Embarking on a road trip from Boston to Orlando is an exciting adventure that offers a diverse range of landscapes, cultures, and experiences. Spanning over 1,078 miles, this journey takes you through the historic Northeast, the picturesque Appalachian Mountains, and the sun-kissed Southeast. With a duration of 7 fun-filled days, you'll have ample time to explore hidden gems, indulge in local cuisine, and create lifelong memories. In this article, we'll guide you through the ultimate road trip itinerary, highlighting must-visit attractions, scenic routes, and expert tips to make your journey an unforgettable experience.
Key Points
- Explore the historic city of Boston and its surrounding attractions on Day 1
- Drive through the picturesque Appalachian Mountains and visit Hershey, Pennsylvania on Day 2
- Discover the charm of Washington, D.C. and its iconic landmarks on Day 3
- Visit the scenic Blue Ridge Parkway and enjoy outdoor activities in Asheville, North Carolina on Day 4
- Experience the vibrant city of Savannah, Georgia and its beautiful beaches on Day 5
- Drive through the scenic Florida countryside and visit St. Augustine, the oldest city in the United States on Day 6
- Arrive in Orlando and enjoy the city's theme parks, restaurants, and entertainment options on Day 7
Day 1: Boston, Massachusetts
Begin your journey in Boston, a city steeped in history and culture. Visit the Freedom Trail, a 2.5-mile red-brick walking trail that leads you to 16 iconic sites, including the Old State House, Faneuil Hall, and the USS Constitution. Explore the vibrant neighborhoods of the North End, Beacon Hill, and Cambridge, and indulge in the city’s famous seafood, particularly the clam chowder and lobster rolls. With its rich history, cultural attractions, and lively atmosphere, Boston is the perfect starting point for your road trip adventure.
Boston’s Hidden Gems
Beyond the famous landmarks, Boston has a plethora of hidden gems waiting to be discovered. Visit the Isabella Stewart Gardner Museum, a stunning Venetian-style palace with an impressive art collection. Explore the beautiful Boston Public Garden, which features the famous Swan Boats and the Make Way for Ducklings statue. For a unique experience, take a stroll along the Harborwalk Trail, which offers breathtaking views of the city skyline and the harbor.
| Attraction | Location | Hours of Operation |
|---|---|---|
| Freedom Trail | Boston, MA | 9:00 AM - 5:00 PM |
| Isabella Stewart Gardner Museum | 25 Evans Way, Boston, MA | 11:00 AM - 5:00 PM |
| Boston Public Garden | 69 Beacon St, Boston, MA | 6:00 AM - 12:00 AM |
Day 2: Hershey, Pennsylvania
On Day 2, drive to Hershey, Pennsylvania, a charming town famous for its chocolate and theme parks. Visit Hersheypark, a family-friendly amusement park with over 70 rides and attractions, including 13 roller coasters. Explore the Hershey’s Chocolate World, a interactive experience that takes you through the chocolate-making process. Don’t miss the opportunity to indulge in the town’s famous chocolate treats and drinks.
Hershey’s Scenic Routes
Hershey is surrounded by picturesque countryside and scenic routes. Take a drive along the Susquehanna River, which offers breathtaking views of the surrounding landscape. Visit the nearby town of Lancaster, known for its Amish community and traditional farmland. For a unique experience, take a hot air balloon ride over the countryside, which provides a bird’s-eye view of the region’s natural beauty.
Day 3: Washington, D.C.
On Day 3, drive to Washington, D.C., the nation’s capital and a city steeped in history and politics. Visit the iconic landmarks, including the White House, the Capitol Building, and the Lincoln Memorial. Explore the Smithsonian museums, which feature a vast collection of art, history, and culture. Don’t miss the opportunity to visit the National Mall, which offers breathtaking views of the city’s monuments and landmarks.
Washington, D.C.’s Hidden Gems
Beyond the famous landmarks, Washington, D.C. has a plethora of hidden gems waiting to be discovered. Visit the Kenilworth Aquatic Gardens, a unique park featuring water plants and flowers. Explore the vibrant neighborhood of Georgetown, which offers a mix of historic architecture, upscale shops, and trendy restaurants. For a unique experience, take a stroll along the Tidal Basin, which offers breathtaking views of the Jefferson Memorial and the cherry blossom trees.
Day 4: Asheville, North Carolina
On Day 4, drive to Asheville, North Carolina, a vibrant city nestled in the Blue Ridge Mountains. Visit the Biltmore Estate, a grand chateau-style mansion with beautiful gardens and grounds. Explore the River Arts District, a former industrial area turned arts district, which features studios, galleries, and restaurants. Don’t miss the opportunity to visit the Blue Ridge Parkway, a 469-mile scenic road that offers breathtaking views of the surrounding mountains and countryside.
Asheville’s Outdoor Activities
Asheville is a haven for outdoor enthusiasts, with a plethora of activities to suit all interests. Visit the nearby Pisgah National Forest, which offers hiking, biking, and fishing opportunities. Take a whitewater rafting trip down the French Broad River, which provides an adrenaline-pumping experience. For a unique experience, visit the Asheville Botanical Gardens, which features a variety of plant species and a beautiful glasshouse.
Day 5: Savannah, Georgia
On Day 5, drive to Savannah, Georgia, a charming city famous for its historic architecture and beautiful parks. Visit the Historic District, a 20-square-block area featuring beautiful antebellum homes, churches, and monuments. Explore the nearby Tybee Island, a charming beach town with a historic lighthouse and beautiful beaches. Don’t miss the opportunity to visit the Wormsloe Historic Site, a colonial-era estate with a beautiful avenue of live oak trees.
Savannah’s Scenic Routes
Savannah is surrounded by picturesque countryside and scenic routes. Take a drive along the Savannah River, which offers breathtaking views of the surrounding landscape. Visit the nearby town of Beaufort, known for its historic architecture and traditional southern charm. For a unique experience, take a horse-drawn carriage ride through the Historic District, which provides a romantic and nostalgic experience.
Day 6: St. Augustine, Florida
On Day 6, drive to St. Augustine, Florida, the oldest city in the United States. Visit the Castillo de San Marcos, a 17th-century fort with a rich history and stunning views of the Matanzas Bay. Explore the nearby St. Augustine Lighthouse, a historic lighthouse with a museum and beautiful views of the surrounding coastline. Don’t miss the opportunity to visit the Fountain of Youth Archaeological Park, a historic site featuring a re-creation of the first Spanish settlement in the United States.
St. Augustine’s Hidden Gems
Beyond the famous landmarks, St. Augustine has a plethora of hidden gems waiting to be discovered. Visit the Spanish Quarter, a historic neighborhood featuring traditional Spanish architecture and charming streets. Explore the nearby Anastasia State Park, which offers beautiful beaches, hiking trails, and scenic views of the surrounding coastline. For a unique experience, take a stroll along the Matanzas Bay, which offers breathtaking views of the city’s historic architecture and the surrounding waterways.
Day 7: Orlando, Florida
On Day 7, arrive in Orlando, a city famous for its theme parks and entertainment options. Visit the Walt Disney World, a massive resort featuring four theme parks, including the Magic Kingdom, Epcot, Hollywood Studios, and Animal Kingdom. Explore the nearby Universal Orlando, a theme park resort featuring the Wizarding World of Harry Potter, the Fast and Furious - Supercharged ride, and other exciting attractions. Don’t miss the opportunity to visit the Kennedy Space Center, a working NASA facility with a museum and interactive exhibits.
What is the best time to visit Boston?
+The best time to visit Boston is during the fall season, from September