Cypress Island Guided Hike

This guided hike runs May through October, when boat conditions and daylight are most favorable for the crossing and full day on the island. Some trail sections on Cypress Island close seasonally, from February 1 through July 15, to protect threatened, endangered, and sensitive species, so the exact route can shift slightly earlier in the season. Because this is a boat-access destination, Stephanie plans each trip around current marine conditions as well as the calendar.

This is the central logistical challenge for most visitors, since Cypress Island has no ferry service and is accessible only by private boat, kayak, or chartered water taxi. Independent visitors typically need to book a water taxi separately out of Anacortes or Bellingham, time it against the island’s trail access, and then hike the largely unmarked, primitive trail network on their own once they land. This tour removes that entire logistics problem: boat transportation is included in the tour price, so you don’t need to arrange a separate charter or navigate 90% forested, DNR-managed terrain without local guidance.

Cypress Island is the largest and least developed island in the San Juan Islands, with roughly 90 percent of it forested and managed by Washington’s Department of Natural Resources as a Natural Resources Conservation Area. Unlike ferry-served islands such as Orcas or San Juan Island, Cypress sees far less visitor traffic, since reaching it requires your own boat or a chartered ride. That combination of size, minimal development, and restricted access gives the island’s roughly 5,000 acres of protected forest, lakes, and beaches a genuinely secluded feel that’s harder to find on the more accessible islands.

This hike is rated easy to moderate, covering 5 to 7 miles with about 700 feet of elevation gain on a well-maintained trail system, so it’s more physically demanding than several of Skagit Guided Adventures’ other hikes. It’s a reasonable fit for seniors and hikers who are comfortable with a full day of walking and some elevation change, but guests with significant mobility limitations may find this a better fit as a future goal than an easy starting point, and should discuss specific needs with Stephanie before booking. Note that Cypress Island’s recreation sites are primitive and not ADA-accessible.

The tour price includes Stephanie as your guide, boat transportation to and from the island, and taxes and fees. Lunch is not included, so bring a packed lunch to enjoy at one of the island’s beaches.

Like the Vendovi Island Hike, this tour is available by request rather than instant online booking. Contact Stephanie directly to check availability, since scheduling depends on boat access and current island conditions, and tour start times depend on the boat schedule rather than a fixed daily time slot.

Groups are capped at six guests, and the tour runs with a single guest at no additional cost. Given the island’s primitive, largely unmarked trail conditions and boat-dependent access, a small group lets Stephanie manage pacing and timing carefully around the return boat schedule.

The guided route explores the island’s northern end through coastal rainforest, maple groves, a freshwater lake, wetlands, and beaches. Along the way, you’ll stop at one of the island’s beaches for a picnic lunch (bring your own food), with sweeping views of the San Juan Islands, the Salish Sea, Mount Baker, and the North Cascades as the backdrop.

The tour meets in Anacortes, where the boat departs for the island.

Both are guided, boat-access hikes to undeveloped San Juan Islands with no ferry service, priced and structured similarly. Cypress Island is larger and more physically demanding, at 5 to 7 miles with 700 feet of elevation gain, rated easy to moderate, and covers forest, a lake, wetlands, and beaches on the island’s north end. Vendovi Island is smaller, at roughly 3 miles with about 200 feet of elevation gain, rated easy, and includes grassland prairies alongside forest and beaches, plus the chance to meet the island’s resident caretakers. Guests who want more distance and elevation choose Cypress; guests who want a gentler, shorter island hike choose Vendovi.

Bring a backpack with lunch and snacks, water, a small baggie and toilet paper since facilities are primitive, comfortable hiking or tennis shoes, and weather-appropriate clothing.