Just 40 miles north of Boston, Cape Ann is less trafficked than Cape Cod but no less beautiful, with rocky coastline, sandy beaches, and colonial fishing towns. Rent a sea kayak at the North Shore Kayak Outdoor Center and paddle 2.5 miles to Thacher Island, or hop aboard Cape Ann Whale Watch's 115-foot boat to watch breaching humpbacks. Dinner is lobster rolls on the rocks overlooking Folly Cove.
NEAREST AIRPORT: Boston, one hour.
EXPENSE REPORT: Two nights at the Sea Lion Motel (sealionmotel.com): $288. Two half-day sea-kayak rentals (northshorekayak.com): $70. Two lobster rolls at the Lobster Pool Restaurant (lobsterpoolrestaurant.com): $25. Two whale-watching tickets with Cape Ann Whale Watch (seethewhales.com): $90. Total: $473