Escape to the Hamptons of the Chesapeake: Your Chauffeured Retreat to the Eastern Shore

Just two hours from the pulse of Washington, D.C., lies a world of waterfront tranquility, historic charm, and understated wealth. The Eastern Shore of Maryland—featuring the storied towns of St. Michaels, Oxford, and Easton—has long served as a discreet escape for power players and patrician families alike. Known as “The Hamptons of the Chesapeake,” it’s where heritage yachts dock beside sprawling estates, and cocktail hour begins with a chilled gin and a view of the bay.

For those accustomed to elevated standards, the journey should match the destination. Dav El | BostonCoach offers chauffeured transportation tailored to the quiet luxury of your weekend retreat. Our meticulously maintained fleet—featuring Mercedes-Benz S-Class sedans, executive SUVs, and private Sprinter vans—ensures your departure from the city is not only seamless, but serene.


A Weekend of Quiet Luxury: Your Itinerary

Friday Afternoon Arrival
Depart Washington, D.C. in your private chauffeured vehicle and arrive at the waterfront Inn at Perry Cabin just in time for sunset. Toast your arrival with chilled champagne and relax with an optional spa treatment.

Saturday
Start your morning with a private charter on the historic Schooner Selina II. Enjoy fresh blue crab cakes and local oysters at a waterside restaurant. Spend the afternoon exploring the Chesapeake Bay Maritime Museum or antique shopping in Oxford. Conclude your day with a wine tasting or a private oyster roast at a members-only club.

Sunday
Take a chauffeured transfer to Easton for a stroll through its historic district and fine art galleries. Enjoy brunch at the acclaimed Bas Rouge, then unwind at the Links at Perry Cabin or a nearby vineyard before returning to the city.


Why Book with Dav El | BostonCoach?

  • Effortless Elegance: Arrive relaxed, refreshed, and on time for every engagement.
  • Tailored to You: From artisanal drinks to curated playlists and Wi-Fi access, your preferences guide the journey.
  • Seamless Connections: We coordinate airport arrivals and transfers on request.
  • Discreet & Dependable: Uniformed chauffeurs, immaculate vehicles, and absolute privacy.

Whether you’re en route to a private dockside dinner or returning from a weekend of yachting, your time matters. Let our professional chauffeurs handle the road while you relax and take in the transition from skyline to shoreline.

Reserve your bespoke transfer today and elevate every mile.

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Dav El | BostonCoach
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