Luxury holidays in Chesapeake Bay

Life in America’s largest estuary is predictably water-centric. Sailing and oyster harvesting are daily pursuits, master craftsmen still build boats with their hands, and fishermen set out from the harbour, returning with laden nets, to stock the restaurants of bayside towns. Bike rides down leafy streets and quiet garden ambles are serious pastimes in this waterworld. Chesapeake Bay's quaint towns attract foodies, antique-hunters and outdoorsy types to their seafood shacks, boutiques and acres of green. Boating adventures are to be had at this preppie paradise of history-steeped houses and colonial-cool design.

When to go

Starting on Memorial Day (the last Monday in May), everything gets a little busier. The influx of tourists continues until October, so if you’re looking for a buzzy bay experience plan on visiting before then. Water activities stop in November, but things don’t really start to slow down until after Christmas. Some stores in St Michaels and other waterside towns are only open during peak season and many shorten their hours as the temperature dips. Easton, however, is open all year long.

Getting there

  • Planes

    Catch a direct flight from NYC, London and Los Angeles to Dulles International in Washington DC, about two and a half hours from St Michaels. Smaller but slightly closer, DC's Ronald Reagan National Airport is a two-hour drive. Maryland's Baltimore Washington International (BWI) airport, visited by a variety of national carriers including BA ( and Air Canada (, is just over an hour away.
  • Boats

    Dogwood Harbour on Tilghman Island offers trips and boat charters for a range of vessels. Go crabbing with a captain, tour a lighthouse or simply cruise the bay (
  • Trains

    Regular Amtrak trains pass through Baltimore’s BWI station (an hour from Dulles) en route to DC, Philadelphia, Boston, New York and Vermont (
  • Automobiles

    Essential for day trips and waterside cruising: rent a car at Dulles Airport through Avis (, or pick up a rental in the Eastern Shore town of Easton.
  • Taxis

    Cabs can’t be flagged in the street. There are two ranks in Easton: Bay County Taxi and Transportation Company on North Washington Street (+1 410 770 9030) and Eastern Shore services on Glenwood Avenue (+1 410 820 8431;