Washington, D.C. & New York City 6-Day Trip Itinerary

Arrive in Washington D.C.

Fly from Greensboro to Washington D.

C. and transfer to your hotel. Settle in and prepare for your D.C. adventure.

Suggest flying into Ronald Reagan Washington National Airport (DCA) for closer proximity to downtown.

Lunch near Hotel

Enjoy a casual lunch near your accommodation in downtown D.

C. to recharge after your journey.

Many casual dining options are available in the Penn Quarter area near Motto By Hilton.

Explore The Wharf DC

Visit this vibrant waterfront neighborhood offering shops, restaurants, and entertainment.

Enjoy a leisurely stroll along the pier.

A lively area perfect for an afternoon walk. Consider grabbing a drink at one of the waterfront bars.

City Cruises Washington DC

Enjoy a relaxing evening cruise with monumental views of D.

C.'s landmarks from the water. Great photo opportunities.

Booking in advance is recommended, especially for popular evening cruises.

Dinner at The Wharf

Dine at one of the many restaurants at The Wharf, offering a variety of cuisines with waterfront views.

Consider fresh seafood options available in the area.

National Mall Exploration

Visit iconic monuments like the Lincoln Memorial, Washington Monument (exterior), and Reflection Pool.

Enjoy a walk through America's front yard.

Wear comfortable shoes as there is a lot of walking involved. Photos are a must!

Lunch in D.C.

Grab a quick and casual lunch before heading to the train station for your journey to New York City.

Travel to New York City

Take an Amtrak train from Washington D.

C.'s Union Station to New York City's Penn Station. Enjoy the scenic journey.

Amtrak Acela Express is faster but more expensive; Northeast Regional is a good balance of speed and cost.

Check-in NYC Hotel

Arrive at your hotel in Chelsea, check in, and refresh after your train journey.

Dinner in Chelsea

Explore the vibrant Chelsea neighborhood for dinner, with a wide array of dining options from casual to upscale.

Chelsea Market offers many food stalls and restaurants if you prefer a lively atmosphere.

Washington Square Park Tour

Take an audio tour of Washington Square Park, a historic and lively hub in Greenwich Village.

Discover the park's history and significance while enjoying its vibrant atmosphere.

Greenwich Village Stroll

Wander through the charming streets of Greenwich Village, known for its bohemian history, historic architecture, and unique boutiques.

Explore Bleecker Street for interesting shops or Grove Court for picturesque brownstones.

Lunch in Greenwich Village

Enjoy lunch at one of the many cafes or eateries in Greenwich Village, offering diverse cuisines.

Plenty of options ranging from pizza slices to upscale bistros.

Museum of Sex

Explore the history and evolution of human sexuality through immersive exhibitions at this unique museum.

A fascinating and thought-provoking visit. Check for specific exhibition schedules.

Dinner near Flatiron

Dine in the Flatiron District, known for its iconic building and varied culinary scene.

Times Square & Rockefeller Center

Experience the bustling energy of Times Square and visit Rockefeller Center, home to NBC Studios and iconic views.

Best to visit Times Square in the morning to avoid the densest crowds. Consider taking photos from the red steps.

Central Park Exploration

Enjoy a leisurely walk through Central Park, visiting famous spots like Bethesda Terrace, Strawberry Fields, or The Mall.

Rent a rowboat on the Lake or a bike to cover more ground if you wish.

Lunch near Central Park

Dine at a restaurant near Central Park, perhaps on the Upper West or East Side.

Shopping or Museum Visit

Choose between exploring the shops along Fifth Avenue or visiting a world-class museum like the Museum of Modern Art (MoMA) or Metropolitan Museum of Art (Met).

Booking museum tickets in advance is highly recommended.

Broadway District Dinner

Have dinner in the lively Theater District, with many pre-theater dining options.

This could be a good night to catch a Broadway show if interested (not included in this itinerary).

George Washington Bridge

Visit the iconic George Washington Bridge.

You can walk across for stunning views of the Hudson River and Manhattan skyline, or enjoy the view from nearby Fort Washington Park.

A great spot for panoramic photos. The pedestrian walkway offers a unique perspective.

Lunch in Upper Manhattan

Enjoy lunch in an Upper Manhattan neighborhood after visiting the bridge, perhaps in Washington Heights or Harlem.

Free Time / Last Minute Shopping

Spend your afternoon doing some last-minute souvenir shopping or revisit a favorite spot in the city. You could also relax at a café.

Consider shopping in SoHo for trendy boutiques or department stores around Herald Square.

Farewell NYC Dinner

Enjoy a memorable farewell dinner in New York City, choosing a cuisine or restaurant that suits your taste.

Consider a rooftop bar for post-dinner drinks and city views.

Prepare for Montreal Travel

Head back to your hotel to pack and prepare for your departure to Montreal tomorrow morning.

Notre-Dame Basilica

Begin your day with a visit to the stunning Notre-Dame Basilica of Montreal, a masterpiece of Gothic Revival architecture.

Admire its intricate details, stained glass windows, and the serene ambiance.

Arrive early to avoid crowds. Check for specific mass times if you wish to attend a service. There is often an entrance fee for tourists.

Explore Old Montreal

Wander through the cobblestone streets of Old Montreal, soaking in the European charm.

Discover historic buildings, charming boutiques, and art galleries.

Wear comfortable shoes for walking. Many hidden gems can be found in the smaller side streets.

Images Boréales Inuit Art Gallery

Visit the Images Boréales Inuit Art Gallery, showcasing stunning contemporary and traditional Inuit art.

A unique cultural experience.

Admission is free. Great place to find unique Canadian art and souvenirs.

Smoked Meat Lunch

Enjoy a classic Montreal experience with a traditional smoked meat sandwich at a local deli.

Pair it with fries and a cherry cola.

Schwartz's is famous but often has a long queue. Many other excellent delis offer similar quality.

Montreal Museum of Archaeology and History

Delve into Montreal's past at the Pointe-à-Callière, Montreal Museum of Archaeology and History.

Explore underground ruins and fascinating exhibitions that trace the city's origins.

Allow ample time for the underground archaeological crypt. Great for understanding the city's foundation.

Travel to Montreal Airport (YUL)

Allow sufficient time to travel from Old Montreal to Pierre Elliott Trudeau International Airport for your departure.