how to plan a big trip
I love traveling (A millennial? Who travels? Groundbreaking.) I find that putting myself in places & situations that I am totally unfamiliar with, and seeing other ways of being, opens my heart & mind, & makes me more empathetic & understanding.
That being said - I am not, nor could ever be, a person who buys a last-minute plane ticket & trusts the universe to provide an adventure. I am a planner by nature, and like to have everything booked before I step into an airport.
Over the years, I have crafted a trip planning routine that makes the planning process enjoyable. I am sharing in the hopes that, even in bits and pieces, these steps can help enable your next adventure.
Select a country/state/region. It can be vague or specific. “Machu Picchu would be cool” is just as valid an excuse to trip plan as “wonder what Utah looks like” or “I just need to be on a beach.”
Set a flight price monitoring/alert. This allows you to determine when it’s best to buy tickets, especially for trips that are more than 3 months out. You can do this on Google Flights or your favorite travel app.
Buy or borrow travel books. Physical media is so much more fun for trip planning - you can flip through and skim, look at maps and photos, and dog-ear anything that sounds interesting enough to research further. Libraries always have the latest versions of travel guides. I myself am brand loyal to Lonely Planet.
Bookmark places that align with interests/seem fun. Think about what you (and others on your trip) enjoy doing. Is this a relaxing vacation, or more of a sunrise-to-sunset/go-go-go vibe, or maybe a mix of both? I like to make a private Google Maps list, so I can get a sense of how close points of interest are & travel by foot or public transit as much as possible.
Make a calendar hold (or two) early. Block off potential travel dates on personal and work calendars and invite anyone who is coming with you. Exact dates will likely change, but a general timeframe (e.g. last 2 weeks of April, early October, Fourth of July, etc.) will allow you to start actually booking things whenever you are ready.
Book flights (or determine your travel days) & lodging. You don’t need a full itinerary planned before booking flights - quite the opposite. Because flight prices may not be best until closer to your departure date, setting specific travel days can help you plan how many days to spend in a location - which then helps you determine how many nights are needed for lodging.
I use a spreadsheet template to help visually map this out:
An exception - sometimes you come across a flight deal that is too good to pass up. If the timing of the flight deal works, purchasing plane tickets should be your step 1.
Book tours/excursions. Some can be booked the day before, some get booked up months in advance - do research based on your interests, and plan accordingly.
Make restaurant reservations/save allergen-friendly restaurants (optional). Not always necessary depending on where you are going. I like to look up good local vegan restaurants on Happy Cow, so I know there are places I can eat well when traveling.
Make a packing list. This makes packing (and doing laundry before packing) so much easier, and ensures you remember important medications, documents, etc.
Clean your entire house the day before you go. Oh wait, that one’s just for me.
Pack your bags and figure out how you are getting to the airport. Parking? Transit? Phone a friend?
Bon voyage!
good things on the internet
Merrily We Roll Along on the Late Show (Tony’s air on June 16!) 🎶
The work of Rockwell Kent, particularly Reader 🖼️
I think about this moment in herstory and this matching Valentino set a lot 💜
currently reading
Greek vacation edition, because I love travel reading on-theme.
Clytemnestra by Constanza Casati: A gripping retelling of the age of heroes most famous murderer.
Elektra by Jennifer Saint: A bit scattered, but a decent read for Greek story lovers. I preferred Casati’s Clytemnestra to Saint’s.
Ariadne by Jennifer Saint: Stronger and more focused than Elektra. I read this right after visiting the ruins of the Palace of Knossos in Crete, where the story begins.
The Song of Achilles by Madeline Miller: The best one of the bunch - a queer love take on the story of Achilles & Patroclus.
this week’s jam
The soundtrack to Greek mountain drives.
photo of my cats
