Travel Planning 101 for Busy Families in 2024
Prioritize, Execute, & Enjoy
Welcome Readers! I’ve re-started this Substack to to share my experiences with travel coming out of the pandemic, and providing useful information to others. Please feel free to comment, ask questions, or otherwise reach out via this newsletter.
As many of us have come out of the pandemic with big trips, whether family gatherings, the typical Disney/beach/big city vacation, or a dream trip overseas, I’m sure many of you have struggled with making decisions on things like flights, hotels, sights, restaurants, and all the purchasing and scheduling stress that can come with that. We often say we are “planning” our trips, but often that can get bogged down in overthinking and “analysis paralysis”.
On top of that, a supposedly detailed, well-crafted travel plan can easily fall apart on your trip. I used to fall prey to this, especially as I am a capital-P planner not only for travel, but also in my professional life. It feels good to have a cool itinerary on paper, but that’s not how
My first big mistake in travel planning
In fact, one of the first trips my wife and I took together after getting married taught me a hard lesson, and unfortunately is was her who suffered more. That pack-as-much-stuff-into-a-plan, go-go-go on the road resulted in her getting sick on our anniversary.
Take a look at the map below. We basically did a whirlwind tour of Vegas and northern Arizona. We used my in-laws’ timeshare at the time to make a resort in Lake Havasu City, on the Colorado River & California border, our “home base”. That allowed us to splurge on a night in Sedona and the Strip in Vegas. But the distances between what we wanted to see was far.
The saddest memory I have is my wife feeling quite ill as we were checking into the Luxor hotel in Vegas on our anniversary. Whether it was a Monday or them feeling bad for her, the hotel upgraded us to a Presidential suite, but it was difficult to enjoy the room or Vegas that evening.
This was a trip of less than a week. In retrospect it was way too much, particularly with long rides. After that trip, it was clear to me that minimizing travel between places, especially driving, and ideally staying in one or two spots, would be the way for future trips. My wife is a big fan of cruises for this reason, and I can appreciate how an all-inclusive environment is less stressful. This is doubly true today with kids in tow.
How I approach travel planning today
As much as I like nerding out on a lot of details for a big trip, I’ve come to understand that the best approach is focusing on a few “big ticket” items, and allow for unplanned time and experiences to come to us. Once you can evaluate and finalize items like flights, hotels, rental car, and maybe a few key sights, it’s best to let go of the rest. I like to frame this as prioritize, execute, enjoy.
Prioritize
If you think about the major expenses and logistical items for a typical trip, it’s often travel to and from the destination, especially via air, and accommodations.
Air travel specifically has to be nailed down because most people buy non-refundable tickets and it hard-bookends your trip on the calendar. There are of course tons of strategies and tactics to get the best deal and value that fits your desires and budget, whether that’s the multiple booking sites, use of points or point-linked credit cards, or even a travel agent especially on overseas trips. But bottom line, I like to set a general budget, perhaps after researching a bit at a booking site, and a deadline for when to purchase. That helps minimize agonizing over whether one should wait or not to book.
For hotels it’s similar, although with cancellation policies you can usually wait and explore a bit more. Again, there are tons of booking sites out there, and now with short-term rental platforms via sites like AirBnB and Vrbo, along with bed-and-breakfasts and even camping sites, this can become an endless rabbit hole. It’s probably best to focus on a few specific criteria like location, amenities, and reviews to make a decision. I personally find TripAdvisor useful to make sure an otherwise promising-looking property is well-rated by customers.
There may be some trips, such as Disney World or a similar popular destination with tickets, where you may want to consider front-loading your decisions. Or even if it’s just a city or beach or national park, pick a couple of must-see things and find out whether advanced tickets or reservations need to be obtained. For example, the recently-reopened Statue of Liberty has specific time slots and tickets you need to purchase, and these can sell out in advance. Additionally, some sites like museums or even the Taj Mahal may be closed certain days of the week, so research accordingly.
A word on food and restaurants, often the biggest uncertainty and variable on trips: this is the one thing I don’t like to over-plan. In a just about about any city, it’s helpful to find a good “density” of restaurants when making a decision on where to visit/stay. Another tactic I like to use, especially with kids and a busy day, is finding hotels where breakfast is included (mainstream business chains like Hampton Inn and Fairfield Inn are good bets in my opinion). Another approach is when you rent an AirBnB or cabin, is to make sure there is a grocery store or Wal-Mart nearby so you can stock up, especially for breakfast.
Execute
You’ve done your research and due diligence. You may have even had fun doing so! But at some point it’s time to pull the trigger. It won’t be perfect, but hopefully you’ve set your boundaries in terms of budget and schedule, and find the right fit. Buy the tickets, book the rental car, book the AirBnB or hotel, etc., and then let go. Be satisfied that you’ve put in the appropriate time and effort on the important stuff, and let the “white spaces” of your trip surprise you.
Enjoy
While you’ll of course want to prepare in the run-up to your trip with packing, confirming your travel, hotel, etc., and documenting the major items, it’s time to kick back and let the adventure come to you. Once you arrive you’ll want to feel you’ve lined up and systematized your trip in a way that minimizes further decision-making. You’ll want to focus on making memories with your family.
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