Great Chesapeake Bay Loop Getaway Guide - 2024 Great Chesapeake Bay Loop Getaway Guide

From sunup to sundown, Maryland is always ready for a close-up. Hop on water taxis, yachts or guided cruises to admire photo-worthy beaches, enchanting lighthouses and jumping Spanish mackerel as you explore this fun-sized state’s super-sized waterways.

Tumblehome Cruises

Cruise out of Oxford Harbor with Storyteller Sandi Pepe for nautical serenity on a private, peaceful sunset cruise. This is slow travel at its best, filled with warm breezes and gentle waves. Pack your cooler and playlist to enjoy the quiet side of the Bay.

“When we take visitors out in Oxford’s harbor or on the river, they say they feel like they’ve stepped back in time and tell us how lucky we are to call this beautiful and peaceful place home.” Sandi Pepe Tumblehome Cruises

Watermark Journey

Whether it’s a water-taxi ride across the Severn River, a guided cruise or a private-yacht charter, outfitters like Watermark Journey make experiencing the Bay easy. And with certified Storyteller Captain Scott Bierman at the helm, you’re guaranteed to return to shore with memorable stories of your own.

“When you’re on a tour boat … you can see it in people’s eyes. It really clicks how awesome the Chesapeake Bay is. Kids get to throw oyster spats over into the reef, and you can see the light bulb come on. That’s exciting to me.” Captain Scott Bierman Watermark Journey