Sarasota to Westwood train

A culturally-rich alternative to the nearby theme parks of Orlando, Sarasota's Gulf Coast location is hard to resist. It became the winter base for many well-to-do families in the early twentieth century, during which time much of the town developed a subtle Italian feel.

Not only is the climate similar to what you might experience in southern Italy, but many of Sarasota's buildings were constructed to resemble the country's renaissance masterworks too. A good example is the Ringling family's Ca' d'Zan Venetian-style mansion.

The Ringlings made their money from circuses before giving their name to the much-celebrated John and Mable Ringling Museum of Art. It contains 21 galleries of European paintings, archaeological artifacts, and American art totaling 10,000 objects.

With weather so fine, you'll probably be looking with more than half an eye at Sarasota's numerous excellent resorts and beaches, many of which lie on a group of keys within the city limits. Bonus: our research ranked Sarasota as the #3 cheapest Spring Break destination, so you can soak up the sun on the cheap.

Arriving in Sarasota is equally easy thanks to its Cattleman Transfer Centre and Fruitville Road bus stations. Between them, travelers can connect by bus everywhere from Tampa to Tucson. Amtrak also operates a Thruway bus service from the defunct Sarasota rail station to Tampa for onward connections by train on the Silver Service. This service runs between Miami and New York City via Washington, D.C.

Westwood, Massachusetts, is a small town about 13 miles outside of Boston. This quaint suburb's high-quality school system and 30-minute commute into Boston make it a popular place for families to live.

Although Westwood maintains a distinct small-town vibe, there are growing shopping opportunities in the University Station area and along High Street. Buckmaster Pond is a popular spot for fishing, picnicking, walking, and in the winter, ice skating. Several working farms in the area welcome visitors to walk around the land, meet barnyard animals, and purchase fresh produce and goods. The historic Bradley Estate in neighboring Canton is also a gorgeous place to explore in the area.

Westwood connects to Boston via the MBTA commuter rail and is located right off I-95. Westwood also has its own Amtrak station, connecting to Amtrak's Northeast Regional line and Acela services.