Heading into Nassau County on the Sunrise Highway (Route 27), you’ll soon come to Freeport, a bustling fishing and boating community that’s the largest town on the South Shore . Freeport’s most famous native son was Guy Lombardo, and a long avenue named in his honor runs through downtown.
Freeport’s main visitor attraction is its “Nautical Mile,” located along the Woodcleft Canal, bordered by a street of the same name. Much of Freeport was built on landfill, and Woodcleft is one of seven or eight canals in town. Along it, you’ll find lots of shops, many selling arts and crafts, and a plethora of seafood restaurants, as well as fishing boats sporting signs advertising “Halfday Flounder” and “Blues AM.” On summer evenings, music beckons from outdoor bars while party boats set sail for dinner and moonlight cruises.
For more information on Freeport, contact the Freeport Chamber of Commerce (300 Woodcleft Ave., 516/223-8840, www.freeportny.com ). For more information on sportfishing, call the Freeport Boatmen’s Association (540 Guy Lombardo Ave., 516/378-4838).
In the fall, the Riverhead Foundation for Marine Research (631/369-9840, www.riverheadfoundation.org ), offers seal-watching cruises that leave from Point Lookout, south of Freeport near Jones and Lido Beaches. Check the website for the cruise schedule; rates are adults $24, seniors $21, and children $19.
Just north of Jones Beach  is Freeport Motor Inn and Boatel (445 S. Main St., 516/623-9100, www.freeportmotorinn.com , $90–105 d), a good, clean choice popular with boaters and landlubbers alike.
One of the best restaurants along the Nautical Mile is the boisterous Hudson & McCoy (340 Woodcleft Ave., 516/868-3411, $18), serving both seafood and steaks. The clientele here tends to be young and trendy. In summer, bands play on a crowded outdoor deck.