WORKING TOGETHER

My Services + Our Process

I’m Chelsi Falcon, founder of Y’all Trippin’, and I help families, couples, and groups trade predictable for unforgettable. My sweet spot is the Caribbean. Over here, we are big fans of those turquoise waters, sun-soaked days, and salty, and windswept memories that make life feel big again.

Most of my clients come to me stuck in the “same resort, different year” loop, nervous to try something new but craving more. I give them the confidence, logistics, and support to step outside the all-inclusive bubble and discover destinations that feel vibrant, real, and still totally within reach.

Because the truth is, the world’s way bigger than one swim-up bar… and with me looking out for you, you’ll finally feel brave enough to explore it.

You’ve done the same all-inclusive more than once, eaten at the same buffet one too many times, and realized you’ve got more photos of the swim-up bar than your kids.

Let’s change that.

let's get trippin'

Bahamas • Barbados • St. Lucia • Jamaica • Virgin Islands • Mexico • Belize • Turks & Caicos • and beyond • Bahamas • Barbados • St. Lucia • Jamaica • Virgin Islands • Mexico • Belize • Turks & Caicos • and beyond • 

Island-hopping itineraries that mix adventure with downtime



Cruises for every vibe



All-Inclusive, Non-AI, and Hybrid Escapes



Luxury Villas & Vacation Rentals



Private Yacht Charters

Where I Work My Magic

If it’s got warm water, sunshine, and a view that makes you close your eyes and finally feel relaxed, it’s my wheelhouse.

Pick Your Planning poison

You’ve got the time and confidence to do your own booking — you just need a pro to point you in the right direction. I’ll handle the heavy research, find the best resort or cruise options, and send you curated recommendations so you’re not drowning in tabs. Perfect for the “I’ve got it from here” traveler who just wants expert insight without the full-service bells and whistles.

basic
Research

You want a smooth, done-right trip without spending your evenings comparing flights and transfers. I’ll handle the logistics, quote your travel insurance, recommend excursions, and make sure everything connects seamlessly. Great for couples or families who want peace of mind and personal attention without going full concierge.

Enhanced Planning

white glove
experience

fee starting at $40

fee starting at $100

Whether you just need a little nudge in the right direction or want me riding shotgun from first click to boarding gate, there’s a travel-planning tier that fits your style (and your sanity level). Think of it as choosing your own adventure. I’ll handle the details, you just pick how hands-on you want me to be.
ready to geaux!
This is the “I want it all handled” tier which is perfect for travelers who’d rather focus on making memories than managing details. I’ll create your full custom itinerary with day-by-day suggestions, coordinate your excursions, dinners, and transfers, and be on call from takeoff to touchdown. Whether it’s a luxe villa stay, yacht charter, or a nonstop adventure, this is your stress-free, concierge-level experience.

fee starting at $50/day

feel free to look around

Totally fine! If you’re still in your “let me just poke around” era, my Destination Highlights page is where you’ll want to go next. It’s full of free travel inspo, real-life trip notes, and all the cool stuff I (and my clients) actually loved, plus a few links that might just make planning your own adventure a little easier.

Not ready to schedule that call just yet?

I’m not your average travel advisor and honestly, I like it that way. I’m equal parts straight shooter, spreadsheet nerd, and hype woman. I’ll tell you if that resort everyone’s raving about online actually has a rocky beach or service that doesn’t match the price tag, and I’ll cheer you on when you finally book the dream trip you thought was out of reach.

My clients call me the calm in their travel storm, the person who actually cares if your flight gets delayed, who stays up late double-checking your transfers, and who believes a well-planned trip can change how you see the world (and yourself).

I’ve been where you are, craving something new but not knowing where to start, and I’ve turned that obsession into a business built on trust, humor, and a little Louisiana grit. If you want someone who’ll treat your vacation like it’s her own, keep it real about the budget, and still find the magic in the details, you’re in the right place.

we are going to get along so well.

Why? Lemme tell you:

ready to work together?

I Build a Custom Plan

02

Let’s Chat

01

my planning PROCESS

Our first chat is all about getting to know you, your travelers, your priorities, and what kind of experience you want to create. I’ll also walk you through my planning fee structure and the flexible options available, so you can decide how hands-on (or hands-off) you’d like me to be. Once we find the best fit, your trip officially gets its wings.

Pack Your Bags

04

You Approve + I Book

03

This is where my rabbit-hole research obsession kicks in. I’ll piece together flights, transfers, stays, and experiences that fit your budget and energy level whether that’s chill, thrill, or somewhere in between.

You’ll get a polished proposal with transparent pricing and options. Once you give me the green light, I handle the bookings and fine print.

You’ll leave with a detailed itinerary, insider tips, and my personal support from “let’s go” to “we’re home.” If something pops up mid-trip, I’m a quick text away! I'm your built-in safety net.

Chelsi did a great job of listening to what we wanted out of our vacation and giving us more than enough options to choose from. She made sure that nothing was overlooked in the planning process. From the second we booked to the second we landed she had everything planned out. The app that she uses for your phone was so convenient and even updated us on any delayed flights. She made traveling a breeze! 

- Peyton R.

nothing was overlooked

Chelsi was so pleasant to work with. We chatted often. both before and during our trip. I look forward to using her services again in the future.

- Lacie L.

We chatted often

From the day we booked, Chelsi was on top of literally every aspect of the trip. From booking all the way to an extremely detailed packing list, and even texting us before our last flight home to check on us. The Trip Plans app was seriously amazing and so useful!! It breaks down every day during our trip and tells us what we need to do and when. Chelsi was also available throughout our whole trip. We had a few questions on our travel days and spoke to her during the week about a few things, and she was extremely quick to answer! I could not have asked for more from a travel agent. 

- Dina C.

seriously amazing

Y'all Trippin' made traveling so easy and non stressful! She had everything so organized and had all the information you could possibly need and more! She is always there for any questions and to make your trip go as smoothly as possible! It was perfect!

- Paige C.

so organized

Chelsi planned a great trip that met all of our wants and expectations! She was available anytime and promptly responded to help us, before, during, and after the trip.

- Nicole M.

promptly responded

Using Y'all Trippin to book our trip to Italy, was as easy as drinking Limoncello! They took all of the guess work out of planning the trip. The hotels, transportation, excursions and restaurant recommendations were well thought out and on point. It was a perfect trip because of Y'all Trippin. We will use them for all of our "real vacations" in the future!

- Justin S.

it was a perfect trip

Chelsi always makes it happen.

- Jeremy L.

makes it happen

Chelsi is fantastic. She puts a lot of time and attention into planning your trip!

- Lindsay H.

time and attention

I will 100% use Y’all Trippin for future travel plans! The process was easy, communication was ideal, and we had a great time!

- Randi S.

had a great time

Trip was perfectly planned!

- Jamie L.

Perfectly planned

Chelsi made it extremely easy to plan a trip for multiple people who all had different expectations. The itinerary and trip information were easy to access, understand, and VERY organized. You can tell that Chelsi wants to provide a great vacation experience to her customers.

- Virginia D.

very organized

Ready to see what your next “we actually did it” trip looks like?

You don’t need another cookie-cutter Caribbean getaway, you need a story you’ll still be laughing about years from now. Whether it’s a week in a luxury villa, a barefoot island-hop with your favorite people, or finally ditching the all-inclusive buffet for a little adventure, I’ll handle the heavy lifting so all you have to do is show up, sip something tropical, and say, “we actually did it.”

let's get started

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