Words by MaryRose Denton and photographs by Richard Schmitz

Initially, the weather forecast for the week in mid-September called for perfect sailing conditions. The app on my phone showed 70-74 degrees, slightly overcast, and slightly sunny weather, with winds 15-17 knots out of the southwest.

Then the smoke from the California and Oregon forest fires moved in. Our Northwest skies became a hazy orange with low visibility. This cloud coverage created an exciting phenomenon of, no wind.

Richard and I continued to ready the boat and set off at a good time that morning, knowing it would be a full day of sailing (or maybe mostly motoring due to lack of wind) down to our first anchor. This will not foil our trip plans to cruise south on the Salish Sea and circumnavigate Whidbey Island. Our itinerary included Coupeville, Langley, Port Ludlow, Port Townsend, then crossing the Strait of Juan de Fuca to spend a few days among the San Juan Islands before returning to our home port in Bellingham, Washington.

While Richard and I along with our companion sailboat “Selkie” reside in Washington and the San Juan Islands are in our backyard, the are different options available to you to experience this Island even if you don’t. If you are an experienced and accredited sailor, or maybe you are more interested in a passenger on a sailing charter, turn to: SaratogaYachtCharters.com or SanJuanCharters.com for assistance.

Our first anchor in Penn Cove and the town of Coupeville.

We anchored just outside of Coupeville in the area known as Penn Cove, just a stone’s throw from the Coupeville Wharf’s historic building. The Wharf is an active marina for boaters with a fuel dock, guest moorage, showers, café, and even kayak rentals.

Downtown Coupeville
Along the waterfront

This water inlet is beautiful, with postcard-worthy views looking back on the small town of Coupeville and its quaint seaside buildings. As quiet and calm as this cove can be, there was a night, August 8th, 1970, when it became an area of distress and tragedy. The night is now known as the Penn Cove orca capture, where a pod of 80, probably Southern resident, Orcas, were rounded up and herded into nets waiting for them inside Penn Cove. Seven of the younger Orcas were taken into captivity and immediately sold to marine parks.

Today, there is one remaining Southern resident orca in captivity, Lolita or Tokitae, known in the native Chinook dialect. She still performs at SeaWorld in Florida while a flurry of activity swirls around the call for her release.

At dusk, we sit above deck sipping a libation and watch the lights come on all over Coupeville as the fading sun turns the sky dark. I think about Tokitae and that night over 50 years ago in the stillness and quiet amongst this cove. These waters of the Salish Sea are sacred to the native tribes who live alongside them, and so are all the beings who swim in them. May Tokitae (Lolita) return home soon and safely.

Waterfront homes


The next morning, we dinghy over to the large, majestic, red Coupeville Wharf and head up into the town and home of Practical Magic, the 1998 movie with Sandra Bullock and Nicole Kidman. If you are a Practical Magic fan, then you will love the quaintness of Coupeville captured in the motion picture.

Walk-up Front Street (the main street in the movie) and poke inside the buildings used as backdrops for this classic story.

Coupeville is the second oldest town in Washington was founded in 1852. This charming slice of an older time offers the perfect taste of that slower island life. Much of the downtown area retains its century-old charm.

We only spent the day here, but Coupeville offers everything one needs for a fun-filled outing from its beautiful beaches, quaint houses, historic buildings, quirky shops, and great places to eat from its artisan bakers local produce. If you like seafood, then the day’s catch comes right from the Penn Cove mussel and oyster beds.

Coupeville Shore
Coupeville Downtown street
Coupeville stores

After taking in the breathtaking views from the dock on the Wharf, we wandered up Front Street, poking about in the gift and antique shops and working up an appetite for a mid-morning coffee and breakfast sandwich. We found both at the Little Red Hen Bakery. We also found a great table to sit outside on the patio and overlook the bay. Pro tip: their bread is all made fresh daily and by hand. Grab a loaf to take with you on your travels. We did and took it back on the boat with us. The café is only open Thursday through Sundays, 9:00 am – 3:00 pm, and there is usually a line, so get there early and bring your patience. It will be well worth it!

We do not eat seafood, but if this is your thing and you are searching for a great seafood dinner, the locals all recommend Toby’s Tavern, located right on Front Street. Toby’s is famous for their Penn Cove mussels, casual bites, and of course, brews. The Oystercatcher is a few blocks away on Grace Street, also specializing in local seafood and Northwest faire.

Tobys Tavern
Little Red Hen bakery

Langley, the village by the sea.

Langley has these beautiful coves and passageways

At the very southern tip of the island sits the charming town of Langley. An artists haven of galleries and shops, an excellent bookstore, an old-time movie theater playing all the new releases along with classic films, and even a set of life-size angel wings painted on a corner wall. Langley has it all and much more.

Sailing into Langley, we moored at their marina, the Port of South Whidbey Harbor at Langley. It’s relatively quiet and a little sleepy on the docks as we pull in, but with 65 miles of shoreline and six public beaches, this marina has all the amenities any sailor could desire.

We worked up an appetite securing the boat, so we decided to venture up to town to now secure some dinner. The road to town is a very steep climb but certainly doable and feels good to stretch our sea legs a bit.


We find not much in town to be open but as we wandered up to Second street, we discovered the Spyhop. The term spy hop refers to when whales half-rise out of the water to view their surroundings. It’s a fitting name for a small-town pub in this small seaside town where whale watching has become a thing and a popular pastime.

The Spyhop Public House is known for its gourmet burgers and tasty pub grub. They have many brews on tap to wash it all down, including the hearty Porter I sampled and the amber IPA which Richard chose.

Sitting outside along their side deck gave us views looking westward. With the skies still smoke-filled, the one advantage was the sunsets, with the sun becoming a glowing orange ball as it lowered itself in the sky. We watched the sky show as we sipped our ales, relaxing for the evening.

The next morning, we hiked back up the hill to town in search of coffee. We found Main Street to be more like a ghost town. It was when we walked up to Second street we found where the locals hang out. And that place is the Commons Café & Books. We ordered our Americanos and pastries at the take-out window and found a table on the far side of the outdoor patio. Every table on the deck was full—friends and neighbors enjoying each other’s company before they hurried to get their day underway. There were a few tourists scattered among the locals looking at maps and discussing their next adventures. One trademark to Langley is the rabbits. There are wild town rabbits everywhere! And this patio was no exception. As we sat, the rabbits hopped around and under the tables fairly unobtrusively, sniffing out a few crumbs or perhaps a leftover scrap.

The Commons is popular with tourists and locals for their delicious coffee and their mission, for they offer a job training program for youth in the community to gain work skills and save for a college education. An effort is certainly worth patronage.

Langley is also known for its many wineries, but that will have to wait for another visit. It is time to set sail for our next destination.

Port Ludlow

Just a jaunt across Admiralty Inlet lies Port Ludlow and the Port Ludlow Resort. A destination we chose purely for its beauty and charm. The 300-slip marina sits inside a lovely bay and offers a calming respite to any travels. There is even a totem pole standing sentry at the entrance. Besides guest moorage, there are shower facilities and a fuel dock. This marina tends to be very peaceful and quiet.

It is located next to the Port Ludlow Inn and Golf course. The Inn is a 37 room waterfront inn inspired by New England charm with an 18-hole golf course that winds through a rolling fairway. Inside the Inn is the Fireside Restaurant, a well-known, local farm to fork restaurant serving fresh Northwest cuisine. It is best to make a reservation for this bistro-style restaurant is very popular, and tables fill fast.

We cooked on the boat instead, preparing our gourmet vegetarian delights for supper. Honestly, life feels pretty sweet eating dinner above deck while the sunset lights up the horizon.

After washing up the dinner dishes, Richard took a stroll along the beachfront, which offers stunning views over Ludlow Bay, while I cozied up with pen and paper to get some writing done.

Port Townsend Harbor

Port Townsend

Now heading slightly west along the Olympic Peninsula, we travel a short distance to one of our favorite cities, Port Townsend, WA. The city motto is “leave ordinary behind, experience extraordinary.” We have to agree.

There is so much culture and history in Port Townsend, from its Native American beginnings to its Victorian architecture and charm to its lively fishing and boating scene. There are weekly Farmer’s Markets, artists and creatives galore, and several festivals throughout the year, including our favorite The Wooden Boat Festival, where everything is about small craft boats and of course, sailing!

We tie up the boat early and take a walk up Water Street, the downtown district’s central area. A stroll becomes an excellent way to soak in the culture and ambiance of this town. I am meeting a writer friend a little late for coffee, so Richard brings his camera along to entertain himself with a spontaneous photoshoot.

Port Townsend downtown on Water Street

We meet back up for dinner at our number one place, The Fountain Cafe. The Fountain is an icon in the local scene providing fresh and creative cuisine, which is truly a masterpiece to be witnessed and eaten. We are always delighted to dine here and generally make our reservations early. They are very popular.

We leave satiated and happy. Despite the smoky haze still lingering in the air, it is a relatively nice evening as we stroll back to the boat.

The Fountain Cafe in Port Townsend

The next day

In the morning, we eat breakfast on the boat and enjoy a leisurely morning with our coffee. The harbor in Port Townsend is lovely and picturesque, so we take a late morning walk along the waterway. There are usually a couple of harbor seals swimming offshore, and this morning, they did not disappoint us as they bobbed their heads up to take a better look at us as we watched them.

Back at the boat, we gathered up a few overnight things, including our toothbrushes, for we were off to spend a night at the historic and possibly haunted Palace Hotel.

Built-in 1889 by retired sea captain Henry L. Tibbals, the Palace Hotel building housed many businesses throughout its years, from a billiard parlor and saloon to a town newspaper. The more well-renowned proprietorship to call this building home lived here from 1925-1933, nicknamed the Palace of Sweets, as it operated as both a hotel and a brothel.

Rumor has it, some of the girls from the brothel never ultimately left after it was shut down in the mid-1930s. The Palace Hotel hosts a few permanent guests, so the story goes, who come out at night, sometimes to mingle with the living. Do not be alarmed if you feel a cool breeze or flick of your hair, for these are just the “girls” being playful.

After checking into our room, named for one of the “girls”, Miss Alice, we ventured down the street to another favorite eatery, the Sirens Pub, “an eatery of distinction”. Located upstairs the view of the harbor from their deck is phenomenal. Truly a sailor’s delight. This is where we seated ourselves for a supper of veggie burgers and brews on tap, 11 to be exact.

Even with a full belly, I had a hard time falling asleep back at the hotel. I kept wondering if Miss Alice would want to use her room or bed. Eventually, I fell asleep and by morning, wondered if all the folklore was just stories until I looked at the far right window pane. Upon the glass were two white handprints. We were three floors up, and these handprints were on the outside of the window. Had they been there before? Hard to know.

There is one possibility. Maybe Alice did visit her room to have a look around after all.

Palace Hotel Port Townsend

Crossing the Strait of Juan de Fuca

We certainly could spend much more time in Port Townsend, but we needed to be on our way for now. The smoke seemed to have cleared slightly as we left the harbor and headed out into the Strait of Juan de Fuca. This was going to be a long crossing where the currents and wind coming in off the Pacific usually run easterly, proving at times to be tricky. But not today. There still seemed to be next to no wind.

What we did not expect was fog! Dense, dense fog surrounded us as we moved out into the bigger water of the Strait. If it weren’t for modern-day radar and GPS devices, we literally would have been blind at sea. The fog was so thick we could not see beyond our own bow. We sailed in a cloud at sea.

This made it relatively slow going. The scary part occurred when a freighter sounded his horn from off our Starbird side. Of course, sound carries in the fog, and I could see on the radar he was more than a mile away from us and headed up his channel. But still…Little by little, we progressed across the Strait and eventually entered the San Juan Channel. Then miraculously, the fog lifted slightly. We saw outlines of trees and coastline. A small school of porpoise ran alongside our Portside, accompanying us for a short distance.

Exquisitely beautiful scenery surrounded us, allowing me for a few moments to imagine myself in the Hebrides or cruising the waterways of Norway, another land with a very similar look.

We timed our arrival up the channel well, for we cruised on an incoming tide meaning the current flowed with us in the direction we were headed.

Our next port of call was Friday Harbor, known as the “Gateway to the San Juan Islands”.

Our traveling companion 'Selkie'

Friday Harbor

This charming seaport town offers a wide variety of cultures, activities, shopping, and food. The best part, everything is within walking distance of either the ferry landing or the marina allowing visitors to experience the slower pace of “island time.”

Coming into port, a resident seal escorted us to slip #22, which would be our home for the next few days. Friday Harbor is known for its marine life, from seals to the resident J, K, and L orca whale pods who call the waters around San Juan Island home. In these pods, the orca whales are direct relatives to Tokitae (Lolita), who was captured and lived and performed at SeaWorld in Florida. If spotting a whale excites you, these islands are the place to be for tours and leave the marina daily.

After that long and somewhat harrowing journey, we were ready for a hot meal, a glass of wine (or two), and an evening of pure relaxation, translated as doing “nothing”.

San Juan Bistro, a well-respected restaurant in town, came highly recommended so we call in our order, letting owner Richard Daly know we can be there in 15 minutes. It is a short walk of about six blocks up through town, and we are happy to be on land this evening.

Back on board, we settle into a magnificent farm-to-table meal beginning with a roasted carrot soup followed by a Thai Red Curry with seasonal veggies as a side dish.

This area is rich in sea life and its agriculture, with San Juan Bistro working closely with local farmers and fishers to bring out this region’s flavors through their gastronomy. We paired our meal with a red Malbec wine and finished the evening off savoring a slice of apple cheesecake for two. All while watching the sunset over the harbor, painting the cumulus clouds a light pink.

Those clouds brought rain during the night, and what a welcome sound it was. After a week of smoke-filled skies, that sound of patter on the skylight meant clearer skies were on their way. A slight autumn chill greeted us in the morning of day two as we headed into town for a walk, reminding us why the trees lining Spring street were turning shades of orange.

Later this same evening we stood at the ferry terminal’s foot and waited for my son to disembark and walk down the gangway. He traveled up to Friday Harbor to spend a few days with us, sailing in and out of the San Juan Islands.

Dinner for three that night came from my go-to eatery on this island, Mike’s Cafe and Wine Bar , an all-vegan restaurant situated in the middle of the shopping district on 2nd street. As a vegetarian, I rest assured the “meat” in the Reuben sandwich is created from plant-based proteins. All their menu items help create a more sustainable and compassionate world. 

Port Townsend downtown
The Fountain Cafe

Things to do

Friday Harbor is a vibrant town with an earthy soul. Being a seaside town, it has a strong connection with the marine life cohabitating this area. One of my favorite places to visit while in Friday Harbor is the Whale Museum. A natural history museum founded in 1979, it was the premier museum in the country devoted to a sole species living in the wild. It inhabits two floors of exhibits and educational resources promoting stewardship, all on marine mammals throughout the Salish Sea. There is a primary focus on the resident orca pods, including a chart showing their lineage throughout the decades. You can even adopt a whale through a monetary contribution.

Friday Harbor is home to many creatives as well as marine life. The San Juan Islands Museum of Art, located right on Spring Street in downtown, is a haven for local art exhibits from all around the Pacific Northwest. They focus on Native artwork and art depicting life in this region.

We stayed over through Saturday, we took in the local Saturday market and stocked up on some fresh greens, vegetables, and flowers for the boat.

There is a sense of melancholy leaving Friday Harbor, but we untie the boat and steer our way out of the harbor towards San Juan Island’s northern end. This time with our sails up for not only did the rain clear, but it also brought wind!

Sailing and Roche Harbor

For the majority of the afternoon, we enjoyed the full sail, running with the wind and streaming through the San Juan Islands’ waters. The skies shone clear and sunny and were a welcome change from this past week’s oppressive, smoke-filled air. Now we had perfect sailing weather. We decided to make our way north to the other side of the island and moor at Roche Harbor

After securing the boat, we meandered our way through the docks and resort to the Madrona Bar and Grill where we enjoyed a pint accompanied by a massive plate of fries. The perfect ending to a day on the water.

Tomorrow we head for home, completing the route which brought us full circle around Whidbey Island.

Hotel De Haro, Roche Harbor
Spread the love
error: Alluring Travel Magazines Content is protected !!