Welcome!
Lots of sailing opportunities abound in this region, for any size sailing craft. Cindy and I have sailed a Sport, Outback and a TI at a wide variety of locations on the Bay - from just above the Bay Bridge at Sandy Point State Park to as far south as Point Lookout State Park, as well as the Eastern Shore and points further afield. We've also gone sailing on the Potomac and the larger Maryland fresh water reservoirs with our yaks.
For your i14t, the sheltered waters of the smaller bays and inlets will be better, but the Bay is rife with them - both on the Western Shore and the Eastern Shore. Excellent sailing around Annapolis and the South River, with good swimming beaches at various locations - just be aware of the Chesapeake chop. The bay side of Assateague National Seashore (very shallow and excellent winds - however, be sure to stay away from the Ocean City Inlet and the rip currents there).
As far as Calvert Cliffs is concerned, it's tough getting there. We want to visit it with our TI, but the closest ramp for us to use as a put-in location is miles away. Instead, we've come to *love* Point Lookout State Park, which is further south. Point Lookout has the Bay, the mouth of the Potomac and an ultra-protected back bay called Lake Conoy to choose from. With the Potomac, I'd be cautious in the waters above the tidal section of the river, as we've had the smaller yaks get yanked around by swift underwater boils that could not be seen from the surface (the Mirage Drives shook like something was grabbing at them and the yaks were partly spun around by the force) and I don't know that I would trust the non-tidal water even when wearing a PFD. We used to canoe on the Potomac without any care or PFDs, but after that last experience we stay well clear of the upper Potomac with our yaks.
With the fresh water reservoirs, care must be taken with some of them due to the invasive Zebra mussels; at least one reservoir (can't remember which one) requires a paid registration and decals for use and the boat can *never* be used in another body of water because of fears related to the Zebra mussels. Other reservoirs aren't so restrictive and just require a thorough washing of the boat or yak between uses.
As a rule of thumb, I'd say your sailing radius with the i14t will be about 7 miles as a limit, so keep that in mind when making your plans.
Here are some videos we've taken with our Sport and Outback using the same size sail as you have:
Thomas Point lighthouse with the Sport and Outback: [youtube]http://www.youtube.com/watch?v=z-tqWY6iWrA[/youtube]
Liberty Reservoir: [youtube]http://www.youtube.com/watch?v=5Bf6oo-nODo[/youtube]
Triadelphia Reservoir: [youtube]http://www.youtube.com/watch?v=07f_AHImDIY[/youtube]
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