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Three Day Fall Itinerary on San Juan Island

driftwood piled up along a beach
Content and Photos by Nikki Schroeder Published on September 6, 2017

The San Juan Island is one of Washington’s best kept secrets during Fall for your October holidays. Thousands flock to the islands during the summer months to enjoy nature, go kayaking, and go whale watching. However, the Island in Fall is where true relaxation is possible. Have you ever had those vacations where you pack so much into it that you forget to relax and really take in your surroundings? We see it happen all the time! Our guests will come in with a mission. They have every moment planned to a T in order to maximize their time here. That’s how my own family travels! But usually vacations like those require a vacation afterwards.

What to do, where to eat, what to see. We have you covered!

The best part about San Juan Island in Fall is that you can still experience the beauty of the Island while relaxing! The key is to give yourself plenty of time to do so. Or to be like my mom, who has now learned to limit my dad to the number of activities he is allowed to plan so they can actually have time to enjoy their vacation. So, to make your life a little simpler, I have devised a perfectly balanced three-day itinerary for what to on San Juan Island during your October holidays!

Day of Arrival

You’ve just been traveling all day, you’re going to want to take it easy! First things first, come and check in at the Harrison House Suites where our staff will eagerly be awaiting your arrival. Once you’re all unpacked, go ahead and take a stroll into town. Our charming three-block “downtown” is sure to delight you. There is a little something for everyone!

The Young at Heart

For the young at heart, there are many “must stop” spots for you. My family friends who have been venturing over to Friday Harbor (known as the “big city” of the islands) from Lopez for years have a strict routine they stick to. They had to stop at the Toy Box to pick out a special toy then had dinner then stopped at the ice cream shop to pick from the many options they have. Even now that the kids are grown and starting families of their own, they STILL stick to their routine! And the boys occasionally get to sneak over to the remote control store.

The Shopper

Although we are not Seattle, Friday Harbor does boast a couple boutiques that are favorites for both locals and tourists. Deer Hazel and Be Chic Boutique are two must visit shops. The owners of Deer Hazel make their own jewelry and carry the latest styles. Even if you’re just window shopping, it’s worth it! And you’ll also want to check out the new kid on the block – the Print Shop. If you want unique souvenir gear to show off your island pride, it’s the shop for you!

The People Watcher

Okay, who doesn’t love people watching? There are a number of perfect, discreet spots to people watch in Friday Harbor! If you want to watch the swarm of people coming off the ferry while warming your hands with a latte, then the Salty Fox is the place for you! If you want to see all of the excited whale watchers go to and from their trips, then the bench by Memorial Park on Front Street is the spot. And to watch all other sorts of tourists go up and down the main street, there are benches all along the streets downtown. Plus, there is a new pocket park that is ideal for this!

A Casual Dinner at Cask and Schooner

jackson beach san juan island

Once you have explored to you heart’s content, meander on down to Cask and Schooner for a casual dinner. This pub-style restaurant boasts a variety of options to feed any pallet. And they do it all well! Plus, they have a variety of beer on tap that is always rotating.

Have a Night Cap

You’re on vacation, right? Meaning, naturally, it’s time for a night cap. Grab a bottle of wine or your favorite beverage from King’s Market. Then, either bundle up and spend and evening watching the sunset at Jackson Beach or relax by your very own fire in you room at the Harrison House Suites.

Day One

Okay now that you’ve had a good night of sleep on our feather top mattresses, you’re ready for the real deal! Start your day off with breakfast delivered right to your door. We offer two delivery times. So whether you’re an early riser or want to spend a little extra time under the covers, we’ll make sure you don’t miss out on our gourmet, multi-course breakfast!

innkeeper susan

Whale Watching

Now that you’ve watched all of the excited people downtown on their way to or from their whale watching tours, it’s your turn! Even through October, there are whale watching tour boats still going out. Three of our favorites, Maya’s Legacy Whale Watching, San Juan Safaris, and Western Prince are offering tours on the weekends this Fall.

Dinner at Coho Restaurant

After your adventurous day, it’s time to relax and treat yourself to an intimate dinner! Once you have taken some time to unwind from your day on the water, head on down to Coho Restaurant, just a block and a half away from the inns and prepare for your tastebuds to do a little happy dance.

breakfast at the harrison house Day Two

Now it’s time to tour the Island! Of course, fuel up on our breakfast once again. Now that you’ve had a taste of what it’s like, you’ll be eagerly waiting our knock in the morning. Consider giving us a call and asking us to send up some of our homemade Greek-style yogurt as well. Then, head towards the South end of the Island to begin your tour.

Hike Mount Finlayson

Your first stop should be Mount Finlayson. Take advantage of our crisp, clean air on a mid-morning stroll. This 3 mile loop takes you to the top of Mt. Finlayson where you’ll have beautiful views of Mt. Baker, Mt. Rainier, the Olympic Mountains, and British Columbia. You can even enjoy a few side trails to the Lagoons if you’re feeling really adventurous.

Lavender, Alpacas, and Parks, Oh My!

Continue on your tour and be sure to stop at all of the highlights along the West side of the Island. Although the lavender farm is not in bloom in the fall, there is still much to learn from their fields! Then, there are the alpacas which are here all year round. And of course, we have multiple parks to check out. Lime Kiln State Park is the best point on land for whale watching. Even if the whales are taking a break from people for a while, the views from this park are unbeatable. You can also check out the county park and English Camp if you haven’t gotten your fill of gorgeous Island scenery yet.

Lunch at Roche Harbor

Now that you’ve worked up a good appetite, stop in at the Madrona Bar and Grill in Roche Harbor for lunch. Weather permitting, you can even sit out on the deck and take a gander at all the “boats” in the harbor. Okay so most of them aren’t really boats. They’re yachts! And for someone who has only grown up around fishing boats, they are truly mind blowing.

Dinner at the San Juan Island Brewing Company

Okay okay. I know I jumped straight to dinner. BUT once you make it back into town and relax from your busy day for a bit, you’ll be ready for what I have in store for you next. Just a block and a half from our property is the brand new brewery! The San Juan Island Brewing Company opened its doors this summer and we are so “hoppy” they did! So even if you haven’t quite worked up and appetite yet, grab a sampler and watch the game or play your own games out on their lawn. Their casual menu will be just what you want after exploring the Island.

Day Three

So for today, I have a couple options for you depending on what you’re looking for your final day of your October holidays on San Juan Island. Of course, you’ll start with breakfast delivered to your door, yet again. Who knows, maybe today you will have switched to the later delivery time if you spent enough time at the brewery last night.

The Adventurers

If you’re ready for more activity today, I have a challenge for you! Bike around the Island. I know, I know, you just saw the Island yesterday. But trust me, biking it is a whole different perspective. Especially since you’ll want to take the roads less traveled by today. If you time it right, you may even catch the last haying of the season. Let your senses guide you!

The Relaxers

If you want to just relax and enjoy a blissful last day of vacation, we have phenomenal spas on the Island. Lavendera, Spa d’bune, and Earthbox are our favorites. If your suite is large enough, you can even have in-suite massages!

Dinner at the Backdoor Kitchen

For your final dinner, treat yourself to another fine dining experience at the Backdoor Kitchen. Just a stones throw away, you’ll be able to reminisce about the wonderful time you have spend on the Island while enjoying a marvelous Island meal and sipping a hand-crafted cocktail.

granola to go from the harrison house

Time to go Home

The day has now come to head home. I know you probably won’t want to leave your new home at the Harrison House Suites, but have no fear, you can start planning your trip for your next October holidays! Or, you can even extend your stay. Our team will be more than happy to suggest even more activities for you. Oh, and don’t forget to take home some of our homemade granola!

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