Boston winters are legendary — nor’easters, icy sidewalks, and below-zero wind chills. These warm-weather road trips head south along the coast or cut inland to reach sunshine and mild temperatures.
Boston → New York → Virginia Beach → Outer Banks → Myrtle Beach → Charleston
Drive the length of the East Coast to reach the warm, palmetto-lined beaches of the Carolinas. Each stop gets warmer as you go, with Charleston’s mild climate and world-class food waiting at the end.
Boston → Philadelphia → Washington DC → Jacksonville → Cocoa Beach → Miami
Follow I-95 south to Florida’s Space Coast where you can watch rocket launches and catch perfect waves, then continue to the tropical heat of Miami and the Keys.
Boston → New York → Washington DC → Savannah → Jekyll Island → St. Simons Island
Georgia’s Golden Isles are one of the South’s best-kept secrets. Quiet beaches, historic ruins, wild horses on Cumberland Island, and Savannah’s world-famous hospitality — all in a warm, subtropical climate.
Boston → Philadelphia → Charlotte → Atlanta → Pensacola → Destin
Cut through the Southeast to reach the emerald-green waters and white-sand beaches of the Florida Panhandle. Destin is known as the ‘World’s Luckiest Fishing Village’ and offers warm weather when Boston is buried in snow.
Boston → Connecticut → New Jersey Turnpike → Richmond → Hilton Head Island
A straightforward I-95 run to one of the East Coast’s premier resort islands. World-class golf, quiet bike paths, and mild winter temperatures make Hilton Head the perfect Boston escape.