The Planning Process
- E.M.
- Sep 29, 2023
- 4 min read
I thought it might be helpful to describe the steps I take in planning each destination in case it might be helpful for others...
First of all, I don't like traveling during high season. I'm a deal-seeker and there are rarely deals during high season. I don't like super hot weather and I'm not crazy about crowded tourist sites and long lines. To make long-term travel more affordable I have unilaterally decided that for this trip we will aim for shoulder season in every location possible.
I also need to remember (and remind my husband quite often) that we will not be able to get to every place we want to go. Not even close. My cost-benefit analysis of getting to more places vs. spending more time in fewer places will be explored in another post. Super fun for me. Big *yawn* for you. Anyway...
Here's where the family gets to contribute...
EM: Hey--where do you want to go?
S: Disneyland.
EM: Ok, I'll take it from here.
1. Look at map/globe. I've been wanting to go to Hawaii with my mother to see Pearl Harbor, where her father was stationed on the USS West Virginia in 1941. Lucky for her (and me), he lived to tell his story, and after hearing the story many times, I want to go with her to see it in person.
NJ to California to Hawaii. Done. When is Disney not super crowded? How about September after kids go back to school.
2. Search Stays/Accommodation on Booking.com and AirBnb.com
in Oahu for 4 people (Use filters! Must have at least 3 beds and Free Cancellation). Use Map view. Peruse Reviews to get a sense of good location/ideal areas. Around $400+/night? Yikes...Let's only stay a few days!
3. Look at map/globe. What is beyond Hawaii? Japan, China, South Korea, SE Asia, New Zealand, Australia. Hmmmm. China and Japan are still "closed" (as of 2022). New Zealand sounds awesome. I've heard it's beautiful and since it's English-speaking it
could be a good place to ease our least enthusiastic traveler into long-term travel.
4. Search blogs. Travel itinerary New Zealand with kids. Wow, at least 3 weeks necessary?
That puts us around the end of September into October. Check WeatherSpark.com
Temps in the 50's. Fine with me.
5. How to get to the next location: Use Rome2Rio.com to find ways to get to from Hawaii to NZ. Check FlightConnections.com and search One-way from Honolulu to Auckland. Yikes...$900! for a direct flight. Oooo there's a cheaper flight through Fiji.....so let's check out Fiji.
Moving from island to island like this means flying, so first I check FlightConnections.com and Kayak.com to get a sense of price, frequency, airlines, direct vs. connecting flights. Then United.com for award flights, then Point.me for other award flights (using credit card points/partner airlines). [More on searching award flights in another post]
Ok you get the picture. It's more art of exploration than science. I get ideas about destinations from podcasts hosted by frequent travelers interviewing guests who travel long-term: Zero To Travel, That Remote Life, Better Travel, About Abroad, The Maverick Show, All the Hacks, The Professional Hobo. These types of podcasts and long-term travel blogs are great for those looking for recommendations on where/when/how to travel. Every time I heard or read a tip/advice/location I wanted to remember I would add it to the Notes page in my phone, which is now incredibly long and includes advice ranging from which months to avoid visiting Thailand (burning season) to how to manage your mail while you're gone for months at a time.
***Main lesson learned early in the planning process: Hotels/Stays fill up much faster than flights!!! You can search and book Stays a year or more in advance, but usually flights are not available until 11 months prior to travel. This altered the way I planned the trip the most. In the past when booking vacations I usually would buy flights first, then look for hotels/AirBnbs (often to find that many are already booked and I end up settling for less than ideal locations or pricier options). First Ah-Hah moment (the first of many): Book Stays early.
TIP: Look for travel blogs by parents of children with similar ages to your children, or travelers with a similar profile to you (single female, digital nomad couples, families with adult children, families with toddlers, etc) . They usually will share the good and the bad, and they aren't trying to sell you anything. I avoid TripAdvisor because it seems to be focused on expensive group tours for singles/couples.
Check a location's weather/precipitation based on the time of year you might visit.
Find direct flights to/from potential destinations
Get an idea of how many airlines and flights exist, general pricing, duration of flights
Watch specific flights for price trends and drops
Filter by Rating (8+), # beds, family friendly, etc. Compare prices to AirBnb.
Use filters (# bedrooms, # beds, superhost, 4*+, etc). Read reviews for clues about location/noise. Compare with accommodations on Booking.com
Compare train travel to air travel for cost, duration, ease of use, quality of experience
How to get from Point A to Point B.
Search award flights to find
See the seat maps of the flight you are booking and see which seats are good/bad according to other travelers
After reserving a rental car, enter the reservation information into AutoSlash. It will alert you if the price drops, and you can cancel and rebook for less.
So many good tips here! You should give a class.