Well, I happen to like rainy days. I would like to caution visitors who believe the publicity that says 270 sunny days per year -- or some such number. Somehow, somewhere, someone read climate information in a meteorological data set and saw that there are 270 (or whatever) "days with sun". My memory may fail me, but when I last read in a similar data set the meaning of "days with sun" it was defined as any day with twenty consecutive minutes or more of sunshine. "Days with sun" does not mean sunny days. Very often the day will be gloomy or rainy and then about an hour before sunset the sky will clear and we'll have a bit of sunshine. I live here; I am used to overcast skies. However, when I travel I prefer a lot more sunshine per day than a few minutes.
Fondest memory: I live here. Since I moved here, I hardly ever travel. On the rare occasions that I leave the island, what I miss most is the quiet -- but then I never go to town in the afternoon. If you like quiet activities, hiking, birding, looking for native plants, etc., you'll enjoy the islands. I also like the pampering one gets at our B&Bs -- when I travel, I always choose to stay at a B&B that offers a fabulous breakfast.
There are many public beaches on the island, and they are all beautiful. South Beach, is great for beachcombing, barbecueing, partying and flying kites. Eagle Cove is a great family beach, especially for small kids. It is a nice sheltered cove, a little bit of a hike down from the parking area. The beach is sandy and the water is pretty shallow pretty far out. San Juan County Park is grassy -- we like it for picnics and frisbee. There are half a dozen more beaches, each with its own strong point.
Fondest memory: Playing with my daughter at Eagle Cove when she was a baby.
Take a drive around the island, and explore the beautiful inland scenery also. We were amazed at the lush but bucolic landscape and how many little farms and homesteads were there. No (or at least we didn't see them) subdivisions! The island is very manageable to drive around, with services at both ends (Roche Harbor and Friday Harbor). Most enjoyable!
Fondest memory: The view of False Bay from our little guest house, Wigeon's Rest (companion guest house to another called Water's Edge) was amazing... and sooooo peaceful. I have never been so relaxed.
Enjoy your trip out here. Riding on the Washington State ferries can be half the fun on your trip! The scenery is wonderful. No matter how many years or trips I have taken on the ferry I always find the rides most enjoyable. Be aware that you must wait in line to board if you are bringing your car...the wait can vary from an hour to several hours. If you are a walk on passenger then you can forgo that wait, but that will limit what you can see once you get to the islands. For more information on the state ferries go to their web site at www.wsdot.wa.gov/ferries
Fondest memory: Whenever the ferry pulls away from the dock at Anacortes I always feel a relief...to leave behind all traffic lights, 4 lane roads and highways, chain restaurants and crime.
Favorite thing: See the only two real tourist attractions, relics of a tense standoff between Britain and the U.S. The British camp is at the north end of the island, the American camp is at the south end. Visit both, and you'll have some vivid memories of a quirky little chapter of US history. The island is fairly small and can be seen in a day. For longer sojourns of just hanging out and doing nothing, there are B&Bs on the island that can help. Also, as the most developed town among all the San Juan Islands, Friday Harbor is the most logical base for an island-hopping holiday. Just don't bother the locals too much--it's a real, working American small town!