It’s no secret that winter cruising in the Pacific Northwest can be difficult. But it’s also an incredible time of year to get out and discover unique holiday events and the beauty of empty anchorages around the Salish Sea.

For sailors with some extra time and a sense of adventure this December, we highly recommend a voyage through the San Juan and Gulf islands when Christmas lights are shining bright, the days are short, and the wind is brisk. Having cruised on both sides of the border extensively during this season aboard our Grand Soleil 39, Yahtzee, we found cruising this time of year to be extremely rewarding. Gone are the crowds of the summer and shoulder seasons, leaving marinas, anchorages and parks begging to be explored in peace and solitude. That many of the quaint towns offer something extra in the form of holiday festivities is just icing on the winter cruising cake.

The key to making it work, though, is paying close attention to the weather and having a plan for when gales sweep in off the Pacific Ocean or down from the Fraser River Valley. A good way to think about a winter cruise through the islands is to draw a straight line across a chart between Guemes Channel and Port Sidney Marina. What you’ll find is a roughly 30-mile east-west stretch that cuts straight through the heart of the San Juan Islands. Now, imagine planning a fluid winter cruising journey that bounces north and south of that line with stops at choice anchorages, state parks, and island hamlets that offer some yuletide flare. In our experience, you won’t be disappointed.

The Holiday Highlights

Get Started in Anacortes

Well known as the Gateway to the San Juan Islands, Anacortes is a logical starting point to launch a winter cruising adventure westward, and it’s easy to see why. Multiple grocery stores, hardware stores, restaurants, and an ample amount of marine services and supplies are within walking distance of nearby marinas.

Anacortes also has a wintertime charm that we grew to love. We’ve made some wonderful “A-town” friends over the years and have taken in several entertaining community events including the Downtown Christmas Tree Lighting and the and the First Friday Art Walk, which is holiday themed at this time of year. Built of crab traps, the lighting of the giant Christmas tree in front of the Anacortes Chamber of Commerce (only one block from Cap Sante) made for a merry evening for the Yahtzee boys, Porter and Magnus. Along with the ceremonial lighting, associated festivities included Christmas caroling, hot cocoa and, of course, an appearance by the big man himself… Santa.

Layover in Friday Harbor

During the winter, our crew quickly found that three to five days at anchor was a suitable number before needing a night or two at a dock to get provisions and plug in the dehumidifier. Accordingly, Friday Harbor turned into a winter home base for us while cruising the San Juans, because of its central location, services, and people.

While in Friday Harbor, a highlight is joining in any of the town’s Winterfest events, including A Very Merry Cabaret and San Juan Community Theatre production of Christmas Memories and Charles Dickens’ A Christmas Carol, Island Rec’s dichotomous duo of the New Year’s Eve Party and Resolution Run/Walk 5k & Salish Splash.

And if you find yourself on the other side of San Juan Island at Roche Harbor, check out the Annual Christmas Block Party at Roche Harbor Resort, which offers a Christmas lighted boat parade, photos with Santa, hor d’oevres and drinks at the Madrona Bar and Grill, and outdoor fire pits to warm your sailor bones.

Experience Victoria and Sidney

For us, stopping in Victoria or Sidney always entails three things: laundry, showers, and groceries. But during the winter season, there is much more to do than the standard chores of boat life. Victoria and the Saanich Peninsula are rife with holiday activities, and you can base yourself in Victoria Harbour, or at Port Sidney Marina and Van Isle Marina to revel in the season.

No stop in Victoria is complete without a visit to the Empress Hotel, and during the month of December you can sit on the veranda enjoying s’mores and hot drinks while overlooking the twinkling lights surrounding the harbor. Join in the celebration and lighting of the provincial Christmas tree and Parliament Buildings. And if you’re sailing with the whole family, savor brunch with Santa at The Hotel Grand Pacific and stick around to decorate cookies and make crafts afterwards.

Whether you take a bus from Sidney or Victoria, or anchor nearby in Tod Inlet, a wintertime must on Vancouver Island is certainly a visit to the famous Butchart Gardens for their Christmas spectacle.

After a gale moved through and the wind went north, we sailed Yahtzee down Saanich Inlet and were the lone boat anchored in Tod Inlet near the Garden’s entrance. From there, our family reveled in the quintessential Christmas charm, spending a starry night experiencing it all. Walking through the enchanting Christmas lights, listening to the traditional Christmas carolers and the Festive Brass Band, sipping cups of coffee and hot chocolate, riding the carousel and doing the “Twelve Days of Christmas” scavenger hunt, all four of us were mesmerized by the scene. Visitors can also ice skate and enjoy fine dining in one of two restaurants. It truly is a perfect holiday activity for any crew, and would be an ideal capstone to a yuletide cruise.

Connecting the Dots

While cruising the aforementioned east-west route to the major ports for holiday cheer is fun, stopping along the way at choice anchorages and marine parks can be the real gift of the season. Many of the popular destinations that boaters know from summertime sailing are eminently suitable during the winter. And in many cases, they’re even better without the crowds. Discovering these well loved spots in the offseason has led to some of our most memorable and cherished moments of cruising in the Pacific Northwest.

Blind Bay

Approaching Blind Island State Park near Shaw Island on a Monday afternoon, the sun wriggled free from the clouds yet a light mist continued to fall. Perched atop a scraggly tree on the island, a bald eagle sat watching the bay and a rainbow arched overhead. For a December day in the San Juan Islands, the scene was nearly perfect.

After securing Yahtzee on one of the park’s moorings, I dropped our dinghy in the water while Jill woke the boys from a nap and got them ready to head for shore. Blind Island is small, so after landing on the beach we left Porter to dig on the rocky beach while we went to see if the eagle was still in his perch.

Porter was soon at our heels to look as well and we crossed the rocky, grass- and tree-covered island together before dropping back down onto the beach as twilight set in. With the sun setting early this time of year, we had just a little time left to explore. On top of that, a forecast southerly gale was approaching, and we needed to move Yahtzee farther into the bay for more protection. We slipped the mooring and then dropped the anchor as a curtain of darkness closed in around us. On came our cabin heater and we made dinner and read books before turning in for the night.

To be sure, Blind Bay offers a fine winter haven to spend a couple of lazy days at anchor or on a mooring. Located on the north side of Shaw Island you can tuck close to shore to reduce fetch and land the dinghy at a nearby park dock to stretch your legs ashore.

Prevost Harbor, Stuart Island

On a brisk Sunday morning, a strong southwesterly wind swirled through the tops of tall pine trees overhead and rain started to fall as we came closer to the end of our hike to the old schoolhouse and museum on Stuart Island. We picked up the pace near Prevost Harbor and while moving through the trees I caught a glimpse of a large, 70-foot powerboat parked next to Yahtzee at the state park dock that wasn’t there just a few hours earlier. In the summer we’d expect this, but we hadn’t come across another cruising boat in a while and, on a blustery day, didn’t think we’d see other boats.

When we walked down the dock, the boat’s owner was going the opposite direction with his dog and we stopped to exchange pleasantries. They had just come from Friday Harbor and said he clocked wind gusts in the 40 to 50 knot range in San Juan Channel. I told him we were waiting to leave for Sidney the following morning when the wind was forecast to lay down, and he eagerly replied. “Perfect timing! You guys should come over to watch the Seahawks game with us!”

Soon after, our family of four was clamoring onto the comparatively palatial powerboat while our Seahawks flag was whipped into a frenzy in the breeze. We don’t have a TV aboard and with no cell service I was resigned to the fact that we wouldn’t be following the game—oh how fortunes change for the lucky winter mariner!

Portland Island

After clearing into Canada by phone at Van Isle Marina in Sidney, we made for Royal Cove on Portland Island on a beautifully sunny day. The cove is exceptionally well protected from the southerly quadrant and, since another gale was quickly approaching, we figured it would be a great spot to tuck in and hang out for a few days.

As expected, we were the only boat in the anchorage and had our pick of spots to drop the hook and put a stern tie to shore. After spending one night uncomfortably close to some rocks at low tide, we moved the next day and added a stern anchor to our stern tie set-up (along with our primary anchor) to hold Yahtzee safely in deep water. With the boat tucked in tight, we spent the weekend hiking throughout the island, exploring fern-lined trails and rocky outcroppings.

This is one of our favorite winter anchorages in the Gulf Islands because, when stern-tied to shore adjacent to the dinghy dock, strong southerlies flow right over the treetops and boat. Also, with the bow pointed north, oncoming ferry wakes are taken on the bow, instead of the beam.

More Offseason Favorites:

Cypress Island

Cypress Head, Eagle Harbor, Pelican Beach – Whether coming from Bellingham or Anacortes, the east side of Cypress Island is a special place. In the winter, the moorings at Cypress Head are a suitable spot to wait out strong southerlies.

Jones Island

Grab a mooring in the eastern cove and walk the islands empty trails. Ewing Cove, Sucia Island: Located in the northeastern corner of the island, Ewing has decent protection and is a gorgeous spot to enjoy a couple of lazy days.

Cabbage Island

We’ve ridden out a gale on the moorings here in relative comfort. The island’s sand beach is a great spot to land your dinghy and set off for a walk around the island.

Princess Cove, Wallace Island

With no other boats here, anchor all the way in the head of the cove and swing with the wind. No need to tie a stern line if you don’t want.

This article was published in the December 2019 issue of 48° North.