SSS #22: Travel Tips


Dia and I love to travel. We've had a good run over the past two years, but things are about to change.

With a baby on the way, we're not sure what our travel plans will look like in the immediate future.

Before I forget them all, I wanted to write down the few lessons learned and share them with you.

Click here if you want to read this post on Otherwise it's pasted below for your convenience.


Traveling Tips

When Dia and I decided we were ready for our first kid, we kicked our travel plans into overdrive.

Over the past 2 years or so, we were lucky to see many new places for various reasons.

  • Weddings: Hawaii, Italy, San Francisco, LA, Dallas
  • Dia’s Work: Dubai, Abu Dhabi, Greater U.A.E
  • My Work: North Carolina, Kentucky, Kansas City
  • Bachelor Parties: Miami, Ibiza
  • Dadchelor Party: Park City
  • Dia’s Girl Trip: Disney
  • Dia’s Mother/Daughter Trips: Paris, Lisbon, Rome
  • Quick Weekend Getaways: Hamptons, Berkshires, Saratoga
  • Visiting Dia’s Fam: Greater Mexico City, Cancun

That’s thousands of miles flown plus weeks, maybe even months, spent in hotels and AirBnBs. I don’t claim to be an expert on travel hacking, but we did learn a tactic or two along the way.

I don’t fully understand how to “maximize” points. Nor do I have “elite” status with any hotel, airline, or travel agency. I’ve just figured out what works for us and thought I’d share it in a way that’s practical for you.

After all, we won’t be using the lessons learned over the past 2 years for quite some time. With BabyShak arriving soon, our travel plans have come to a screeching halt.

I imagine most of our travel in the immediate future will be limited to places we can drive or going to Mexico City to see Dia’s family.

BTW: Dia’s entire immediate family just obtained their Travel Visas. We’re going to need a bigger place!

Without further adieu, here are some of the lessons learned from the past couple years of traveling.

Travel Efficiently

  • Apply for Global Entry (Cost: $100 to apply)

Global Entry is the E-ZPass of flying internationally. Compare saving seconds or a few minutes at a toll booth to saving an hour or more at Customs & Border Protection after a long international flight.

Global Entry is a U.S. Customs and Border Protection (CBP) program that allows expedited clearance for low-risk travelers upon arrival in the United States. Members enter the United States through automatic kiosks at select airports.

To become a member, you must first fill out an online application. If you pass the online application portion, you advance to an in-person interview. We did our interview at Newark Airport, Terminal B.

ProTip: Some credit cards, like the Chase Sapphire Reserve, will reimburse you for the Global Entry application cost.

Global Entry expires 5 years after your next birthday following the date you receive membership for Global Entry. If you plan it correctly, you can get close to 6 years of use by applying right after your birthday.

I wouldn’t wait to apply, though. The benefits far outweigh the cost after one or two flights.

If you don’t travel internationally often, Global Entry is still worth it. Why? Because it comes with TSA PreCheck. If you apply for TSA PreCheck alone, it will cost $85. Why not get both for $15 more?

The TSA PreCheck program expedites traveler screening through TSA security checkpoints.

Most airports have a separate line for travelers using TSA PreCheck. There are only a few tangible benefits. The line is usually shorter. You don’t have to take off your shoes or belt. You can also leave one major electronic device (tablet or laptop) in your bag.

The real, intangible, benefit of TSA Precheck is the company you join. You go through airport security with a different type of traveler. These people understand efficiency, and they don’t look lost as the security guard asks them to walk through a metal detector.

  • Travel Light: Don’t Check a Bag

Aside from being an added expense, it’s inconvenient. I’ve seen too many friends lose their bags or receive them delayed due to airline mistakes out of their control.

Even if you have the ability to check a bag for free, there’s a time cost. You have to arrive extra early to the airport to check in the bag at the counter. The length of the line to check bags is a crapshoot.

I’m oddly satisfied by our ability to take a 10 day trip with nothing but a carry-on and backpack.

One of my friends bags got lost on his way to a wedding we attended in Italy. The bag didn’t make it in time for the event so he had to buy a brand new suit, among many other things.

Thankfully, I overpacked and had enough clean clothes to share with him. It was, however, a huge inconvenience for him.

To make matters worse, when it came to reimbursing him for his troubles, he received less than half of what he spent on new clothes from the airline & credit card company.

Flexible Planning

  • One Major Activity Per Day

When I first started traveling, I tried to pack as much as I could into each and every day. I’d basically copy and paste the “Top 10 Things To Do” list from TripAdvisor into my itinerary.

I was operating from a scarcity mindset. I thought we had to see everything a city offered in the limited time spent there. It was exhausting.

Going on vacation to explore a new place is supposed to be fun and relaxing.

Dia got tired of me pulling her around, so she helped me switch into a lower gear. We decided one activity per day was enough. If we don’t have time to see everything we want, we can go back.

Here’s our itinerary from Italy.

The red cells are fixed, the yellow are flexible. We broke the day into three parts and tried to visit one major attraction per day. This gave us the freedom to explore and really take the culture and environment in.

  • Schedule Rest

One of my biffs, Rags, routinely takes off from work the Monday after returning from a vacation. He likes to ease back into the grind. Pure genius.

Dia, on the other hand, went straight to work at 7am from Newark airport after a ~9 hour overnight flight from Hawaii. Straight savage.

The best approach is probably somewhere in the middle of these two strategies. I try to build rest into our travel plans in one of two ways:

  1. Take an extra day. Arrive to our destination one day before we have to be there. Come home one day before we have to be back.
  2. Hang back in the room. Watch a movie on TV after a long day of exploring a city. Order UberEats. Every meal doesn’t have to be at the highest rated spot on Yelp.

We went to Dallas for a wedding on Saturday, October 12th, 2019. We arrived the prior Thursday night. We spent the first half of Friday in bed at the hotel watching Halloween movies like Hocus Pocus. Still can’t believe Sarah Jessica Parker is one of the sisters.

  • Making a Decision is More Important Than What You Decide

When you’re visiting a new city it can seem like the options are endless. What kind of food should we eat? Which activity should we do? Which site should we visit?

Mexican? Sushi? Pho? Ramen? Let’s just eat!

Rent ATVs? Scooters? Jet Skis? Hop on/off Bus Tour? Let’s just go on an adventure!!

Museum? Hike? Food Tour? Let’s just do something!!!

The real problem when weighing all the different options is this: the more time you spend making a decision, the higher your expectation becomes for a successful outcome. Chances are you’re going to be let down.

I’m complaining, but I’m also a huge part of the problem. I’m so indecisive it’s ridiculous.

My most recent trip to Park City, Utah was riddled with indecision. I went with 3 of my oldest friends. We’ve known each other since we were 12 years old and we’re all cut from the same cloth.

We spent more time arguing about what to eat than eating. We spent more time arguing about what to do than doing anything. We all gave our strong opinions and then ended each suggestion with, “ doesn’t matter to me, though. Down for whatever.”

We were all equally frustrated with each other. Thankfully, we spent the bulk of our time on the slopes. We only had to figure out the one thing we were going to do after.

Each night, someone ended up “putting their foot down” on what we were going to do and I think the rest of us were thankful for that person at that moment.

Save Money

  • InstaCart (Groceries) + Eat At a Restaurant Once Per Day

If traveling domestically, use an app called Instacart to send groceries to wherever you’re staying. We used this app on our recent ski trip to Park City, Utah. We had two cases of water and snacks like fruit, granola bars, and chips, sent to the hotel the day we arrived.

We spent $40 across 4 guys for 4 days. We avoided spending money on drinks and snacks from the hotel vending machine. We also avoided spending money on lunch on the mountain.

Instead, we had a full breakfast at the hotel. We packed two granola bars for lunch. We had a ton of water on hand to stay hydrated.

When we went to Hawaii, we did the same thing. Instead of using Instacart, all 8 of us went to Target and stocked up on our favorite breakfast foods and snacks. We cooked breakfast at our AirBnB, packed a few snacks in our bags to get us through the day, and then ate out for dinner.

A case of water could be $3-5 for 24 16-oz bottles. Each one of those bottles can be $2-3 in a vending machine or convenience store. Same goes for Clif Bars and bags of Chips. It adds up.

  • Book in Advance

The further you book something in advance, the cheaper it will be. Flights, hotels, tickets, etc. This is Economics 101: Supply and Demand. As supply goes down, price goes up.

I booked our lift tickets for Park City more than a month in advance and received an “early booking” discount. I also reserved our equipment rental early online to take advantage of a buy one get one free coupon.

Companies love making money today for a service they have to provide tomorrow. They’ll ask for less money the earlier you pay.

  • Weigh the (opportunity) Costs of Rideshare vs. Rental Car

Rental cars seem cheap when you’re browsing online. There are many ancillary costs to consider:

  • Taxes & Fees
  • Insurance
  • Gas
  • Parking
  • Extra Mileage

For me, rideshare is more convenient and less stressful. Uber & Lyft can be cost effective, especially when you are traveling with a full car. 4 people fill up a regular car; 6 for XL.

You can do the math: Uber & Lyft have a “Ride Estimate” feature that will tell you how much a trip will cost.

It definitely made sense to rent a car in Hawaii. It definitely did not make sense to rent a car in Park City.

Renting a car in Italy would have been less expensive than taking trains and Uber everywhere. But the small roads, limited parking, and unfamiliarity with the territory were enough for us to choose the more expensive option.

Other Thoughts

  • AirBnB vs. Hotel

I personally prefer hotels. I’m ready to pay a premium for privacy and not having to share a bathroom with 7 other people.

  • Hyatt Place

I’ve been a Hyatt fanboy ever since our wedding. The Hyatt Ziva in Puerto Vallarta, Mexico made for an incredible stay for us and all of our guests.

The Hyatt Place is my favorite tiet because of the value it provides when booking through points.


I transfer my Chase points to my Hyatt account to book these rooms at roughly 50% off. Hyatt Place also has a legit free breakfast.

  • Make a Packing List in Advance

I usually pack my bag one night before leaving for a trip. Before putting anything into my bag, I lay everything out in separate categories to make sure I have what I need. I no longer worry about forgetting something.

The list template I use is probably only useful for guys. I say that because my guy friends appreciate it when I send it their way. Dia’s packing system is completely different than mine. She does it by outfit per day per event.

Here’s the packing list I use every time:


Underwear: 1.5 per day

T Shirt / Sweater: 1.5 per day

Socks: 1.5 per day

Jeans: 1

Formal (if necessary):

Button Down: 1.5 per event

Pants: 1 per event

American: Suit, Tie, Belt, Socks, Shoes: 1 per event

Indian: Dress + Shoes: 1 per event

Gym (if available)

Gym Underwear: .5 per day

Gym Shorts: .5 per day

Gym Shirt: .5 per day

Swim Trunks: 1


iPad, AirPods, Charger

Gift (if necessary)

Card, Envelope, $$

Toiletry Bag

  • Upgrade After Purchase

If you want to enhance your travel experience by flying in premium economy, business class, or first class, upgrade after purchasing a basic economy ticket.

Paying for an upgrade is usually cheaper than buying the premium seat from the get-go. The cost of upgrading fluctuates, so be sure to check it periodically.

Use to look at which seats on the aircraft` are the best. SeatGuru will tell you which seats are wider than others, which seats don’t recline, which seats are too close to the bathrooms, etc.

Wrapping Up

Dia and I got bit by the travel bug on the same trip. It was the Summer of 2009, when we studied abroad in Europe together. Since that trip, we’ve prioritized traveling well.

We fully anticipate the arrival of BabyShak limiting our travel plans in the immediate future. However, it won’t be long before we’re the annoying couple on the plane that’s trying to calm down a screaming baby.

Maybe my next post on traveling will be “Top 10 Tips to Traveling With a Toddler”.

Until then… let me know what I missed!

What’s something you recently learned that made for a better travel experience?

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