Available by request · Late spring through early autumn
A private journey beyond the Bay’s familiar cities, visiting working-waterfront communities, historic maritime sites, unusual landmarks, and the quieter Eastern Shore.
Request Passage InformationThe quieter Chesapeake
Five days create room for places rarely combined in one private journey, with daylight cruising, meaningful time ashore, and private yacht hospitality throughout.
The five-day passage
The itinerary is subject to weather, visibility, navigational conditions, marina availability, and captain approval. Tangier is a planned tender visit and is not guaranteed.
If Tangier conditions are unsuitable, TPP will provide an expanded Cape Charles and Eastern Shore itinerary.
Cruise the Mathews shoreline and view New Point Comfort Lighthouse from a safe, captain-approved distance. Planned deep-water dockage at Fishing Bay Marina is followed by a visit to the Deltaville Maritime Museum, sunset cocktails, gourmet dining prepared by an onboard chef, and an overnight aboard the yacht.
The yacht remains in captain-approved water for a planned tender transfer to Tangier. Visit the Tangier History Museum, take a planned private island or golf-cart tour, explore the working-waterfront community, and enjoy a local lunch. An overnight near Tangier occurs only with the captain’s approval.
Cross the Chesapeake for planned deep-water dockage at Cape Charles Yacht Center, then explore the historic district, boutiques, beach, and waterfront before dinner and an overnight aboard the yacht.
A planned chauffeured visit to Kiptopeke State Park includes approved views of the nine World War II concrete ships, the beach and maritime forest, and seasonal bird- or hawk-watching when appropriate. Return to Cape Charles for a final chef-created dinner aboard.
Breakfast aboard followed by a scenic daylight passage across the Chesapeake and arrival at Gloucester Point.
Suitable late-spring, summer, and early-autumn dates are available by request.
Request Passage InformationThoughtful passage details
Useful printed details, local perspectives, and carefully chosen keepsakes help guests understand the communities and landscapes along the route.
A printed route chart identifies the working-waterfront communities, historic sites, and unusual landmarks along the passage.
Each guest cabin includes a concise Chesapeake guide, with binoculars available for guest use throughout the journey.
Daily printed menus and schedules keep the group oriented while allowing the pace of the journey to remain relaxed.
The private group receives a keepsake route map showing the destinations and landmarks visited.
An optional local historian, waterman, or naturalist may join part of the experience depending on guest interests and availability.
The route is offered during suitable late-spring, summer, and early-autumn weather rather than assigned a fixed calendar date.
Created around suitable conditions
TPP will shape the final route and shore arrangements around safe conditions, local access, and partner availability.
Request passage information →