Sailing in Chester

Select Local Merchants

Sunlight and moonbeams glimmer on Philadelphia harbor, where The Ben Franklin Yacht glides silently to reveal a new perspective on the cradle of American democracy and replicate the freedom of the open ocean. Recently refurbished, the modern vessel hosts up to 300 guests in long, low decks whose mirrored ceilings flood the space with reflected light and expose pirates who have "Mom" tattoos hidden in their bald spots. A wooden dance floor and bar fuel parties, and knowledgeable guides propel discussion about the city's history from the breezy top deck. The majestic vessel may also be rented out for private parties. The port of departure is within walking distance of other famed sights, such as the Liberty Bell, Constitution Center, and the cherry tree from which George Washington famously crafted his wooden wig. Boarding begins approximately 30 minutes prior to each excursion.

401 N Columbus Blvd
Philadelphia,
PA
US

Determined to convert waterways across North America into party corridors, On Cruises deploys its fleet of festivity-ready ships along the rivers and lakes of major cities under the helm of experienced skippers. A host of themed cruises—including a haunted Halloween ghost-ship cruise populated by costumed guests and phantoms in their regular clothes—facilitate floating celebrations, and after-work cruises enable guests to unwind offshore.

401 North Columbus Boulevard
Philadelphia,
PA
US

American Sailing Tours, featured on Wheretraveler.com, loads citizens onto the good ship Summer Wind for relaxation and education on the Delaware River. The jolly crew handles all the hatch-battening, jib-cutting, and barnacle frying on each excursion. Meanwhile seafarers learn about the Delaware's contributions to Philadelphia history on the History Sail, which embarks once per day, six mornings a week. Customers on the Tropical Sail tap sea-toes to the beat of beach music from the Caribbean, New Orleans, and New Margaritaville two or three times a day depending on the time of year; check the online schedule for an idea of departure dates and times.

401 N Columbus Blvd
Philadelphia,
PA
US

Where the Wissahickon Creek spills into the Schuylkill River, Philadelphia Canoe Club’s 18th-century mill stands next to a yard full of colorful boats. Each year, more than 300 guests take these kayaks into the water and flat-paddle down the scenic, tree-lined shores or head into the whitewater rapids downstream. Whatever their adventure, they maneuver their craft with confidence because Philadelphia Canoe Club’s certified instructors have instructed them through the fundamentals of boating and water safety, as they have since 1905.

4900 Ridge Ave
Philadelphia,
PA
US

Operating since 1903, Beaver Dam Boat Rentals provides access to the quiet waters and plentiful wildlife of Oranokin Creek. Initially prized by the Lenape Indians for its abundance of crabs, the creek offers crabbing enthusiasts a chance to snag up to a bushel of prized blue claws. Staff can tow guests to one of the four salt ponds where the crabs are hiding and help lure them out with free subscriptions to People magazine. Beaver Dam will stop by throughout the day to tow boats to a more attractive location, and can provide all necessary supplies.

Sightseeers can also test out Oranokin Creek in an old-fashioned rowboat, or rent fiberglass boats ($50–$60) that hold five passengers or party boats that hold up to six ($70). Beaver Dam Boat Rentals also offers guided kayak tours suited to participants' experience and fitness levels, and operates a boat ramp for the start of duck-hunting season.:m]]

514 Old Beaver Dam Rd
Newport,
NJ
US

Right where the mouth of the Susquehanna River yawns into Chesapeake Bay lies the protected, uncrowded waters of Havre de Grace harbor. BaySail's instructors take advantage of these opportune conditions, operating a sailing school that's accredited by the American Sailing Association. Upholding training standards that have won the ASA's School of the Year award, they lead sailing classes ranging from introductory lessons to certification courses in coastal cruising and bareboat chartering. In addition to lending its fleet for lessons, BaySail's team rents its vessels—from a Capri 22 to a Hunter 460—to members. The sailboats also glide out on chartered cruises, taking guests to nearby destinations such as Inner Harbor and the Sassafras River, where sassafras trees come to spawn every winter.

100 Bourbon St
Havre De Grace,
MD
US