How I Plan for a Trip (Especially to NYC)

New York is my favorite place to go alone. To be completely anonymous, not just in a foreign place but among so many strangers who respect your space in response to you respecting theirs. Moving fluidly from metro stop to destination, one neighborhood to the next, a new world opening up before me as I climb the stairs from underground. 

The last time I went to New York, I was 19 and seriously under-prepared. There happened to be a spontaneous minor blizzard the day I arrive with nothing but some Target-brand Oxford dress shoes, jeans, and a cardigan. That trip saw a lot of shopping for winter/weather gear, much of which I still have. 

This year, I'm more confident in my planning and packing skills, having traveled to many states and a couple countries since then. Long before I book my flight and accommodations, a trip is typically percolating at the top of my mind and in my Google Maps. 

Whenever I'm on Instagram and I see a person traveling to a place I'd like to visit, I star the geotag in my map for later.

New York has been accumulating stars and the combination of a friend's hospitality and an unmissable event pushed me to set the dates. Below, I detail how I plan trips, focused this time on NYC. Each time I travel, I find myself a little more organized, a little more prepared, and as a result, a lot more excited to be embarking.  

Preliminary Planning & Budget

In light of my recent adoption of minimalism (and subsequent conscious consumerism), this trip's budget saw a serious decline in allocation for shopping. Does that mean I won't shop at all? No - but it means that I a specific set of items which I hope to find, New York being the prime place for them to be. I separate my budget as such: 

Flight: $211

Accommodation(s): $200

Transportation: $32/ 7-day unlimited metro

Food Cost per Day: $325 ($50 x 5)

Events & Attractions: $129 + (see below)

Shopping: $300

Gifts: $50

Emergency: $150

Total: $1,322

It seems like a lot when you first look at it. But, better to over-budget than to to show up unprepared. While I know I will be staying with a friend for two nights, greatly decreasing my cost of food (and my access to shop), I have a few doozies on my itinerary (see: Brooklyn Flea) that I will want to spend time perusing for a fewer high-ticket items unavailable in the tropical south. 

I found my flights using Kayak (though I often try Skiplagged first to see what they find), and my accommodations via AirBnb. If you haven't already, AirBnb provides a huge discount from hotel prices and positions you in the neighborhoods you want to be in (or in this place, can afford). Having access to a kitchen and the opportunity to make new friends are indispensable to me on a trip. 

Special Events

Waitress, starring Sara Bareilles @ Brooks Atkins Theatre

Sara Bareilles creates music unlike any other singer-songwriter I've ever heard. Her lyrics are dense but digestible. Her melodies are carefully crafted, piano-based, and unique. Yet, you'll find a few of her hits on the Muzak and they sound just as poppy and light-hearted as the rest of them. Without getting too serious or sappy, Sara Bareilles has been a part of my music library for close to a decade and she's touched my life in so many ways.

I learned of her debut Broadway show at the beginning of 2015. It would be premiering in Massachusetts in August, 2015 - I just had to be there. In short, life got in the way and I didn't make it. For the next year (and a half!) I watched the press roll through as to how incredible the show was, devoured the soundtrack and her solo recording of the tracks. 

Three weeks before I booked this trip, it was announced that she would step into the leading role for 10 weeks only, starting in April. That was it. I booked my trip.


Book Signing for The New Paris, by Lindsey Tramuta @ Rizzoli

I pre-ordered The New Paris well before it was ready to ship, beyond excited for Lindsey Tramuta's - whose blog, Lost in Cheeseland is on of my favorite weekly reads - first full-length book. The photos, by Charissa Fay, are stunning and have only further fueled my Franco-lust for a Parisian excursion. 

By happenstance, I saw in this infographic that she would be speaking at the Rizzoli flagship store in New York while I was in the city - add it to the itinerary! 

Click the image to enlarge and see if Lindsey is coming to your city!

Where I'm Headed

This map started as a mass conglomerate of places that interested me in NYC. I tend to gravitate toward different themes in different places. Wild vs City are the major distinguishers - I'm less stoked on shopping and matcha lattes as I am on hiking and whale-watching when it comes to Alaska. 

NYC Themes:

Photography - Coffee & Matcha - Makers/Making - Sustainable Shopping - Japanese & Scandinavian Textiles - Gluten-Free Bakeries

I then organized my schedule my day, giving myself a general idea of how my day (time, especially) would progress and what neighborhoods I'd visit on the same day to promote streamlined travel. What I anticipate doing is getting to my mapped landmark, enjoying it, and then wandering the surrounding area with my themes as my guides.

Travel Capsule

I surprised myself packing last night. Packing is typically my greatest stressor. Too much? Not enough? Am I prepared for the weather? Do I have enough room in my Osprey Sirrus 36 Pack? I'm chalking the easy packing up to my recent fervor for capsule wardrobes and my acceptance how much I love wearing three colors. I naturally love to wear black, white, and denim.

Did I mention I love denim?

On this trip, however, I am shopping for a few items that will better this capsule and are a necessity to my regular life: 

Sustainable Leather (or vegan leather) daily walking boots

Ethically-made canvas walking shoes

The perfect white tee

A new pair of ethically-produced sunglasses*

*that don't break the bank

Shopping Style Inspiration


On my way out,

Do you have any suggestions for places to go, shows to see, food to eat, or people to meet? Leave your suggestions in the comments below or reach out on Instagram. I'll be sharing photos + updating my Story throughout the trip - stay tuned! 

With love from me, across the internet,