

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: ​
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Practical navigation & seamanship (compass work, helming, sail handling, tides)
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Chesapeake Bay ecosystem & restoration (oysters, crabs, water quality)
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Historical & cultural literacy (St. Mary’s, St. Clement’s Island)
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STEAM skills (data collection, charting, simple marine science)
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Confidence, leadership, teamwork, and decision-making skills.
Our adult courses vary between vacation mode and detailed sail training, your pick!
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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...
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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)
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​Cast off from The Slips after final gear check. Short training sail on Yeocomico → Potomac approach.
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On-deck rotations: helm, sail trim, bow lookout, knot practice. Teach hand-compass basics and how to take a bearing.
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Learning module (seamanship):
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“Steer by compass” exercise: students follow a short compass course between two waypoints (teacher times & coaches).
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Chart plot: students mark position on paper chart and estimate speed via log/time.
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Afternoon
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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.
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Evening
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Team debrief & leadership reflection: roles rotated (skipper-for-hour); leadership journal prompt. Play the get to know you game "The Envelope Game".
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Day 2 — Sail to St. Clement’s Island; treasure hunt + lighthouse & museum
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Morning — transit
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Early sail toward St. Clement’s Island / Colton’s Point. Short navigation lesson on course plotting and reading channel markers.
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Late morning — St. Clement’s Island
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Land on St. Clement’s Island (state park & museum area). Explore the island, lighthouse and the monument marking Maryland’s first landing (1634).
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Activity — Compass Treasure Hunt
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Learning outcomes: compass reading under pressure, puzzle solving, team roles (navigator, recorder, leader, lookout).
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Afternoon
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Visit the St. Clement’s museum; short interpretive talk on early Maryland settlement. Return to boat; practice reefing & anchoring exercises.
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Evening dinner followed by board games and/or cards.
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Day 3 — Sail to Historic St. Mary’s City: Dove + waterfront history + oyster lesson
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Morning — transit
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Sail north toward St. Mary’s River / Historic St. Mary’s City; students log mileage and tidal trends.
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Late morning — St. Mary’s City
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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
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Afternoon — oyster restoration & crabbing lab
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Mini-lesson on blue crabs: anatomy, life cycle, and a demonstration of safe sampling (crab pots or ID shells).
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Evening: Dinner, movie, board games, star gazing, constellation ID from deck of Boundless.
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Day 4 — U-boat transit (viewing) → Shark’s Tooth Island fossil hunt → beach STEM
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Morning — transit & U-boat view
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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
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Midday — Shark’s Tooth Island (Hollis Island)
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Proceed back upriver toward Shark’s Tooth (Hollis) Island for beachcombing. Anchor off to search for fossilized shark teeth and other fossils.
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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.
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Back to boat; Reflection: how did navigation + teamwork succeed under fatigue?
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Day 5 — Return to Kinsale (The Slips) — capstone projects & departure
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Short sail back to The Slips, Kinsale.
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Dock at The Slips; boat cleanup and gear out. Debrief week, talk of future adventures together! Farewells and safety checkouts.
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Possible mini-lessons
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Compass & Coastal Navigation: hands-on bearings, triangulation from shore features, pacing, and basic dead-reckoning.
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Seamanship: knots (bowline, clove hitch, figure-eight), sail trim basics, reefing, helming, man-overboard drill (practice with a floatation dummy).
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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
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History & Interpretation: St. Clement’s landing story, early colonial navigation, Maryland Dove vessel history at St. Mary’s. Maryland Dove+1
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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.
