The Ultimate Two-Week East Coast Road Trip: From Maine to Florida

Quick Reference Timeline

Days 1-3: New England

• Maine Coast

• White Mountains

• Boston

Days 4-5: New York

• Hudson Valley

• New York City

Days 6-7: Mid-Atlantic

• Philadelphia

• Washington D.C.

Days 8-10: The Carolinas

• Blue Ridge Parkway

• Charleston

• Savannah

Days 11-14: Florida

• St. Augustine

• Kennedy Space Center

• Miami & The Keys

Detailed Itinerary

Days 1-2: Maine Coast

Start: Portland International Jetport Drive time to Acadia: 3.5 hours (175 miles) Drive time to White Mountains: 4 hours (230 miles)

Begin your journey in Portland, Maine, where the Old Port district showcases classic New England charm. The cobblestone streets and brick buildings house seafood restaurants and local boutiques. Take a morning ferry to nearby Peaks Island for stunning views of Casco Bay and the city skyline.

Drive up the coast to Acadia National Park, where mountains meet the Atlantic. The Park Loop Road provides access to key sites: Thunder Hole's booming waves, Sand Beach nestled between granite cliffs, and Cadillac Mountain's panoramic views. Drive the entire loop, stopping at Jordan Pond House for traditional popovers with views of the Bubbles mountains.

Your second day explores Mount Desert Island thoroughly. Start with sunrise from Cadillac Mountain - the first place to see the sun rise in the United States (October through March). The historic carriage roads, built by John D. Rockefeller Jr., provide excellent car-free cycling opportunities. End your day in Bar Harbor, watching lobster boats return with their daily catch.

Days 3-4: White Mountains & Boston

Drive time from Acadia to White Mountains: 4 hours (230 miles) Drive time to Boston: 2.5 hours (150 miles)

Begin your White Mountains experience on the Kancamagus Highway, one of New England's most scenic drives. This 34-mile route winds through White Mountain National Forest, offering numerous hiking trails and scenic overlooks. Stop at Sabbaday Falls for an easy hike to a three-tiered waterfall. The Conway Scenic Railroad provides another perspective on the mountains' grandeur.

Arrive in Boston by mid-afternoon of Day 4. Begin at Boston Common, America's oldest public park, and follow the Freedom Trail's red brick line through history. The trail connects 16 significant Revolutionary War sites, including Paul Revere's House and the USS Constitution. End your day in the North End, Boston's Little Italy, where historic churches share narrow streets with authentic Italian restaurants.

Days 5-6: New York City

Drive time from Boston: 4 hours (215 miles) Base: Manhattan

Manhattan deserves focused exploration. Start your first day in Lower Manhattan at the 9/11 Memorial, then walk across the Brooklyn Bridge for magnificent skyline views. Return via subway to Central Park, where the Mall's elm-lined promenade leads to Bethesda Fountain. The Metropolitan Museum of Art provides a cultural finale to your day.

Your second day explores different neighborhoods. Start in Greenwich Village's historic streets, then walk the High Line, an elevated park built on former railway tracks. The afternoon takes you to distinct neighborhoods: SoHo's cast-iron architecture, Chinatown's bustling streets, and the Lower East Side's immigrant history. End atop the Empire State Building or Top of the Rock for sunset views across the city.

Days 7-8: Philadelphia & Washington D.C.

Drive time from NYC to Philadelphia: 2 hours (97 miles) Drive time to Washington D.C.: 2.5 hours (140 miles)

Philadelphia's historic district concentrates America's foundational story within a few walkable blocks. Start at Independence Hall, where both the Declaration of Independence and Constitution were debated and signed. The Liberty Bell, Reading Terminal Market, and the Benjamin Franklin Parkway leading to the "Rocky Steps" round out your morning.

Arrive in Washington D.C. by late afternoon. Start at the Lincoln Memorial, walking along the Reflecting Pool toward the Washington Monument. The Vietnam Veterans Memorial provides a moving end to your day.

Dedicate your full day in D.C. to the National Mall's highlights. The Smithsonian museums offer free admission - focus on the National Air and Space Museum and the American History Museum. The afternoon takes you to Georgetown's historic streets and vibrant waterfront. Consider an evening monument tour when the marble structures glow against the night sky.

Days 9-10: Blue Ridge Parkway & Charleston

Drive time from D.C. to Blue Ridge Parkway entrance: 4 hours (250 miles) Drive time along Parkway sections: Variable Drive time to Charleston: 7 hours (450 miles)

The Blue Ridge Parkway, "America's Favorite Drive," winds through the Appalachian Mountains. Start at Shenandoah National Park, taking Skyline Drive to connect with the Parkway. Notable stops include Mabry Mill, one of the most photographed sites on the Parkway, and Mount Mitchell, the highest peak east of the Mississippi.

Arrive in Charleston by mid-afternoon the next day. The historic downtown peninsula showcases antebellum architecture at its finest. Start in the French Quarter, where historic churches and hidden gardens transport you to another era. The Battery promenade offers views across Charleston Harbor while Rainbow Row's colorful historic homes provide perfect photo opportunities.

Days 11: Savannah

Drive time from Charleston: 2 hours (108 miles) Drive time to St. Augustine: 3.5 hours (280 miles)

Savannah's historic district unfolds around 22 peaceful squares, each a shaded retreat lined with moss-draped live oaks and historic homes. Start at Forsyth Park, with its iconic fountain and weekend farmers' market. The park's wide paths, lined with massive oak trees dripping Spanish moss, showcase why Savannah is considered one of America's most walkable cities.

River Street, paved with ballast stones from colonial-era ships, represents the city's historic maritime trade. The renovated cotton warehouses now house shops and restaurants, while cargo ships still pass by on their way to the modern port.

Days 12-14: Florida

Drive time from Savannah to St. Augustine: 3.5 hours (280 miles) Drive time to Miami: 5 hours (310 miles)

Begin your Florida exploration in St. Augustine, America's oldest city. The Castillo de San Marcos, the oldest masonry fort in the continental United States, stands guard over the historic district. The Spanish Colonial architecture creates a distinctly European atmosphere unique in North America.

Continue south to Kennedy Space Center, where the history of space exploration comes alive. The Rocket Garden showcases the evolution of American spacecraft, while the Space Shuttle Atlantis exhibit demonstrates the complexity of space travel.

Complete your journey in Miami and the Florida Keys. Miami's South Beach Art Deco Historic District presents the world's largest collection of Art Deco architecture, particularly stunning during golden hour. The Wynwood Arts District showcases Miami's contemporary creative energy through massive murals and innovative galleries.

Spend your final day driving the Overseas Highway to Key West, where the Continental United States meets the tropics. Stop at Key Largo for world-class snorkeling, Islamorada for sport fishing, and end at Key West's Mallory Square for a classic sunset celebration.

This two-week East Coast journey connects America's historical roots with its natural beauty, from New England's rugged coast to Florida's tropical keys. While covering significant distance, each stop provides unique insights into American history and culture.

Travel Tips:

• Book accommodations well in advance, especially in major cities

• Consider a mix of urban hotels and coastal B&Bs

• Many historic sites are free or offer combination tickets

• Use public transportation in major cities

• Weather varies significantly from Maine to Florida - pack accordingly

• Best seasons: Late spring or early fall for moderate temperatures

• Consider flying into Portland, ME and out of Miami

• Build in flexibility for traffic in urban areas