chapter 5: start with "why?"
my trip planning process and why you should travel with intention
🏆 little wins & offer for you – let me plan your next trip!
Before I get into today’s topic of intentional travel planning, this was a big week in the world of You Are Where You Go – I’m all about celebrating little wins, so here they are:
Just one week after announcing this trip, 8 adventurous people have booked to join me in Los Cabos, Mexico on June 1-5 where we will scuba dive and swim with mobula rays, hammerhead sharks, and the rest of the rich marine life in the Sea of Cortez. The trip is now half full, and spots are first come, first served – so get your deposit in ASAP if you want to join me on this underwater adventure!
I was invited to give an author talk at Cavallini Middle School via Zoom since my book is integrated in the curriculum for the students’ “Beyond the Classroom” course that encourages them to be thoughtful about travel and experiencing the world around them. Nothing makes my heart feel more full than sharing my story and perspectives with children and young adults – I strongly advocate for traveling while you’re young!
If you or anyone you know works at a school and thinks your students could benefit from me sharing my inspiring story about visiting 70 countries and 7 continents during college and learning so much about myself and the world around me along the way – reply to this email, I would love an introduction :)
My book is getting stocked in local bookstores in Los Angeles! One of my favorite coffee shop/bookstores called Village Well in the Culver City main drag will soon have copies of my book available for purchase in person. I have yet to campaign to many bookstores to stock my book, but it’s one of my goals for this year to expand beyond direct sales online… so this is a small step in the right direction! :’)
If you’re planning a trip soon, reply to this email to tell me about it and let’s see if I can help! I have a hefty repository of all my past itineraries and starred locations on Google Maps for every destination I’ve visited. I’ve had many friends reach out recently for trip recommendations and I’ve been experimenting with how I can offer customized itineraries and recommendations as a service, so would love to help you plan an upcoming trip as a beta test, completely free of charge. Just reply and let’s chat!
back to our regularly scheduled programming of travel planning tips and musings about travel philosophy...
start your travel planning by asking yourself “why?”
In my travel memoir, the first chapter titled, The Decision: Prioritizing Travel, starts with the call to action to determine your why:
“Ask yourself, what is the reason you want to travel? Do you want to learn about new ways of life in different corners of the world? Do you want to experience new foods and new cultures? Do you want to challenge yourself in a new environment and learn more about the natural world? Would you rather see a place with your own eyes than hear about it a hundred times from friends or in the media? Keep that purpose top of mind.”
When I go about planning a trip, I try to think through these questions and set an intention or purpose for my travels. Almost always, my travel goal is to experience things I’ve never experienced before.
Usually, this translates to getting out of my comfort zone and trying the most outrageous new local cuisine that I could never get back home, doing activities or sports that are only possible in that locale, or talking to locals like my Uber drivers or bartenders or walking tour guides to try to really understand a diverse perspective of how people live their lives in this new corner of the world.
Most people tend to plan their trips in a different way – perhaps they saw a beautiful scene on Instagram that they want to be able to take photos of themselves in, or they are checking off a list of “must-see” attractions in major cities around the world.
make a “to-be” list
I offer this advice in my book and am sharing it here again as well, because it rings so true with my core travel philosophy:
“Instead of a to-do list, or a to-see list, make a to-be list. When you focus your travels around the emotions and states of mind you want to embody, rather than just the activities or attractions you want to do or see, you will be more fulfilled in your travels.”
What are the emotions or perspectives you want to experience on your next trip? How can you plan activities that will enable you to feel that awe, that discomfort, and that revelation about a different walk of life that you would not get simply from checking off a list of monuments you’re “supposed” to take a photo of yourself next to?
a quick anecdote…
One of my coworkers is taking a 3-month sabbatical and I grabbed a quick virtual coffee with her to learn more about her travel plans for this time off and see if I could provide any recommendations.
I asked, “So what’s the objective of this extended trip?”
She replied with a laugh, “This feels like you’re my therapist or something! I’ve never been asked that before.”
We then dove into a deep, somewhat personal conversation about how she wanted to be intentional with her time off to take a break from being overworked and return to nature and a state of being relatively unscheduled, just letting herself enjoy a place to its fullest – a direct contrast to the tightly packed daily schedule of a VP at a growth-stage venture-backed startup.
With those intentions in mind, I gave my thoughts and evaluations for the places she was considering traveling for the whole month of April: Patagonia, South Africa, New Zealand, and Japan.
All seemed to really align well with her intention of getting out into nature, but I offered some other considerations such as timing of the year in terms of best weather in each location, relative pricing for shoulder season vs peak seasons, and natural seasonal phenomenon such as the cherry blossom bloom in Japan.
She thanked me for the intel and intention-setting prompt, remarking again that it was so refreshing to have this purpose framing her trip.
my general trip planning process
At least once a week, I get a request for travel recommendations from a friend or acquaintance who is about to visit a country or city I have already visited (there are over 80 of those, so this happens very often nowadays!).
Often times, I will just list out recommendations for what to see, what to eat, and where to stay that are generic and applicable to everyone, as a quicker answer.
More recently, I’ve been taking the time to schedule a quick 5-10 minute phone call with friends who ask for recommendations as a way to understand their intention and preferences for the trip, so that I can tailor my own recommendations to best fit their goals.
Roughy, this is the questionnaire that I’ve been working through when putting together customized travel recommendations:
Where do you want to go? (If you already have a destination/country you’re traveling to, what cities or regions?)
How long are you traveling? (If you already booked flights/hotels, what are the dates? Or is this trip more open-ended thus far?)
What is your intention for this trip? (Are you seeking relaxation, adventure, trying new things, sightseeing?)
What are your priorities; what do you enjoy most on a trip? (Are you a foodie, history buff, photo op fiend, nature lover, local market explorer, etc?)
What are your “musts” for this trip? (What experiences or sensations do you want to be experiencing?)
What are your food preferences or dietary restrictions? (Can I recommend you as authentic cuisine as possible, perhaps even a local cooking class experience?)
Are you comfortable taking public transit? Or renting a car?
Do you want to take any day trips nearby or just stay in the one city?
With those answers in mind, I can then start to map out an itinerary one-pager that summarizes where they are each day of their multi-leg trip, what activities I suggest in certain neighborhoods or cities each day, what restaurants I recommend, and any other tips that are relevant to maximizing joy and learning from the trip.
Next week, I’ll share the more granular details of how I turn these intentions and preferences into the actual essential puzzle pieces of an itinerary – by booking flights, accommodations, figuring out logistics, making restaurant reservations, etc. And I’ll share my template for how to keep all this information nicely organized as an easy reference while you’re on the go during a trip!
xoxo your *intentional* Type A travel bestie,
Caitlyn
🚨 If you enjoyed this newsletter, forward it to your friends! I am doing this all completely free and out of the kindness of my heart because I want to share my knowledge to help as many people as possible travel more economically, more sustainably, and more intentionally…
so forward this email, share the link, post it on your IG story… share it far and wide, please, if you find this valuable :)
📝 travel hack of the week
Look out for free layover programs! Often times, when you fly an airline that has a layover in a destination that’s trying to boost its own appeal as a tourism hot spot, that airline will partner with the country’s tourism board to offer free extended layovers.
This was perhaps most popularized by Iceland, where travelers from the US to Europe or vice versa could extend their hours-long layover into a multi-day stopover for no additional cost – allowing them a few days to explore the natural wonders of their layover destination instead of never leaving the airport.
Most recently, I’ve seen the Azores islands (owned by Portugal) offer this layover program via their local airline. But the one that has excited me the most is the brand new *free visa* layover program offered by Saudi Arabia.
Saudi Arabia only in the past few years opened itself up to general tourism, and the government is really trying to put itself on the map as a tourism destination by offering travelers a free visa (normally over $100 at least) and a free night stay in a 4 or 5 star hotel if they book a flight that has a layover in Saudi Arabia and choose to extend the layover for a few days.
I’ll be flying from Egypt to Los Angeles this September via Saudia airways (for only about $300 🤯), so am taking advantage of this free 4-day layover to add another new country and new cultural experience to my trip instead of just proceeding straight from Egypt back to my home.
I encourage you to take a look at any free layover or stopover extension offerings the next time you book a flight with a layover in a country you are interested in exploring!
🌎 where in the world is caitlyn?
It’s about to potentially snow in Los Angeles 🥶… so I am ecstatic that I am heading out of town this weekend to host a group trip in Mexico City! Our main goal is to experience the magical sight of the monarch butterfly sanctuaries in the mountains of Michoacán, where every single monarch butterfly instinctually flies each year to spend the winter hibernating among millions of other monarchs.
I heard about this phenomenon a few years ago from a boat driver in Lake George who visited and highly recommended it… which just goes to show that travel inspiration can come from anywhere and one conversation can really change your life later on! The seven people who are joining this group trip might have never met if not for this trip – I am so excited to form deep bonds with everyone and experience this natural wonder together.
👯♀️ group trip opportunities
As mentioned at the top of this newsletter, my Los Cabos diving trip on June 1-5 – which is open to both experienced divers and anyone who wants to get scuba certified for the first time! – is now half full, and spots are first come, first served.
Check out the video below if you need some inspiration and a preview of what we will get to experience in person during the mobula ray migration season… get your deposit in ASAP if you want to join me on this underwater adventure!
I’ve partnered with Your Friends Are Boring, a trip-planning platform centered around travel-centric sports like surfing and scuba diving, to serve as their first guest host for this dive trip.
Check out the full trip outline I put together to get the full details and you can book your spot to join this epic bucket list dive trip by submitting just a $450 deposit on Your Friends Are Boring!
📱app of the week
An AI-powered travel recommendations app that will make you a personalized itinerary in 5 minutes? Sign me up!
I heard about this new app called Tern this week and think they could really change the game for lazy and experienced travel planners alike. Their beta goes live on March 3 – sign up below to get on the waitlist.
🪣 bucket list inspo
I’ve said it before and I’ll say it again – Death Valley is way more than just the hottest, driest, lowest place in the US… it’s one of the most diverse and underrated national parks out there and is SO worth adding to your bucket list!
From sand dunes, to majestic mountain peaks, to salt flats, to badlands, to slot canyons you can climb and shimmy through – Death Valley makes you feel so alive.
Check out the photos below and set an intention to go experience these natural wonders for yourself someday soon!
📖 read with me
We’re wrapping up this month’s book club, where about a dozen of us read What I Was Doing While You Were Breeding. It is HILARIOUS and highly relatable for someone who wants to prioritize exploring the world rather than settling down.
I’m going to find a time to Zoom and discuss the book with everyone who read it in the next week or two and then will kick off another book of the month for March/April!
Starting to think that a book every 2 months might be more feasible for most people (myself included) considering busy travel and work schedules.. but we’ll see!
Click here to join my virtual book club on a social reading app called Fable that I’m trying out – if you choose to read the ebook in the app, you can write comments on specific chapters or paragraphs that the rest of the book club members can also see!
But if you’re old school like me and want to buy and read the physical copy of the book, you can do that too – just reply and let me know that you’ll be participating so I can include you in a book club group chat :)
💭 self reflection prompt of the week
One of the students from my author talk at Cavallini Middle School asked me, “What are your thoughts on traveling somewhere twice?” and coincidentally, I had just returned from my Death Valley trip last weekend, which was my second time visiting that national park in the span of 2 years.
Usually, I prefer to visit brand new destinations because there are SO many places to see in this big ol’ world and hardly enough time… but I am more recently realizing that re-visiting the same place can be so impactful.
The first time I visited Death Valley, I had been living in San Diego as part of my nomadic year of 2021. I was a different person back then – a recent grad, figuring out what I really valued in life, not knowing what job or type of role I wanted to be in, and being unsure about who I wanted to keep as close friends and where I wanted to live. A ball of indecision and slight depression, basically.
But now, two years later as I once again explored the stunning landscapes in Death Valley, I couldn’t have felt more different than my 22-year-old self who had previously soaked in these same views. I now love what I do for work and feel good at it, am also making strides with this passion project I have around travel and writing, and absolutely love all the people in my life that is straddled between NYC, SF, and LA.
It is definitely beneficial to visit a place twice, especially if you are going to that place with different people – because as much as you are where you go, it can also be said that you are who you travel with.
It can be really insightful to experience the same things you once experienced, but in a different context with different friends bouncing off their different perspectives that might make you process the events and activities of the trip in a unique way.
What is a place you have visited twice, or would like to visit twice? How did/would your experience differ the first versus second visit?
Leave a comment or hit that reply button and let me know your answer!
📱let’s connect
If you’ve got feedback on the format of this newsletter, or suggestions for travel topics you want to hear more about, don’t be shy! Reply to this email or DM me:
Instagram: @caitlynlubas / @you.are.where.you.go
Twitter: @caitlynlubas
TikTok: @you.are.where.you.go
LinkedIn: Caitlyn Lubas (feel free to reach out if you want to talk about working remotely, transitioning careers, etc!)
That’s all for now…
Remember, you are where you go – never stop exploring the world and yourself! 🌎 🌍 🌏
If you enjoy my writing in this newsletter, you’d love my book called You Are Where You Go: A Traveler’s Coming of Age Journey Through 70 Countries and 7 Continents During College. Feel free to pick up a copy on Amazon, Barnes & Noble, or reply if you’re interested in me sending you a signed hardcover or paperback copy :)
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