Whidbey Island visitors know that they can come back time and time again and always see and do something new, and depending on the time of year you visit, this is especially true! Each season brings something special to discover, and whether you’re visiting in the heart of winter or in the middle of a hot summer, our island is the perfect spot for a weekend getaway.

In this post, we’re sharing our recommendations for where to stay, where to eat, and what to do depending on the season!

How to Spend a Winter Weekend on Whidbey Island

• Stay: Snuggle up in a picturesque cabin at Captain Whidbey. Nestled on the Penn Cove waterfront, this historic inn offers cute cabins, Scandanavian-inspired rooms, a lodge, a restaurant, and an idyllic setting perfect for relaxation.

• Eat: Oystercatcher is always cozy, and this tiny restaurant is easier to get a reservation at in the winter. Request a window table and look out over Coupeville and Penn Cove! We also recommend heading to Saltwater Fish House and Oyster Bar—its dark, cozy atmosphere is perfect for the winter.

• To Do: Bundle up and enjoy shopping in our many cute downtown areas. We especially recommend strolling through Downtown Oak Harbor, Downtown Coupeville, and Downtown Langley.

How to Spend a Spring Weekend on Whidbey Island

• Stay: The Inn at Langley offers a totally luxe waterfront experience! The guest rooms, suites, and cottages offer waterfront views, and you can indulge in spa packages and fine dining without leaving the indulgent comfort of the inn. Plus, the immaculately maintained grounds are lovely and filled with vibrant blossoms to enjoy.

• Eat: Visit Flower House Cafe at Bayview Farm & Garden for breakfast or lunch, and check out the iconic Laburnum Arbor when it’s in bloom while you are there. For dinner, head to Ultra House, a hole-in-the-wall type of place and an absolute gem. If you love ramen, it’s okay to set your expectations extremely high when you visit Ultra House—they aim to impress the palate.

• To Do: Spend some time exploring Whidbey Island’s stunning gardens. Meerkerk Gardens in Greenbank features scenic trails surrounded by a huge variety of plants and flowers. Meerkerk is especially known for their rhododendrons, which bloom from early to late spring.

How to Spend a Summer Weekend on Whidbey Island

• Stay: Comforts of Whidbey is a summertime oasis, and views of vineyards, bucolic pastures, and the shimmering Puget Sound are aplenty. This bed and breakfast is also conveniently a winery, so you can enjoy their wines in the tasting room before you head upstairs to your lodgings.

• Eat: Callen’s Restaurant is right on the water in Coupeville, and not only do they have excellent food, they are close to the ferry to Port Townsend in case you are island hopping. In Langley, the Prima Bistro upstairs deck offers a gorgeous space to enjoy French-inspired Northwest fare, and you can finish off the evening at Captain Whidbey Inn’s outdoor deck. Captain Whidbey offers phenomenal views + delicious cocktails.

• To Do: One thing on Whidbey Island that’s only available during warmer months is kayaking tours with Whidbey Island Kayaking. You can choose from several different types of tours—head out on a half-day adventure paddling to see wildlife and classic PNW scenes, go on a guided bird-watching kayak tour, or even head out at night for a memorable bioluminescence kayaking tour.

How to Spend an Autumn Weekend on Whidbey Island

• Stay: Auld Holland Inn offers a totally unique experience in Oak Harbor. This old-world gem features Dutch architecture, beautiful gardens, charming accommodations, and an onsite restaurant.

• Eat: For a pricey but memorable experience, Orchard Kitchen is known for their rustic, “farm-to-table” experience. During non-COVID times you can enjoy family-style dinners at community tables.

• To Do: Whidbey Island is known for its many small farms, and autumn is the perfect time of year to enjoy our bountiful harvests. Sherman’s Pioneer Farm is a popular destination for locals this time of year, and you can take a tractor tour through the pumpkin patch, stock up on fresh local produce, and meet the resident cows, all in a festive fall atmosphere.

For more Whidbey Island recommendations, keep exploring our blog!