Planning & Booking
Time: 2 Weeks
*with 350k airline points and 4 travelers
Locations: Athens, Santorini, Naxos, Milos
Budget: $5k/week*
We have always wanted to go to Greece. We’ve seen the photos of the iconic blue and white domes, heard about the incredible people, and have dreamed of the fresh seafood and cuisine. When considering our kids’ first trip to Europe, we knew we wanted a mix of beaches and water, approachable food with many options, and somewhere that many people spoke English. We considered our interests as a family – being outside, having a mix of adventures and relaxation, food we are interested in, and unique accommodations. Greece checked the box!
We try to strike a balance between opportunistic travel (i.e. book the deal not necessarily the location first), but Greece was somewhere we picked the accommodations before the flight. We booked all of our accommodations using AirBnb. I cross-checked all of them with Vrbo and Booking.com, as many of them are run by third-party travel companies and are listed across sites; looking for differences in price, cancelation policies, and to read reviews. We blocked 2 weeks of time and chose to focus on the Aegean Islands, using Athens as our base to fly in and out of. We chose three islands – Santorini, Naxos and Milos – to explore.
Getting around:
We used a combo of points and cash to book and upgrade (premium economy) our flights on United for Turkish Airlines (Star Alliance – using United miles). This unusual way of booking through a code share partner often offers fixed/cheaper mileage booking (85k miles/person), compared to booking directly. (Read More on this from the Points Guy) Airlines and opted for the bulkhead seats so we could take a chance on using the inflatable seat extenders for the overnight flight out of O’Hare. Flights with a connection were much cheaper than nonstop, so we opted for a flight with at 3 hour layover in Istanbul and utilized their lounge (shower, food, play area). Within Greece, we used domestic airlines (Skyexpress and Olympic Air) to travel from Athens to and From the islands. Then within the islands we used ferries. Ferries, seemed kind of daunting to book remotely, but booking in advance (>3 months) in this season was helpful. Notably, there are a few ferry companies all of which can be booked from FerryHopper. Also, there are often multiple options of travel on ferries, with names like “SuperExpress” or “World Champion” being the fastest options. We chose the fastest options and didn’t upgrade our seats – overall an easy and good option.
One oversight we made was booking our trip during August when ALL of Greece (and Europe) is on holiday. We didn’t realize that Greeks have two weeks (the exact time we went) every August, so not only were we with all the European tourists but also the Greek tourists. I’m sure the nightlife was very busy, and the beaches were busy, but we were still able to make reservations without a problem, likely because we eat at 6pm which is very early by Greek standards. If we do it again, we would choose June before Europe gets out of school. Early summer also means less impact of the maritime winds, which progressively get worse as the summer goes on. Fortunately, no flights or boat rides were canceled due to the winds for us, but definitely something to consider in planning. September would have been another option if our kids weren’t in school.
Bodhi needed a new passport for this trip. No visas or vaccinations were required, but we chose to complete his Covid vaccination series just before the trip as he had just turned five. We also took this chance to complete Global Entry for the kids and Julia, as Kabeer has had it for a few years. We used credit card reimbursements and paid for the three global entry applications ($100/per person). On re-entry to the US we used the “Enrollment on Arrival” in EWR, which was really fast and easy. We are looking forward to less lines and waiting during future trips.
Packing
We heard the horror stories about traveling this summer in Europe so we really tested our packing skills with this trip in hopes of sticking with carry-ons only. We chose an AirBnb for the middle week of our trip that had laundry so we could minimize how much we packed. We still overpacked and didn’t wear everything! Greece is casual and hot during the summer, so many days we were in swimsuits and coverups. One of our rules is – bags in bags – I always take a few reusable grocery bags, reusable ziplocks, and smaller totes for the beach. We have recently discovered these reusable zip bags and they are so versatile; this trip we used them to house all kid activities on the plane.
How to Pack: Each kid has their own packing cube color, and Kabeer and I have our own packing cube colors. We roll our clothes to maximize our space. I like the packing cubes that are nylon and compressible, as they’re more durable than the mesh ones.
What to Pack: Greece is a place you can buy most everything you need once you’re there – laundry pods, toiletries, beach toys + towels, snacks. I took a few personal toiletries we couldn’t buy, but otherwise bought it there. Saves us space and weight. We focused on versatile pieces, lightweight shoes, and one warmer piece for cool nights. Each kid got to choose a comfort object to bring.
We selected one goto bag for quick access needs during the flight, so we are not constantly pulling bags out of the overhead. Turkish provided us each with toiletry bags that included eye masks, socks and toothpaste gel. Notably, United on the return did not. We chose not to take kid neck pillows to save space and did not regret it. Turkish did not allow us to use our inflatable seat extenders which was a definite bummer. It really seems like this is a crew-dependent decision but some airlines do have policies on the inflatables.
Otherwise, our goto bag included:
- Extra outfits for kids
- Passports and credit cards
- Snacks: dried fruit and nut mixes, granola bars, gum, crackers, PBJ roll-ups.
- Tablets and wireless headphones, chargers
- Kid activities: coloring books + thin markers, Uno, SpotIt, activity books
- Phone chargers
- Kid basic first aid -bandaids and kid Tylenol
- Toothbrushes and toothpaste
- Lipbalm and Facial Spray (for mama)
- Socks and sweatshirts
- Eyemasks
- Turtl neck pillow
- Water bottles with flip straws
Once we got to the airport and our gate, we gave the kids surprise toys. It’s amazing how much they cherish anything labeled a “surprise” and certainly anything “mini”. We stock up on these items during the year at various sales. Our kids like the monster truck and LOL toys but there are so many different kinds!
We encouraged the kids to sleep on the first flight after meal service followed by some tablet time. Once we were told we couldn’t use the seat extenders (after Veda was asleep!), we had to adjust. Veda sat up to sleep -what a champ- and Bodhi laid on my lap. Following some solid whining and readjusting, both slept for a good amount of time. Once in Istanbul, we kept them awake so we could actually sleep our first night in Athens.
Athens
We had minimal problems on our flights and finally arrived in Athens! We stayed in this Airbnb and our host arranged a driver to pick us up at the airport. There was a flat taxi rate of €60 that we paid with credit card in local currency (ALWAYS pick local currency over US$! Otherwise the local business conversion rates will apply). We only had two nights in Athens so wanted to be within walking distance to the major monuments. The Airbnb was comfortable and clean, it felt safe, and was in a perfect location.
For many, Athens is a stopover before the island. We only had 1.5 days in Athens so we stuck to the highlights: the Acropolis and the Panathenaic Stadium (map). At the bottom of the post, there’s a map of most of the places discussed here. After sleeping in til 10am due to jet lag, we knew we would have to deal with the Athens heat. It was hot as Hades, you guys. We found Victory for breakfast – absolutely delicious and epitome of Greek hospitality. They sent us with extra waters and pastries. The Acropolis is worth seeing, for sure, but there is zero protection from the sun in 90+ degree heat, so you have been warned! We spotted the Cave of Acropolis next door as a great option for a cold beverage after a tour. There is a new museum next to the monument that appeared beautiful to explore, but our kids’ jet lag was catching up with us so we had to skip.
Our one night in Athens we spent in the Acropolis district and walked to our restaurant Arcadia. Kabeer regrets not ordering the octopus here, but the gyro, yogurt, and fries all were a hit with us. For dessert we went to Django gelato and it was some of the best gelato we’ve ever had.
Day 3: Woke up early and packed for Santorini. We arrived at the Panathenaic Stadium right as it opened (just a 10 minute walk from our Airbnb) and it was pretty special to be there with only a few others. It was early enough that it was warm but not uncomfortable and the kids could run freely on the track. We did family races, pretended to be royalty observing the games, and explored the small museum inside. We saw tour buses arriving around 9/9:30 so it was time to go. We stopped at the Coffee Joint for breakfast and everything was delicious – good pastries, delicious yogurt and eggs, and fresh juices. The hospitable owners sent us with extra pastries and water for the road.
Santorini:
We flew from Athens to Santorini, a quick flight on Sky Express. We used the Ride Safer Vests for taxis and rental cars. These are *not* EU approved because they’re a US product, but there is a EU version that is approved. We chose to roll the dice on this as we trust the US standards. We upgraded to the “Lounge Access” ticket on Sky Express which was worth it as we breezed through security, had flexibility to check bags, and had access to a lounge with chargers/snacks/comfy seats. Internal/Domestic bag check was easy and these local airports are less likely to lose bags compared to international terminals/airports. Athens airport was super congested, so upgrade this was worth it for us. (Ticket Totals: €280 with upgrades)
Our Airbnb in Santorini was wonderful and the host fantastic. We really wanted the view seen from our spot, and we were so happy to have it. Airbnbs have upped their game in Europe and their hosts can arrange meals, transportation, and luggage transfers. We chose to stay in Imerovigli as it is south of the busy port of Oia (ie: Cruise ships and their 1000s of passengers). We did not regret it and still had, in our opinion, an unbeatable view of the iconic domes and sunsets over the caldera. Santorini is very expensive, so we splurged on two nights at this Airbnb before heading out to Naxos. It was so worth it to us – the sunsets were undeniably gorgeous and the views will take your breath away.
What to Do: It is hot in Greece and there is no shade. Book a boat tour if you don’t have a pool at your accommodations (we had a small soaking pool inside ours, but was not a swimming pool). It was very fun to do this and to see the caldera. We booked with Odyssey which was recommended by our host. They were excellent; the staff were so kind to our kids, the price (150€/adult, 75€/kid) included food and transfers. We visited the red and black beaches and had a blast.
Where to Eat:
Fly Away Creative. Walked from Imerovigli, excellent staff and food, perfect sunset view. Definitely a honeymooner’s spot that catered to us and our kids. We fed our kids beforehand, they snacked on bread during the meal and hung out with us/on their tablets while we did the coursed meal.
Blue Note: Good view, decent food. Highlights included the saganaki, tapenades and the lamb.
Confetti: Great brunch, ice cream and coffee just down the walkway from our Airbnb.
Naxos:
We traveled to Naxos via ferry from Santorini. The port was pretty easy and has a few small restaurants and shady spots to wait. We kept our luggage with us but there are holding pens underneath the ship. Wi-Fi available for a few euro. Ferries can arrive/depart somewhat unpredictably, so checking ahead of time and getting to the port 10 minutes early is advised. We were shown this website to track the ferry: Ferriesingreece.com. A little cumbersome, but is very accurate.
Once at port, our Airbnb was just a short walk and our host Litsa met us in the road to make sure we could find it ok. For us, Naxos meant amazing beaches and delicious seafood! We chose a convenient Airbnb close to the port in case we wanted to day trips to others small islands, but we ended up staying in Naxos the entire time. The accommodation was great and had laundry, an essential for a two-week trip. It had an incredible view of the Temple of Apollo which is the iconic view of Naxos as you arrive or depart. There are plenty of good sized markets in Naxos, so we bought groceries for the week to supplement eating out so much.
Naxos has a very authentic feel once you get off the main port boardwalk with your typical tourist restaurants and shops. There are many locals who have grown up on the island still there today. You hear a lot of Greek spoken in the streets. Our Airbnb host has lived in the flat above what we rented for over 40 years. It is a very large island and we recommend having a rental car for this portion of the trip. We rented it (from Hertz, at the port) for half of our time on the island and focused on day trips the days we had the car. On a day we didn’t have the car, we used the bus system without problem (kids under 6 ride free and don’t need tickets). The bus stop is right in the port and you have to buy round trip tickets before getting on.
We spent the majority of our time in Naxos at the beach or eating, both being what Naxos is known for! Our favorite beach was Agios Georgios. We rented chairs with umbrellas for €30 each (peak season rate) at Trata on both days we went there. Because we have kids, we would get there early and beat the midday tourist rush with the prime pick of seats. The food was delicious, the kids were happily in the water all day, and the service so friendly. Another great kids perk, is a long shallow surf break, which allowed the kids to go way out into the ocean and only knee deep. We took a few trips to the grocery store to get drinks and snacks to offset our bill at the beach restaurant. Other beaches we visited include:
Plaka: Good clean beach with a long break. Chair rental €30. We had a lot of fun here and there were lots of restaurant and shop options.
Agios Prokopios: We thought this beach was just ok. The beach was rocky and the water was really chilly. There were few food options and you had to walk a ways to them.
Pyrgaki: Small beach on the southern part of the island. It was windy here the time of day we were there (early evening) and the sand was blowing against skin. Due to the distance, there were less crowds and offers a quieter scene than some of the others. Also this is the spot we went cliff jumping, though there are likely many others around the island!
Where to Eat:
- Oasis – Mom ‘n Pop stop that we found on our first night.
- Apothecary – Within a block from our Airbnb. Small menu but delicious and perfect view of Temple of Apollo for sunset. Easy to miss at it’s at the end of the block.
- Doukato – Beautiful outdoor setting with large portions of homemade classic Greek cuisine.
- Nissaki Beach Hotel – incredible homemade pastas, fresh seafood, right on the beach.
- For gelato – Milkato and Waffle House – get the Fererro Rocher
What to do besides beaches? August is hot, so we didn’t do any hiking but definitely would have during a shoulder season. Naxos is known for great hikes as it it has plenty of beautiful mountainous areas. We took the rental car up to Filoti to explore and had a sunset dinner at Rotunda which is famous for sunsets. Next to the restaurant is an old windmill that made for a beautiful photo spot.
Shops under the old castle in Naxos town ha some very beautiful high quality souvenirs. Stop at the restaurant Avaton 1739 for coffee/breakfast or cocktails/apps in between shopping!
Cliff jumping! We found a place on Google Maps literally labeled “cliff diving” so had to check out what it was about. We read many accounts that it was a very safe cove, and we watched for a while before doing it ourselves. Veda decided she also wanted to do it, so Kabeer and I went first and then our brave girl did it, too. One of our favorite memories.
Pool Hack- go to a pool restaurant! One disadvantage of many Airbnbs is that they don’t have pools. We found Aegean Land Pool bar (in Plaka) on our last day in Naxos and spent the whole day there. If you order something at the bar you can access their pool and showers. It was a nice break from having sand in all of our business before hopping on our ferry to Milos.
Milos
We took an evening ferry to Milos (only one scheduled per day) and it was delayed by a few hours. Our Airbnb host Christos met us at the ferry port at midnight anyway (again with the hospitality), took some of our luggage in his car because ours did not fit with all of us in the tiny rental car we got, and led us to the house. The rails came off a bit here and the late night and bumpy roads for the kids was a great setup for a meltdown. Still, the hospitality of the Greek people continued to wow us and quickly enough we were settled in our new spot.
Our Airbnb – the Cove – was an old fisherman’s house called a Syrma. To get to this spot, you will need a car and will need to be comfy driving on bumpy roads. Our host Christos booked the car for us at a comparable rate. This Airbnb is off the beaten path but was so worth it to us. This private cove had fish, swimming, sea glass collecting, and the most incredible view of a full moon over the water. We spent hours relaxing here and enjoying our private spot on the water. We met several other families and our kids made friends with a local Greek girl whose family has also owned a Syrma (home) in this cove for generations.
One of the draws to Milos was its very unique volcanic landscape. We booked a boat tour through Excellent Yachting. Overall, we had a great experience, but there were a lot of people on a small boat, and the seas were rough this day due to high winds. The first hour of the ride was nerve wracking and not for those easily prone to seasickness. Once through the open sea and into the coves, the day was smooth sailing. There were lots of stops with beautiful beaches and coves/caves to snorkel. The kids were fascinated by the stories about how pirates used to hide in these areas and raid passing merchant ships.
We had three days in Milos. One day was for our boat tour, one day was adventuring through Pollonia, Papafragas, and back to Adamantas. There are all kinds of spots to stop and explore caves, coves, and cliffs. Use Google Maps to explore where you want to go and make a route to follow. We always “download offline maps” before we go, in case of poor gps/cell service. We had a rental car for the 3 days of this part of the trip and would not have gotten by without it.
Two fantastic meals we had during these few days were at Yialos and Mikros Apopulos (still dreaming of the seafood pasta).
To return to the USA, we flew from Milos to Athens to stay near the hotel prior to our flight home. Milos airport is tiny and security/boarding happens about 15 minutes before the flight departs – no need to arrive 2 hours early. We stayed at the Aethon Hotel Project. There were a few cats on the premises and they likely had been in the rooms, because both Kabeer and Bodhi had allergic reactions in the hotel room. Otherwise the hotel was well located near the airport, included a transfer to and from Athens International Airport. We completed Global Entry for Julia and the kids upon arrival into Newark which included a pre-registration online and a quick interview and fingerprinting at immigration. This was easy to do and Global Entry is good for 5 years.
The kindness and hospitality in Greece was incredible. Restaurants designed for honeymooners welcomed our kids and carried their sleepy bodies to the taxi. Our boat captains let the kids drive and take naps in their cabins. Our Airbnb hosts personally transported our luggage when it didn’t fit in our tiny car. Another dropped it off at the ferry for us so we wouldn’t have to haul it ourselves. They showed us how to correctly eat fish on the bone and never sent us away empty handed. And here’s the the thing: no one asked us to leave them a positive review or personal mention at any point. We left Greece amazed by its beauty, landscapes and food, but beyond that, we felt so welcomed and cared for by its people.
