Charter Itinerary
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Day 1
Annapolis
On this southbound itinerary, you’ll cast off on your luxury Chesapeake Bay yacht charter in Annapolis, arguably the most stunning belle of the ball. Do make sure to include a few days here, before you set sail, to explore the enticing markets and exceptional art galleries, boutiques and restaurants. Visit the respected United States Navy Academy and drop into the Maryland State House, before getting lost in the maze of cobbled streets of this historic town. A must-do lunch spot is Chick & Ruth's Deli, a revered pie institution in Annapolis, renowned for its skyscraper sandwiches and mouth-watering crab cakes.
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Day 2
Camridge
One of Maryland’s oldest and most atmospheric old towns, Cambridge is home to an outstanding Maritime Museum, which reflects three centuries of illustrious history. Waterfront cafés, an excellent art district, gorgeous boutiques and a delectable mix of international fine-dining establishments will no doubt capture you for an entire day.
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Day 3
Oxford
The first entry port of the colonial states, Oxford is a charming town revered for its relaxed and serene vibe. Oxford lacks the dazzling modernity of some of the other bayside towns yet this is what makes it so alluring. Arrive early enough and you’ll see local fishermen unload their daily catch, stroll downtown to explore the quaint shop and choose one of the waterfront cafés for a superbly fresh seafood lunch.
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Day 4
St. Michels
This picturesque colonial seaport town is a must on all Chesapeake Bay yacht charter itineraries. St/. Michaels, much like Oxford, is an old-world town that’s immensely beguiling. Cast your eyes on the magnificent restored Boats at the Chesapeake Bay Maritime Museum, where you’ll discover the largest collection of maritime artifacts and indigenous boats in the region. Town center, brimming with shops, galleries and eateries, entices families and couples alike, with enough options for sightseeing and activities to keep enthralled for days on end.
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Day 6
Rock Hall
Day 6 of your Chesapeake Bay yacht charter itinerary will see you reach Rock Hall, an artisan hideout and an unrivalled boating haven where wildlife viewing reigns supreme.
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Day 7
Baltimore
Baltimore’s Inner Harbor is a picture-perfect welcome into what is perhaps the most famous Chesapeake Bay hubs of all. With a bevy of cultural and historical attractions and a vibrant foodie scene, Baltimore is a wonderful end-point for your Chesapeake Bay yacht charter itinerary and, much like Annapolis, deserving of a couple of extra days’ exploration, at the very least. Over 16,000 species await you at the National Aquarium, and if you visit during baseball season you shouldn’t miss a game at Orioles Park. Indulge in more mouthwatering crab at Phillips Seafood, one of the city’s most celebrated restaurants, and pay homage to the “Star Spangled Banner” anthem with an afternoon visit to Fort McHenry.
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Day 8
Disembarkation
Today, it’s time to farewell your crew and disembark…and to start planning your next Chesapeake Bay yacht charter trip.
