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!*

Leave a Comment


  1. Lilly wrote:

    Isn’t 50 the new 39?.? 🙄. I feel great been *39*…..happiest and healthiest of birthdays and beyond.

    PS: I am glad lost passports didn’t stop you from traveling elsewhere…you are unstoppable 🥰

    Posted 11.11.22 Reply
    • Cassie wrote:

      I was determined to be somewhere that *wasn’t* my house on my actual birthday, ha!!! xo,C

      Posted 11.11.22 Reply
  2. Kristin wrote:

    I am 56, and have been loving my 50s. My husband retired early this past summer, and it’s fun having him around (usually!!). He can go for his runs when I am available to bike along, and that’s been great. He’s got me going on longer bike rides with him. Our kids have finished their grad degrees and have jobs and INSURANCE. I am getting better at saying no to things I really don’t want to do, and am enjoying focusing on things I am passionate about, whether that is hobbies, social justice or political issues, etc. Overall, it’s GREAT! I think you’ll LOVE your 50s.

    Posted 11.11.22 Reply
    • Cassie wrote:

      The best part of all of that sounds like the insurance!! Hah! xo, c

      Posted 11.11.22 Reply
  3. Patricia wrote:

    Loved reading about your trip to Whidbey Island, brought back memories of mine. I did do the Ebey hike (weather cooperated that day) and spotted wild turkeys in the fields. And seals offshore along the beach.
    Sounds like you had a great time too with friends.
    My 50th birthday trip was a week at Rancho La Puerta with Pilates, Yoga and morning hikes. Alas, requires a passport.

    Posted 11.11.22 Reply
    • Cassie wrote:

      Oohh your Whidbey trip sounds dreamy! And so does your 50th birthday!!! xoxo, C

      Posted 11.11.22 Reply
  4. Maryanne wrote:

    Happy Birthday, Cassie! I turned 51 last week and I can confirm that age is just another number. (Menopause, however, is a tough one. Eek!) I hope that you all have a great time in Cali!

    Posted 11.11.22 Reply
    • Cassie wrote:

      Thank you so much, Maryanne! I hope you had a wonderful birthday!! xxoo, C

      Posted 11.11.22 Reply
  5. Sandy wrote:

    Gurrrrl! You still look college-y age! Just be in denial about the age thing. That’s what I do.
    This trip seems so gorgeous and worth it. That whole area, and a car ferry=my fave!
    Ohhhh, yes on Big Sur! Details please, lots of details!
    Did u look absolutely everywhere for those passports?? I know you did.
    Any chance they were stolen? (hot commodity). : (
    This is a beautiful post-thank you, SPs.

    Posted 11.11.22 Reply
    • Cassie wrote:

      We have looked high and low in every nook and cranny of our house, multiple times! It’s like they vanished into thin air!!! xoxo, C

      Posted 11.11.22 Reply
  6. Kim G wrote:

    Happy Birthday! You will breeze thru your 50’s! You are health conscious and in shape! I’m almost 58 and sadly not in shape! My brain says I’m still in my 20/30’s, but my body says otherwise. I do try to exercise, but I love tacos (and any tex-mex) way too much! Have a great trip. Hope y’all find your passports. ~Kim in Austin, Tx

    Posted 11.11.22 Reply
    • Cassie wrote:

      Tex Mex is too good not to eat!!!! And yes, I hope we find our passports too! #ugh x0x0, C

      Posted 11.11.22 Reply
      • Rhonda wrote:

        Happy birthday! So sorry you couldn’t find your passports but I’m a firm believer that things happen for a reason. Wishing you a wonderful time in Big Sur! And 50 is just a number. I’m 51, but still feel 25, other than the hot flashes 🤣

        Posted 11.11.22 Reply
        • Cassie wrote:

          Yes maybe there was a reason we needed to head to Big Sur instead! Positive thoughts! xo,C

          Posted 11.14.22 Reply
  7. Mary Allison wrote:

    I can only imagine the chaos at your house on that day. Good save by Mr SP. We are on our way to Mexico next week. Although we have a home in Tulum, we will be staying in Cancun (which we just land and get the heck out of there) at The Vine. But, we will be taking a few explore days and one of them is Holbox…I read your entire post on that, so we are prepared. Just one question, how do you keep your hair from frizzing out in the humid weather of Seattle and Mexico. Any product update on that would be appreciated…Have a great weekend in Big Sur, Cassie!

    Posted 11.11.22 Reply
    • Cassie wrote:

      What a fun trip, Mary!!! My hair tip on most every trip is a hat! You’ll notice I”m wearing some sort of headgear in pretty much every pic, ha!

      Posted 11.15.22 Reply
  8. lynn wrote:

    I love to see you where scarves because I have so many and I always feel like I look like my grandma in them….LOL. Thanks for the idea!

    Posted 11.11.22 Reply
    • Cassie wrote:

      Ha! Scarves are cute! And sometimes they are a necessity! xo, C

      Posted 11.11.22 Reply
  9. Rhonda wrote:

    Happy birthday! 50 is an awesome age and you look amazing. Glad you had a relaxing and peaceful time in the Pacific Northwest. I live just 30 min south of Seattle. You dressed perfectly for this area which is a lot different then Texas. My son moved to Dallas 4 years ago so we are always comparing the weather. Also he misses our mountains. But he loves the hot weather in Texas.
    Also another thought on the missing passports. Could it be in a jacket pocket or sweater pocket that has not been recently worn? My friend lost my credit card we thought and then 3 months later she found it in a sweater pocket that she rarely wears. She had my card to return something.

    Posted 11.12.22 Reply
    • Cassie wrote:

      We have truly looked everywhere!! And yes… not sure if trading Dallas heat for Seattle mountains is a fair trade, ha! xo, C

      Posted 11.14.22 Reply
  10. Lisa wrote:

    Happy 50th to you, welcome to the club! Sorry about the passports, but so glad you got back to CA and Big Sur (are you at the Post Ranch Inn? Such a beautiful spot). My 50th was during the pandemic so we spent a weekend in Las Vegas – no shows, but it was nice to eat out and shop without the usual crowds. I’m filing away this trip report; this spot looks amazing and reminds me of visiting Vashon Island years ago. xo

    Posted 11.12.22 Reply
    • Cassie wrote:

      We have been at Alila Ventana Big Sur! xoxo, C

      Posted 11.14.22 Reply
  11. Colleen wrote:

    Happy Birthday Cassie. I just turned 64 and I absolutely hated it when I arrived at 50 and still hate getting older. My mind still feels like I’m in my 20’s and I feel good and I’m healthy, but the speed at which a year flies by is not fun at all! Life starts getting shorter very quickly and that saddens me. I did like it tho, when the kids left the nest and we could get back to being just “him and I”…Menopause sucked and everything that goes along with that. (Mother Nature played a dirty trick on women with that part of life) but, we haven’t slowed down and are currently enjoying 4 months of travelling around south east Asia. Is there some way you can cancel a passport? That sounds a bit scary if they dropped out somewhere along the way and someone is using them!

    Posted 12.4.22 Reply
    • Cassie wrote:

      Wow! The traveling for four months around Southeast Asia part of growing old makes up for all the other yucky stuff!!! xo, C

      Posted 12.5.22 Reply
  12. Sandy M-L wrote:

    Happy 50th!! I know you made the best of it, and that’s just one more sign that you have “matured”. 🙂 Being flexible is everything. We had the same thing happen a few years ago, and lo and behold, at a friend’s suggestion, I finally found my passport in my fireproof safe where it should always be, but I’d forgotten I’d tucked it safely away there.

    With every stage in life, there are pros and cons. Pros – you’ve mentioned some great ones! Cons – you have more time in the rearview than ahead, BUT still, that gives you the perspective and motivation to be your very best and live your very best life NOW!! Besides, you look fantastic and are healthy. Keep moving, keep planning, and keep bending when you need to. Enjoy every minute, every taco, and every hug.

    Love your trip report. You always give us fresh ideas. Thank you. Great hat and utility jacket too.

    I hit cinco cinco on Thanksgiving day, and my best advice other than the above is to take care of your body, soul, and spirit now so you don’t look back later and wish you had. I think you already do this well so keep it up!

    Posted 12.5.22 Reply
    • Cassie wrote:

      Thank you so much, Sandy! <3 <3

      Posted 12.5.22 Reply