Issue #24: An Intentional Travel Guide, Part 1.
Issue #24: An Intentional Travel Guide, Part 1.
Summer Travels, A Flight Website I Love, and a Discount Code. ✈️
In Central Park, the cherry blossoms have reached their peak, we’ve enjoyed our first picnic of the season, and the Weather App has boasted its first 70+ degree day in the city. It's fair to say that spring is in full swing, and summer is well on its way!
For many of us, that means travel is also upon us. Travel has always been a passion of mine. I find trying new foods exhilarating, meeting people from other cultures a gift, and seeing sights I dream about an immense privilege. When I was fresh out of high school, I’d often take road trips—hiking a trail in Tucson, camping in Joshua Tree, or maybe an overnight trip to San Diego to jump into the saltwater.
When I was 19, I went to another country for the first time, immersed in the suffocating Yucatán June heat as I gazed up at Chichén Itzá. At 20, I took out an extra $5,000 in student loans and saved every sacred penny to backpack Europe for a month — a trip that was both the most difficult and most rewarding thing I’ve ever done.
I’ve been lucky enough to do a handstand (kind of) in front of the Eiffel Tower, jump off a boat in turquoise Sardian waters, and climb a rope ladder up the side of an Arizona mountain. While so many stars had to align for those events to take place, a good chunk of it happened due to my organized tenacity + ability to “just kind of know” about places and events that always left my friends asking me how on Earth I found out about this or that.
For years, I’ve fielded questions about how I knew about this hidden restaurant or that unique experience. While I attribute it to being one of my inherent gifts — how did I even discover those? — I’ve tried to break down some tips to help you plan your future adventures today.
I hope they help, and my wish is that they inspire you to feel the same sense of fulfillment I feel so often when I travel, even if you’re going no further than your backyard oasis.
To the art of discovery,
Kayli
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Charleston 2024 // Positano 2022 // Puerto Rico 2023 // Colmar 2019
Okay, so numbers one and two can be interchangeable. It really depends on what’s more important: Who you’re traveling with, or if you’d rather prioritize a destination. I’ve done both! For the sake of this guide, we’ll start with choosing your travel crew.
First, decide who you’d like to travel with. A group of old friends? Your partner? A solo trip? This will influence where you go, your budget, and the overall vibe of the trip which is so important.
Some Things to Consider
Temperament. Have you traveled with this person/people before? Do you know their travel style? I speak from experience when I say not everyone travels well together. And that’s okay! But keep that in mind when picturing an adventurous trip to Costa Rica with your pal who prefers lounging on the beach.
Budget. I get it, it can feel weird to talk with loved ones about money. But you know what can feel more sticky? One of the parties going on a trip they can’t afford, and heading home feeling the effects of a strained friendship or an empty bank account.
Schedules. How much time can you both take away from work? Can one of you work from anywhere? If so, what will their time to explore look like? Do you each want to go for the full length of the stay?
Your destination will often set the vibe of the trip. Are you imagining plopping down poolside for five days without a care in the world? A Mexico all-inclusive could fit the bill! Want to zipline through gorgeous rainforests in the morning and swim under a waterfall by afternoon? Costa Rica could be your spot.
I Recommend
Creating a vision board using magazines or Pinterest to tap into how you’d like the trip to feel and experiences that invigorate you + get you excited.
Determining “the vibe” you’d like for your getaway. The vision board is a great tool for this! Once you have those guidelines down, make a list of 3-5 destinations that delight you.
Keep in mind how much time you have! For example, if you have 3 nights, I’d recommend staying closer to home than spending 5 hours of precious travel time in transit.
The budget is often set in tandem with choosing a destination, but I put it at number three because I truly believe you can do most spots at many budget points, it just will mean a different kind of trip.
For example, I went to Positano on my backpacking trip at 20 and survived off of Caprese salads and cafe sandwiches while swimming at the public beach. On my honeymoon, my husband and I splurged on a hotel that has been on our bucket list for years + imbibed on gourmet experiences aplenty. Each was an incredibly special experience but at very different price points!
Transit. Transit is often the aspect that will eat into your budget the most. Determine how you’re getting to your experience: Car, Airplane, Bus? Will you need a rental car upon arrival? Does the location you’re visiting have passable public transit? Are you going on an experience that will require a driver (ex: winery hopping)? All of these should be looked at when setting the budget.
Accommodations. We’ll get more into choosing accommodations in number four, but this is a good time to determine your maximum accommodation spend. I put this in the budget section because it is a major letdown to fall in love with a hotel only to discover it’s totally not in your price point. I’ve been there, but I can also say that there are so many gems at just about every price point! I’ve stayed at a bed and breakfast with gorgeous countryside views for around $100/night and in luxury hotel suites that cost far more, and both can be equally memorable.
Experiences. Like accommodations, you can dive into the meat and potatoes later, but this is a good point to start pondering what it is you’ll want to do. Will you want most of your money to go toward French brocante finds, hostel be damned? Flush this out a bit!
Okay, it's time to book transit. I know it’s not sexy or glamorous—unless you’re flying Delta One or Emirates Business, in which case, can I snag an invite?
I recommend Kayak for comparing flight costs, Avis for car rentals (however, please look into booking via a travel credit card for best deals/insurance purposes!), and RyanAir + Trainline for easy location-hopping in Europe.
Alright, partner. We made it this far! It's time to decide where you want to stay during your adventures. Do you desire a unique stay? Could you care less, knowing you plan on being out and about anyway? I’ve been in both camps and the only one who can truly decide this is you.
I’d say, regardless, it’s important to consider:
Neighborhood. Is the neighborhood you’re staying in walkable? If you’re in a more remote area, is it close to the experiences you hope to have?
Private Stay vs. Shared Accommodation. Will you be staying in a shared accommodation like a hostel or a private hotel room?
Safety. Like anywhere, there are safe parts of places and not-so-safe spots for tourists. I like to stay up to date with the news in the area I’m traveling in, do some Google searches, and speak with locals if I have access to determine whether I stay in a particular area.
Make a Pros & Cons List. If you’re between accommodations, the famous pros/cons method exists for a reason! I make these and when I do it always helps me decide, if not least because it’s like flipping a coin — sometimes you realize your one pro outweighs 5 cons. :)
Okay, onto the fun stuff!
Poolside in Tuscany
The Fun Stuff™️ — the part of travel planning that is the reward for jumping through the hurdles of logistics! You’ve booked your flights, gotten your hotel lined up, and all participating parties are celebrating.
Now, where to begin?
Firstly, I absolutely go feral on my IG and TikTok Saves as well as my Notes App (where I sometimes jot down bits I learn about a place when I’m in a rush). I highly recommend saving things that look interesting/beautiful/fun as they come up on your feeds. I sort by country, or if it’s a larger metropolitan city, by city.
As I go through these, I add them to a Google Map to visualize priorities. As an example, we’re going to Provence this summer, and as much as I’d love to paddle boat down the Gorges du Verdon, it’s too far from our other “musts” to justify this trip.
When traveling, I also like to have most of my meals booked—especially during high seasons! It used to be that you could walk into most places at a reasonable hour and snag a table or, at the very least, be put on a waitlist while you enjoyed a cocktail. At many locations now, not so much! I love finding email newsletters, social media accounts, and blogs of people who live in the spots I’m visiting + perusing to see what the locals think is worth it! David Lebovitz is a classic for Paris, Venita Aspen and Grace Atwood give superb Charleston recs, and there is no YouTube channel I love more than Aselya Fortin’s, where she shares her life along the Cote d’Azur.
My favorite trips have all had a similar three-part cocktail.
Leisure Time
Great Food in Lovely Places
Unique Experiences
For cultivating unique experiences, I have found two things to be incredibly helpful.
One, doing research about the specialties of the area you’re traveling to. For example, when in Arizona, don’t skip a Prickly Pear margarita and if the weather permits, choose a gorgeous hiking trail like Pinnacle Peak.
Second, Airbnb Experiences. Airbnb Experiences allows locals to host experiences and I have booked some of my best memories using the search engine. Aaron and I snowshoed Mount Rainer in the moonlight, friends and I have made sangria in an ancient garden in Barcelona, and I’ve truffle hunted in a Roman forest.
Check it out on your next jaunt!
Truffle Hunting Outside Rome
Over the years, I’ve accumulated so many incredible traveling resources. Here are a few I highly recommend looking into to see if they fit into your trip-planning style!
1. Kayak. As mentioned above, I absolutely love Kayak for setting flight price alerts and finding the best deals between the various airlines.
2. Chase Sapphire Reserve. I have the Chase Sapphire Reserve and can’t say enough good things about it. It’s Chase’s top-tier travel card, and while it boasts a high annual fee ($550 for the Reserve, and there’s also a more entry-level Preferred card), I travel enough that it gets paid off times over. The Chase Sapphire Reserves gives you access to Priority Pass lounges, TSA Precheck, Global Entry, a complimentary $300 travel credit annually, 3 x’s points on travel (the big draw for me), and much more. You can compare cards, using this tool too!
3. Send My Bag. I have used Send My Bag upwards of five times, and its efficiency is unmatched for long travel stays or times you’ll need more luggage than usual! I wrote a whole blog post on it here, and they were kind enough to give readers a 5% discount to try it out.
4. Birdie. I personally have a Birdie + feel so much safer when I travel with it! It’s like having a fire alarm in your pocket — talk about grabbing attention when you need it.
5. A Small Notebook. I’m always traveling with a small notebook to jot down memories I don’t want to forget or quips in cafes when inspiration strikes. I’ve picked up notebooks in local shops in cities I’m visiting or love a good pocket notebook.
