The sun is shining bright on a warm, fall-weekend road trip from Seattle to Anacortes, Washington. We have a small caravan of cars filled with friends and are giddy as we trade our parental responsibilities for a night and two days of fun and relaxation in the peaceful oasis of the San Juan Islands. We are celebrating a special birthday and a wedding anniversary. Tunes blast from the radio, and the sunroof is open as we savor our sudden freedom on a Saturday that is typically filled with sporting events, kids’ birthday parties, household chores, and bedtime routines.  

The drive to Anacortes is less than two hours from Seattle (depending on traffic). Anacortes is the launching point for our adults-only, fall sailing adventure in the San Juan Islands. Our friends rented a private charter and our captain will be navigating us through the shimmering Pacific Northwest waters to dock the night in Friday Harbor before island-hopping from San Juan Island to Lopez Island and Orcas Island, and then back to Anacortes. Someone pinch me. 

Once aboard, our captain from Crown Yacht Charters gives us the rundown of the boat, its rules, and our adventure ahead (we promise to behave ourselves). We push off from the dock and instantly the blue water and breeze off the bow blow away any stress from the morning logistics of farming out the kids to the grandparents.

Viewfinder Tip: Consider splitting the cost of a rental charter boat with friends for a slow sail through the San Juan Islands.

Fall is a great time to visit the San Juan Islands. We’ve taken the ferry numerous times in fall, but it is a whole new experience sailing on a private charter among these majestic cliffs and homes adorning the island beaches. Turns out, mid-September is a great time to sail, as the weather is still nice and the rates and crowds are thinning out to reasonable levels.

According to Crown Yacht Charters, rates on boat rentals are lower in midseason fall, which typically runs September 10–30. So if you are considering a slow sail through the San Juan Islands, or you want to spend an autumn weekend island-hopping by ferry, here are a few of our favorite places to explore, eat, and play off the dock.

Friday Harbor, San Juan Island 

We arrived late in the afternoon, docked in the Friday Harbor Marina, and spent most of our remaining daylight on the island exploring the immediate downtown area. Some of us went paddleboarding around the marina (carefully avoiding the incoming wake of the ferry traffic), while another group of us shopped at some of the local boutiques before returning back to the boat to get ready for dinner.

Our dinner reservation was at The Place Restaurant & Bar, just a short walk from the marina where our boat was docked. The Place is the place for a delicious meal with spectacular views and small-island ambiance. The menu features a variety of savory dishes from steak and lamb to fresh seafood, and—wait for it—they bake their own pies. Much to our dismay, they didn’t have enough pie left to serve our big brood, but a few of us got a quick nibble of their sweet treats. For the record, you must try the Pacific Rim Bouillabaisse, but just make sure to order more bread to soak up the delicious sauce.

If you are more in the mood for some casual pub food on Friday Harbor, consider grabbing a burger and a beer and hanging out with the locals in the laid-back atmosphere of Herb’s Tavern. 

Staying on the island? Check out Friday Harbor House for luxury accommodations that are walkable to the ferry terminal and marina.

Orcas Island 


After spending the evening in Friday Harbor, we had time for one quick stop for lunch before heading back home.

We meandered through the islands with our sights set on Orcas Island. As our boat approached the Rosario Marina, the majestic Rosario Resort & Spa—a historic Orcas Island luxury resort known for playing host to numerous influential leaders and countless weddings—was commanding our view from high on the hill overlooking the water. We docked and made our way to the resort’s restaurant, The Mansion, for a late brunch, where we enjoyed fresh fish and chips and the most delicious BLTA I’ve ever tasted.

If a slow sail through the Puget Sound by private boat or an hour ferry ride from Anacortes to the San Juan Islands is in your future, the fall season can be an incredible time to visit. The crowds and ferry traffic will be lighter, and you just might snag a sunny blue sky to contrast the San Juan Islands’ fall colors.

What is your favorite place to explore in the San Juan Islands?