Ten thousand? Even Luie Boone knows that's a big number. Ten thousand pets? Yes, please. Ten thousand treats? A dream come true. Ten thousand walks? His tail might never, ever, ever stop wagging. But ten thousand islands? Now that's a whole different kind of adventure. Luie can only imagine how long it would take to swim around all those islands. Fur-ever, probably. Luckily, exploring the Ten Thousand Islands of Florida doesn't require a doggy paddle marathon!

When Luie Boone heard Chesapeake Bay, he thought his hoomans said Cheesecake Bay. Unfortunately, Annapolis, Maryland is not nestled along Cheesecake Bay, but rather Chesapeake Bay. Regardless, he'll be getting a cheesecake or two on his vacation to Annapolis. It is historic waterfront city, which offers the perfect mix of walkable charm, maritime character, and open-hearted hospitality for both people and their pups.

Luie Boone believes every vacation is better with your dog, and he's sniffed out the perfect getaway for you both: Maryland's Eastern Shore. This laid-back region is full of walkable towns, waterfront paths, and plenty of spots where pups are more than welcome.