South Boston

With miles of sandy swimming beaches that are now the cleanest urban beaches in the nation and the best - and most affordable - hot dogs in the city, South Boston is one of the most popular destinations for Bostonians and the region's many Southie Alums.

Start your trip at the Dorchester Heights National Historic Park (which is in Southie, not DOT) to take in the views and get an historical perspective.

Then head to the harbor and take a stroll along the HarborWalk towards fashionable M-Street beach. Be sure to keep your eyes open for the L-Street Brownies swimming on even the coldest winter days and kite surfers and fisherman as well.

To warm up - or cool off - stop in at the L-Street Tavern, South Boston's friendliest neighborhood bar, and then continue on your way to Castle Island, where you can explore Fort Independence and great views of Boston Harbor and our working port. Then enjoy a hot dog, fries and a shake (or a great clam chowder)  at Sullivan's at Castle Island. Then take a walk around Pleasure Bay to work off the calories (2.1 miles) and head to the Harpoon Beer Hall to enjoy a cold, refreshing - and well earned - Harpoon beer and the best pretzels on the planet.