ARRIVE: Make the drive east from the Maryland mainland over the Verrazano Bridge early: there’s competition for backcountry permits, so you want to be there when the ranger station opens at 7 a.m. (weekend permits, $6; nps.gov/asis). Rent a kayak from SuperFun Eco Tours ($50 a day for a sit-on-top, paddles, drybags, and life jacket), which will deliver the boats right to the launch site at Bayside Drive, half a mile from the ranger station. Leave your car in a lot by the launch, and bring two days’ worth of camping gear, food, and water, plus a nautical map of the island (map number 12211); the sheltered coastline’s abundant eelgrass makes for great birdwatching but difficult navigation.
PADDLE: The island’s back bays provide sheltered paddling through shallow marshes. From the launch, paddle five miles south, hugging the shoreline until you reach Pine Tree, one of the park’s four bayside campsites, where you may get a visit from the island’s most famous residents—a 300-strong herd of wild ponies. Watch the sun set over Chincoteague Bay, then wake up before dawn and pack a breakfast. Hike through loblolly pine to the Atlantic side of the island and chow down as the sun rises over your own stretch of beach. Then hop back in your boat; there’s a deep gut just south of Pine Tree and miles of deserted coastline to explore.
RECHARGE: When it’s time to leave, keep Tingles Island to port and head north via the Tingles Narrows, where you can slide through a slender channel, watching for Assateague’s 300 bird species. Drop the boats at the launch and make for the Assateague Crab House in nearby Berlin for a cold beer and all-you-can-eat crabs.