As the forests of masts and rigging in Friday Harbor and Roche Harbor  can attest, sailing and cruising is the preferred pastime on San Juan Island . If you don't have a boat of your own, there are a number of charter and cruise companies available to take you out on the water in style.
If you're looking to splurge, Caramel Cruises (360/378-9816 or 888/875-1774) offers three-hour afternoon sails aboard a 37-foot Hunter Legend sailboat for $384 per couple. Sunset sails, dinner cruises, and multi-day sails are also available.
Another fun (and more affordable) option for history buffs are the dinner cruises run by Scamper Charters (360/370-5133 or 877/314-3532, www.scampercharters.com ) aboard the lovingly maintained 1920 wooden yacht Scamper. If you want more time to check the boat out, it is also available to charter for $100 per hour with a four-hour minimum.
For fishing and other boat charters from Friday Harbor, contact Trophy Charters (360/378-2110, www.fishthesanjuans.com ) or Buffalo Works (360/378-4612).
Additional fishing charters—and day trips to Victoria—are available at Roche Harbor Marina (360/378-2155 or 800/451-8910, www.rocheharbor.com ), the largest marina in the San Juans and a U.S. Customs port of entry for boaters coming in from Canada. Facilities here include permanent and guest moorage, showers and laundry, a store, restaurant, bar, and full-service resort. Motorboats, canoes, kayaks, and paddleboats are available for rent.