Greece has never really been on my radar. It was always France, the UK, Italy and we checked all of those off within the past year. We wanted to explore a new country and Greece stuck out because we'd be taking an 11 year old and a 13 year old - both whom enjoy Greek mythology and have read tons of books inspired by it (I loved mythology growing up too). Seeing how Nathaniel was in his element at the Colosseum, the idea of touring the Acropolis seemed pretty magical.
If we were already heading to Athens, we had to add Santorini to the list too. Although we weren't sure any of us were stare-at-the-pretty-blue-waters type of people, we weren't sure if and when we'd ever be back in Greece. Our motive was a new experience, right?
3 kids. 2 countries (3 if you count an airport). 6 cities. No checked baggage. Yes, we did.
I'm not a big fan of checking in baggage.. the lines at the counter, the potential for lost luggage, the waiting at baggage claim. The inefficiency and the time it takes drives me crazy. I've been on the path to minimalism so it made me question if we really need to pack all of the things we wanted to. We didn't. We don't. Ever since we started traveling internationally, we learned how to pack lighter and simpler. It's become a goal to pack as light as we can.
We managed to fit everything for 5 people in 4 carry-on duffles, 2 backpacks, and 1 compact stroller for a two week trip. Everyone's wardrobe revolved around 1 pair of shoes. We chose clothing in the same color palette so that everything worked with everything. We rolled all of our clothes instead of traditionally folding it. We also planned to do laundry once during the second leg of our European escapades.
We were meeting my uncle, his family, and my sister in the French Riviera during that second leg, so we booked nonstop, roundtrip tickets for Paris using CC points and would figure all other travel plans from there. We decided to start off the trip in Santorini, which meant two 3-hour layovers (there is a nonstop from Paris, but it only runs about once a week). Any which way, we knew the flight to Santorini was going to be a long haul; we splurged on a hotel because of this.
The kids did amazing during the flights and the layovers. iPads and entertainment systems definitely helped. I always try to load the iPads with new things beforehand. When we made it to Santorini, we took a taxi straight to our area, had to walk up and around to find the hotel, got lost, iPhone maps weren't helping, asked for directions, and FINALLY made it in time to catch the sunset below. Worth it.
We, originally, looked at hotels in Oia because it's supposed to feature the best views of the caldera. Not very many hotels in Oia allowed children. We had 3 kids, needed room for 5 people, and wanted a private pool so that the kids could enjoy it to themselves - nonexistent in Oia.
We stumbled upon Day Dream Luxury Suites in Fira. The Dream Villa could hold up to 6 people, allowed children, had 2 bedrooms/2 bathrooms/a living room, and its own private infinity pool that overlooked the volcano and the Aegean Sea.
We loved it here! The room included daily breakfast. The staff was incredible and so accommodating. One thing to note: their website and every other booking websites says private pool for the Dream Villa, but the concierge said it was a sharing pool for the hotel. No one, aside us, ever used the pool in front of our room, but I thought that was rather weird. There are only about 4 rooms total on the premises with another pool that's described as a sharing pool and a hot tub. Regardless, the kids' favorite part of Santorini was the pool. We spent the majority of our stay lounging in or around the pool.
For us, Fira > Oia. We rode a taxi over to Oia for a day trip and it was just so HOT. It was about a 30 minute ride from where we were. The landscape and the views were great, but like I've read in other reviews, you really can't go wrong with the view on any side of the island. We wanted to try a seafood restaurant by the shore line, but the thought of 3 kids climbing back up the winding stairs didn't seem like a good idea. We walked around, explored, had lunch, found some gelato and went back to Fira. Fira just felt more lively.. with a lot more shade. I guess that's the city-lover in us.
Most of our meals in Santorini were restaurants we just bumped into. We didn't do prior research.
Our first and last meal was Rastoni. The beef mille-feuille was a favorite. The pastas were good. The view is breathtaking. We got to enjoy it for a dinner and a lunch. We're creatures of comfort, so Rastoni was our safe place where we were guaranteed everyone liked something from here.
As we were walking up near the cable cars in Fira, we tried China restaurant because the boys were craving some asian food. It wasn't the best, but it wasn't the worst.
We tried to go to Parea Tavern on the first night of our stay because it was by our hotel, but they said there wasn't room for the 5 of us that day. We tried again for lunch another day. Mussels in white wine sauce are one of our go-tos. We preferred the pastas at Rastoni.
Thalami was the one restaurant we tried in Oia. I recall waiting awhile for the food to be served or it was that there was a huge gap in between dishes being brought out. I think this was our least favorite restaurant out of the ones we tried.
You can't go wrong with gelato though. We stopped into Lolita in Oia because it was the cutest spot. Their branding and marketing were on point. The pink logo on the wall + Olivia's pink outfit that day.. we had to stop. Of course, Olivia ordered pink. The gelato was good too!
In Fira, we would go to Caffe Hausbrandt. Pistachio is my usual and it did not disappoint. We made a pitstop here whenever the kids wanted dessert.
We wanted to try other restaurants around the island, but the logistics of transportation held us back. There aren't that many taxis and we didn't want to be stranded further out.
I never thought we'd be relax-by-the-seaside people, but being in Santorini was amazing. We would watch the sunset every evening. The cynical side of me used to say: seen one sunset, seen them all. I was wrong. I was in awe. The pool made it seem as if we were sitting on the edge of the Aegean Sea. I thought Santorini might bore the kids, but being at the hotel was one of their favorite parts of the entire trip (their favorite part was spending time with the entire family in France).