The Over Thinker's Guide to Planning a Weekend Trip

The Chappell Experience:
NYC phase 1: Planning


As with most of our grand adventures, New York City started as a conversation about a month ago. I was put in charge of planning "the next trip" which, I happen to excel at. If you ever want to see the inner workings of an over thinker's brain, tell her to plan a weekend trip away and give her a note pad. You may or may not know this but over thinkers are excellent planners and budgeters because we take literally everything into account and we compare the deals to get the absolute best prices. Don't you worry though, I will share my knowledge with you along the way.

          Being a couple who consists of a photographer and her wonderfully inspiring husband / assistant, I always look at our trips as "photographic excursions". Therefore, everything around the planning of this trip had amazing photo-ops in mind. I wanted to make sure we got in some super touristy attractions, like the Empire State Building and the Rockefeller Building as well as doing some general hoofing around the city. After careful consideration and lots (when I say lots, I mean an entire front and back side of a steno note page filled with comparisons) I chose a city pass that would suffice. 

The options I had narrowed it down to were:

  • citypass.com - $132 per person OR $83 per person if you choose the C3 pass

  1. The regular pass gives you access to 6 attractions. The C3 pass will get you in to 3.

  2. You have 9 consecutive days to use either pass from the first time you use it. Giving the regular pass an awesome value if you're staying for several days. However, if you're only staying in the city for a weekend like we did, you're much better off with the C3 pass.

  • newyorkpass.com - at the least expensive this pass will run you $134 for one day. Prices range all the way up to $329 for 10 days.

  1. See as many attractions as you possibly can within the purchased time frame.

  2. If you purchase multiple days, they need to be used consecutively. Use it or lose it!

  3. Passes are valid from the first use until midnight. So if you don't use your one day pass until 4pm, you have 4 hours to use your pass!

  • smartdestinations.com - (New York City Explorer Pass)  3 Attractions = $89 / 4 = $124. Prices go right up to 10 choices at $219.

  1. They offer a "Build Your Own" bundle, which allows you to choose how many attractions you would like to see. Each selection saves you a little more money.

  2. The regular pass does not require you to choose your attractions prior to your visit. 

  3. "Visiting your first attraction activates your card. Then, you'll have 30 days to use your pass." (This is actually an excellent feature!)


              I personally went with the city pass C3 ($168 total). It saved me a few dollars and gave me everything I wanted. Last year, we drove to Atlantic City and stopped in NYC on our way home and between tolls, gas and parking, we spent a fortune just by having our car with us. This time, I decided to find other means of transportation. After doing a quick "Providence to New York" google search, I found wanderu.com . Wanderu gave me both bus and train options and assisted me in booking the absolute best deal. If you're wondering, you can get a bus for as little as $26 (one way)! For a little over $110 (with fees and taxes) our toll-free tuna can was booked! (If you're keeping up, we're now at $278 for 2 days in the city) Last, but certainly not least; the hotel...

              This part was daunting, to say the least. Any time I book a hotel, I go to priceline.com (period, end). As far as I was concerned, priceline had the absolute best deals. And after looking through their results for 2 days (because I'm an obsessive freak) I was sure that I would be paying $180 for a decent hotel room. When I say 'decent', I mean - we won't be sharing a bathroom with strangers but our room will be, at best, a pod room with a full-sized bed. The cheaper places, ranging from $40 - $135 reminded me of the European places that were depicted in the movie "Hostel". Ever seen it? Don't. If you're the type that doesn't mind sharing bathrooms, don't see this movie. It just might make you want to change the way you look at "these kinds of places". So when I bring the price up to my dotting [at the time] fiance, he scoffed at me. That' right! SCOFFED! At ME! Frugal frick'n Franny! "What do you mean, the best you can do is $180?!". Needless to say, I looked into other options. Queue hotels.com ! I found a great deal on a king room in the Comfort Inn Times Square Hotel. $105!! AND we get our own bathroom! Ok, so I had to wait a day to book it (for monetary reasons) and when I finally booked it, the price bounced up to $135. Still though, a great deal none-the-less. ($413 total)

             With all of the details booked, I was left with one thing to plan. The itinerary. Bread and butter, baby. Bread and butter. My notepad very precisely outlined the whole thing and it looked something like this: 

Excuse my neuroses here.

  • (Friday)

  • 6:30 am - Peter Pan Bus departs Providence, RI

  • 10:30 am - Arrive at Port Authority, NYC

  • 11:00 am - Eat like starving hostages

  • 12:00 pm - 6:00 pm - General sightseeing, check-in at the hotel

  • 6:30 pm - Top of the Rock (I had this dead-set, planned for sunset.)

  • 9:00 pm - The Empire State Building

  • 10:30 pm - Go back to the hotel and die of exhaustion

  • (Saturday)

  • 10:00 am - Ferry to Liberty Island & Ellis Island

  • 2:00 pm - head back to Port Authority area

  • 4:00 pm - Greyhound it back to Providence

              As you can see, I had everything planned to the "T". How much would you bet that everything went smoothly? Stay tuned, kiddos. I'm going to tell you all about it in our next post. Thanks for checking out our brand new blog at chappellphoto.com . And feel free to browse our site to check out the pictures that I captured on our trip. Do you know of any other bargains that would have helped cut the costs of this trip? Leave your comments! Share your frugality!