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Chesapeake Bay

Three to seven day live-aboard sailing adventures for families, adults, cruising couples or our premier educational program for students/teachers! 

Our 5-day educational trips for 6 students + 1 teacher focus on: â€‹

  • Practical navigation & seamanship (compass work, helming, sail handling, tides)

  • Chesapeake Bay ecosystem & restoration (oysters, crabs, water quality)

  • Historical & cultural literacy (St. Mary’s, St. Clement’s Island)

  • STEAM skills (data collection, charting, simple marine science)

  • Confidence, leadership, teamwork, and decision-making skills.

Our adult courses vary between vacation mode and detailed sail training, your pick!

  • Sail training from beginning through advanced. Chart reading, route planning, weather sources/planning, heavy weather preparation, provisioning, long distance voyaging, anchoring, boat preparation, ICW prep, electronics aboard from EPIRB's to Starlink, watch keeping, night passages, and more...

  • Vacation trips are the ideal getaway for a chance to reconnect with family and friends. Spend a few to several days sailing to coastal towns and uninhabited islands. Explore ashore for an afternoon and eat dinner at a local seafood restaurant. Have time to read while sitting at anchor in a quiet cove or go for a swim and shower off on deck. We will help you design a perfect getaway...

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Day 1 — Arrive Kinsale (Sample itinerary)

  • ​Cast off from The Slips after final gear check. Short training sail on Yeocomico → Potomac approach.

  • On-deck rotations: helm, sail trim, bow lookout, knot practice. Teach hand-compass basics and how to take a bearing.

  • Learning module (seamanship):

  • “Steer by compass” exercise: students follow a short compass course between two waypoints (teacher times & coaches).

  • Chart plot: students mark position on paper chart and estimate speed via log/time.

  • Afternoon

  • Anchor in a quiet cove for lunch and a shoreline mini-lesson: Potomac estuary basics (salinity, tidal influence, what makes a Bay). Collect a simple water sample (turbidity tube + salinity refractometer) and record.

  • Evening

  • Team debrief & leadership reflection: roles rotated (skipper-for-hour); leadership journal prompt. Play the get to know you game "The Envelope Game".

  • Day 2 — Sail to St. Clement’s Island; treasure hunt + lighthouse & museum

  • Morning — transit

  • Early sail toward St. Clement’s Island / Colton’s Point. Short navigation lesson on course plotting and reading channel markers.

  • Late morning — St. Clement’s Island

  • Land on St. Clement’s Island (state park & museum area). Explore the island, lighthouse and the monument marking Maryland’s first landing (1634). 

  • Activity — Compass Treasure Hunt

  • Learning outcomes: compass reading under pressure, puzzle solving, team roles (navigator, recorder, leader, lookout).

  • Afternoon

  • Visit the St. Clement’s museum; short interpretive talk on early Maryland settlement. Return to boat; practice reefing & anchoring exercises.

  • Evening dinner followed by board games and/or cards. 

  • Day 3 — Sail to Historic St. Mary’s City: Dove + waterfront history + oyster lesson

  • Morning — transit

  • Sail north toward St. Mary’s River / Historic St. Mary’s City; students log mileage and tidal trends.

  • Late morning — St. Mary’s City

  • Visit Historic St. Mary’s City and Maryland Dove (replica tall ship exhibit). Tour the Dove (if docked) and waterfront exhibits; docent talk covers 17th-century mariner life and settlement. Maryland Dove

  • Afternoon — oyster restoration & crabbing lab

  • Mini-lesson on blue crabs: anatomy, life cycle, and a demonstration of safe sampling (crab pots or ID shells). 

  • Evening: Dinner, movie, board games, star gazing, constellation ID from deck of Boundless.

  • Day 4 — U-boat transit (viewing) → Shark’s Tooth Island fossil hunt → beach STEM

  • Morning — transit & U-boat view

  • Early departure toward the Piney Point / Potomac U-1105 area. From an appropriate safe distance and following navigation channel rules, slow-pass the marked wreck area so students can observe (discuss wreck history and WWII context). NOTE: this wreck sits deep; observation is from surface only—no diving without certified operator/permits. marineprotectedareas.noaa.gov

  • Midday — Shark’s Tooth Island (Hollis Island)

  • Proceed back upriver toward Shark’s Tooth (Hollis) Island for beachcombing. Anchor off to search for fossilized shark teeth and other fossils.  

  • While beached/anchored, run a short sampling lab: sieving sand for microfossils, measuring sediment grain size, and discussing the paleo-environment that deposited those fossils. Discuss erosion and human impacts.

  • Back to boat; Reflection: how did navigation + teamwork succeed under fatigue?

  • Day 5 — Return to Kinsale (The Slips) — capstone projects & departure

  • Short sail back to The Slips, Kinsale.

  • Dock at The Slips; boat cleanup and gear out. Debrief week, talk of future adventures together! Farewells and safety checkouts.

  • Possible mini-lessons 

  • Compass & Coastal Navigation: hands-on bearings, triangulation from shore features, pacing, and basic dead-reckoning.

  • Seamanship: knots (bowline, clove hitch, figure-eight), sail trim basics, reefing, helming, man-overboard drill (practice with a floatation dummy).

  • Chesapeake Health: water sampling (pH, turbidity, salinity), plankton tow demo (safety—no dangerous lab handling), oyster filtering role & reef ecology. Cite local oyster restoration partners for program options. Chesapeake Bay Environmental Center

  • History & Interpretation: St. Clement’s landing story, early colonial navigation, Maryland Dove vessel history at St. Mary’s. Maryland Dove+1

  • Field Paleontology: fossil search protocols, identification of shark teeth vs. other fossils, recording finds.

Cost: $1,275 per student (based on 6) and includes 5 days/4 nights lodging on Boundless, a Captain and First Mate, all educational materials, instruction, museum entrance fees, dockage, fuel, and all meals on board. Meals ashore (group's choice), extra museums/events not on our itinerary, and/or airport pickup, additional. Transportation to/from our departure location in Kinsale, VA, not included. A teacher attends for free including airfare with six students.

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