San Juan Island Sunset

I don’t know about you, but I love creative and adventurous dates or getaways! With Valentine’s Day right around the corner now is the time to start planning your romantic getaway to San Juan Island.  Within the last couple of years Friday Harbor and San Juan Island have become better known in the travel-sphere for our beautiful summer season, but the winter months here on the island have slid under the radar as a prime time to visit the islands.

In the winter the islands transform from their dry, yellow, summer hues to a vibrant green that so well accents the dark gray and black shades of our rocky shores. There is wildlife teeming in our waters throughout the winter, and there are very few visitors on the streets in town! This time of year you practically have the place to yourselves, plus it’s super cozy to curl up under a blanket by a fire to warm up after your adventuring!


Here are some suggestions on planning your romantic getaway.

Mt. Baker and a Washington State Ferry
Mt. Baker and a Washington State Ferry
Sarah McCullagh


Island Inn at 123 West

The Island Inn is a great high-end hotel option right in the heart of Friday Harbor. Offering sweeping views of the Harbor and suite-style accommodations, the Island Inn is a great option for a cozy home base right in town.


Harrison & Tucker House

Looking for a bed and breakfast experience? The San Juan Island Inn Collection might be the place for you! Offering cottages, suites, and typical queen or king inn style rooms, Harrison and Tucker Houses are well regarded as one of the coziest spots on the island. The real highlight to your stay will be breakfast! They offer can’t miss, in-room, gourmet three course breakfast every morning!



Earthbox Inn and Spa is advertised as the most complete accommodations on San Juan Island. Located within a five-minute walk from everything in downtown Friday Harbor, this lovely hotel offers and indoor swimming pool, jacuzzi, sauna, and a host of modern amenities per room. In addition to all of that... Earthbox also has an on-property spa.


Roche Harbor

Roche Harbor is a great option for guests who want the small resort experience. Located at the north end of San Juan Island, about a 20-minute car ride off the ferry, historic Roche Harbor is a stunning launch point to the rest of the island. The resort features a full spa, restaurants, and beautiful views. Take a walk on the docks to check out all of the yachts tied up for the winter!


Pelindaba Lavender Farm

Though their visitor center is closed for the winter, you are more than welcome to take a walk through the fields. In some shape or form, Pelindaba has been on San Juan Island since 1998, and has become an island staple. Take a short walk around their beautiful fields.


American Camp

Bundle up and take a walk on the south end of San Juan Island! You will be treated to sweeping views of Haro Strait, the Olympic Peninsula, and, on these crisp, clear, winter days sometimes even a view of Mt. Rainier. The main loop is about two miles long, taking you through the prairie landscape and down towards the rocky shore line. My recommendation? Start high, walking past the historic structures and taking a right on a well-groomed path. Follow that all the way down towards South Beach, hang another right and walk along the bluffs overlooking the pocket beaches.


Lavendera Massage

Book a luxurious massage at Lavendera! Offering couples massages for your romantic Valentine’s getaway, their studio space is right in the heart of Friday Harbor.


Whale Watching – San Juan Safaris

Looking for a fun way to spend a day out in nature? Join our sister company at San Juan Safaris for a whale and wildlife tour! In February boats are running weekend departures starting on February 10th, with additional departures on both Valentine’s Day (Wednesday the 14th) and President’s Day (Monday the 19th). This time of year expect to see migrating seabirds and marine mammals, like sea lions! When you’re cruising in the San Juan there is always the chance of finding whales too, whether they be orcas or humpbacks!

Killer whale surfacing
Orca Surfacing
Sarah McCullagh



Coho Restaurant

Coho prides itself in farm to table style dining, utilizing the freshest ingredients that the island can offer. Make sure you order from their award-winning wine cellar. On Valentine’s Day (and other holidays throughout the year) the restaurant offers a five course tasting menu. Seating in limited, make sure you make your reservation in advance.


Tops’l Sushi

Delicious and fresh, locally sourced seafood overlooking the harbor? Yes, please! With one of the best views in town, looking right out over the harbor, Tops’l is one of my favorite spots in town. Master Sushi Chef Hee Han creates beautiful and tasty plates that are sure to wow you! Make sure that you call ahead to make a reservation!


Mike’s Wine Bar

Mike’s is the most incredible vegan restaurants I’ve ever had the pleasure of visiting. With a varied menu and a great local wine selection, a night out at Mike’s is a can’t miss for herbivores and carnivores alike. Mike and his crew often offer special menus for holidays, I recommend calling ahead to see what they have going on!




Cynthia’s is a great little café tucked away next to the additional ferry parking. Cynthia cooks up amazing and unique breakfast options that are always a great start to the day. My favorites include her skillet baked eggs and the sweet Dutch baby! In the winter, Cynthia’s is open for brunch Thursday through Sunday 7:30am-2:00pm.


Rocky Bay Café

All I can say is yum! This is my go to spot for a quick and easy breakfast. I usually order their veggie benedict, but if they have crab cake benedict as their special, you better believe I’ll order that and lick my plate clean. This café is a great stop if you have other plans through your day… the service is great, the coffee is strong, and you’ll have plenty of time to get out and explore. Rocky Bay is located in downtown Friday Harbor, right on Spring Street.



Cask and Schooner

With a new menu Cask has upped the ante! Keeping local favorites like the stout-spiked chicken sandwich and the bacon-wrapped cheese-stuffed dates, but adding so much more! Stop in to warm up with a cup of soup and a great view.


Market Chef

Market Chef is hands-down my favorite deli I have ever visited. With a rotating case of handcrafted salads, mac-and-cheeses, and local meats I would be happy if that was all they offered! This amazing team has also put together a thoughtful menu of made-to-order sandwiches that will knock your socks off. I recommend their curried egg salad sandwich, Pat’s Special.


We always love to help visitors plan their visit to the islands. Feel free to give us a shout; one of our staff members will be happy to point you in the right direction! We hope to see you soon, Happy Valentine’s Day!