San Juan Islands

4 Nights / 5 Days from Anacortes through the San Juan Islands

This extended private charter aboard Bear Paw is a fully immersive exploration of the San Juan archipelago — blending wildlife-rich cruising, remote anchorages, vibrant island communities, kayaking, crabbing, and thoughtfully prepared onboard meals featuring local Pacific Northwest ingredients.

Cruising routes are intentionally designed through productive marine habitat. The waters surrounding San Juan Island are world-renowned for whale activity and diverse marine life.

Two distinct types of orcas frequent this region:

Southern Resident orcas – fish-eating family pods most commonly seen in summer months.
Transient (Bigg’s) orcas – marine mammal hunters that travel widely and may be encountered year-round.

Other possible wildlife sightings include humpback whales, minke whales, harbor porpoises, sea lions, harbor seals, bald eagles, and a variety of seabirds.

Onboard Dining & Local Catch

All meals are prepared onboard by Bear Paw, highlighting seasonal produce, regional farm-to-table sourcing, and fresh Pacific Northwest seafood.

Guests may also participate in Dungeness crab fishing (season permitting). Enjoying freshly caught crab prepared onboard is one of the most memorable ways to experience these waters.

Dietary preferences and special requests are accommodated in advance.

Day 1: Anacortes to Roche Harbor

Scenic Cruising & Whale Watch Opportunities

Depart Anacortes and cruise north through island-studded waterways, passing Speiden Island. This rugged, forested island is a wildlife hotspot: Mouflon sheep and deer roam the hillsides, sea lions haul out along rocky shores, and bald eagles perch high in old-growth trees. Kayaks can be launched nearby to explore quiet coves where seals rest and seabirds nest.

Throughout the afternoon, your captain monitors established whale travel corridors, with time intentionally set aside to search for Southern Resident and transient orcas, as well as humpbacks and porpoises. Evening arrival in Roche Harbor offers a tranquil setting to explore the historic marina or unwind onboard.

Day 2: Roche Harbor to Stuart Island

Remote Beauty & Coastal Trails

Stuart Island offers quiet, off-the-grid anchorages surrounded by dense forest and rugged coastline. Guests may hike scenic trails, including Turn Point Lighthouse, and enjoy kayaking along sheltered inlets and rocky coves.

Seal colonies are common along shorelines, and eagles and herons frequent the wooded areas. Crab pots can be set in promising waters (seasonal), offering a hands-on coastal experience.

Day 3: West Side San Juan & Optional Offshore Passage

Cruise along the western shoreline of San Juan Island — one of the most consistent whale-watching stretches in the region. Pass Lime Kiln Point State Park, often called “Whale Watch Park,” known for resident orcas in summer months.

Weather and conditions permitting, the voyage may extend toward Smith Island, a tiny, uninhabited island and protected wildlife refuge. Smith Island is especially important for seabird nesting, harbor seals, and occasionally haul-outs of sea lions. Its rocky shores provide a remote environment where transient orcas and other marine mammals are frequently observed in surrounding waters, adding a sense of true open-water adventure.

Evening arrival at Friday Harbor allows optional shore excursions: winery visits, distillery or brewery tastings, scenic hiking trails, or a stop at Westcott Bay Shellfish Co. to see a working oyster farm.

Day 4: Orcas Island – Deer Harbor & Island Interior

Cruise to Orcas Island and moor at Deer Harbor. From here, guests may hire a local taxi to explore:

Mount Constitution – panoramic views across the archipelago.
Eastsound – charming village shops, galleries, and waterfront.

Return to Bear Paw for a relaxed evening, enjoying fresh seafood or your own Dungeness crab catch. Eagles often soar overhead as the sun sets over the harbor.

Day 5: Wildlife Passage & Return to Anacortes

Cruise south toward Anacortes through productive marine habitat. This final morning provides one last opportunity to encounter Southern Resident or transient orcas, humpback whales, porpoises, seals, and seabirds before returning to port by late morning.

Disembark refreshed, having experienced the islands’ wildlife, remote anchorages, and the unmatched natural beauty of the Pacific Northwest.