Special shout-out to my husband and favourite travel partner who has taken most of our travel photos.

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New York itinerary in 5 days

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Hotels

Hotel 414

♥♥♥♥

Located in the Hell's Kitchen neighbourhood. This lovely, small, boutique hotel is comprised of two nicely renovated, historical townhouses with an inner courtyard. It is located on a quiet residential street. Bonus - they include breakfast and afternoon wine and cheese!

Guides and Tours
  • Harlem Heritage Tours.  This tour company offers walking tours, as well as a variety of other tours, of Harlem. The tour was both entertaining and informative. We learnt about the African American and Latin American history in the neighbourhood and the gentrification that is slowly transforming the area.

Our family loves road trips so we decided to drive from Toronto to New York for a few days of sightseeing, museums, music and good food. 

You can never get tired of New York. There are countless things to see and do no matter what your travel style.

Day 1

 

Afternoon

We arrived in New York and checked into Hotel 414 located in the Hell's Kitchen neighbourhood. This lovely, small, boutique hotel is comprised of two nicely renovated, historical townhouses with an inner courtyard. It is located on a quiet residential street. Bonus - they include breakfast and afternoon wine and cheese!

We took the train to trendy Williamsburg, Brooklyn to wander around. This hip neighbourhood was once home to orthodox Jewish immigrants but is now filled with  fashionable boutiques, cafes, restaurants and clubs.   

We grabbed lunch in a diner there.

Evening

When we're in New York we like to catch some live music, especially Jazz. This evening we had a reservation at Dizzy's Club Coca-Cola at Lincoln Centre. It really is a perfect place to listen to great jazz and have a nice dinner. There are great views of Manhattan as well. Reservations are required.

Day 2

 

Morning 

After breakfast we went headed toward Lower Manhattan and the Ground Zero 9/11 memorial. The memorial was built to honour the victims of the September 11, 2001 terror attack on the World Trade Centre, in Pennsylvania and the Pentagon as well as the six people killed when the World Trade Centre was bombed in 1993.

The memorial consisting of two reflecting pools and a large waterfall sit in the footprints of where the twin towers once stood. The names of the victims are inscribed in panels along the perimeter of the memorial. It is very moving and powerful.

Next to it, there is now a museum which was not complete when we were there but I've heard is excellent.

From there we went to South Street Seaport which is nice to walk around. From here you can take a ferry to Staten Island or a sight-seeing boat to see the Statue of Liberty. The high-speed boats are fun but the ferry is certainly much less expensive.

 

Tip: South Street Seaport is a good spot to purchase half-price tickets to Broadway shows. The lines here are much shorter and the ticket office opens earlier so you have a better selection of tickets.

Afternoon

We took the subway all the way up to Harlem - there are express trains which are quite quick.

 

Our destination was Sylvia's Restaurant - an iconic Harlem eatery. Sylvia is known as the Queen of Soul Food and her restaurant has been serving this comfort food for over 50 years. Some of her specialties include fried chicken, grits and collard greens.

Following lunch we had a walking tour of Harlem by Harlem Heritage Tours.  The tour guide was a native resident of Harlem and was both entertaining and informative. We heard about the African American and Latin American history in the neighbourhood and the gentrification that is slowly transforming the area.

Evening

This evening we had dinner reservations at Marseille Restaurant in the Hell's Kitchen neighbourhood. This was good and convenient as we had tickets for a Broadway show.

Day 3

Morning

After breakfast we took the subway down to Greenwich Village. We wandered around the area, browsing in and out of interesting shops and boutiques.

We had lunch at Monte's Trattoria in the heart of Greenwich Village. This authentic restaurant opened in 1918 and continues with its rich tradition of homemade pastas and dishes.

Afternoon

We spent the afternoon walking around Chelsea. We went to the Chelsea Market for a little dessert/snack and then climbed up to the High Line for a beautiful walk along this elevated park and rail trail.

 

The High Line extends all the way from Gansevoort Street – three blocks below 14th Street – in the Meatpacking District, through Chelsea, to the northern edge of the West Side Yard on 34th Street near the Javits Center. This should be on everyone's list of things to do in New York.

We also spent some time visiting the private art galleries in Chelsea.

Evening

This evening we went to the Blue Note in Greenwich Village for dinner and music. Many famous jazz musicians have played at this well-known jazz venue.

Day 4

 

Morning 

This morning we walked to Central Park and strolled through the park visiting Strawberry Fields, the area dedicated to the memory of the former Beatle, John Lennon.

Afternoon

We stopped for lunch in a deli and then spent the rest of the afternoon at the MoMA (Museum of Modern Art) which has an incredible collection of modern and contemporary art.

Evening

This evening we went to Fig and Olive in the Meatpacking district for dinner. I like this restaurant as it serves delicious, fresh, Mediterranean-style food.

Day 5

 

Morning

This morning we took the subway down to the Lower East Side of Manhattan. This area is where many immigrants arrived and lived in their first years in the U.S., in particular the Jewish immigrants from Europe.

We did a walking tour organized by the Tenement Museum. The tour included visits to some of the crowded apartments and stories of the tenants who lived in these buildings and worked in the neighbourhoods' factories under horrible conditions. 

It is highly recommended that you book tickets in advance as these tours get quite busy and often sell out.

Afternoon

After the tour we went to the iconic Katz's Delicatessen for lunch. Their legendary smoked meat sandwiches and Jewish classics are delicious. For some added fun, you can sit in the same seats from the famous scene in the movie When Harry Met Sally. This scene was shot there.

After lunch we decided to walk off our food and head to Canal Street, in the centre of Chinatown. This area is known for its bargain shopping - especially designer knock-offs.  We spent some time browsing and then walked to SOHO with its trendy shops and cafes.

Evening

This evening we had a reservation at Becco, one of Lidia Bastianich's  restaurants (of the cooking show Lidia' Italy). This restaurant is located in Restaurant Row not far from our hotel. Their dinner menu includes a reasonably priced "all you can eat" pasta special which is a great deal, but there is also an a-la-carte menu available.

Day 6

Morning 

After breakfast we packed our car and started our road trip back home. 

For more ideas of things to do in New York check my New York itinerary in 3 days.

Noteworthy Restaurants
  • Dizzy's Club Coca-Cola at Lincoln Centre. This is a perfect place to listen to great jazz and have a nice dinner. There are great views of Manhattan as well. Reservations are required.

  • Sylvia's Restaurant is an iconic Harlem eatery. Sylvia is known as the Queen of Soul Food and her restaurant has been serving this comfort food for over 50 years. Some of her specialties include fried chicken, grits and collard greens.

  • Marseille Restaurant is located in the Hell's Kitchen neighbourhood. It is good and convenient particularly if you are going to a Broadway show.

  • Monte's Trattoria located in the heart of Greenwich Village. This authentic restaurant opened in 1918 and continues with its rich tradition of homemade pastas and dishes.

  • Blue Note is a famous dinner and jazz club located in Greenwich Village.

  • Fig and Olive serves delicious, fresh, Mediterranean-style food. It is located in the Meatpacking district for dinner. 

  • Katz's Delicatessen. Their legendary smoked meat sandwiches and Jewish classics are delicious. For some added fun, you can sit in the same seats from the famous scene in the movie When Harry Met Sally. This scene was shot there.

  • Becco. One of Lidia Bastianich's  restaurants located in Restaurant Row. Their dinner menu includes a reasonably priced "all you can eat" pasta special, but there is also an a-la-carte menu available.

Favourite Museums
  • Ground Zero 9/11 memorial The memorial was built to honour the victims of the September 11, 2001 terror attack on the World Trade Centre, in Pennsylvania and the Pentagon as well as the six people killed when the World Trade Centre was bombed in 1993.

  • MoMA (Museum of Modern Art) This museum has an incredible collection of modern and contemporary art.

  • Tenement Museum. This museum in the Lower East Side offers walking tours of the old tenement buildings as well as stories about the immigrant families who once lived and worked there.

 
Itinerary Add-ons

​For more ideas of things to do in New York see my New York itinerary in 3 days.