Trip Report | Santorini, Greece

Hey friends, and happy Wednesday!! I spent the day previewing the Nordstrom Anniversary Sale yesterday…and by day, I mean 12 hours! Yes ma’am, I was at the Mother Ship for 12 straight hours yesterday! Mama Sugarplum was with me, so you know we had a ball. Someone might have wet her pants laughing, but we won’t mention names.

The bottom line is, we found TONS of amazing deals and darling new Fall pieces that will make your closet sing. And even better, the majority of the pieces we loved most are under $50!! #bamwhat

My Sugarplum Top Picks will go live tomorrow (Thursday) at 11:30am, when Icon and Ambassador members can shop. Other cardholders will be able to use the post as a lookbook to prepare for Friday’s launch. My hope is it helps you thoughtfully add new pieces to your wardrobe, without impulse shopping or getting lost in 1000s of products.

But let’s move on to today’s post…another Trip Report!! I’m so excited to start sharing our Greece trip, starting with arguably the most picturesque island, Santorini!

oia town

We’ve all seen the images on Instagram, Pinterest, travel magazines and more…Santorini is splashed all over the place! And believe it or not, none of those pictures actually do it justice. It really is one of the most awe-inspiring places I’ve ever seen.

Built into the side of what was once a volcano, the towns are clustered along the edge with sweeping views down to the water. When we arrived, instead of looking around, I kept my eyes glued to our kid’s faces…seeing them experience that view for the first time was something I’ll always remember. They froze mid-step with jaws gaping.

Literally every view, every nook and cranny, is picture-perfect.

We spent our days wandering the alleyways of Oia, lounging by our hotel’s pool, eating greek salad (so much feta!!), and just soaking in the Greek culture.

Santorini is packed with tourists, but the majority seem to be day-trippers arriving on cruise ships. To beat the crowds, we’d explore early (before the ships arrived), then relax in our peaceful hotel pool for the bulk of the day, then venture back out near dusk.

We also booked a half-day catamaran excursion, and loved the chance to be on the water.

my loves

Henley Tank Top | Wide Leg Pants | Sandals

0ia at dusk

Embroidered Racerback Tank  | Shorts

catamaran tour

sunset in oia

One Shoulder Ruffle Top  | Tiered Skirt

Seersucker Short Set | Vans Sneakers

oia town at night

poolside lunch

Embroidered Racerback Tank (XS) | Shorts (XS)

Seersucker Short Set | Vans Sneakers | Similar Tropical Shirts | Birkenstocks

Henley Tank Top (XS) | Wide Leg Pants (XS)

One Shoulder Ruffle Top (XS) | Tiered Skirt (XS)

Embroidered Racerback Tank (XS) | Shorts (XS)

One Shoulder Ruffle Top (XS)


What to Pack for Santorini

The sun and heat can be intense, so lightweight, breathable fabrics are a must for Summertime. I lived in cotton tanks, linen shorts, and gauzy skirts and sundresses…all from the Nordstrom Vacation Shop, of course! And almost always wore a hat and sunglasses. #vacationhair

The dress code most everywhere was casual, but you’ll want to take a million photos, so maybe insist your son leave his black Motley Crue t-shirt at home! 😉

Most pathways and alleys are smooth, but there are a ton of steps, so pack comfortable sandals! We were also grateful we traveled with just carry-on bags, as getting off and on the ferry boats was fast-paced and a little hectic. (More on the actual travel details and itinerary later.)

See everything I wore and packed in this post, and find my travel essentials here.

Dress (XS on sale!) | Roller Bag | Weekender Bag


What We Did in Santorini

It’s funny I even included this category, considering we spent almost every day lounging by our hotel pool, or wandering the alleyways of Oia! But we wanted to see Santorini from the water, so we booked a half-day sunset catamaran excursion via Get Your Guide, and loved it!

They picked us up from our hotel and drove us to the other end of the island. From there, we boarded a large, pristine catamaran and cruised the length of the island. We stopped a few times to swim and snorkel, while the crew grilled fresh meats and veggies on the open-air grill. We wrapped the day watching the famous Oia sunset from the water. It was magical!

We had quite a few other things on our list, like hiking from Fira to Oia…but poolside and view-gawking got the better of us!

Sugarplum Travel Tip: Santorini Dave was a really helpful site in planning the trip and activities.


Where We Ate in Santorini

Atrina Canava // Our hotel! They served a huge 3-course breakfast every morning, which usually held us over much of the day. Then we’d have a light snack from the pool bar mid-afternoon.

Pitogyros // Near the waterfront on the backside of the island, this gyro stand is always busy with locals and tourists alike. It’s casual and seriously the best gyro and greek salad of my life! Dine in, or get it wrapped for strolling and eating.

Skiza Pizza // In Oia town, the smell of this casual pizza place lures you in. Eat in the open air patio overlooking the water, or in the rooftop patio with a sunset view. Lunch was super busy, but dinner had a smaller crowd (especially if you go before the sun sets).

Amoudi Fish Tavern // In Amoudi Bay, at the bottom of Oia, this waterfront restaurant literally sits inches from the sea. Fresh fish is brought in daily and served table side whole. It’s pricey (but still casual), but the portions are huge and the setting is straight out of a movie. We ate dinner here after our boat excursion, then walked the stairs back up to Oia.


Where We Stayed in Santorini

Atrina Canava // This family-owned property exceeded all our hopes, and was a huge part of our love for Santorini! Oia is a bustling little town, with many tourists, but the moment you pass through the gate of Atrina Canava, all the noise and chaos disappears!

Incredibly peaceful and meticulously maintained, the rooms were spacious, clean, and comfortable. You start the day with a huge 3-course breakfast, and the pool bar serves heavy snacks and drinks until late at night. The staff is incredibly friendly and eager to serve.

We had a two-bedroom suite with patio, which was the perfect place for morning breakfast and evening stargazing.

Santorini is all about the views, so I highly recommend splurging for a hotel with a caldera view…and if traveling in the summer, you’ll really appreciate a pool, too!

daily breakfast delivered to your room!

view from our patio

Her Tank | Henley Tank Top | Shorts

Santorini was the perfect kick-off for our trip, and definitely a highlight. But experiencing it with my people was what made it extra special!

I hope this post is helpful in planning your own Greek adventure, or inspired you to add Santorini to your travel list! My plan is to recap each island we visited, then share the full itinerary with travel details like flights and ferries, routing info…the works!! Let me know if you have specific questions.

See you back here tomorrow at 11:30am CST for my first Sugarplum Picks from the Nordstrom Anniversary Sale! (I can tell you this cardi and this one will both make the short list!)


*See all my Greece outfits, plus my packing tips, in this post, and find my travel essentials here.


*This post created in collaboration with Nordstrom and ShopStyle, but all product selections, styling and wandering spirits are our own. Thank you for supporting Hi Sugarplum sponsors!*


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