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)
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!*
I am so excited for your Greece reports! I’ve always wanted to go there. We’re hoping for next summer. It looks so beautiful! We’ve debated doing a cruise or staying on a couple of islands like you did. Now that you’ve been there would you say one would be better than the other?
I think staying in a few islands is the best way to really sink in to the experience of Greece. Cruises are great, but you only had a few hours in each spot. The joy of Greece for us was sitting leisurely in taverns or on our patio gazing at the water. Santorini is a must, but I’d throw in the more lesser known islands like Naxos and Paros, too.
Thank you so much for this post! I’ve been waiting on it. Next year my husband and I will celebrate our 20th wedding anniversary, and we’ve narrowed down our celebration to a road trip thru Italy or the Greek Isles. I initially thought about cruising the islands, but it doesn’t seem like there’s enough time actually on the islands, and that’s what I really want. So I think you just helped make that decision. One question . . . do you use a travel agent or just research/book everything yourself? We’ve traveled a lot across the US, and I always do everything myself. But I’ve considered using an agent for this trip because I’ve never traveled internationally before. At the same time, I don’t know that I can let go of the planning myself!
You can’t go wrong with either trip…both sound amazing! I planned and booked the trip myself, but I love that part (and don’t like to hand over the control and decisions!). I’ll be sharing all the details of the travel and full itinerary, so hopefully that’s helpful, too!
Thank you for this! I’m starting to plan a trip next June to Greece, I’m nervous but with your posts and Dave’s help (already started my research with his help!) I think I will feel week prepared! Can’t wait for all the details!!
Your trip recaps are the best! Hope to visit some day. I love that you share your tips and recommendations so openly – I’m sure you help lots of readers and travelers. 🙂
I’m thrilled they’re helpful!
Could you give specifics on which catamaran half day cruise you took? I pulled up the sight you suggested and there a a handful to choose. Wanted to take advantage of your great experience and look for the same same tour. Thank you. And thanks for sharing tour info. It is very helpful.
Hi Cathy! I just pulled up our receipt, and this was the official name…hope it helps!!
‘Santorini Gems: Small Group Sailing Cruise on a Catamaran’
12 hours on the Mothership-LOL!
Forwarding this post to everyone I know, to put on their bucket list!
Thank you for sharing your wonderful, awesome trip, SP’s!
Only one missing was Mama SP, ha,ha.
Thanks so much, Sandy!! I really appreciate you sharing! xo
Me and my husband spent our honeymoon in Santorini. Last year we took a two weeks roadtrip in Italy. These were our favourite vacations. Definitely recommend both. We planned both trips ourselves, more work but half the fun is in the planning.
Hi,
These pictures are stunning! I was wondering if you used a camera or managed to get these with an iPhone? Also, on vacation do you keep up the intermittent fasting or take a break? Love your blog! 😘 thanks!
Thank you so much! I took all these pics on my phone!!
Your pictures are just gorgeous! I could totally plan a vacation based solely on your blog. You do such a good job!
Are those adorable buildings houses? I feel that’s what Heaven might be like. 😁
Gorgeous photos, Cassie!
I think the bright and ethereal landscapes of Santorini are jaw-dropping like nowhere else.
Ps- I cannot believe these photos! U spoil us!
The photos are gorgeous. I’ve always wanted to visit Santorini. I especially loved the town at night photo….kind of magical that one.
I love the colors of send to Reaney. It has such vibrance & life. All the food has me drooling. :]
Spent my honeymoon there 25 years ago! Explored the whole island by scooter and loved every minute of it. This post really makes me want to get back!
oh no those white shorts are cute but SEE THRU!!! Yikes! Can i return them to the store
Oh no, I wear them all the time and don’t have any issues!? I wear nude undies, just like with any white jeans, skirts or shorts. But yes, Nordstrom will accept the return. I’m sorry to hear they didn’t work out for you! xo
I’ve been anxiously awaiting your details on your trip since I saw you were there. We are headed to Greece in 18 days and don’t have all of ours plans fully flushed out yet since we will be staying with family in Athens and Patras, but trying to plan island trips now. It looks magical!
I wear nude undies too ….but it’s my tucked in shirt you see clear as day! I like my white bottoms to be lightweight but not see thru. Thanks for the info on the return!
I’m going in a few weeks! Hopefully it won’t be too hot for a hike from Oia to Fira, but I’m sure it will be amazing no matter what we do. Thanks for the tips!
Hello from Athens Greece. Santorini is very beautiful , thanks for the post ,all greek people are blessed we live here .
I’m so excited to hear All the details. Planning to take my 3 kids next summer. Really want to hear all hotel, restaurant and excursion, activities details. Did you go to Athens? I feel like if I travel that far I should go to Athens too.
Yes! We flew in and out of Athens, and stayed one night each time. I’ll include that in my overall itinerary post! (We didn’t see/do enough in Athens to warrant a stand-alone post) xo.
Anxious for your overall itinerary post….flight info, etc…..Planning a trip soon….Will you be posting this anytime soon? Thanks for all the wealth of information here on this post!!
Hoping to wrap the individual island recaps in august, followed by the full trip!
One week until we leave for our family vacation to Greece. We are going to the same islands. I love all of your information. We are staying in Fira. I have planned family photography session while in Santorini. Thank you for posting this. Looking forward to Naxos recommendations!
How much does a trip like this cost?
It totally depends on the time of year, where you’re flying from, where you stay, how many people, etc. So many factors! We saved by booking our flights several months out with mileage points, and booked our hotels for discount via hotels.com. Also, but choosing hotels with large breakfasts included, we usually only ate one additional meal and a snack, so that cut down on our food budget.
LOVED this post – your photos are gorgeous. And I’m super impressed you looked so cute throughout with just a carry-on 🙂 Looking forward to more posts about your trip. Greece is a maybe for us next summer but I really don’t know where to begin. But I bookmarked your resort in Santorini for starters!
Hi! I am new to your site and love all the details. I am also very interested in your full Greece itinerary. I’m a new fan!
Cassie, really looking forward to your itinerary on this trip! Looks amazing. When will you post your itinerary or do you mind sending?
Hi Nadia!! I’ve gotten so behind on that trip!! I’m not sure when I’ll have it all up, but I did save video highlights to each island we visited on my Instagram profile!! That will show you everywhere we stayed and what we did! xo. C
Hi Cassie
Have been following your blog for years and love you travel posts. I recently went to NYC with my 15 year old daughter and used many of your recommendations! Loved the food tour! What time of year did you go to Greece
I’m so happy to hear it, Tina!! We went to Greece in June!