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The word "trail" has never been less rough and tough: The Brandywine Valley Wine Trail features eight estate vineyards located in the rolling hills of Chester County, Pennsylvania, just east of Philadelphia. Spend a relaxing day discovering charming tasting rooms and barrel-aging cellars - and enjoying wine after wine.

Six years ago, the Black Walnut, Chaddsford, Penns Woods, and Twin Brooks Wineries banded together with Pantone Cellars, the Kreutz Creek, Paradocx, and Stargazers Vineyards to create the Trail, which you can hop on or off at any point. Since most of the wineries are within about 20 miles of the Sheraton Great Valley Hotel, you can take your pick. Some highlights: The 30-acre Chaddsford Winery is the state's largest, and bottles an impressive range of grapes - taste everything from a multiple award-winning Syrah to a Super Tuscan-style blend of Cabernet Sauvignon and Sangiovese to unoaked Chardonnay in its renovated colonial barn. If Italian wines appeal to you, you'll want to check out the Penn Woods Winery. Winemaker Gino Razzi was awarded 95 points by Wine Spectator for his 1997 Montepulciano d'Abruzzo, and brought that impressive talent to Pennsylvania, purchasing this winery and its 30-year-old vineyards in 2004. Among his offerings are the Traminette, a Gewurtraminer hybrid, and the zesty "No Name" rose. A relatively new winery, Black Walnut officially crushed its first grapes in 2006 - try the light and crisp Vidal Blanc or, if the season is right, sip on the Spiced Apple wine.

The Liberty Bell and Independence Hall draw scores of history-seeking visitors to Philadelphia every year, but a lesser known site offers an even better picture of what life was like for Americans in the 18th century. Constructed in 1702, Elfreth's Alley is the oldest continuously inhabited street in the United States, and its meticulously preserved Georgian and Federal-style houses and narrow, cobblestone street can easily make you feel like you've traveled back in time 300 years. Named after Jeremiah Elfreth, an 18th century blacksmith, the alley was once the province of furniture builders, glass blowers, and silversmiths. While today's residents tend toward contemporary careers, visitors will see few of the trappings of modern society on its 32 buildings. Start with a visit to the Elfreth's Alley Museum, which occupies two buildings, Jeremiah Elfreth's house and the Chairmaker's House. Take a guided tour of the museum and then stroll up and down the street using one of several free Cell Phone Tours with themes like "A Community of Artisans" and "Women and Community in 18th Century Philadelphia." The alley is especially enchanting around the holiday season, as the Deck the Alley celebration lends the street a festive atmosphere with caroling, holiday treats, and special tours of houses not normally open to the public. It's a great way to experience American history. Starwood has hotels throughout Philadelphia, including the nearby Sheraton Society Hill Hotel.

[image via gophila.com]

Philadelphia's Schuylkill Banks is one of the best places in the city to stretch your legs while appreciating its natural beauty, with a 1.2 mile landscaped walking path and plenty of open spaces to toss a Frisbee or kick a soccer ball. When you're done with your hike, run, or bike ride, why not cool down with a romantic cruise along the Schuylkill River? Boat tours depart from the park and visit historic sites along the river. The Secrets of the Schuylkill, for example, is a one-hour tour on the (bar-equipped) RiverLoop that highlights the past, present, and future of the "hidden river," visiting Bartram's Garden (pictured), the Fairmount Water Works, and a number of cutting-edge skyscrapers that represent the newest addition to the Philadelphia skyline. Tours run through October and depart from the Walnut Street Dock. Those with an adventurous spirit, meanwhile, might prefer to explore the river in a kayak on a Schuylkill Banks Kayak Tour. Several guided tours are available, including daytime and moonlight tours to the Fairmount Water Works. There are few better ways to appreciate the beauty of this classic American city. Starwood has hotels throughout Philadelphia, including the Sheraton Society Hill Hotel.

[image via Schuylkill Banks]