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Biking Vacation Maryland: Cycling the Chesapeake Bay​

Activity Level: Easy  |  Daily Mileage: 13 – 32 mi  |  Daily Biking: 2 – 4 1/2 hr
Land only
6 days from only
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The lure of the sea tugs deep into the soul of Chesapeake Bay, a rising tide of maritime tradition, close-knit communities, protected seashores, marshes, and coastal islands, and regional cuisine as distinctively flavorful as any in the world.

The towns and villages of Maryland’s bay region have given rise to generations of devoted and creative shellfishermen, craftspeople, and culinary artisans who will welcome us like family. From elegant 18th-century brick mansions to weathered crab shacks by tidal ponds, we’ll feel the warm glow of daily life as only possible on bike and on foot, on an active vacation that features the most welcoming bicycling landscape of any in the country.

What's Included

  • 5 nights in historic inns
  • 11 meals – 5 breakfasts, 3 lunches, 3 dinners
  • FREE use of our custom VBT bicycle and helmet
  • Service of two VBT Trip Leaders
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Transfers
  • 5% Frequent Traveler Credit to use on your next VBT vacation
  • Special Good Buy Discount

Cultural Highlights

  • Sail the eastern shores with Captain Ed onboard the skipjack HM Krentz
  • Feast on the region's famous crab and seafood
  • Be entertained during an evening of local storytelling and music
  • Amble the wooden boardwalk at the Eastern Neck National Wildlife Refuge, a haven for more than 240 bird species
  • Browse the restored crab shacks, now artisans' shops, in Rock Hall – “where nice people live”
  • Engage with history past and present at a working boatyard at the Chesapeake Bay Maritime Museum

What to Expect

This tour offers options for easy rides throughout the trip. The terrain includes very few gradual hills. It’s possible to ride this entire week without the need for van shuttles. However, our VBT van support shuttle is always available in cases of inclement weather or for those who wish to shorten their rides. 
  • Activity Level: Easy
  • Average Daily Mileage: 13 – 32 miles
  • Average Daily Cycling Time: 2 – 4 1/2 hours
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