The Chesapeake, in its moment
Limited private passages created around the gardens, waterfront traditions, festivals, flavors, and celebrations that belong to a particular time of year.
Private by design
Each passage reserves the yacht for one private group. Most multi-day journeys are designed for 2–6 guests, with up to 8 considered by custom arrangement. Pricing is developed after the dates, group, route, and shore experiences are confirmed.
Gardens, maritime stories, and the quieter Bay
Begin with Virginia’s brief garden season or choose suitable dates for a private passage shaped around the lower Chesapeake.
Selected 2027 datesApril 19–22, 2027
A limited late-April passage through Gloucester, Yorktown, Williamsburg, and Norfolk, created around Virginia’s Historic Garden Week.
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Available by requestSpring through early autumn
Historic lighthouses, maritime stories, waterfront towns, and scenic cruising, with the final route shaped around safe conditions and local access.
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Available by requestLate spring through early autumn
Working-waterfront communities, unusual maritime landmarks, and the quieter Eastern Shore, with Tangier planned only when conditions permit.
Explore this passageWaterfront festivals, music, and Independence Day
Limited summer passages pair private yacht hospitality with the Chesapeake’s most memorable waterfront weekends.
Provisional calendar holdJune 4–6, 2027
A private passage from Gloucester Point to Norfolk planned around Harborfest’s maritime displays, waterfront entertainment, and fireworks.
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Event details pendingJuly 3–5, 2027
A private holiday passage to Norfolk with waterfront time, gourmet dining prepared by an onboard chef, and a planned captain-approved fireworks view.
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Provisional · Performers pendingAugust 5–8, 2027
A Thursday-to-Sunday journey connecting planned waterfront music experiences in Yorktown, Norfolk, and Cape Charles.
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Provisional · Performers pendingAugust 19–22, 2027
A second limited summer journey connecting Yorktown, Norfolk, and Cape Charles through three planned music experiences.
Explore this passageOysters, harvest dining, and late-season Chesapeake scenery
A richly Chesapeake passage created around oysters, waterfront towns, and the colors and flavors of the late season.
Festival dates confirmedNovember 4–7, 2027
A journey through Irvington and Urbanna centered around the confirmed November 5–6 dates of the 2027 Urbanna Oyster Festival.
Explore this passageWaterfront lights, festive dining, and private traditions
A late-season private journey combining the Chesapeake’s holiday atmosphere with the warmth and privacy of your own yacht.
Provisional calendar holdDecember 3–5, 2027
A holiday passage connecting Norfolk’s waterfront celebrations and Yorktown’s traditional Christmas events, pending official 2027 calendars and final arrangements.
Explore this passageUnderstanding the calendar
The passage has a defined date window on the current whole-yacht calendar.
The route is created around suitable conditions and dates that work for your group.
The calendar hold may change when official event schedules or operating arrangements are finalized.
Tickets, performers, reservations, transportation, and individual activities are not confirmed until arranged in writing.
A season that matters to you
Begin with a family tradition, annual event, holiday, anniversary, client gathering, or part of the Chesapeake you want to experience. TPP will explore the right dates, route, dining, and shore plans for your private group.
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