I still remember my first time flying on a plane when I was 15 years old. I was alone; cell phones weren’t that smart yet, and it was my first taste of independence. Since then, I’ve been fortunate to travel hundreds of thousands of miles with best friends, coworkers, and romantic partners. Each travel experience has played a pivotal role in shaping my perspective on the world. When approached with an open mind, traveling teaches you a great deal about yourself and how you interact with others.
One of the people I’ve traveled with is Baylie Robinson, Founder of the newly launched travel subscription box ClubRoam. I recently met with Baylie and said: Let’s talk about travel planning! Here’s a glimpse into our conversation.
[This interview has been edited for clarity.]
Recently, Conde Nast Traveler’s Deputy Global Editorial Director, Jesse Ashlock, said, “Travel is a gift to be shared and that passing it along enriches the lives of both the recipient and the giver.” I wonder, what you think anyone should consider when selecting a friend to travel with?
Baylie Robinson: Growing up, I was always told, “Everyone is not for everyone.” The same thing applies here. Not every friend of yours will make the ideal travel partner, and that’s okay.
Questions to ask yourself: Do your vacation priorities align with theirs? For example, do one of you want to party while the other wants to relax and sunbathe the entire trip? Are one of you on a significantly tighter budget than the other?
When traveling with someone for the first time, I’d recommend starting with a 2-3 night trip to ensure you enjoy their travel companionship. We all work too hard to risk letting a poor companion choice ruin a trip.
Research from Expedia shows that roughly half of Americans don’t plan on using all their time off this year (53%), and the top reason why was “life is too busy to plan or go on vacation.” What are your top tips for planning a trip?
Baylie Robinson: The two most important things to plan first are your flight and hotel! It will cost you a lot of money in the long run. If I know I want to go on a summer vacation, I always book my flight in December/ January to avoid price hikes and to get the aircraft, airline, and class of my choosing. The same thing applies to hotels. Many don’t require payment upfront, so why wouldn’t you book a free cancellation hotel as soon as possible to ensure you get the best option?
My top tip for trip planning is to use an itinerary tool. There are so many to choose from, but I use TripIt. Anything I book regarding restaurant reservations, flights, hotel confirmations, and activities, I just forward to a designated email address, and it’s automatically created into an itinerary that you can easily print or share with others. It really keeps me organized and gives me a visual of where some gaps in my itinerary may be.
You’ve been to approximately 30 countries and have visited so many cities. What’s one place you recommend every American visit?
Baylie Robinson: One place everyone should visit is Hawaii. No passport is required; Hawaii is America’s own paradise. Each island has its own flair, with Maui being my personal favorite. As a New Yorker, I really enjoy the escape to a slower-paced lifestyle surrounded by rich cultural heritage and a lush environment.
From the stunning beaches and lush rainforests to the vibrant local cuisine and warm hospitality, Hawaii truly has something for everyone. Important to note – I would eat their poké every day if I could.
I’ve recently learned how small things can suddenly make all the difference when traveling. A few months ago, I was influenced by an Instagram Story from travel editor Lyndsey Matthews about using compression packing cubes in your suitcase. I’ve been missing out this whole time! I have to know, what can’t you travel without right now?
Baylie Robinson: My travel hat clip! I love a hat moment with my outfits and always bring at least two on every trip I go on. The clip lets you attach a hat onto your bag without damaging it, so you’re not forced to wear it or risk putting it in your suitcase.
I think you’re such a tastemaker across so many areas of life. Can you tell me more about ClubRoam?
Baylie Robinson: I have always been the go-to travel friend or person who creates bomb itineraries for my friends when vacationing. Over the years, I’ve learned tricks and hacks and picked up routines to level up my traveling experiences. Posting some of these experiences on social media prompted me to receive many messages like, “Where’d you get that? What’s that?” or “Saving this for when I travel.” I realized: What if I could offer some of these things at a grander scale?
ClubRoam has enabled us to do precisely that. It’s a luxury subscription box curated with travelers or people wanting to start traveling. We curate items that maybe you never thought to buy, but once you have them, you’ll never travel without them – truly elevating your travel moments.
Missing an airplane skincare routine? ClubRoam has you covered. Need a more efficient way to pack a wet swimsuit? ClubRoam has you covered. Want to be introduced to high-quality new and emerging brands? ClubRoam has you covered. With curations being the most essential part of what we do, we intentionally highlight women, Black, Latino, and Asian-owned businesses. This is the differentiator we’re most proud of.
Want to add more travel and relaxation into your life? I’d love to talk with you!
Jarryd Boyd, Clarity + Communication Coach 