Ocean to Bay Bicycle Tour
📅 Dates: May 16-22, 2027
🚴♀️ Duration: 7 Days, 6 nights | 25-45 miles per day
📍Locations: Cape Charles, Onancock, and Chincoteague Island
💲 Cost: $2,995 (double occupancy) + $500 for single supplement
Experience the unspoiled beauty of Virginia’s Eastern Shore on this relaxing coastal cycling adventure. Ride quiet roads between the Chesapeake Bay and the Atlantic Ocean while exploring charming waterfront towns, scenic marshlands, working harbors, and miles of breathtaking shoreline. Highlights include a three-night stay on Chincoteague Island, fresh local seafood & opportunities to spot the region’s famous wild ponies. This tour combines coastal charm and unforgettable scenery in one of the Mid-Atlantic’s most unique destinations
What’s Included:
6 nights in premium accommodations in Cape Charles, Exmore & Chincoteague, VA
Daily breakfast, 5 lunches, and 5 dinners at handpicked, locally owned restaurants. We give you one day to pick your own food when options are plentiful
A dedicated support team and mobile mechanic
Transportation when biking isn’t feasible
Hassle-free luggage transfers
Support vehicles stocked with water, snacks, and mechanical aid
A Pony watching boat tour around Assateague Island
A guided bike tour through Assateague Island Wildlife Refuge
Highlights:
Peaceful, lightly traveled roads ideal for relaxed riding
Explore the rich ecosystems of Chincoteague Island and nearby Chincoteague National Wildlife Refuge, home to migratory birds, native wildlife, and the island’s iconic wild ponies.
Time to explore charming seaside towns of Cape Charles & Onancock with shopping, art & baked goods
Walkable restaurants, ice cream shops, bakeries & sightseeing just outside our hotel door in Chincoteague
All levels of cyclists welcome. We take care of the logistics—just show up and ride!
Wild horses visible on the beach while on our boat tour