Trip Report | Greece — plan it petersons

Overview

Greece has been on my bucket list for as long as I can remember! With family roots that trace back there, I’ve always pictured it as one of those places that would feel both magical and meaningful - rich history, whitewashed villages, blue water stretching endlessly. This trip was all of that! And also…a little more. I think of this trip as a combination of a dream, real life moments, and everything in between.

We traveled to Greece as a group of seven - our family of five, along with my mom and aunt. Like most family travel, it was a mix of unforgettable highs and a few unexpected challenges.

Here’s a day-by-day look at how we made it work, what we loved, and little tips we learned along the way. We will also provide a points and miles breakdown to show how we saved nearly $9,000 on our flights and hotel! Proof that with a little strategy and organization, you can explore the bucket list destinations on your list too!

Our Itinerary

Day 1: An entire day of travel

We flew direct from Pittsburgh to London on British Airways and landed at Heathrow at 10:00 a.m. local time. Our flight from London to Athens was supposed to leave around noon, but when we touched down in London, we got a text saying the flight had been canceled. Gulp. We navigated over to the British Airways counter, spoke with a ticketing agent, and were rebooked on an Aegean Air flight that left at 4:00 p.m. Not exactly how we planned to spend our first day abroad, but grateful that we didn’t need to stay the night in London.

We persevered by lounging around the airport, having lunch, and just passing the time until our flight took off. Luckily, the Aegean Air flight was uneventful, and we landed safely in Athens around 10:00 p.m. (after a 4-hour flight and a 2-hour time change).

We made our way to the Grand Hyatt Athens, grateful just to be there after a long travel day. This property isn’t quite centrally located - you can’t walk to the main sites - but that wasn’t a huge priority for us. The hotel itself was great and the rooftop pool was outstanding! More to come on that. We checked into our rooms (a suite for our family of five and a standard room for my mom and aunt) and went straight to bed, ready to officially begin our adventure the next morning.

Or so we thought! 🙃

Killing time at Heathrow. Aunt Martha’s deck of cards came in so handy this trip!

Day 2: Sightseeing after a late start.

The day kicked off with a classic travel reality check: we accidentally slept through breakfast! “We” meaning our family of five - not my mom and aunt, who were waiting for us at breakfast and beginning to get concerned. We woke up to them knocking loudly on our hotel room door, which made us jolt out of bed Home Alone-style. That got our blood pumping, all right! Add in that our youngest woke up queasy, and let’s just say our trip wasn’t kicking off the way I had hoped. Still, we persevered and quickly got ready, then headed down to the lobby to meet our tuk-tuk tour drivers.

I love a good tuk-tuk tour. We took our first one in Paris last summer, and I’ve been excited to do another one ever since. I will say, our tuk-tuk tour in Athens was hot, long, and a little chaotic with tired (and one sick) kiddos - but also genuinely fascinating and a great introduction to the city! We had two tuk-tuks for our group of seven, one driven by Joseph and the other driven by Manos. I would compare Joseph to the dad in My Big Fat Greek Wedding - the pride for his country really came through. He told us how things like politics and theater all began in Greece, way before the rest of civilization. Greeks are the best, etc. 😉 Manos was younger and spoke better English, so he sometimes served as translator. We drove all over Athens, stopping several times to walk around and explore. One highlight was when they allowed the kids to drive the tuk-tuks in a huge empty parking lot area. It was a fun little surprise that the kiddos really enjoyed!

After our tuk-tuk tour, we returned to the Grand Hyatt Athens and ventured to the rooftop pool which overlooks the Acropolis. That moment really felt good - sunshine, history in the distance, and a much-needed pause. We grabbed lunch there, spent some time swimming, and just relaxed for a bit. It was really special and the photos we captured from that spot are some of my favorites.

After our pool time, we ventured into Plaka for dinner at a place called Lyra - great food and a relaxed pace.

We capped the day off with a sunset visit to the Acropolis, which was breathtaking even through jet lag and heat. In hindsight, I would recommend booking a guided tour to fully appreciate the history - but the views alone were stunning and unforgettable! I love that we saved this for the end of our day because I’m sure it’d be quite hot in the afternoon sun. A stroll through the Acropolis during sunset was just perfect. 10/10

Henry chose this Greek snack from the convenience store

Courtyard of the Numismatic Museum of Athens

Agios Dionysios Areopagitis Church in Athens

Inside the Agios Dionysios Areopagitis Church

Lighting candles and saying prayers for our family

Living her best life at the rooftop pool

My buddy - still not feeling well, but making it work!

A close-up of the Parthenon’s marble columns

The Porch of the Caryatids, six female figures which serve as columns of this ancient Greek temple. Apparently these are casts, and the original statues are preserved in the Acropolis Museum.

The view from the Acropolis, looking down the ancient stone steps.

I snapped this photo of the description of the Parthenon. Everything was in Greek (of course) and English.

Day 3: Santorini, aka the postcard moment we were waiting for

On our third day, we made it to breakfast (hooray!) at the Grand Hyatt Athens, which was very well done. And even better since it was included by the hotel staff at check-in!

We were still navigating a bit of illness with our youngest, but we made the most of our travel day to Santorini. We flew from Athens to Santorini on Sky Express, which is an affordable no-frills airline in Greece. It suited our needs just fine, though, for a quick (less than an hour) trip. And the moment we arrived, everything shifted.

We checked into our Airbnb in Oia (pronounced “ee-uh”), called the Anemi Villa, and it was immediately one of those “wow” moments. The traditional cave house was super charming and the kids were absolutely thrilled with the views from the rooftop and with the private plunge pool right on our patio. The location - truly in the heart of the town - made it easy to step straight into those iconic views and winding streets. I would highly recommend this Airbnb, which was large enough for the seven of us. If you’re traveling in a smaller group, the host has other properties just as charming and centrally-located as ours. He was so warm and welcoming and made our stay just perfect. Take a look if you’re planning a visit to Santorini!

Santorini really did feel like a postcard. We spent our first evening walking through Oia, taking it all in - whitewashed buildings, blue domes, and views that genuinely stop you in your tracks. It truly was everything I had pictured!

Unfortunately, that evening came with a slight hiccup: a misunderstanding at a restaurant where I believed we had a reservation, but apparently I hadn’t completed the final confirmation step. The interaction with a rude host at the restaurant left me feeling quite unhappy and caught off guard, but I tried to let the moment pass because - hello, we were in Santorini! We ended up pivoting to another beautiful spot with caldera views and had a wonderful, peaceful dinner while the sun set. Crisis averted, but also, why are people rude? One of the things travel teaches quickly is how often you need to adapt - and this was definitely one of those moments.

We ended our first night in Santorini on a high note, though. I could have walked around Oia on those beautiful, winding cobblestone streets overlooking the caldera all evening. It was my favorite part of this unique city. I would love to go back someday!

Arriving at our Airbnb - this was the porter that our host arranged to transport our suitcases. An absolute lifesaver with all the winding cobblestone streets and steps.

The patio of our Airbnb (and view of the caldera in the background!)

The plunge pool at our Airbnb. The kids loved that it had steps on the right side, and then got very deep on the left side. And Louie with a smile (finally)!

The rooftop of our Airbnb! Hello Santorini! Absolutely incredible views.

The Church of Panagia Platsani, located in the main square of Oia.

Our lovely sunset dinner overlooking the caldera - too pretty for words!

The infamous Greek salad, which I ordered at every restaurant possible.

A man in Oia wearing a traditional Greek folk costume.

I could have enjoyed these views for days and days…

The picturesque pedestrian street to get to our Airbnb. Elise and Louie holding their Santorini donkeys, purchased as souvenirs.

Day 4: Sailing Santorini

Our second day in Santorini was one of the absolute highlights of the entire trip. We planned a private half-day catamaran cruise with Spiradakos Sailing Cruises, and from the moment we stepped aboard, it felt like the pace of the trip slowed down in the best possible way.

The crew, which included our host Stavros and his team, were just the best. We sailed all the way around the island, learned about the history and geography of Santorini, and stopped to snorkel in the cool blue water - something the kids really loved. It was their first time snorkeling!

Stavros’ team prepared lunch on the boat, which was quite the spread of grilled chicken and shrimp, pasta, grape leaves, Greek salad, crusty bread, and more! It was so over the top and we’ll never forget it. Shout out to our friends and neighbors who passed along the cruise recommendation to us!

That evening, we kept things low-key with pizza at a restaurant in Oia right near our Airbnb. After a day on the water, it was exactly what we needed. I just loved that we could walk everywhere from our house. So convenient!

Mark and the big kids went snorkeling at the first stop.

Enjoying the breeze - you can see some whitecaps in the water here. It was quite windy at times.

Taking turns navigating was a highlight for the kiddos.

Ready to go snorkeling with mom at our second stop.

I was intrigued by these colorful doors carved into the volcanic caves.

The Santorini steps - we did not attempt to climb them, but rather enjoyed the view from our boat.

A really beautiful beach club we spotted from our boat

More snorkeling in Santorini’s beautiful waters.

The incredible lunch the crew made for us! Wish I could go back and have this meal all over again.

The selfie I didn’t know I needed - Stavros and Mark

Our casual dinner spot, post catamaran cruise.

Day 5: Saying goodbye to Santorini & our ferry ride to Naxos

We ventured out on foot for a quick breakfast before sadly leaving Santorini. We stopped at the Blue Domes restaurant and were seated on the rooftop, which was unreal. We ate pancakes, bacon, eggs, avocado toast, fresh juice and lots of coffee and enjoyed (yet again) the breathtaking views. Afterwards, we walked back to our Airbnb where the porter was waiting for us to take our suitcases out to our driver, who took us down the hill to the harbor. There, we waited for the ferry to arrive, and it was right on schedule.

Taking a ferry in Greece is an experience in itself - boarding a Greek ferry is nothing short of chaotic and overwhelming. Picture a huge crowd narrowing in on one small staircase to get into the ferry, a blaring siren (why???), and dragging your suitcase along the bumpy terrain, all while trying to ensure the kids didn’t get lost or pulled away from our group. As a fellow American traveler muttered to me during the insanity, “This is like a zombie apocalypse.” Sheesh! Once we got to our reserved seats aboard the ferry, though, the kids loved the ride and we all leaned into the adventure of it. We reserved upgraded seats (for an insignificant cost) which I would do again. It felt more like we were riding in an airplane than a ferry. Also, there was a snack bar in our section and a waitress to serve the passengers. It was a pretty cool experience!

We checked into Sundunes, an incredible resort right on the beach. Due to our group of seven, we reserved two “maisonettes” with private plunge pools, which were just awesome. The resort had a stunning pool, a beach just steps away, a complimentary buffet breakfast, and a rooftop restaurant. They also assisted us with several rides in and out of town, to the airport, etc. The service here was really amazing. Everything was super clean, modern and very zen-like.

Our first night at Sundunes, we ate at the rooftop restaurant for convenience’s sake. The food was good, but it didn’t blow us away. The evening breeze, however, almost did. Luckily, the restaurant gave us cozy blankets to keep us warm and comfortable during our dinner - a nice touch!

Henry ordered pastichio (which he was very excited about) and it was served in a non-traditional de-constructed manner. He did not approve because it was nothing like Yiayia’s! 😂 Also, the food came out very sporadically, and it wasn’t a tapas or family-style restaurant. Elise got her pasta probably 20 minutes before the rest of us got our entrees. But it was okay because we were in Greece!

These smiles combined with these views are almost too much for me to handle.

My buddy taking a break after that stressful boarding process.

Doing what they do best - eating snacks.

I always love snapping photos of the local food packaging - the kids loved these cookies.

Taking a load off at Sundunes’ aesthetic reception area.

Our second plunge pool of the trip (spoiled children) - this one is outside of our maisonette at Sundunes. The other plunge pool (outside of my mom and aunt’s maisonette) is to the left, beyond that half-wall.

Here’s a view from the other side, showing our maisonettes.

The view from our second-story balcony - here you can see the two plunge pools. The resort pool is in the distance.

The most beautiful resort pool I think I’ve ever seen.

Day 6: A beach surprise and dinner in Naxos Town

Naxos brought a very different energy than Athens and Santorini, which is part of the reason we wanted to visit. Our days here slowed down significantly - beach time, pool time, and easy dinners. There was a calmness to Naxos that felt restorative after the busier pace of Athens and Santorini.

There was no rushing out the door, no packed sightseeing schedule, and no need to make every minute count. We spent the day at the beach, floated around in the private plunge pools at our maisonettes, and let the kids do what kids do best on vacation (swim, snack, repeat). It was glorious!

There was, however, one little surprise waiting for us at the beach…

We quickly discovered that some of the beachgoers, mostly from an older generation, had a very different definition of appropriate beach attire than we were accustomed to. As in…completely nude. Including the men.

Meanwhile, our kids were happily playing nearby, so cue the parental exchange of, “Okay…how are we going to handle this?” We decided to lean into it as a cultural learning opportunity.

One of the best things about traveling with kids is that they get to see firsthand that the world doesn’t operate exactly like their little corner of it! Different countries, different customs, different norms. Sometimes, those lessons come from museums, guided tours, or historic sites. And sometimes, they come from a beach in Naxos that you definitely weren’t expecting to be clothing-optional!

That evening, we took the hotel shuttle into Naxos Town for dinner, and this ended up being one of my favorite nights of the entire trip!

We ate at Taverna Naxos, and everything about it was incredible. The restaurant itself was beautiful, with an outdoor patio that felt quintessentially Greek. They even surprised us with Ouzo shots to round out the meal. The food, service, and atmosphere were exactly what you hope for when you picture a family dinner in Greece. 10/10 for this one!

Quick photo op with Yiayia before heading into town.

The bougainvillea was everywhere - chef’s kiss.

Snapped a few photos while walking around before our dinner reservation.

Happened upon this quaint little church in Naxos Town - I’m not sure of the name.

Really enjoyed the views of the water from Naxos Town.

The picturesque patio of Taverna Naxos. Delicious and charming!

More grape leaves, another staple we ordered at every possible place. Just to die for!

My “orzo risotto” entree with fresh veggies, a tomato-based broth, and lots of fresh Feta cheese.

Louie and his sour cherry juice - this is a common drink on the menus in Greece, and he was a big fan!

How cute are these curved stone benches overlooking the water?

Waffle House ice cream after dinner, recommended to us by our driver.

We didn’t go inside, but I loved the vibe of this mural.

Day 7: Beach club life

By day seven, we had really settled into the Naxos pace, and we were not mad about it.

The beach club was just steps from the pool area at Sundunes, so it was very easy to spend the day going back and forth. The beach club is open to the public, so even though we were staying at the resort, there was a fee to reserve chairs and an umbrella, which is not uncommon in Europe. As hotel guests, we received a discount, and I believe we paid around 30 euros per day for two chairs and an umbrella. We ended up getting two sets each day so the adults had a place to relax (not that that happened very much).

The beach itself was beautiful - clean, well-maintained, and surrounded by the most incredible water. The sea was crystal clear, and while it wasn’t very warm (we were there in mid-June), it was refreshing and gorgeous.

One of the best things about the beach club is that we didn’t really have to do anything! Servers came right to our chairs to take food and drink orders and brought everything directly to us. The kids could swim and play, we could sit under the umbrella, and nobody had anywhere they needed to be. The kids loved the pizza at the beach club, and ate it every single day for lunch.

That evening, we kept things casual and ate at a little beachside restaurant near the resort called Seaside Souvlaki. It wasn’t necessarily a meal that will go down in the family travel hall of fame, but it hit the spot. The food was good, the setting was casual and right near the beach, and sometimes that’s all you need after a full day in the sun.

The breakfast at Sundunes (and more card games), where we started each day in Naxos.

We ate lunch on the beach each day. The kids loved the margarita pizza, fries, and chips and guacamole.

Dinner at Seaside Souvlaki - this was my falafel.

Walking back to Sundunes and admiring the beautiful scenery.

Day 8: One last pool day

Our last morning in Naxos was intentionally uneventful. We had our usual breakfast at the resort, packed up our rooms, and then spent our final few hours hanging out by the pool.

There was something really nice about ending our time there without trying to squeeze in one more activity or one more sightseeing stop. We had experienced the beaches, explored Naxos Town, enjoyed some great meals, and had really slowed down.

Eventually, it was time to head to the airport. The Naxos airport was tiny (really tiny), and the kids got a kick out of how small it was. Our flight from Naxos to Athens left on time, and thankfully, this travel day was completely uneventful. We made it safely back to Athens and checked into the Sofitel Athens Airport, which I would absolutely recommend if you have an early flight out of Athens.

The hotel is directly across from the airport, making the logistics very easy. Our rooms were super nice and comfortable, and after checking in, we had dinner at one of the restaurants in the hotel lobby before heading upstairs for an early night…because the next morning was going to be an early one!

We were always the only ones in the pool!

Leaving this beautiful and magical resort.

Snapped at the airport. Have you ever seen Pringles flavors like tzatziki or prawn cocktail?? I kind of regret not trying them.

Day 9: The longest day home

Our flight from Athens to London left at about 6:00 a.m. Thankfully, staying at the Sofitel meant we didn’t have to worry about transportation to the airport. We simply walked across the street, which made the early departure about as painless as it could possibly be.

From Athens, we flew to London, where we had a long layover before our afternoon flight back to Pittsburgh.

Spending most of the day in an airport wasn’t exactly how we would have chosen to spend our last day of vacation, but at that point, we were pros at making the best of it. We grabbed food, found ways to entertain the kids, and reminded ourselves that the only thing standing between us and our beds was one more flight!

Our flight to Pittsburgh finally departed London that afternoon, and after what felt like the longest day ever, we finally made it home.

Tired? Absolutely. Happy to be home? Also absolutely. But most importantly, we felt so grateful! Greece had made it off our bucket list and into our family photo album, and that is a pretty awesome feeling.

When stuck at Heathrow all day, you go to the Jellycat pop-up shop.

Another snack at the airport - just made me laugh that they’re called “wee chunkies.”

Points & Miles Breakdown

Accommodations:

Grand Hyatt Athens: Booked the Grand Suite (1 king bed + pullout sofa) for 46k points (23k points/night for 2 nights). A real steal! Also worth noting, since this is a Category 4 hotel, you can cash in a Hyatt Free Night Certificate to book a standard room. Cash price would have been $1,463 for the two nights.
Our Santorini Airbnb and Naxos resort were paid for in cash. If you have Capital One Venture miles, you can use those to “erase” anything that codes as travel on your statement. We, however, didn’t do this for this particular trip.

Flights:

British Airways: For our outbound flights, I paid 193,750 Avios for five tickets from Pittsburgh to Athens with a layover in London. Total taxes and fees were $505 ($101/person). The cash price would have been $4,395 ($879/person).
British Airways: Coming home, I also paid 193,750 Avios for five tickets from Athens to Pittsburgh with a layover in London. Again, the total taxes and fees were $505, ($101/person). The cash price would have been $3,762 ($752/person).

Total Savings:

By using points and miles, we saved a total of $8,610!

Accommodation Savings: $1,463 (Grand Hyatt Athens)
Flight Savings: $7,147 (we would have paid the $1,010 in taxes either way)

Earning Points

We accumulate Hyatt points mainly by transferring Chase Ultimate Rewards to Hyatt. British Airways is a transfer partner of all four major banks, so points can be racked up relatively easily and then transferred over to BA.

If you are interested in learning more about racking up points and miles to take a dream trip, let me know! I’d love to help strategize credit card welcome bonuses with you and I’m happy to answer any questions.

Is Greece on your family’s bucket list??

Trip Report | Greece

Overview

Our Itinerary

Points & Miles Breakdown

Earning Points

❤️ Liz

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