Outlook Inn, Eastsound, WA on Orcas Island

Washington State’s Best Kept Treasure: The San Juan Islands

(Last Updated On: April 24, 2020)

Washington state is located in the pacific northwestern corner of the United States and is home to the stunning islands that collectively make up the San Juan Islands.

Before I moved out to Oregon six years ago from Vermont I had never heard of the “San Juan’s”.

In fact, if you had uttered the words to me back then I probably would have assumed you were mispronouncing the Puerto Rican capital of San Juan, and trying to make it plural by adding an “s”

So over the years of living in Portland I would often here people at work mention just how magical and stunningly beautiful the San Juan islands were. It’s not that I didn’t believe them, I was sure that the islands were beautiful, its just that the trek to get to them from Portland was a nearly six hour drive, including a ferry ride.

It seemed too far away for a quick weekend jaunt.

But, when our dear friends told us they were getting married there, it provided the perfect opportunity to visit. And quite frankly a nice excuse to drive ourselves north to experience not only their happy wedding ceremony but also the pacific northwest landscape of the San Juans.

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Before I jump into telling you all about Washington’s San Juan Islands I thought I would share a little about me incase you haven’t stopped by my blog before.

Hi! I’m Jane and I started Plain Jane Lifestyle as a fun creative outlet to write about food, travel and blogging!

If you are thinking about starting a travel blog, or any type of blog for that matter, here are a few of my most popular past posts that will help you get started: What Every Blogger Needs To Know About Blogging Legally and Start A Blog In Less Than 10 Minutes With Siteground (affiliate).

Okay back to the San Juan islands of Washington…

Friday, October 12th

My husband and I got up early to begin our road trip from Portland, Oregon. Our SUV was packed and we began to dive north on interstate I-5 toward the San Juan islands!

I should mention that after completing this long three day weekend that it is very, very doable. In fact I can’t believe it took me six years to finally make the trek!  But since doing so, I would happily go back.

One very important thing to note is that you must take a ferry to get to the islands.

We were specifically headed to Orcas island, the biggest of the San Juan Islands. The best thing to do is to make a reservation at least a month ahead of time. You don’t need to pay at that time, just simply reserve, and if you do not show up for your reservation than a $10 fee will be charged.

The ferries that operate out of the Anacortes, WA terminal are very large, but also extremely popular.

Trust me when I say that you don’t want to just hope that you can get a reservation that same day. It’s better to be safe than sorry.

You don’t want the ferry to be full, and then find yourself waiting for hours to get on a ferry, or worse of all, not make it at all. Here is a link for the Washington state ferry guidelines where you can make reservations.

The ferry also asks that you arrive at least 45 minutes prior to your ferry leaving the dock.

I was happy to arrive early and spend about 30 minutes walking around the nearby waterfront to give my legs a much needed stretch.

Anacortes, WA ferry terminal
Anacortes, WA ferry terminal

I found the nearly hour long ferry ride from Anacortes to Orcas Island so fun!  The Washington state ferries that operate out of Anacortes are very large!

It reminds me of the ferries that Dr. Meredith Grey on Grey’s Anatomy would take to work! My husband and I enjoyed spotting a sea lion, taking pictures of the stunning snowcapped mountains and looking at the cute homes that occupied the neighboring islands we were passing by.

Riding the ferry from Anacortes, WA to Orcas Island, WA
Riding the ferry from Anacortes, WA to Orcas Island, WA

Once we docked on Orcas Island the drive to our accommodations was exactly a 20 minutes. The landscape was filled with lavender and sheep farms, and also lots of wild deer. Be sure to drive careful!

We saw more deer on this weekend then we previously had in our whole life! We were staying in downtown Eastsound, WA at the Outlook Inn.

Outlook Inn, Eastsound, WA on Orcas Island
Outlook Inn, Eastsound, WA on Orcas Island

I highly recommend staying at the Outlook Inn if you venture out for a vacation on Orcas Island.

It is in a central location in the most bustling part of the island. You can easily walk to nearby coffee shops and restaurants. It aso happens to lookout over the waterfront.

Suite inside the Outlook Inn
Suite inside the Outlook Inn

To our surprise, when we checked into our room we had received a complimentary upgrade from the owner Sarah Farish! So special shout out to Sarah for our amazingly beautiful guest suite!

Not only did we have a spectacular waterfront view, but we had a nice sitting porch, king size bed, Jacuzzi tub and separate standing shower. We had no complaints!

Acapulco Restaurant, Eastsound, WA
Acapulco Restaurant, Eastsound, WA

For dinner that evening we walked a few blocks for some tacos, chips and guacamole from Acapulco restaurant.

After dinner we got ourselves to a pre-wedding festivity with the happy couple and all of their friends and family at Island Hoppin’ Brewery!

Driving from the Outlook Inn to Island Hoppin’ Brewery only took 5 minutes. I highly recommend stopping here if you wind up vacationing on Orcas Island.

This is a small but intimate brewery. It has a lounge area, a heated patio and a fun ping pong table to use.

I got a glass of the blond ale “Feel The Bern” brew while my husband tried the Elwha Rock IPA.

Island Hoppin Brewery, Eastsound, WA Orcas Island
Island Hoppin Brewery, Eastsound, WA Orcas Island

Saturday, October 13th

Saturday we awoke to a welcoming sunrise over the sound. We got dressed and headed to the Outlook Inn’s restaurant the New Leaf Café for breakfast.

The food was excellent from start to finish. We were seated in a quiet corner of the café, with a window view to people watch and take in the water view.

Coffees came out quick and we both ordered our delectable dishes. I got the crab cake Benedict and loved it. I just wish I had enough room to finish the large portion!

New Leaf Cafe, Eastsound, WA Orcas Island
New Leaf Cafe, Eastsound, WA Orcas Island

Pre-wedding festivities continued with a charted whale watch sightseeing tour and lunch.  This was such a memorable and fun part of the weekend! We were lucky to have spotted both Orca and Grey whales.

Nate and I on the whale watching boat.

Whale watching excursions are popular activities in the San Juan’s, so please check it out if you are staying here for vacation, as it is well worth it!

Me in front of a Orca whale statue the morning before the whale watch.

Next, it was time to get ready for the main event,…to see our happy friends get married! The ceremony was absolutely perfect and took place at Doe Bay Resort & Retreat. Once the wedding ceremony was complete we moved from outdoors to indoors for a delicious reception meal from the talented chefs at Doe Bay Café.

View from Doe Bay at sunset
View from Doe Bay at sunset

This restaurant sources local ingredients to create the most stunning dishes and craft cocktails! We ate family style with the other guests and consumed flank steak, scallops, crisp salad, delectably seasoned potatoes and carrot cake, chocolate caramel and macaroons for desert!

A trio of deserts from Doe Bay Cafe
A trio of deserts from Doe Bay Cafe

Sunday, October 14th

The last day of a fun vacation is always a sad one…packing up and getting back to reality, however, we embraced the short morning we had before checking out by taking a short morning walk to the popular Brown Bear Bakery.Pastries, breads, muffins and scones are made in house every morning.

In fact the moment you walk in the bakery you are privileged to a direct sightline of the bakers in the kitchen preparing various breads and treats. The sweet smell of this bakery is heavenly. I opted for the chocolate muffin which was about the size of my head and told myself I was only going to eat half…and before I knew it the entire muffin was gone! The coffee here is also delicious!

Next, we left our room keys off with the Outlook Inn’s front desk and loaded our suit cases into the car and drove to the ferry terminal to begin our trip back to Portland.

The ferry terminal on Orcas Island has a really nice convenient store that is way more than your typical convenient store, in fact it seems more like a boutique organic grocery store. We strolled through because I needed another morning coffee to be properly caffeinated for the trek home.

Coffee in hand at the Orcas Island ferry terminal
Coffee in hand at the Orcas Island ferry terminal

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