3-Day Whidbey Island Itinerary for Women Over 40

Amazing Puget Sound Views, Historic Forts, and Small Town Vibes

This 3-day Whidbey Island itinerary for women over 40 turned out to be a super fun, scenic girls’ trip for my sister, me, and our mother… and it could be for you as well.

If you’ve been craving a quiet, beautiful escape that doesn’t require a ton of planning, this Whidbey Island itinerary might be exactly what you need.

This trip was a bit of a girls’ getaway… a chance to get outside and spend some time together away from the hustle and bustle of our daily lives.

I am writing this for women over 40, because we are all over 40, and we were going for a more relaxed, quiet trip.

However, this could easily be a trip for all ages.

Our 3-Day Whidbey Island Itinerary Overview

We were looking for a relaxing getaway… where we could hang out, enjoy some scenic walks, and do a bit of sightseeing.

We needed something easy… not fancy or exhausting.

We stayed in a cozy VRBO on North Whidbey with incredible views of Puget Sound and Mount Baker.

We explored Coupeville, Ebey’s Landing, Fort Casey, Fort Ebey, and the Deception Pass area.

We packed a lot into three days, while still allowing plenty of time to play games around the table in the vacation rental.

If you’re planning a women over 40 “girls’ trip” in Washington and want something that blends scenery, history, and a relaxed pace, this is a perfect option.

Where is whidbey island WAshington

Whidbey Island is a long, narrow island in the Puget Sound of Washington State… about 30 miles North of Seattle.

Being the largest island in Washington, it feels far quieter than you’d expect.

Most of the “big town” area seems to be in a single main stretch in the Northern part of the island, Oak Harbor, where the Naval Air Station is located.

What whidbey island is like

While our trip was centered on quality time together, the backdrop of the island itself played a starring role.

Beyond the bridge and the charming ferry docks, Whidbey unfolds into a delightful blend of…

• Rolling prairies
• Coastal views
• Quiet beaches
• Forested trails
• Historic sites
• Charming waterfront towns
  • Langley
  • Coupeville
  • Freeland
• It is also home to Ebey’s Landing National Historical Reserve…the nation’s first national historical reserve.

How to get to Whidbey island

You can drive from the Seattle-Tacoma area in just a couple of hours, depending on traffic, of course.

You can also get there by taking the ferry from Mukilteo, which is always fun.

If you decide to drive there, you will be able to drive over the dramatic Deception Pass Bridge at the North end of the island.

This is what I typically do, as the Deception Pass area is one of my favorite places in Washington.

Where we stayed on Whidbey island

We wanted a vacation rental rather than a hotel room so we’d have space to sit around a table, play games, and enjoy coffee together in the mornings, so I booked our stay through Expedia.

This coastal rental home was the perfect thing.

It was in the North end of Whidbey, just a short drive from the Deception Pass Bridge.

The rental unit was in the bottom half of a lovely house, with its own entrance and a patio overlooking the rolling hills down to the water.

The views of the Puget Sound, the islands, and Mt. Baker were absolutely stunning.

The cost of this stay was about the same as local hotels… granted, this was in January, the middle of winter.

Even while being in the midst of winter, we found ourselves bathed in golden light, watching the sun dance across the surface of the Sound.

You never know how the winter will be in the Pacific Northwest.

Our 3-Day Whidbey Island itinerary

Day 1: Snow Geese, Deception Pass & Coupeville

the drive to whidbey island

I live on the very end of the Key Peninsula in Washington, so the drive time to Whidbey was almost 3 hours.

The initial drive took us over the Tacoma Narrows Bridge, and I was happy to see that the mountain was out in all her glory.

We drove through all of the typical freeway nonsense, past Seattle, Everett, and Marysville.

Marysville is when I start really enjoying the drive… the scenery shifts from city life to farmland and open spaces.

The fields are empty this time of year and are blanketed by snow geese and trumpeter swans, who migrate to the area each winter, and can be seen eating roots and grain out in the fields.

In fact, the Skagit Valley is a fascinating place to visit on its own if you are a bird watcher like me.

Quick side note, I didn’t care about watching birds until after turning 40. What is that about?

After passing the fields of birds, we turned onto Highway 20, where you can go East to the North Cascade Highway or West to Anacortes…we went left.

This takes us to Fidalgo Island, where we make the first stop on our little getaway at one of my favorite places in Washington… Rosario Beach.

first stop | Rosario beach

Rosario Beach is part of the Deception Pass State Park, and is one of my personal happy places.

Here, you can explore the tide pools at low tide, take trails that lead out along the rocky cliffs with sweeping views of the saltwater below, or walk along the beach where the gentle waves roll over the pebbly shoreline, creating a soft, rhythmic sound that is incredibly soothing.

The best thing about this place is that you can return many times and make each visit a different adventure.

The trail here connects to the Bowman Bay portion of the park, which includes…

• Small park
• Large beach
• Fishing pier
• Multiple trails

The trails there lead into the dense, coastal forest and rugged outcrops where you can gaze upon the wonder of the Deception Pass Bridge.

exploring rosario head & beach (at an easy pace)

For this trip, since our mother isn’t able to do long hikes, we simply enjoyed the beautiful scenery of Rosario Head and Beach.

I was incredibly proud of my mom for taking the trail out to the large cliff area at Rosario Head.

It is a loop trail with a slight incline to the main open area and a slightly more challenging descent back to the beach.

We helped her along the way, and she enjoyed the scenery very much. She was rewarded with a gentle walk along the soothing beach with plenty of time to sit, watch the water, and take it all in

Jets overhead from nearby naval air station

While we were there, we were fascinated watching jets from the nearby Naval Station fly overhead.

We noticed three of them, and the sound was wild and slightly intimidating.

We did hear and see them throughout the rest of the trip, but it wasn’t constant, and for us, it wasn’t annoying.

Driving across Deception pass bridge | one of the Best views in washington

After enjoying time at Rosario, we headed back to Highway 20, then south to cross the iconic Deception Pass Bridge.

Although we always mention Deception Pass Bridge, there are actually 2 bridges here.

They look similar yet are separate bridges with distinct construction styles.

The first bridge we passed was the smaller, Canoe Pass Bridge; the second was the longer, Deception Pass Bridge.

I’m not sure why Canoe Pass Bridge is often left out of the conversation, but it is there and deserves a little attention, too.

This is such an incredibly beautiful stretch of road with stunning views of the water and surrounding islands.

There is an area before the first bridge where you can pull over to view the structure, and there is a small parking lot after the second pass where you can park and walk over both and enjoy the expanse of water beneath.

Leaving the pass | next stop… coupeville

We drove on for about half an hour, passing through Oak Harbor, before arriving in the charming town of Coupeville.

This adorable town is the second-oldest town in Washington State (Steilacoom is the oldest) and sits in the heart of Ebey’s Landing National Historic Reserve, making it a must-see for history lovers like me.

Downtown Coupeville is lined with small, colorful, historic buildings near the water, many dating back to the 1800s.

There is a short, walkable, quiet main street with locally owned shops and cafes tucked into simple wood-frame buildings that feel well-used yet well-cared-for.

At the end (or beginning) of the main street is the Coupeville wharf, a historic 500-foot pier that extends out into Penn Cove.

The weathered red building at the end houses a marine education center, café, and gift shop.

There are bones of a gray whale, stellar sea lion, and Dall’s porpoise on display.

I never realized how large Stellar Sea Lions were until I saw these bones up close… they are massive.

Okay, as much as I love historic little towns, the main focus of our visit to Coupeville was that it was the main filming location for the movie Practical Magic, starring Sandra Bullock and Nicole Kidman.

There’s a bit of magic in all of us

Practical Magic is one of my favorite movies, and my sister and mother also love the movie and are just movie buffs in general, so we just had to spend some time here.

The real time to come here for Practical Magic vibes is the fall and Halloween, of course, where they do Practically Magic Halloweekend, have movie screenings, and of course, Midnight Margaritas… well, not quite midnight.

We may come back in October, but we were there in January and enjoyed our quiet, calm self-guided tour of the town.

This included purchasing a small souvenir from Back to the Island Gift Shop… matching Practical Magic shot glasses.

We finished our stroll and tour with some appetizers and beers at Toby’s Tavern.

Toby’s has the kind of relaxed, slightly worn-in feel you’d expect from a restaurant that has been serving locals and visitors for years.

We sat down at a booth overlooking the water and enjoyed local beer, a vegetable basket, clam chowder, and an oyster shooter.

Well, only I got an oyster shooter, as I am crazy about oysters; my mom and sister were not nearly as enthusiastic.

It was all quite good, a nice little spot to relax and discuss the movie and the location.

The sun was setting, and it was time to head to the VRBO, where we spent the rest of the evening playing games and enjoying snacks and drinks we picked up at a grocery store in Oak Harbor. It really was a lovely time.

Day 2 of our 3-day Whidbey Island getaway

It felt like Christmas morning when I opened my eyes and saw faint light coming through the blinds.

I jumped up and opened them, letting in the glory of the sunrise coming up over the Puget Sound.

I made a cup of coffee
Put on a hoodie
And stepped out into the crisp morning air.

It was so perfect.
I couldn’t help but smile.
I stood there, breathing it all in, feeling my soul fill with gratitude.

These are the moments I live for.

After some time enjoying coffee, a light breakfast, and some morning conversation, we headed out for a sunny day of exploration.

Jacob and Sarah Ebey’s Historic Homestead

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Instead of going into downtown Coupeville, we explored more of the Ebey’s Landing National Historical Reserve.

Our first stop was a walk along the loop trail past Jacob and Sarah Ebey’s historic homestead and out toward the prairie overlook.

The views over the bluff were absolutely stunning, and standing there, looking out over the wide-open land, made it easy to imagine what this place must have been like more than a hundred years ago.

I’ve always been fascinated by the lives of our pioneers, and Ebey’s Landing really brought that history to life for me in the best way… quiet, scenic, and full of story.

Historic forts

Fort ebey state park

First up was Fort Ebey State Park, one of the smallest forts in Washington, which sits above the water, with wide-open grassy areas and sweeping views of Puget Sound.

It was one of those perfectly clear, sunny days when everything feels brighter than expected, and the water below caught the sunlight, making it sparkle.

These are the type of days that bring out the full beauty of the Pacific Northwest.

Fort casey state park

From there, we headed to Fort Casey State Park, which has a much more expansive feel.

The fort sits right along the water, and the contrast between the solid concrete batteries and the bright blue sky made the whole place feel especially striking.

We spent time walking through the dark corridors and open gun emplacements (phone flashlights on), enjoying how easy it was to explore at our own pace.

Fort Casey feels peaceful now, but there’s still a stark sign of history as you move through the old concrete structures tucked into the landscape.

We wandered through the entire area, pausing to look at scraps of metal, railings, and openings in the walls, trying to guess what each one might have been used for.

It was one of those places where history doesn’t feel formal or museum-like; it invites curiosity and a little imagination.

That said, they have also been restoring and maintaining the central concrete batteries, with signs explaining how the structures were used and what they once looked like.

All this after we had already been concocting our own theories.

Admiralty head lighthouse

Just beyond the fort, Admiralty Head Lighthouse stands overlooking the water, adding another layer of history to the stop.

With the sunshine, open views, and deer grazing on the lawn, it was easy to linger longer than planned, wandering, talking, and taking photos.

It quickly became one of our favorite parts of the entire Whidbey Island trip, even for my mother, who did much more than she thought she could.

dinner in oak harbor

Needless to say, Mom was exhausted and hungry, so the last stop before retiring to the rental for more games was dinner in Oak Harbor.

Mom chose Mexican. Honestly, you can never go wrong with Mexican food, and Esteban’s Mexican Eatery was just the thing.

The space was colorful and spacious, the staff was super friendly, and the food was on point. The variety of Margarita flavors didn’t hurt either.

Day 3 of our 3-day Whidbey Island getaway

Time to head home

The day started with another gorgeous sunrise.

My sister joined me outside for coffee and morning conversation. (It was too cold for Mom.)

We soaked up as much of the view as we could while listening to nearby chickens crowing to signal the start of the day.

I didn’t want to leave that spot, but I was grateful to enjoy the calm, quiet moment with my sister.

After everything was packed and the place was tidied, we said goodbye to our rental and began our journey home.

A couple quick stops on the way

A must-mention near the VRBO is the Dugualla Bay Preserve, a tranquil 200-acre preserve that includes a saltwater estuary, tidelands, and freshwater wetlands.

It is a picturesque setting for a morning walk and bird watching.

My sister and I enjoyed the crisp morning air and panoramic views as we watched and listened to a wide variety of birds.

I used my trusty bird-identifying app, Merlin Bird ID, to identify a few new ones.

It is so handy to identify birds by their sounds.

It is a great app for bird lovers, and this is a great place to use it.

A Walk Across The Deception Pass Bridge

So… we had to stop at Deception Pass one more time and walk across the bridge to fully take in the views.

It was a bit cold and windy, but the view is truly amazing!

The color contrast between blue water and green forest was striking, even though it was not as sunny as the day before.

A Drive Through La Connor

Rather than going straight over to I-5 from SR 20, we took a detour through the town and the surrounding farmland of La Connor.

We did not stop, simply drove through, but it is worthy of an hour or so of window shopping along the waterfront and staying for a bit to eat.

There are many cute little shops and cafes downtown that make the stay well worth it.

Home Sweet Home

We survived the chaotic traffic going through Everett, Seattle, and Tacoma, making our way safely back to my house, where we finished off the day with a few more games before parting ways.

It was a lovely little getaway.

I thoroughly enjoyed the quality time with family and the chance to breathe in the fresh air and take in a bit of nature and history.

This 3-day Whidbey Island getaway was exactly what we needed: beautiful scenery, meaningful history, good food, and quality time together.

It proved that you don’t need a far-off destination or an elaborate plan to create something memorable.

Sometimes a simple island drive, a historic trail, and a waterfront sunrise are more than enough.