Weekend Trip to San Juan Island: Part I

Thanks to Lakedale Resort and Visit San Juans for hosting our trip.

Although you can make your way around San Juan Island in probably two hours or less, just because it’s small doesn’t mean it isn’t one of the more spectacular destinations in the Pacific Northwest. Located inside the rain shadow between the Olympic and Cascade mountain ranges, it’s about 80% sunnier than most of the Seattle area making it a great way to get away in the spring and summer. It pours on the charm in its small port towns of Friday Harbor and Roche Harbor, but the adventure really begins before you even arrive.

Sailing on Washington State Ferries

If you’re not flying in, you’ll most likely be taking the ferry from Anacortes, which follows a stunning route through the island passages. To give yourself a smooth start to your weekend, make sure you book your ferry reservation well in advance—but do keep in mind that open reservations are released in waves, so keep tabs on the Washington State Ferries website.

Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane

Best Restaurant on San Juan Island

Floating in just in time for happy hour, Michele and I headed to Downriggers for drinks and appetizers on the pier. It became our favorite restaurant on the island—we went a total of three times in three days. Sorry, not sorry! Their spicy margaritas, crab tots, and tacos were absolutely worth it. We had a lot of great food during our weekend, but you can’t beat the views and the vibes at Downriggers.

Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane

FROM Friday Harbor to Roche Harbor

My dad happened to be working on nearby Henry Island the same night we arrived. Driving from Friday Harbor to Roche Harbor to meet him, we got to enjoy a full overview of the two main towns on our very first night! Having been a few times in my life, I was pretty familiar with Friday Harbor, but Roche Harbor was new to me, and I was blown away by its charm.

As we learned later at the San Juan Museum of History, Roche Harbor was dominated by lumber and lime mining until it was privately purchased and turned into tourism paradise. The marinas are breathtaking, and all of the businesses and buildings dotting the shoreline are a beautiful weathered white. Getting to meet it for the first time at twilight just as the twinkle lights were switching on was absolutely magical.

Stopping at the go-to Roche Harbor hangout, Madrona, we enjoyed a few more snacks and drinks while catching up with my dad, who then took us on a quick harbor cruise just before the sun went down.

Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane

RELAX AND EXPLORE AT Lakedale RESORT

After our busy afternoon and evening, we finally checked into our home for the next two nights—Lakedale Resort. I detailed our yurt glamping stay in this post, but there is so much more to the resort I want to share! They have such beautiful grounds and so many options of places to stay. One of my favorites were their glamping tents, located right on one of their three lakes.

They have activities for every age level all throughout the summer and plenty of places to tuck yourself away with a good book or just to sit with the sun. Roast marshmallows, make tie-dye t-shirts, play giant chess…Lakedale really is a summer paradise!

Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane
Weekend Trip to San Juan Island | truelane

If you’re more interested in staying in town, there are a ton of adorable hotels and B&Bs both in Roche and Friday Harbors. Visit San Juans has made it super easy to find available accommodations on their website no matter what you’re looking for.

Now that we’ve got all the basics down—where to stay and where to eat—I can’t wait to share Part II of our trip next week! I couldn’t fit the bazillion photos we took in one blog post, so next up I’ll be highlighting a few of my favorite things to do on the island and more. Stay tuned!




Huma Blanco Shoes

Huma Blanco Shoes | truelane
Huma Blanco Shoes | truelane
Huma Blanco Shoes | truelane
Huma Blanco Shoes | truelane
Huma Blanco Shoes | truelane
Huma Blanco Shoes | truelane
Huma Blanco Shoes | truelane
Huma Blanco Shoes | truelane

Photography by Michele Equitz


Tula Boutique tee (
similar) | Levi’s denim shorts (sized up two sizes) | Sandals c/o Huma Blanco | Soludos handbag (similar)


Peru has been quietly working its way up my travel wishlist to become one of the places I’m most excited to visit one day. Huma Blanco shoes are designed by Adriana Crocco and created in her home country of Peru with a goal of creating more long-term jobs. I’m all about supporting businesses that are about much more than profit and loss, and these perfect ankle-tie sandals are a chic reminder of the companies that are out there trying to make the world a better place.

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Louis Vuitton Favorite MM

This post is sponsored by Bag Borrow Or Steal.

This little Louis Vuitton Favorite MM shoulder bag in Damier Ebene is one of my favorite bags I’ve ever rented from Bag Borrow Or Steal. We went to New York together. We enjoyed coffee and mini tarts along the river. I brought him to every concert I went to in June. The size was perfect for my wallet, phone, a few make-up products and house keys. In addition to having a short shoulder strap and a long crossbody strap, I figured out a way to create an in-between length for the crossbody strap by hooking both ends to the same corner of the bag and hiding the extra length underneath the flap opening.

Below are a few ways I styled the Louis Vuitton Favorite MM pouch from Bag Borrow or Steal. Start browsing for your next (or first) bag rental here!

Bag of the Month: Louis Vuitton Favorite MM | truelane

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Bag of the Month: Louis Vuitton Favorite MM | truelane

Shop the Look:


Bag of the Month: Louis Vuitton Favorite MM | truelane

Shop the Look:


Bag of the Month: Louis Vuitton Favorite MM | truelane

Shop the Look:


Borrowing a designer handbag from Bag Borrow or Steal every month has become one of life’s little pleasures I look forward to most. They have been one of my brand partners since 2015 and their selection, service, and convenience is why I keep coming back to them year after year! If you have any questions about the rental process, feel free to leave a comment below or visit their social media.