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5-Day Road Trip Adventure from Durham to NYC Itinerary

Last updated: 2024 Jun 14

Exploring Durham's Rich History

Morning

Start your day with the Durham African American History Tour. This tour will take you through significant sites that highlight the contributions and experiences of African Americans in Durham. It's a deeply educational and moving experience that sets the tone for understanding the city's rich cultural tapestry. For breakfast, head to Elmo's Diner, a local favorite known for its hearty and affordable meals.

Afternoon

After the morning tour, take a break at Cocoa Cinnamon, a highly-rated coffee shop where you can enjoy a variety of unique coffee blends and pastries. Then, embark on the Downtown Durham Historian-Guided Walking Tour. This tour will give you an in-depth look at Durham's historical landmarks and stories from its past. You'll walk through downtown, learning about the architecture and events that shaped this vibrant city.

Evening

For dinner, dine at Mateo Bar de Tapas, which offers delicious Spanish tapas with a Southern twist. Afterward, engage in some fun with the Durham Scavenger Hunt. This activity is perfect for winding down your day while still exploring more of what Durham has to offer in an interactive way.

Bedtime

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Richmond's Historic Charm

Morning

Drive from Durham to Richmond (approx. 2.5 hours). Begin your Richmond adventure with the Richmond Hollywood Cemetery Lore and Civil War Walking Tour. This tour provides fascinating insights into Richmond's role during the Civil War and highlights notable figures buried in this historic cemetery. For breakfast, visit Perly's Restaurant & Delicatessen, known for its Jewish deli fare.

Afternoon

After your morning tour, stop by Lamplighter Coffee Roasters for a refreshing coffee break. Then explore Carytown, one of Richmond’s most eclectic neighborhoods featuring unique shops and boutiques. Don’t miss out on visiting Carytown, where you can stroll through colorful streets filled with local art and culture.

Evening

For dinner, try out The Roosevelt, which offers Southern-inspired dishes made from locally sourced ingredients. End your evening with some spooky fun on the Richmond Capitol Hill Ghost Walking Tour with A Guide. This guided ghost tour will take you through some of Richmond’s most haunted locations while sharing eerie tales from its past.

Bedtime

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Scenic Drive to Annapolis

Morning

Depart Richmond early (approx. 2 hours drive) towards Annapolis while avoiding major cities as requested. Upon arrival in Annapolis, start your day with breakfast at Chick & Ruth's Delly, famous for its hearty breakfasts and quirky atmosphere. Next up is the engaging Best of Annapolis Walking Tour, which will introduce you to key historical sites and charming streets of this sailing capital.

Afternoon

Take a break at Bakers & Co for some delightful pastries and coffee before continuing your exploration with the self-guided audio tour -Annapolis Walking In App Audio Tour in Sailing Capital. This allows you to explore at your own pace while learning about Annapolis' rich maritime history.

Evening

For dinner, head over to Carrol's Creek Cafe which offers stunning waterfront views along with delicious seafood dishes. Cap off your night by joining the spooky yet entertaining activity -Phantoms of Annapolis Ghost Walking Tour-, perfect for getting acquainted with local legends and ghost stories.

Bedtime

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Exploring the Charm of Annapolis

Morning

Start your day with a hearty breakfast at Iron Rooster, known for its all-day breakfast menu and homemade pop-tarts. Afterward, embark on the Best of Annapolis Tour. This comprehensive tour will take you through the city's most iconic sites, including the United States Naval Academy and historic downtown Annapolis. It's a perfect way to get an in-depth understanding of this charming city.

Afternoon

For lunch, visit Mason's Famous Lobster Rolls for some delicious seafood. Afterward, enjoy a relaxing afternoon on the water with the Annapolis: Electric Boat Rental - Duffy Sun Cruiser - 10ppl. This activity allows you to explore Annapolis from a different perspective while enjoying the scenic views of Chesapeake Bay.

Evening

For dinner, dine at O'Learys Seafood Restaurant, which offers fresh seafood and waterfront dining. End your day with some spooky fun by joining the Annapolis Crabtown Boos and Booze Haunted Pub Crawl. This guided tour combines ghost stories with visits to local pubs, making it a unique way to experience Annapolis' nightlife.

Bedtime

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Arrival in New York City

Morning

Depart from Annapolis early (approx. 3 hours drive) towards New York City. Upon arrival, start your day with breakfast at Clinton St. Baking Company, famous for its pancakes and brunch menu. Begin your NYC adventure with a visit to Central Park, one of the city's most iconic landmarks. You can take a leisurely stroll or rent a bike to explore this vast urban oasis.

Afternoon

For lunch, head over to Katz's Delicatessen, an iconic NYC deli known for its pastrami sandwiches. Afterward, dive into some culture by visiting the renowned Metropolitan Museum of Art (The Met). Spend your afternoon exploring its vast collection of art from around the world.

Evening

For dinner, try out Joe's Pizza, a classic New York pizzeria that offers some of the best slices in town. End your evening with an unforgettable experience by joining the NYC Sightseeing Cruise with VIP Dinner, Drinks, and Service. This cruise offers stunning views of NYC's skyline along with a gourmet dinner and drinks.

Bedtime

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