Sail to the San Juan Islands!

Departing from Skyline Marina, we begin our journey by crossing Rosario Strait for James Island. Along the way, always be on the lookout for local wildlife like harbor seals, porpoises, bald eagles, and, if we’re lucky, orcas.

We’ll anchor for lunch and explore the islands before heading out for our next paradise, Watmough Bay, where you can explore the shoreline, hike to the lookout, swim, or try paddleboarding near the kelp beds, all while soaking up the summer sun.

On the return sail, you’re welcome to join Captain Paul at the helm and learn the basics of sailing or sit back and enjoy the peace of the wind in the sails as we make our way back to Anacortes.

Timeline:

9:30 AM – Check-In: Meet your crew at Skyline Marina in Anacortes and settle aboard for the day’s adventure.

10:00 AM – Depart for James Island, crossing Rosario Strait to James Island, where we’ll anchor for lunch and enjoy time to stretch our legs and explore the island’s trails and beaches.

1:30 PM Hoist the sails and head for scenic Watmough Bay on Lopez Island, arriving around 2:30 PM.

4:30 PM – Depart Watmough Bay and enjoy the evening light as we sail back across the strait, arriving at Skyline Marina around 6:00 PM.

Private:

Duration 8 hours

1- 4 Passengers: $ 975

Please get in touch with us below to plan your trip!

Eligibility for booking this tour requires prior sailing experience and/or sailing with us on Penn Cove.

Available dates:

Aug 21st, Aug 23rd, Sep 12th, Sep 13th, 2025