Ride
The primary way out to the Island is via the WSDOT ferry from Anacortes, WA. If you can find someone who is willing to take you out on a private plane, boat, or water plane, by all means, take them up on their offer. But if you are like the rest of us and don't happen to know someone with one of those fancy gadgets, take the ferry, and make a reservation before you go.
Pro Tip: Take the early ferry, the 8 or 9am, and bring your breakfast on board. There are plenty of cute coffee shops in Anacortes; buy your coffee and pastry, climb up on the top deck, and let the wind whistle through your hair as you enjoy your treats.
Stay
There are quite a few nice places to stay on the island. Airbnb has some good options if you are planning more of a long term stay, but if you are just going for a visit, nothing beats the Hotel de Haro in Roche Harbor.
The ferry arrives in Friday Harbor, about a fifteen minute drive across the island from Roche Harbor. This sleepy town is worth the drive: with a cafe and diner, two additional dinner eateries, boutiques, a general store, a swimming pool, tennis courts and many other exciting attractions, Roche is the perfect "homey" counter-part to Friday Harbor.
Pro Tip: The hotel is gorgeous and perfectly placed with all necessities within arms reach. Do yourself a favor and ask for a room with an ocean view, seeing the sunset from your balcony is worth the upgrade.
Eat
I LOVE food from around the world, seriously, I dream about it. But there is nothing like fish n chips, clam chowder, tacos, and margaritas to remind me that it is (finally!) summer on the west coast.
If you decide to stay in Roche Harbor, there are some places you must try out if you're trying to tantalize your taste buds.
Lime Kiln Cafe: This place is great for an affordable breakfast and they make the best f-ing donuts, fresh, everyday. Vanilla with sprinkles is a favorite.
The Madrona Bar and Grill: Located on the deck overlooking the harbor, the grill offers great surf and turf options, tons of veggie choices, and drinks that will make your head spin (in a good way!). A sweet tradition that can be viewed from the deck is Colors, the taking down of flags as the end of the day. Announcements with birthdays and graduations are made over the loud speaker during Colors, so be sure to enter your announcement prior to dinner if you want to embarrass your loved one. :)
The Salty Fox: A simple and delicious cafe; the perfect place to get your morning coffee as you wait in line for the ferry.
Brickworks Farmer's Market: This market is adorable and impressive, with a lovely array of both local arts and crafts as well as fresh veggies, eggs, meat, and baked goods. The fresh summer pizzas are my favorite!
San Juan Island Brewing Company: Despite its new-ness to the island, SJIBC has already become a local favorite, especially on those cloudy island days. They offer a great flight for $13, and great looking food too!
Pro Tip: Order the $13 flight (the brewery's five classic beers), but order a taster of their current cider as well. When I went it was blood orange and SO delicious!
Jacket, head scarf, and t-shirt are all from Madewell!
My sister and I grew up spending our summers on the island, picking blackberries, eating ice-cream, visiting the lavender fileds, and taking long walks through the woods. There is nothing quite like a little cottage in the trees, over-flowing with cousins and laughter, that makes a childhood extra sweet. Visiting the island always reminds me to take time to play in the sun, swim in the sea, and seek out the very juiciest summer fruit.
*Thanks to Bobby Stewart for helping me out with these photos.