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4 Days in Santorini

4 Days in Santorini

Directly after our October 2016 wedding, we decided to take a more relaxing "mini-moon" in Santa Barbara wine country with plans to take a more active honeymoon the following August. For us, five days eating, drinking and exploring the quaint towns of Solvang and Los Olivos was exactly what we needed and gave us another, larger trip to look forward to.  In planning our trip to Greece, we enlisted the help of our friend, Emily Prentiss from Valerie Wilson Travel.

Emily worked with us closely from ideation through execution. She had an initial call with us to discuss what we wanted to accomplish on our trip and with her expertise in the area, she knew immediately which accommodations would make the most sense given our budget and expectations. She also off-hand knew the best spots for dinners with a view and delicious Mediterranean food. Working with Emily took all the research and logistical work out of planning, which can often be a daunting task and can sometimes add unnecessary stress to something that should be fun. 

We chose to stay at Canaves Oia Sunday Suites, which is situated right in the heart of Oia. We also heard good things about staying in Imerovigli, a village next to Oia that is more residential and quieter. However, staying in Oia allowed us to be walking distance to the best restaurants, sunset views and local shopping - all things we were hoping to experience without hopping in a cab.

We arrived from London late at night and barely squeezed in time to have dinner at Fino, a restaurant tucked away on a side street near Canaves Oia. It was a delicious welcome to Santorini and the decor was perfectly white and minimalist; everything I would have imagined Greek restaurants to be! We set our alarms so to not sleep the day away and woke up in the morning to the most tremendous view right from our suite terrace. 

(Day 1) - We were told that the best way to see the island was to hike from one end (Oia) to the other (Fira). We almost went with casual sandals but thankfully we didn't. Though there are a fair amount of walking paths along the way, there are some areas of the 6.2mi trek that definitely require sneakers. 

Fira is the bustling capital of Santorini and where all of the ships and cruises dock. Immediately upon reaching it, it was obvious we had made it to Fira - there were people everywhere. Working up an appetite from our hike, we sat down to lunch at Dionysos in Atlantis. No matter where we went to eat while in Santorini, everything was the best thing we ever ate. In terms of potentially falling into a "tourist-trap," you might pay a premium for doing so but you won't sacrifice the taste of the food. It is all so fresh!

[Day 1 Sources: Pajamas, Gap; Athleisure, all Lululemon; One-piece gingham suit, Asos; Panama Hat, J.Crew]


Ready to lounge by the pool after hiking and eating, we caught a cab ride back to Canaves and spent the rest of the afternoon poolside overlooking the Aegean Sea and allowing Panos, our favorite and talented bartender, whip up tequila and basil-based drink concoctions.


Dinner was meant to be right before sunset at Floga but instead we caught the tail end of it since we made some friends by the pool and chose to hang for a bit longer. When we sat down to dinner, our table was out on the patio, and just as Emily had described, it had the most beautiful unobstructed views of the famous Oia sunset. It is definitely a good idea to plan this dinner around the sunset hour and ensure you are seated outside. You will not be disappointed. 


(Day 2) - We booked a semi-private morning catamaran cruise ahead of time through Sunset Oia. The semi-private has max 16 passengers and on our boat, it was mostly all couples. T and I are the type of travelers that like to meet new people and exchange stories so the semi-private was just our speed. We often end up meeting people that somehow are friends of friends or are in some way tied to our circle of people. That "six degrees of separation" is real!

The cruise provided lunch and drinks and we would recommend the morning cruise over the sunset. It can get cold on the water once the sun sets and later on while having dinner at Ammoudi Fish Tavern (located right near where our catamaran dropped us off), we could see people getting off the sunset cruise looking miserably cold!

After dinner, we ran into our friends we met while hanging by our hotel pool so the four of us proceeded to MaryKay's Bar. This is a must! I felt like we were transported to a different time and really got to experience Greek culture. Even though Oia is a big destination for tourists, this bar, albeit welcoming, had mostly locals, a large friendly dog and good dance music.

[Day 2 Sources: Red bikini top, Solid and Striped; Beach pant, Tory Burch]


(Day 3) - Our last full day, we intentionally made no plans but to have an unofficial wine tasting at Sigalas Winery around lunch time. It was the first time we actually were able to catch up on some much needed sleep and after a night out dancing at MaryKay's, we were so happy we did. Sigalas was a quick cab ride from Canaves in Oia. We took a table on the back terrace, which was practically empty aside from us and this stray cat and ordered a wine flight and meats and cheeses to pair with them.

[Day 3 Sources: Blue Skirt, Club Monaco; Top, Lovers & Friends]


Later on, T surprised me with drinks on the rooftop of our hotel to watch the sun set before we headed off to dinner at Candouni. Dinner was a hidden gem of a place and completely candlelit in a courtyard setting. Candouni is a family owned spot like many of the restaurants in Greece but it always feels a bit more special when you learn that most of the recipes on the menu are old family recipes that have been passed down.


(Day 4) - Our last day, we had a couple of hours before catching our ferry to the island of Naxos. We strolled over to Passagio for the most delicious Greek coffee and took it to go so we could shop a bit before heading out. Oia has lots of cute shops for homemade goods. I got a nice pair of leather sandals, a top and some olive wood cooking utensils. T and I have oddly been collecting little animal figures wherever we go so we also brought back a horse carving made of volcanic rock.

Our next stop, Naxos! Stay tuned for where we stayed on this beachy, laid back island. 

The Island of Naxos, Greece

The Island of Naxos, Greece

Loaded Veggie Scramble

Loaded Veggie Scramble