Trip Report | Whidbey Island

Happy Friday from California, friends, and cheers to the weekend! That was actually supposed to say…from Mexico…but since we can’t find our passports ANYWHERE, we had to make a last-minute pivot!

For months we’ve been booked at the dreamiest jungle resort in the hills above Puerto Vallarta, but when we went to check in for our flight Wednesday afternoon, we realized neither of us had seen the passports. Full mayhem ensued, and we spent the day and half the night tearing up the house looking for them, to no avail. We finally threw in the towel, and cancelled the trip.

But Mr. SP was determined to usher in my new new decade somewhere fun, so we re-routed our plans and are on the way for a quick weekend in Big Sur! Tomorrow I’ll be 50! #gulp Honestly, I’m not really struggling with it, mostly because it truly does feel like just a number.

For some reason I’ve disassociated with the whole ‘FIFTY’ thing, and I’m just so grateful to be healthy and alive. I think the idea of 50 carries a bigger weight than actually being 50. I don’t look or feel anything like what my younger self assumed 50 would be… so really what is there to dread? Other than the fact that I’m clearly past the halfway mark of life, I wouldn’t go back to being any other age.

The confidence and peace that comes with getting older truly is a gift. Not to mention, the experience of profound loss and grief have taught me to appreciate each day as it comes and to celebrate all of life’s moments. I may tell you differently once I hit menopause or throw my back out, ha… but for now, that’s how I feel!

I’d love to hear from those of you already in the 50+ club! How much fun lies ahead?!

Now let’s get to today’s post! I’ve shared peeks of our quick weekend in the Pacific Northwest (see it HERE and HERE, with more outfits HERE), but today I’m taking you along to Whidbey Island… a picturesque spot in the Puget Sound, just north of Seattle, where you’re just as likely to spot deer as you are people.

Whidbey Island, Washington //

From the moment we checked in to the cozy Captain Whidbey Inn, we felt transported back to another time. One with no rushing or crowds, just peace and nature. The Inn is over 100 years old, and although it has all the modern amenities, it somehow managed to keep the feel of history.

From the crackling stone fireplace in the lobby to the squeaky floorboards in the original rooms, Captain Whidbey feels like the summer camp of your dreams!

Utility Jacket (Size: XS) | Straight Leg Jeans (I cut the hem) | Panama Hat (Similar HERE) | Similar Sneakers

Crewneck Sweater (Size: XS) | Utility Jacket (Size: XS) | Straight Leg Jeans (I cut the hem) | Panama Hat (Similar HERE) | Scarf

Our trip was short, and we were there mostly to see old friends, so we spent the majority of our time catching up on the porch of the Inn, or exploring nearby Coupeville and Langley towns.

Captain Whidbey Inn

Loose Roll-Neck Sweater (Size: Small, prefer XS) | Similar Hoop Earrings | Beanie is from the hotel gift shop

Performance Joggers | Canyon Insulated Vest | Halo Essential Hoodie | Similar Beanie

No surprise I spent most of my time decked out in Vuori, with the occasional jeans and sweater outfit (from Nordstrom, where else?!). Everything on Whidbey Island is incredibly casual and laidback, where cozy and comfy rules!

Halo Essential Hoodie | Canyon Insulated Jacket | Similar Boyfriend Joggers | Similar Beanie | Similar Sneakers

Do you recognize any of these faces? These are our dear friends we met traveling the world with Princess Cruise! (See those trips HERE.) We’ve been everywhere together, from France and Italy to Ireland and Russia… those kinds of experiences really bond a friendship, and it did my heart good to see them again after four long years.

Livvyland | Cassandra Lavalle | Sugar & Charm

This outfit was my favorite of the weekend! Remember these pieces from my Fall’s Essential Seven post with Nordstrom? (See it HERE.) I’ve gotten so much wear out of them, and I love how everything mixes and matches easily with the rest of my closet for perfect Fall combos.

Crewneck Sweater (Size: XS) | Utility Jacket (Size: XS) | Straight Leg Jeans (I cut the hem) | Similar SneakersPanama Hat (Similar HERE) | Scarf

Captain Whidbey has an incredible restaurant on-site for an amazing dinner overlooking the water, and this cute cottage serves up the yummiest coffee, pastries, and a few breakfast sandwiches. And I couldn’t resist a Captain Whidbey beanie and sweatshirt from their little shoppe.

Performance Joggers (Size: XS) | Canyon Insulated Vest (Size: Small) | Halo Essential Hoodie (Size: XS) | Similar Beanie

Crewneck Sweater | Utility Jacket (Size: XS) | Straight Leg Jeans (I cut the hem) | Panama Hat (Similar HERE)

Where We Stayed // 

The Captain Whidbey Inn has three room selections, each so cozy and decorated in the quintessential preppy PNW styles. We stayed in the Lagoon Rooms, which overlooked the small pond and gazebo on the back of the property. It’s reminiscent of a motor lodge, with two floors of motel-style rooms, each with private back and large windows.

They also offer three cabins, which sit nestled in the trees overlooking the cove. Each is decorated in its own unique style, with a living area, small kitchenette, porch, and bedroom.

Rooms in the Historic Lodge are unlike anything I’ve seen, and I was smitten!! The log cabin-style rooms are in the main building and overlook the cove. They are the epitome of cozy, and it felt like stepping back in time.

Each room has a wash basin, sink, and mirror, but the toilets and showers are across the hall and communal. Which honestly wasn’t as odd as you’d think!! I’d totally stay in them for a night or two, just for the experience!

Where We Ate //

Captain Whidbey Inn // The restaurant at the Inn uses all locally-sourced, fresh ingredients, with mussels straight out of their waters. The menu has a little something for everyone, and we ate, drank, and laughed well past closing over the most incredible dinner!

Saltwater Fish House & Oyster Bar // One of the hottest tables in town, the Fish House serves some of the best oysters and champs around. But their fish & chips is other-worldly!

Orchard Kitchen // If you love food and the whole experience of dining, then Orchard Kitchen is a must! It’s a set-menu dinner, determined by the chef and what’s fresh that day, and every bite had us swooning.

The Star Store // Darling little grocery, perfect for grabbing snacks, wine, and basic groceries.

What We Did //

Let’s just say there was a lot of lounging!! There are chairs sprinkled all over the property, with fire pits and gazebos, along with the cozy lobby with the roaring fire and stack of games. We spent the majority of our time catching up while hanging around Captain Whidbey.

We also explored the towns of Coupeville and Langley, each with a handful of darling shops, cafes, and spots for sweet treats.

There are a few notable hikes, like Ebey’s Landing and Deception Pass, that we had full intentions of tackling, but the weather and our desire to lounge won out!

Waffle Weave Pajama Set | Barefoot Dreams Crew Socks | Beanie

Getting to Whidbey Island //

The extra-special places are usually a little harder to get to, but Whidbey Island and Captain Whidbey are worth the travel! The easiest route is to fly in to Seattle (American has a non-stop from Dallas), then head about an hour north to Mukilteo.

From there, the Mukilteo Ferry runs about every 30-minutes, for the quick 20-minute ride to Whidbey. Once on the island, it’s another 45-minutes, depending on where you’re going.

Sugarplum Travel Tip: You’ll definitely want to rent a car (they’re allowed on the ferry!), for not just the journey to Whidbey, but exploring once on the island. We stopped at University Village in Seattle on our way to the ferry… it’s a hotbed of the best shops and eats!

Halo Essential Hoodie (Size: XS) | Canyon Insulated Jacket (Size: Small, but need to size down) | Similar Boyfriend Joggers | Similar Beanie | Similar Sneakers

Whidbey Island definitely stole our hearts, and I’d love to go back for more exploring, and the chance to experience different seasons! There’s all kinds of water sports for warmer months, but the cozy fires in Fall is hard to beat!

Captain Whidbey was booked our final night, so we headed in to Seattle where we stayed at State Hotel (overlooking Pike Place Market, there is no better location!), and had another incredible dinner at Restaurant Homer… both places I highly recommend if you’re visiting Seattle. We also had the treat of seeing my talented friend Cassandra’s shop, Casa di Lavalle, which is not to be missed!

I hope this Trip Report is helpful for your future trips, or at least brightened your Friday! Feel free to leave any other questions in the comments, and I’d love to hear what we need to add to our list for next time! Happy weekend, lovebugs!



Trip Report: Maui, Hawaii
Trip Report | Isla Holbox, Mexico
Trip Report | Pine Cay, Turks & Caicos
Snapshots from Mexico
A Day in Santa Cruz
Snapshots from Big Sur
Trip Report | Vieques, Puerto Rico
What to Pack for a National Parks Trip
Trip Report | Santorini, Greece
Anna Maria Island
Trip Report | Exuma, Bahamas
Swimming with Pigs in Exuma
All Cruise Posts HERE



*This post is created in collaboration with Nordstrom and ShopStyle Collective, but all product selections, styling, and PNW obseessions are my own. Thank you for supporting Hi Sugarplum sponsors!*

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