Available by request · Spring through early autumn
A private lower-Chesapeake journey connecting historic lighthouses, maritime stories, waterfront towns, and scenic cruising aboard your private yacht.
Request Passage InformationMaritime stories in their setting
Each day pairs scenic daylight cruising with a new waterfront destination, thoughtful interpretation, and the privacy and hospitality of your yacht.
The four-day passage
The final route is subject to weather, visibility, navigational conditions, and captain approval. Lighthouse viewing distances will always be determined by the captain.
Cruise past New Point Comfort Lighthouse and Wolf Trap Light, with a planned private lighthouse or maritime historian aboard for part of the passage. Enjoy gourmet dining prepared by an onboard chef and planned overnight dockage at deep-water Fishing Bay Marina.
View the Stingray Point lighthouse replica before crossing the lower Chesapeake to see Cape Charles Light from a safe, captain-approved distance. Planned dockage at Cape Charles Yacht Center allows time for the historic district, boutiques, beach, waterfront, dinner, and an overnight aboard the yacht.
Pass Thimble Shoal Light and view Newport News Middle Ground Light before planned dockage at deep-water Waterside Marina. A planned chauffeured visit leads to the Cape Henry lighthouses, where eligible guests may climb the original 1792 lighthouse, subject to access requirements and availability.
A planned chauffeured visit to Fort Monroe offers an exterior view of Old Point Comfort Lighthouse and time to explore the historic fort before returning to the yacht for the daylight cruise to Gloucester Point.
Thoughtful passage details
Small, carefully prepared details help guests understand the route while preserving the relaxed rhythm of a private yacht passage.
A planned private lighthouse or maritime historian joins one major cruising segment to bring the Bay’s navigational history to life.
Guests receive a printed route chart identifying every lighthouse and a small illustrated lighthouse guide in each cabin.
Binoculars are available for guest use whenever the captain determines conditions and viewing distances are appropriate.
Daily printed menu cards feature a short history of the principal lighthouse alongside gourmet dining prepared by an onboard chef.
Each private group receives a keepsake route map showing the lighthouses and waterfront destinations visited.
The passage is created for suitable spring, summer, and early-autumn weather rather than assigned a fixed public calendar date.
Created around suitable conditions
TPP will shape the final route and shore arrangements around safe conditions and partner availability.
Request passage information