How to Plan Any Trip (But in this Post, I'm Planning NYC)

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On a whim I bought tickets to see Taylor Swift at MetLife Stadium this summer.  So, apparently we are now headed to New York for a summer vacation!  Here's a look at how I am planning for this trip, which is how I tackle all my travel planning. 

Start with Instagram- I must admit most of the 
Brooklyn Bridge. Photo Cred: Michael Sessum
accounts I follow on Instagram are not friends and family (isn't that what FB is for?).  I follow travel accounts- either people who travel or places far away I want to visit one day or have visited in the past.  As soon as I know a trip is in my future, I search Instagram for accounts to help me plan my trip.  Doing this helps me discover unique things to do, where the locals go, where to eat and for any trip with my teen daughters, the best photo opps for social media.  Here's some of the accounts I am following for NYC:
That last account is for a photographer, Michael Sessum, who is based in the DC area, but frequently posts amazing photos of New York.  When I see them pop up in my feed, my first thought is always "I want that view! How do I get there?"  He's graciously allowed me to use his pictures for this post.  Give him a follow for inspiring photos from NYC, DC and other locations. 

What does Dumbo stand for you ask?
Down Under Manhattan Bridger Overpass
(a.k.a. Awesome views of Manhattan)

How do I find the accounts to follow?  In case you are not super savvy with Instagram, here's the breakdown. I start with my destination name and look under "Top" and "People".  I do a quick skim of their feeds to decide which will fit my needs.  Once I follow one account, Instagram  suggests other similar accounts.  Next, try typing "New York City foodies," or "New York city for locals" to see what comes up.  I look for foodie accounts, typical tourist spots, photographers, bloggers, neighborhoods, monuments, museums, etc.   

Book our Flights-  It's good to get this out of the way first so you know what days and nights to plan for.  The awesome part of this trip was that since my dates were a bit flexible, I was able to actually book all five of our round trip tickets using my saved Delta miles.  I purposely put in my dates and found the flight requiring the least amount of points. Another trick is to put in "New York City area airports."  On top of that, be willing to fly into one airport and out another.  If we'd have only used one airport it would have been an additional 10,000 miles each.  In the end I ended booking each of our five flights for 18,500 points and $11.20 in taxes.  How did I earn all of those miles?  I fly Delta every chance I can and I finally got their Delta American Express card.  I use my card for anything over $100 and pay it off right away with the cash I normally would have used.  I take advantage of any offers they put out there.  I also earn miles every time I use Lyft and when I book an airbnb (I got a $25 airbnb credit  just for linking my accounts).  It all adds up.  I also just found out I have a free Delta companion pass (from the credit card) good for the next year- bonus!  Explore what cards make sense for you.  Look at what airlines you tend to use most.  Or maybe you don't fly enough and it makes more sense to get a card that earns you points toward hotel stays.  Here's a referral link to sign up for a card with a 50,000 mile bonus if you spend $1,000 in the first 3 months.  Another 10,000 miles if you book a Delta flight in the first 3 months.  That's at least two free flights right off the bat.

Roosevelt Island.  Photo Cred: Michael Sessum

Book our Hotel- I'm not booking a hotel just yet.  I want to see what part of Manhattan we will headed toward first each morning and stay closer to that location (teenagers) and then I'll try to find a Marriott in the vicinity.  Then I'll just look at all Marriotts in NYC to see which I can get the most nights using my saved points.  Same idea as Delta.  I've been staying at a Marriott or SPG hotel anytime I can and saving my points all year.  I have two more trips, so I will also wait to book after those points are awarded.  At Marriott you can forgo the housecleaning after night one to earn 250-500 points per night.  Finding a hotel this way means we may not be in the heart of the action, or at a super cool hotel brand, but we can now spend more money on the fun stuff.  We wont' be in the room at all anyway.  Going this route when you travel with kids is always a good idea.  When it's just my husband and I we might lean more toward a better brand or a unique hotel.  

Get some Old School Travel Guides- I tend to pick up travel guides anywhere I see them- library used book sales, thrift shops, Goodwill, airports, Anthropologie (they have some unique ones!).  I pick them up for any destination I may want to venture to down the road.  So when I'm planning a new trip, I check my bookcase first and then hit Amazon if needed.  Nothing beats a paperback book in your hands- especially once your trip starts and you can tuck it away in your bag. 

Central Park. Photo Cred: Michael Sessum
Create a Pinterest board and start saving ideas (once called "pinning")- If you haven't been on Pinterest in a while, you need to get back there as it's no longer just a home for DIY ideas and pretty pictures.  Use it as a search engine.  In the search field type in your destination by itself, then try "best food in NYC," "locals guide to NYC," or "top ten things to do in NYC."  Better yet, get more specific "Neighborhoods of Manhattan," "Walking tours of Manhattan." Anything you'd type into Google.  Only with Pinterest you will find a lot of links to articles and blogs.  Real people sharing their real suggestions.  You can also find boards that others have already curated and follow them and see what great finds they've been saving.  Check out my NYC board and give it a follow!  

Map out our trip- It's a science.  It's serious and can take time.  Nothing worse than plan a Tues museum visit, only to find out it's closed on Tuesdays.  Or the tour or restaurant you wanted to go to is already booked.  Or worse that you only planned for 2 hours to see the Statue of Liberty, but it's really a 4 hour deal.  

  1. I start a vacation notebook, usually a physical one AND
    It ain't pretty, but it works.
    one in Evernote so I can access it whenever inspiration strikes.  On one page I write out 
  2. each day of our trip and for every day I break it down by Morning, Afternoon, Night to get an idea of what we can fit into the trip. 
  3. Then I survey the kids.  Super formal: "Text me your top 3-5 wish list items for NYC."  I start a list, add my items and my  husbands.  This gives me a start. 
  4. Next I begin the research.   This could be several pieces of paper.  For each attraction or idea I figure out the following:
    • How much time it will take- an hour? half a day? full day? 
    • Are they closed any days we are there?  What are their hours each day? 
    • Cost?  Who offers discount tickets?  Are kids free? Is it part of a pass?
    • When I buy a ticket do I have to pick a date and time or no?  If so, what days and times are available?  (Tip- going up to the Crown of the Statue of Liberty books out five months in advance.  We won't be doing that this trip.  Two months out most morning tickets are already sold)
    • Where is it located?
  5. Build in enough time to get in between destinations and to eat.  Then add a little buffer based on your transportation.  
  6. Leave some time to just explore, but remember in the city you are doing a lot of walking in between places.  So add a little extra time for shopping and enjoying it. 
    1. Our Family NYC Wish List:
      • Statue of Liberty/Ellis Island
      • 9/11 Memorial and Museum
      • Broadway Show
      • New York Yankees Game
      • Empire State Building
      • Central Park
      • Shopping
      • Today Show
      • Eat pizza
      • Ride the Roosevelt Tram
      • Laduree for Macarons
      • Brooklyn Bridge Park and/or Dumbo
      • Time Square
      • See the Flat Iron Building

My Google Maps
Google Maps- this is another important part.  If you don't already have the Google Maps app on your phone, get it now.  First thing I do is search for each of the places on our wish list and then Save them as a "Favorite" 
which marks them with a red heart on the map.  I don't use "Want to Go" or "Starred Places" because they are green and yellow and blend in too much on the map.  Once I've saved all the places I want, I now have a great visual for where everything is located and can group things together which helps with mapping out our trip.  Then when we are in NYC I use will Google Maps for directions because everything is in there already.  After the trip I keep all of the locations saved for future trips or to make recommendations to family and friends.  Or on my Blog!  

Researching Tours and City Passes- When venturing on a city vacation, check to see what tours are offered that combine multiple locations and check if there are passes available to get you into multiple attractions for a discounted rate.  I started by googling New York City tours and then began comparing them all, based on our list above.  They all work a little differently.  I ended up having to print up each of their attraction lists to compare, because it was so confusing.  I'm trying to spend the least amount of money to get us to most of where we want to go.  

Here are a few of the passes and tours I checked out for NYC (prices as of May 2018): 
  • CityPASS- set deal- 6 places, 42% total discount if you were to purchase them all separately; cost $126 adult/$104 youth 6-17
  • NewYork1- they offer several different options, but they have a One Day Tour that fits in a lot of our places, along with walking, riding the subway and the ferry ($74/pp).  They also offer Statute of Liberty tours and neighborhood tours.  
  • NYC Sightseeing Pass- two options.  Pick the number of attractions you want from their list, or the number of consecutive days you want a pass to do any of the items on their list. 
Or is it cheaper for me to book just the places we want to see individually? The other important thing to remember is to not get sucked into a pass that offers a hundred things to do and thinking it's the best deal.  You may not have time to get to them or or even want to.  It's worth it to price it out individually.  Also, if you have kids be sure to see which places allow them in for free.  So far, it looks like I will be purchasing our tickets individually.

Bethesda Terrace.  Photo Cred: Michael Sessum
Up Next: I'm going to research some self-guided walking tours and try to build one out for us.  Then I will figure out transportation (from airport to hotel, Metro, walking, ferry's, Uber, etc) and ideas for restaurants based on where we end up.  Then I will book the hotel.  

My go-to resource for planning this trip so far: Walks of New York is one of my favorite websites for learning everything about visiting New York. 

What's your special tip for planning your travels? 
I'm always looking for new ideas!


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  2. I am also planning to explore NYC therefore, I will take the bus tours from new york city. I am sure this article will prove useful for me while my trip.

    1. I am sure that this article will prove useful for you. Anyhow, which places of this city you will visit there?


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