mykonos, but may not match the Average Joe’s budget. Though very beautiful (we checked out the famous Scorpios during our stay), prices are steep. In my personal opinion, I don’t think the boujee Mykonos experience is necessarily worth it if you’re not in the position to splurge and go full out.

Walking around the main village is a fun time, as it does give you the full Greek island look and feel. The village is connected to and walking distance to some must-see spots, like the Windmills, Little Venice, and the old port. With a lot of big-name and mom and pop shops around, you could get anything and everything in this tiny town. That being said, it is also quite a small town, so unless you’re walking into every single shop and cafe, you’ll walk all of it in less than a day.


We were only in Mykonos for 3 nights, so we didn’t have the opportunity to try all the places that were recommended to us, but I’m happy to report back on a few.

Eat: Raya

Raya is a restaurant along the old port, a cute little marina in the main Mykonos town. When we went in May we found we didn’t necessarily need a reservation, but I’m sure it picks up in the high season. Anything we tried on the menu was great, and they also have a lovely cocktail and dessert menu in house.

Eat: Vegera

Another gem along the marina, Vegera offers a delicious menu as well, and a really quirky and friendly host to go with it. Though I don’t remember his name, he made conversation with every single patron in the place, and also gave us incredible recommendations for our remaining time in Mykonos.

Party: Scandinavian Club

Also situated in the old Mykonos town, the Scandinavian Club was PACKED by 11:30pm, despite it being a little early before the high season began. I’m not sure if this would work in July or August, but we were able to bypass cover fee and the line by getting a drink at their bar on the ground floor before heading up to the club.

Drink & View: Caprice Bar

Because my husband was hangry, we didn’t stay, but Caprice Bar is a drinks location right on the harbour in Little Venice. With the ideal view of the Mykonos sunset, this is a great place to have any drink of your liking.

Drink, Swim, & More: Scorpios

If you have a vehicle (which you should have in Mykonos!), Scorpios is one of the boujee beach clubs that is worth a visit. We probably didn’t budget for Mykonos as well as we could have (to be honest, we didn’t expect it to be so expensive), but we allowed ourselves to splurge for one afternoon here. At 20 euros a cocktail, it’s not for the faint of heart, but the set up, beach views, and vibe is amazing.


After the expense of Mykonos, we were relieved to arrive in Ios for a couple days. A fair warning: as 26 year olds, we found ourselves to be amongst the oldest visitors on the island, and most certainly the oldest people frequenting the bars at night. A good summary of our stay in Ios would be “it’s like we were 19 again.” I would consider the best part of the island being its lack of cell phone reception, forcing you to actually enjoy the moment as if it’s the ’90s. Bear in mind my recommendations below are based on our experience in the middle/end of May, and aren’t a reflection of what there is to do during high season.


We arrived in Ios by ferry, and much to our pleasure, we were walking distance from our accommodation, Hotel Kritikakis. The hotel is like a village of its own, with winding roads and steps, just like what you see in movies set in Greece. Equipped with two pools, and terrific sunset views, the hotel was a nice oasis from the crazy nightlife just a 15 minute walk away. One thing worth noting anywhere in Greece: hills and mountains. This is something that’s hard to understand on a 2D map, and let me tell you, it was not fun spending those 15 minutes climbing wide steps into the main village. Otherwise, the location was great due to its proximity to the main port, allowing us to hail a cab or rent a car (if we had an international license… which we didn’t) steps from our hotel.


Sadly, due to not having an international license ordered on time, we weren’t able to rent a car or ATV, which stopped us from being able to explore the various beautiful beaches Ios has to offer. That being said, we made the best of it and booked a tour with Meltemi Watersports, taking us on a boat with 10 other (Canadian!) people to a small cave along the water, snorkelling to see a shipwreck, and lunch on a deserted beach. The tour made for an amazing day out to sea – though I must credit the crowd we ended up with on the boat.


It’s pretty slim pickings for sit-down restaurants in Ios, but we found a few that accommodated our tastes. As for late night eats, there is one gyros place alongside all the bars in the village, which does the job when you’ve had too many shooter shots at the surrounding bars.


We happened across this place accidentally, when we arrived in Ios and at 5pm went searching for dinner in the main village. An older gentleman sat outside and prompted us to go in, and given my husband’s hangry state, we obliged. An order of a litre of white house wine, chicken tzatziki, and grilled squid (highly recommend!) cost us 32 euros total and also garnered us a couple free liquor shots.

Drakos Tavern:

Slightly more expensive than other places in Ios (but not more than Mykonos), we sat at Drakos Tavern due to its convenient proximity to Mylopotas Beach. We ended up having a great view and a great filling meal! Word of the wise: portions are large here, so be wary even if you’re ordering plates to share.

Dodoni Ios:

Situated conveniently near the main port, Dodoni was a great breakfast, snack, and coffee destination for us especially given our hotel location. We found ourselves having breakfast here both mornings, as well as stopping by for an ice cream or coffee during the day or early evening before heading into the village for the nightlife.


Nightlife in Ios deserves a category mention of its own. The drinks are cheap and plenty, and there’s many bars filling the streets of the quaint village. You really can’t go wrong with any of the bars, but here are a few honourable mentions:

Vesuvius Bar:

As I mentioned, we were a little early for the true high season in the Greek islands, so when we ended up being amongst the only few people at the bar that night, the bartender (and part owner) kept pouring us new shots to try. With her fun shooter shots recipes, it took a lot of willpower to leave and try something else out.

Lost Boys:

Owned by Australians and inspired by Peter Pan and Neverland, Lost Boys was a beautifully decorated popular bar that felt a lot more luxurious than it cost. We made it here on their opening night for the season. I highly recommend one of their 20 euro bowls if you’d like to start (and potentially end) your night off strong.



Having not known what to expect from Santorini, we booked our stay at Astir Thira Hotel, a place that fit our budget but also allowed us to be walking distance from Thira, one of the two (Oia being the other) main tourist villages in Santorini. This worked out in our favour, as even though we had an ATV for 48 hours, we were able to walk to and from the majority of the nightlife without worrying about driving impaired. Additionally, the hotel staff were incredibly accommodating with my husband’s birthday, and surprised him with a full cake and bottle of champagne. As we were leaving the next day and weren’t able to finish the cake, we left half of it to the amazing reception staff. PS. Booking vehicles and tours is best through the reception desk!


Santorini has SO MUCH MORE to offer than just Thira and Oia, which sadly is what cruise tourists are only exposed to. With our ATV we took the opportunity to drive out to Faro, the lighthouse at the complete opposite side of the island from Oia. The Faro/Akrotiri area is beautiful and offers hikes that give you incredible views of the water and passing boats.

Additionally, we used the opportunity to check out the Red Sand Beach (though found no reason to stay), and Black Sand Beach where we stayed in Perissa at The Beach Club. We came here for two of our three afternoons, as we were able to get lounge chairs by just hitting their minimum spend for food and drinks.

If you’ve heard anything about Santorini, you may be wondering about watching the sunset in Oia. We drove over on our ATV about an hour and a half before the scheduled sunset, only to find the streets already overcrowded with people. Realizing that our cliffside drive didn’t exactly have the best lighting, we decided it best to skip out and head back to Fira. To be honest – no regrets on our decision. We ended up catching the sunset at Santo Wines Winery another night; more details below.

As it was our first time in Santorini, we decided it best to cross visiting the volcano island from our list. We booked our tour through our hotel front desk, and it included transportation to and from the hotel, the boat tour to the volcano as well as a guided tour through the hike, an opportunity to jump off the ship into hot springs, and a stopover at Thirasia, a separate island that used to be part of Santorini before the volcanic eruption.


For the most part, we would just choose places based on menu, whether it was at least a little crowded (if it was empty it was usually a sign it wasn’t that great), and price. We mostly had luck with wherever we went, but here are a couple worthy mentions:

Santo Wines Winery:

I made a reservation here in advance for my husband’s birthday, and asked in advance to be seated “beside the glass”, giving us an unobstructed view of the sunset. With a flight of 16 wines to share, a cheese board, salad, and seafood, we filled our bellies with wine and tasty bites, and had one of the best evenings of our trip here.

The Good Heart:

On our drive back from Faro, we saw this cute little restaurant along the side of the road so decided to stop by and check it out. It ended up being one of our best meals in Greece. Having ordered lamb chops, I learned that the lamb was “super fresh”, which turned a spontaneous meal into an authentic farm to table experience. A nice touch was the restaurant provided a small tasting plate before we even ordered, giving us an opportunity to try some of their homemade wines and treats.

Hopefully our detailed itinerary helps you in planning your next adventure! Though Greece was beautiful overall and a great experience, I did find it to be overrated having been exposed to so many photoshopped photos and sugarcoated blogs and videos. That being said, to each their own, and you may fall in love with it a lot more than I did!

P.S. if like me you plan to pack a carry on only, I highly recommend buying packing cubes, as it’ll help you stay organized and avoid unpacking and repacking at every stop. Another helpful product while travelling was my iPhone/camera tripod, as it allowed my husband and I to get some photos of the two of us without having to ask any strangers to take our photo.

P.P.S. Keep checking back for updates on this post – photos coming soon!

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