chapter 2: if you fail to plan, you plan to fail (part 1)
are you team 'plan' or 'no plan' when it comes to travel? let's debate...
Quick housekeeping: shoutout to everyone who replied to my email last week. I loved hearing about your favorite places you’ve traveled! It’s not too late – help your email provider know that you value these emails from me by hitting reply and telling me your favorite travel destination. I’ll share a summary of everyone’s answers next week!
be the man (or woman!) with a plan 📝
If I could choose one lyric that describes my entire outlook on life and travel lately, it is the subject line of this email – if you fail to plan, you plan to fail (shoutout to my girl Taylor Swift for putting it so poetically in her song Mastermind).
When it comes to travel, I am a firm believer that planning is superior to not planning. You may disagree with me (and I’ve had MANY healthy debates on this topic, especially with long-term travelers) but hear me out:
Why plan and book trips well in advance?
The cheapest flights and flash deals tend to sell out the fastest. So, not planning in advance costs you valuable money that you could’ve put toward your next trip or toward indulging yourself while traveling in your destination. Last minute flights are almost always guaranteed to be exorbitantly expensive as airlines’ dynamic pricing preys and profits on fliers who seem like they are desperate to travel and will pay any price. 💸
With the exception of occasional random day-of deals in shoulder season when hotels might offer discounts to fill empty rooms that would otherwise go unsold, accommodations in prime locations tend to also get booked up far in advance. Hotels will often employ dynamic pricing to price-gouge last-minute planners, especially during holidays or special events. Not only that, but the later you book, the slimmer your chance of finding an accommodation that is centrally located within walking distance to all the main things you want to see, do, and eat in a new city.
The best restaurants and best times (like sunset) to enter and experience popular attractions can get fully booked weeks or months in advance. This is just the reality of so many people wanting to (and being able to) travel and experience the same amazing sites and tastes… we can dive into over-tourism as a whole separate topic in a future newsletter. Let me share a few examples:
When my family visited Paris on my 14th birthday, which happens to be the same day as the French holiday Bastille Day, you can imagine how many people also wanted to be at the top of the Eiffel Tower that night to witness fireworks at eye level — this birthday surprise required extreme advance reservations and planning from my mom (shoutout Mom! I know you’re reading this!)
When I visited Lima, Peru and wanted to check out some of the world’s top restaurants located there (Maido, Central, Astrid y Gastón), some bookings opened 3 months in advance and sold out immediately. I didn’t plan ahead fast enough to snag a Central reservation and have always regretted it… although now at least I have a valid reason for eventually booking a trip back to Peru ;)
Let me further put the above rationale into context with a recent example from my travels:
Before I even waited for anyone else to confirm their interest and get their schedules aligned, I knew I wanted to visit Oaxaca, Mexico so I booked a 6-person Airbnb (it’s a great one and the host was fantastic — highly recommend staying here if you’re ever in town!) 6 months in advance of Día de los Muertos, a holiday that draws massive crowds to the normally peaceful city. I knew lodging availability even that far in advance was rapidly declining due to the popularity of the cultural holiday, in which locals celebrate their dead ancestors in the most traditional and vibrant way with street parades juxtaposing quiet yet cheerful family gatherings in the cemeteries that surround the city.
After some time, when more people than I initially expected wanted to join this group trip, we booked a second Airbnb for 4 more people – but the noticeably worse quality of that Airbnb and its non-walking distance from the city center were direct negative impacts of booking later.
Once I found 10 people who committed to splitting the Airbnbs, I encouraged everyone to book flights as soon as possible – then turned on personal Google Flights price tracking alerts for that same date range of flights I had already booked.
Why would I set a price alert *after* booking the flight? Call it schadenfreude, perhaps – I liked watching with satisfaction as the price continuously shot up hundreds of dollars as the holiday approached, reaffirming we had made the right choice to book early and feeling sorry for any suckers who were playing the waiting game and paying way more.
Once we knew how many people had booked their flights and were definitely coming on the trip, I moved on to booking memorable group lunch and dinner reservations. The greatest restaurants in Oaxaca (especially the intimate dining experience at Alfonsina and the highly-rated tasting menu at Criollo, from which the gloriously fluffy conchas live rent free in my head) get booked up months in advance, especially for groups of 6-10 people looking for reservations together.
If we had made a spontaneous, non-planned-out, last-minute decision to celebrate Day of the Dead in Oaxaca, we still could have gone and had an amazing time surrounded by rich culture and city-wide festivities. I’m always going to be an advocate for a last-minute, unplanned trip if the alternative is not going anywhere at all.
But – without planning in advance, our experience would have been dramatically worse, with inconvenient housing options and no availability at restaurants that allowed us to experience the city’s rich and famed connection to its unique regional cuisine. And, we for sure would not have been able to keep the weeklong trip within a $700 budget for fixed expenses like flights, accommodation, key tours, and intercity transportation.
Planning in advance helps lock in cheap flights and accommodations, and ensures you can experience the best fine dining (if that’s what you’re looking for… budget-friendly street eats have my full support too!).
But it’s about more than the monetary and logistical benefits…
You’re going to have to spend time planning or figuring things out eventually – it’s mainly a matter of whether you put in this time before, or during your trip.
Would you rather waste time looking up restaurant reviews and googling how to use the public transit in Seoul while stumbling around the city?
Or would you rather be smoothly gliding around with your eyes roaming the bustling streets of Seoul (not staring down at Google search results on your phone) due to the knowledge and research from your planning which allowed you to spend more time and active brain power soaking up the culture?
Planning things out in advance can reduce pre-trip and during-the-trip nerves and fears you might have when you launch yourself outside of your comfort zone into a foreign country where you don’t even speak the language.
With a plan, you can be confident and less worried while traveling, knowing that you’re following your ideal itinerary and maximizing your time exploring a new place, not wasting time google searching or wandering around lost.
(However, I fully believe in *planning* out a time to wander and get lost in a new city. This is a practice I like to call planned spontaneity, which I know sounds like an oxymoron, but I’ll talk more about that philosophy of mine in a future newsletter!)
Planning also helps make the lead-up to a trip more rewarding:
Beyond helping you remain present and at-ease *during* your trip, planning also helps make the *before* phase of a trip all the more exciting and rewarding as anticipation actually increases happiness.
I’ll phone a friend here and quote Gretchen Rubin, author of The Happiness Project, to explain in her own words:
Anticipation is a key stage; by having something to look forward to, no matter what your circumstances, you bring happiness into your life well before the event actually takes place. In fact, sometimes the happiness in anticipation is greater than the happiness actually experienced in the moment—that’s known as “rosy prospection.”
– Gretchen Rubin, The Happiness Project Blog
There’s a lot of studies out there citing the positive mental health impact of having things to look forward to. Anecdotally, I can say (and I’m sure you can relate) that the coronavirus pandemic stay-at-home period was a tough time particularly because the future was unplannable and there was often nothing on the horizon to look forward to – no upcoming trips, no meals with friends, no concerts or community gatherings.
I felt thoroughly depressed during much of the pandemic up until the world started opening up again and I could finally populate my social calendar and travel calendar without fearing for my personal safety and the health of the more vulnerable people around me.
But post-vaccine and to this day, I feel happier than ever with an entire year of travels mapped out ahead of me. There’s so much to look forward to, and I get more excited about each consecutive trip as I plan out the details of each itinerary and create a clearer vision of how I’ll be spending my time sightseeing, eating, and exploring my way through a new place.
I thoroughly enjoy living my life a few steps ahead of myself. If we’re following this analogy, there’s nothing greater I relish than looking ahead at myself, envisioning how much fun I’ll have on all my upcoming plans, while also looking back at my past self and thanking her for the planning in advance that led me to have so much fun and be fully present in the moment during my trips.
xoxo your *extremely* Type A travel-planning bestie,
Caitlyn
🚨sneak peak! — hopefully this inspired you to be the planning type… in the next newsletter(s), I’ll be including TEMPLATES for an annual travel calendar and annual travel budget that will tactically help you plan out a year full of travel!
📝 travel hack of the week
Know your consumer rights as a flier! This varies based on country or region – the European Union passenger rights are particularly favorable to the traveler, forcing airlines to compensate for delays, for example. But whenever something goes wrong with your flight, you should feel empowered to google search your rights by law, as well as demand compensation from customer support departments that abide by good business ethics.
Yesterday, I arrived at the airport an hour before my 6pm flight only to find out at 5:45pm that the flight had been delayed over 4 hours due to “aircraft maintenance.” The company, Alaska Airlines, stepped up and offered $24 food vouchers to travelers stuck in the airport waiting through the delay, and also sent out this lovely text:
It’s not technically required by US law for the airline to compensate for delayed flights so this is a good start… but I know they can do better since they are a business focused on retaining happy customers.
Previously, when I have reached out to airline customer service departments on the phone following a significant multiple-hours delay, I’ve explained how the flight delay incurred additional costs for me – such as missing ticketed events or activities, no longer being a convenient time for a friend to pick me up forcing me to pay for a rideshare from the airport instead, etc.
I’ve previously successfully (and very nicely – respect your customer service agents, Karen!) negotiated to receive a $250 flight voucher after a cross-country NYC-SF flight was delayed a few hours. So you can bet I’ll be on the phone with Alaska Airlines later today negotiating a higher discount than $75 due to the inconvenience last night’s 4 hour delay caused me.
When life gives you lemons, make lemonade 🍋 (shoutout to Isa for requesting me to share tips about this topic!)
🌎 where in the world is caitlyn?
This week, I’m bouncing around my current and former homes – I spent the first half of 2021 living nomadically throughout California which meant 2 months in San Diego, 3 months in San Francisco, and 1 month in Los Angeles.
This past weekend, I was in my old stomping grounds in San Diego visiting some new friends who live there, catching up with an old friend from my previous time living there, and even grabbing food with a scuba diver from Chile who I crossed paths with back in Miami in December who happens to be studying in San Diego.
After the weekend away, I came back to my current home of Los Angeles for a few days and spent time with many of the people who make the city truly feel like home to me, while also reconnecting with a friend from high school for the first time in years since she had just moved to Santa Monica and shares my love of travel and zest for maximizing your time in a new place.
Now, I’m in San Francisco visiting my old SF roommate and favorite travel buddy who still lives here, and we’re going skiing/snowboarding in Lake Tahoe this weekend – an activity that I have not yet done despite having lived in the Bay Area for a cumulative ~8 months over the past few years.
Meeting new friends in old homes, reconnecting with old friends in my new home, and visiting old homes to do brand new weekend activities really feels like the perfect balance of nostalgia, growth, and stability. I’m grateful for every second of the past week and all the memories I’ve made in these cities that surface as I walk down familiar streets, dine at restaurants with familiar favorite tastes, and surround myself with both foreign and familiar faces.
👯♀️ group trip opportunities
My February group trips are fully booked, planned, paid, and ready to go!!
For the next 3 weekends, I’ll be traveling with groups of people who all know me but don’t know everyone else they’re traveling with. I love surrounding myself with these types of people who are just down to meet new people, experience new places, and say “yes” to things outside of their comfort zone.
The February trips that are now full include:
Feb 8-14: Mardi Gras in New Orleans ⚜️ (5 people)
Feb 17-20: road trip through Death Valley ⛰ (8 people) – this one filled up from word of mouth before I ever even shared it out on social media or this newsletter!
Feb 25-28: millions of monarchs near Mexico City 🦋 (6 people)
In another world, I would’ve just fully planned out these trips and gone solo. But since I did all the planning already, it was easy to just extend an invite and now I know I’ll have even more fun traveling with these groups of adventure-seeking souls!
But now the exciting news – first dibs going exclusively to newsletter readers… my next group trip you can join is a ski/snowboard weekend trip to Mammoth Mountain, CA from March 24-26! ⛷🎿🏂🏔
I snagged a beautiful Airbnb with a balcony, fireplace, and hot tub that is mere steps from the mountain for easy access to the slopes. With 8 people capacity, it works out to $156 per person for the 2 nights there (a steal!). I’ve only been to Mammoth during the spring, but it’s a quaint little town tucked away in the Sierra Nevadas and is known to have less crowds then Tahoe and Big Bear, which are closer to the major California population centers.
Since this is a road trip just for a weekend, it probably only makes sense to join if you’re already located in California during March… but reply to this email if you’re interested and want more details!
🪣 bucket list inspo
I ate a lobster roll in San Diego this past weekend that reminded me of another former home of mine – Mount Desert Island, Maine. 🦞
Home of Acadia National Park, the best lobster rolls, an abundance of blueberry pies, and some of the greatest fall foliage leaf-peeping opportunities, the Bar Harbor area was where I spent the entire month of October 2020 working remotely with some friends and living our best ~New England fall~ lives.
I cannot more highly recommend a destination that you should add to your autumn seasonal bucket list!
📖 read with me
BOOK CLUB ANNOUNCEMENT! If you’re anything like me, you’ve been wanting to read more… yet we’re 1 month into 2023 and you haven’t picked up a book yet 🫣
Let’s change that! I heard rave reviews about this female traveler-narrated memoir called What I Was Doing While You Were Breeding. A few friends and followers have already joined this book club after I shared it on my Instagram stories. We’ll all serve as accountability buddies since we have the goal of finishing the book by the end of this month to then discuss it all together on a Zoom call.
If you’ve never done a (virtual) book club, but want to start, please join! I did this with some of my best friends during the pandemic – it really motivated me to read and helped me more deeply appreciate a book after discussing it with others.
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 – I’ll host a Zoom meeting for everyone who joins the club during the last week of February for us all to discuss the book together. Can’t wait!
💭 self reflection prompt of the week
I absolutely LOVED reading your answers to last week’s question: What would you title this chapter in your life?
My answer: Perfecting the Balancing Act. I finally feel like I’m striking the right balance between both frequent travel and frequent recurring touch points with a community and home base that I love.
This week’s question came to mind after the recent Lunar New Year shooting in Monterey Park, a shooting crime scene I happened to walk past in my own neighborhood last week, and a recent earthquake (my first time experiencing one!):
What is the last time you witnessed, experienced, or heard about something that reminded you how important it is to live your life to the fullest every single day?
Hit that reply button and let me know your answer!
Tomorrow is never a guarantee, as events like this clearly show, so channel that slight fear from events like these into motivation for carpe-ing the heck out of every diem 🤘🏽
📱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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