We set out from the town of Anacortes, WA from Seafarers Memorial Park with a group of 6 people. Two in single kayaks and four in two tandem kayaks. After setting out into the water, keep to the west of Guemes island and follow the shoreline for a shorter trip or follow the east side for a longer day of paddling. 

About five miles in and after following the shoreline of Guemes for about three, you will begin the open water crossing to Cypress Island. Only do this section if the current and wind are low otherwise it will be very hard or even impossible if they're strong enough. Check the NOAA conditions to decide when the right time to cross would be and stick with that schedule. Once you are across, paddle to the little sand bar on the east side of the island, called Cypress Head. Here there is a free campground area and it is also the start of many trails around the island. Set up your camp around here and enjoy the sunset and the sound of the water here. 

In the morning, if you're lucky enough, you may see pods of Orcas swimming in the open water around the island. Upon return, roughly follow the same route you took to get there and arrive back at Seafarers Memorial Park. The entire trip length is roughly 16 miles roundtrip.