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San Juan Islands Sailing Itinerary

San Juan Islands Sailing Guide: Ultimate 10-Day Itinerary

by Bucket List Places Contributors

After over a year of imposed lockdowns and staring at tedious, four-walled rooms, setting sail into the unknown and feeling the wind embrace you like an old friend is a comforting freedom. Our San Juan Islands sailing guide focuses on the best state marine parks and populated islands; but there are 172 islands in the region, ranging from small rocky reefs to lands reaching approximately 2,500 feet. 

Famous as one of the best places to spot Killer Whales in the wild, the San Juan Islands are a truly unique destination. The area is a hot spot during the migratory whale season for Humpbacks traveling from Alaska south. Each island offers something unique for endless exploring opportunities.

Our 10-day San Juan Islands sailing itinerary comprises rolling terrain interspersed with lush, sinuously-forested ridges, leafy glens, and vivacious villages with restaurants serving local cuisine. Beyond land, sailors can spot seals sunbathing and orcas or humpback whales patrolling the waves, while rare bald eagles soar in circular motions above. To reach the more remote islands, kayaking or canoeing to shingle or sand beaches and unspoiled coves is a great way to get the blood pumping before hiking the dramatic surroundings. 

San Juan Sailing Guide Friday Harbor

The Ultimate 10-Day San Juan Islands Sailing Itinerary

Day One: Bellingham 

Sailing in the San Juan Islands typically starts in Bellingham or Anacortes. We suggest Bellingham for its delicious restaurants and thriving brewery scene. With seaside admission to the San Juan Islands and its spectacular views of the 172 isles, Bellingham also offers some of the best outdoor recreational activities. Within its borders are numerous local shops and museums, boasting even the Western Washington University, which adds a college vibe to the town. 

Whether you’re walking the vibrant streets or searching for unique wildlife on one of its many trails, Bellingham will keep you occupied until the sun goes down. Then, it’s imperative to try one of the many Bellingham restaurants in the bay. The Chuckanut Cracked Crab Dinner Cruise (running Friday to Sunday between June to September) and Bellingham’s Bay BREWERS Cruise, which takes travellers to the best local breweries, are the most unusual on offer.

Best things to do in Bellingham

  • Whale- or bird-watching excursions have naturalists helping travellers locate rhinoceros auklets, Caspian terns, great blue herons, and bald eagles
  • Visit the Whatcom Falls Park, which has maintained hiking trails, waterfalls, Whatcom Creek and the Stone Bridge that has the best viewpoint in the park
  • Alternatively, pop to Boulevard Park, which has a performance stage for local concerts
  • Walk around Lake Padden Park, which has an adjacent golf course 
  • Marvel at Lake Whatcom, which is a hotspot for many recreational activities, including boating, fishing and swimming
  • Explore the SPARK Museum of Electrical Invention 
  • Visit the 19th-century architecture of the Fairhaven Historic District
  • In Fairhaven, there are many artisan shops to splash your cash
  • Alternatively, head to Bellingham Farmers Market in Depot Market Square

Anchorage Options in Bellingham, Washington

  • Bellingham Port provides dock space for commercial and recreational vessels
  • There are no overnight moorage options in the Fairhaven area, but there are mooring buoys and plenty of space for anchorage

Day Two: Matia & Sucia Islands

Sucia Island San Juan Islands Travel Guide

Day Two of our San Juan sailing guide and itinerary should be split between visiting Matia and Sucia Islands, spending the evening in the latter. Matia is one of the smaller state park islands, offering 145 acres of protected land safeguarded by the San Juan Islands National Wildlife Refuge. This means you’ll see various wildlife, including puffins and eagles, and its interesting geological features include rock formations and pristine beaches. However, most of the island is a natural reserve and is off-limits to visitors. 

Sucia Islands is considered the number one park in all the San Juan Islands with a whopping 77,700 feet of shoreline. Once on land, the hiking trails will take you along the Fossil Bay beach before heading to the southwest woodland. A longer route goes to Ev Henry Point, but the pebbly beaches lined with spectacular sandstone formations are exquisite for those looking for an easier excursion. This outer San Juan Island offers the best camping experience in the Pacific Northwest but has no ferry service, meaning while boating there you can be sure to have more privacy compared to some of the places that ferries go to.

Best things to do on Matia Island

  • A lot of the island is not open to visitors, but there is an incredible walking trail starting at the dock, featuring ferns and coves taking you into the magical forest filled with big trees.
  • Explore Rolfe Cove 
  • Camp under the stars (although campfires and wood collecting are not allowed)

Best things to do on Sucia Island

  • There are several camping areas with firepits and picnic tables
  • Hike some (or all) 10 miles of this state park, featuring unique rock formations, coves and beaches 
  • If you have your own kayak, bring it to Sucia and kayak around the island’s many bays and extensive shoreline 
  • Marvel at the wildlife including seals often found lounging on the floating docks
  • Explore the many beaches on Sucia Island, the most popular being Fox Cove or Snoring Bay
  • Fish or shellfish on Sucia Island (but you need a fishing licence before you do this)

Anchorage Options on Matia Island and Sucia Island

Matia Anchorages

  • Matia Island has Rolfe Cove, which has a small dock with a capacity for four boats. There are also a couple of mooring balls if the docks are full. Be advised this is a very small anchorage so during busy times you should plan to arrive early to get a spot.

Sucia Anchorages

  • Fossil Bay has two extensive docks with a huge anchoring area and buoys 
  • If the mooring buoys are full, you’ll find anchorage between the westernmost dock and western end of buoys 

Day Three: Stuart Island

Stuart Island Best things to do

On day three of our San Juan Sailing Guide, you will visit Stuart island. This sparsely populated island has 433 acres of terrain and water channels on and around the isle, offering two parks with rocky shores and dense woodlands. The Reid and Prevost Harbors (north and south sides of the island, respectively) are connected by a narrow strip of state park land, and at Reid Harbor, if you want a break from boat living, you can stay at the campground.

The shoreside camp sites have excellent crab and clam fishing opportunities. In addition, there’s a long trail to the Turn Point Lighthouse Museum where, if you’re lucky, you’ll spot some orca. For something a little easier, there are two short loops around the park between the harbors. However, the rest of the island is private property. 

Best things to do on Stuart Island

  • Hike to the Turn Point Lighthouse Museum
  • A popular pastime is fishing, crabbing, swimming or diving in the islands two harbors 
  • Kayakers or canoeists can set up camp near Prevost Harbor
  • Marvel at the cliffs known as “Lover’s Leap’ 
  • Visit the Teacherage Museum, which displays the island’s teaching history 
  • There are many beaches to explore, and beachcombing is a popular pastime
  • Hike some of the shorter trails on the island for incredible views and a fun workout

Anchorage Options on Stuart Island

  • The Prevost Harbor on Stuart Island has a large dock and big bays, featuring a good amount of anchoring possibilities and mooring balls 
  • Prevost Harbor also has easy dinghy entry to the county dock 
  • An alternative is Reid Harbor which has its own dock and bay with mooring balls

San Juan Sailing Itinerary Day Four: Roche Harbor Marina

About four miles from Stuart Island is Roche Harbor Marina, on of San Juan Islands’ top spots to relax the sails. With up to 377 slips, the Roche Harbor Marina is usually where jetsetters spend their summer months as it has an ambience of “old money”, steeped in tradition, with a sunset flag ceremony. It’s a far cry from the other island campsites, and travelers should use Roche Harbor Marina to replenish food supplies, wash clothes, and shower in decent facilities.

Roche Harbor marina is one of the top stops on our San Juan Islands sailing guide to enjoy a sumptuous meal. There’s also a transit bus running during the day that’ll get you around the island. 

Best things to do on San Juan Island and Roche Harbor

  • Visit the islands’ historic village, which has remains of a lime kiln and Our Lady of Good Voyage Chapel
  • Explore the San Juan Islands Sculpture Park
  • Visit Lime Kiln State Park for a chance to spot orca whales from shore
  • Discover the McMillin Memorial Mausoleum (the resting place of the family who used to own the lime works)
  • Go and see the pioneer cemetery
  • Guests can hike the trails around the Roche Harbor quarries, through forest land
  • If you’d like to try your hand at water sports; kayaking and paddle boarding are popular activities on the island 
  • There are many whale-watching tours to go on
  • Swim in one of the islands’ outdoor heated pools 

Anchorage Options at Roche Harbor Marina

  • Roche Harbor Marina has 377 slips for large and small boats.

San Juan Islands Sailing Guide Day Five: Lopez Island

Lopez Island San Juan Islands Travel Guide

Lopez Island is situated at the easternmost point of the San Juan Islands, which can also be reached by ferry from Anacortes. It is 15 miles long, featuring 2,500 year-round residents and a staggering 63-mile-long shoreline. The best way to explore the undulating farmlands, forests, beaches with vast mountain ranges, or peaceful bays is by bike. There are several bicycle rental outfitters on the island that can even meet you at the dock to drop off a bike.

The simple life is also a crucial feature on this island, and some of the best things to do on the island involve you slowing down. With many various hiking trails as well as small shops and restaurants, spend the afternoons taking in the incredible views.

Best things to do on Lopez Island

  • Make sure to see Agate Beach on the South End of the island or Otis Perkis beach near Fisherman Bay
  • Try clamming or crabbing
  • Visit Lopez Village, which has many restaurants, galleries, a bookshop, a historical museum, a library, and many shops to stroll around 
  • Visit Point Colville, which has incredible views of the Salish Sea
  • Visit Watmough Bay (you can hike here from Point Colville)
  • Visit Spencer Spit State Park, which is a popular spot for camping 
  • Hike up Lopez Hill
  • Try your hand at kayaking (there are a variety of routes according to time and difficulty)  
  • There are many campsites in Odlin County Park with waterfront views, beach-access restrooms and picnic tables 
  • Tour Lopez Island by bike 

Anchorage Options on Lopez Island

  • You can anchor or dock at Fisherman Bay, but this is a relatively shallow area, so sailors need to enter it cautiously and slowly and make sure to follow tide charts.
  • Spencer Spit has a large anchoring area with many moorings on both sides of the spit
  • Odlin Park has its own dock that allows you to tie up your boat for two hours as well as a number of mooring balls for overnight anchorage.

Day Six: Friday Harbor, San Juan Island

Friday Harbor San Juan Island Best Things to Do

The next stop on our San Juan Islands sailing guide is Friday Harbor Marina, on San Juan Island, a popular tourist destination with many fine dining experiences and ice cream parlors ashore. Friday Harbor is the largest town in the San Juan Islands, with a huge grocery store. There are many shops, including a chandlery on Main Street, and visitors can rent mopeds to get around the island.

On a more practical note, there are also showers, laundry facilities, and places to refuel, and the sea life here (including shrimp, cod, and crab) is extraordinary. If you’re looking for something cultural, the summer months hold events like a jazz festival, adding a musical flair to your San Juan Islands sailing itinerary.

Best things to do in Friday Harbor

  • Visit the Friday Harbor Laboratories, which is one of the oldest marine research institutions
  • Go shopping on Spring Street, exploring a range of galleries, boutiques and bookshops
  • Go and see the Whale Museum 
  • Explore The San Juan Historical Museum
  • Go to one of the charter companies and fly around the island
  • Watch local marine life at the Spring St. Landing mini-aquarium 
  • Visit the San Juan Islands Museum of Art 
  • Visit the islands’ winery
  • Explore a lavender farm
  • Take a whale watching tour which will give you the chance to see orcas, humpbacks, harbor seals, sea lions and bald eagles. 

Friday Harbor Anchorage Options

  • The Friday Harbor Marina has slips for over 150 boats, ranging in size from dinghies to yachts
  • For those in town only for a short stop there is a free anchoring option. Tie up at the breakwater for a complimentary 2 hours.

Day Seven: Jones Island

Jones Island San Juan Islands Itinerary

The next stop on our San Juan Islands sailing guide and itinerary is Jones Island which can be easily reached from anywhere in the San Juan area. This island is in the centre of the San Juan Islands. It has a 188-acre park with 25,000 feet of shoreline, forest, an orchard and green clearings.

Coming onshore, you might be welcomed by otters or a rare breed of deer. There are little beaches, tide pools, and several short trails to stretch out your legs and 24 primitive campsites. Deer Harbor is close by, should you need to replenish your supplies.

Best things to do on Jones Island

  • Hike trails going through a forest of moss, logs, and towering trees
  • Pick fruit from the pear and apple orchard
  • If you’re looking to stay overnight, the cliffside campsites are close to the dock and allow evening fires

Anchorage Options on Jones Island

  • On the north side of this state park is a protected cove that has a dock and mooring balls 

Day Eight: Orcas Island

San Juan Sailing Guide Orcas Island

The locals refer to this horseshoe-shaped island as “the gem of the San Juans”, as it has 57 miles of green landscape, pristine lakes, underwater treasures, curving roads that are ideal for cyclists, apple barns, art studios, and much more. On the island is the Rosario Resort – a historic mansion with a pub, fine dining restaurant, spa with a hot tub and pool, and tennis courts.

An alternative to Rosario Resort and Marina is Deer Harbor Marina, situated at Orcas’ westernmost point. There is a little town with a restaurant and quaint cottages, and according to sailing veterans, Deer Harbor is the best spot to refuel and buy provisions. There are also friendly seals swimming around the boats which can regularly be seen lounging at the docks.

While on Orcas, we suggest renting a car to explore the island. The local car rental agency will bring the car right to you making it easy to connect from boat to wheels. Make sure to go to Eastsound, the main town on Orcas island which has some of the most delicious restaurants in all of the San Juan Islands. This hip downtown area also has an amazing cocktail bar and a brewery for those looking for a night cap.

For those into hiking, be sure to visit Moran State Park. You can hike the tallest mountain in the San Juan Islands or if you’re short on time, drive to the top and see views all the way to Canada.

Best things to do on Orcas Island

  • Try horse riding or swimming in Moran State Park
  • Go chasing waterfalls in the Moran State Park
  • Hike to the highest point in the San Juan Islands – Mount Constitution
  • Explore the Rosario mansion, which features a museum with the house’s old rooms, a historical slideshow, and a pipe organ concert
  • Drive the San Juan Islands Scenic Byway 
  • Hike Turtleback Mountain, which is situated on the western end of the island
  • Go on a whale-watching tour (the best time to do this is April through October)
  • Explore the Eastsound Village, which has many artisan and boutique shops and eateries, and a history museum
  • Visit Obstruction Pass State Park and relax on the best public access beach on the island
  • Try kayaking or paddleboarding on one of the islands two large lakes
Orcas Island San Juan Islands Sailing Itinerary

Anchorage Options on Orcas Island

  • Westsound Marina has the largest moorage facility on the island, featuring 180 moorage slips and has the most extensive repair facility 
  • Rosario Resort (closest to Eastsound) has 30 slips, plenty of safe anchorage and eight mooring buoys 
  • There are public docks in Eastsound at Madrona Point
  • There’s also Cayou Quay in Eastsound, which has dockage options, while anchorage and moorings are nearby 
  • At Orcas’ westernmost point, you can dock at Deer Harbor Marina

Day Nine: James Island

James Island San Juan Islands Sailing Guide

At 113 acres, James Island is one of those with no residents or drinkable water, and it is the foggiest place on our San Juan Islands sailing guide. However, it has over 12,000 feet of saltwater shoreline and multiple beaches, providing excellent views of the Rosario Strait. James Island can be easily accessed from Lopez Island, and there are three Cascadia Marine Trail campsites with a toilet. In addition to this, there’s an additional 10 campsites linked by a loop trail, but one is for kayakers only (usually coming from Anacortes, which is close by). The northern side of the island is closed to visitors as it is a designated a natural forest area. 

Best things to do on James Island

  • Go crabbing (but make sure you have a crabbing permit), shellfishing, or fishing 
  • Camp under the stars at one of its 13 campsites
  • Hike and explore the islands forested trails, coves and two white-sand beaches

James Island Anchorage Options

  • In the East Cove, four mooring buoys remain in place all year (all boaters must register and pay required fees upon arrival)
  • The West Cove has a dock featuring a 128-foot moorage float

Day Ten: Cypress Island & Back to Bellingham 

Cypress Island Washington State

The final stop on our San Juan Islands sailing itinerary is Cypress Island which has no ferry service. Its Eagle Harbor or Pelican Beach offer hiking trails left in their natural states, feeling very remote and serene. Beyond the Douglas-fir forests is a 7-acre lake, an excellent photography spot, while the south of the island has a protected bay containing a salmon fish farm. Due to its proximity to the mainland, kayakers tend to day trip here. From Cypress Island, head back to Bellingham, where you can enjoy some local cuisine before heading back home.

Best things to do on Cypress Island

  • Hike to the island’s summit along the official DNR trails 
  • Kayak the island’s circumference (the island is considered the best kayaking destination in the San Juan Islands)
  • Spend the night camping on the island
  • Go out looking for the island’s abundant wildlife 
  • Try some fishing

Anchorage Options on Cypress Island

  • On Cypress Island, you can find mooring buoys throughout various spots of the island. A local favorite is Eagle Harbor where you can spot seals swimming right near your boat.

Final Thoughts on our San Juan Islands Sailing Guide and Itinerary

There are many incredible San Juan Islands. You could spend a lifetime exploring their diverse ecosystems, quaint villages, incredible nature, and remote campsites. But this 10-day San Juan Islands sailing itinerary will give you the best of both worlds – freedom at sea and dreamy, once-in-a-lifetime experiences on remote islands. 

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