Up to 8 hours
Set sail on an unforgettable 8-hour journey across Maryland’s iconic Chesapeake Bay. Whether aboard a luxury yacht or a classic trawler, explore historic harbors, secluded islands, and vibrant waterfront towns with ample time for fishing, swimming, and relaxation.
More ways to explore the area's outdoor wonders
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Difficulty
moderate
Duration
8 hours
Fitness Level
Moderate fitness recommended to enjoy active swimming, light kayaking, and onboard movement safely.
Wildlife
History
The Chesapeake Bay has been a critical waterway for centuries, with settlements dating back to the colonial era and a rich Native American history along its shores.
Conservation
Local efforts focus on restoring oyster populations and reducing pollution to maintain the bay’s delicate ecological balance.
Chesapeake Charter Experiences
Up to 8 hours
Chesapeake Charter Experiences is a charter company based in Pasadena, Maryland, offering curated boat trips on Chesapeake Bay. Featured on The Adventure Collective, the company specializes in signature full-day and half-day excursions designed for small groups, families, and friends seeking scenic and activity-focused outings.
The Signature Full Day trip embarks guests aboard a luxurious yacht or a charming trawler for an extended Chesapeake Bay adventure. Guests can explore iconic landmarks, visit secluded islands, and tour vibrant waterfront towns. The full-day experience includes opportunities for fishing, enjoying gourmet meals, and relaxing in serene coves while taking in panoramic water views.
The Signature Half Day option gives guests a choice between a 71-foot motor yacht for a lavish escape and a 38-foot Mariner Trawler for an intimate exploration. Both half-day experiences offer wildlife viewing, coastal scenery, and flexible itineraries tailored to the group’s interests.
Chesapeake Charter Experiences operates on Chesapeake Bay waters accessible from Pasadena, Maryland, and focuses on delivering memorable, scenic outings that combine comfort and local coastal exploration. The company’s offerings emphasize quality time on the water, photographic vistas, and hands-on activities like fishing and island visits. Clear trip summaries, distinct vessel options, and a range of half- and full-day choices provide transparency for guests planning an outing. For travelers seeking a curated Chesapeake Bay boating experience with multiple vessel options and varied day-lengths, Chesapeake Charter Experiences presents straightforward, activity-rich trips suited to group leisure and exploration. Available vessels support relaxed sightseeing, fishing, and private group celebrations on the water.
Base Location
Pasadena, MD
Launch point for Chesapeake Bay charters
Vessel Options
71-ft yacht • 38-ft trawler
Luxury and intimate vessel choices
Trip Lengths
Full & Half Day
Flexible day-length options offered
Featured On
The Adventure Collective
Recognized on a curated travel platform
Select a Signature Full Day or Signature Half Day trip to experience scenic cruising, fishing, and island visits from Pasadena, Maryland.
Bring Sun Protection
The Chesapeake Bay offers expansive open-water exposure—pack and regularly apply sunscreen to protect against intense sun.
Pack a Swimsuit and Towel
Anchor in quiet coves to swim and paddleboard—having swimwear ready maximizes your enjoyment during water stops.
Wear Non-Slip Deck Shoes
Boat decks can be wet and slippery; sturdy, non-slip footwear improves safety while moving around the yacht or trawler.
Prepare for Variable Weather
Weather can change rapidly on the bay; bring a light waterproof jacket even on sunny days.
Sunglasses
Protect your eyes from glare reflecting off the water throughout the day.
summer
Light Waterproof Jacket
Keep dry and comfortable during unexpected spring showers or wind.
spring
Swimsuit
For swimming and water activities while anchored in secluded coves.
summer
Non-Slip Deck Shoes
Ensure safe footing onboard the vessel regardless of season.