Yellow Umbrella Events
Cheryl & Shea at Palace Pro Awards 2019

You Asked, We Answered. Welcome to Q&A with Cheryl & Shea!


What exactly does a Destination Wedding Travel Planner do anyway?

A Destination Wedding Travel Planner will help you find a destination, resort, and wedding package that matches your wish list and spending plan as closely as possible. Once they narrow down the options for you and you make your resort choice, a destination wedding travel planner will normally assist you in confirming your wedding date and wedding package choice with the resort through a wedding day contract. From there, they will assist you with confirming a group rate for your wedding room block and begin educating and assisting your guests on how they can book their room in your contracted room block.

In most cases, the resort’s on site wedding coordinator will assist you from there on your wedding specific details. Or you can hire an outside wedding planner for this role.


What makes you different than everybody else?

Good question! We have a lot going for us, so let me lay it on the line for you –

1.) Shea and I are a husband and wife destination wedding travel and planning team, so you always get the two of us (and depending on the size and scope of your wedding, maybe even some assistants and helpers, too).  Cheryl is the one that you will work with first to help you choose a resort for your wedding. You’ll also work on on one with her through the entire wedding planning and design process if you select out total destination wedding planning service. Shea is the one that creates your one page wedding website and works directly with you and your guests to book their room, facilitate deposit and room payments, and explain their travel options.

We feel like we make a really great destination wedding travel and planning team since we’re able to help you with both the wedding room block/travel planning services and full service wedding planning in one spot.

We’ve been married for 13 years and work in the office (and on the road) together every day and we love it!

2.) We’re really big on YOU having the wedding that YOU want to have – not our wedding, or your mom’s wedding, or your maid of honor’s wedding – your wedding! “That’s just the way it’s done” is not likely to be a remark you ever hear us make. We love tradition as much as the next person but we really want you to end your wedding day feeling like it was a total reflection of the two of you, in whatever form that takes.

We’re okay if you don’t want your dad to be asked: “Who gives this woman” or if you want your dog to be your ring bearer or if you think the garter toss is uber tacky or the greatest thing about the whole day. If that’s the way you want it, that’s what you’ll get. We’re very open to trying ideas that haven’t been done before. And we won’t look at you weird or give you a hard time if you’re not super traditional. 

We’ll help you determine the best resort that makes the most sense for the specific style of wedding that YOU and your significant other are hoping to have.

3.) We’ve been voted the Best Destination Wedding Planner in Texas for the last 5 years in a row! I know, kind of cool, right!?

We work with couples all over the United States – only about 10% of our couples actually live near us. The majority of our couples live in D.C., Houston, New Jersey, Florida, you name it (someplace other than where we live in Austin) and we help them plan their destination weddings in Mexico. Kind of weird, I know. But we love destination weddings and it works for us – and it works for our couples too!

4.) We will be honest with you about your budget – Big budget, little budget, somewhere in between – it doesn’t matter, everyone has one. One of the first things we do with our couples is to decide on a realistic budget for your wedding and for the travel portion for the guests attending your wedding, and start putting it into an action plan. 

We’ll be very honest and to the point with you about what you can truly afford. If you’re describing a $50K wedding and you only have $20K budgeted, we’re going to let you know in the beginning – before we move forward, so you can make wise decisions. And we’ll make great suggestions to help you get the essence of what you want, without the resulting tears from inaccurate expectations.

With all of that being said – it’s really YOU that either sticks to the budget or strays. We can’t spend your money for you. And we can’t stop you from spending your money either.

5.) We have a private meteorologist on staff. Nope, not joking. Since a majority of our events are outdoors there is no way I’m leaving such a huge detail, like the weather, to chance on your wedding day. And Rob is amazing! He does everything from giving us the likelihood of inclement weather when we’re reviewing potential dates to updating us hour by hour (and sometimes minute by minute) on the actual wedding day as to weather-related situations. We’ve moved locations, ceremony times, and more based on his expert knowledge. In all of the years we’ve worked with him we’ve only had to use the Weather Back-Up Plan B twice!

6.) We’ve been doing this a long time! We’ve been wedding and travel planners for 10 years. This is our full time career and we LOVE what we do! We’ve seen a lot of things in our 10 years as event planners and our experience can help you easily navigate the destination wedding processes. We’re also well respected in the destination wedding travel industry and often speak and train other wedding and travel pros at industry events worldwide.

7.) There’s more. I could keep going – but in the interest of time, I won’t. You should just hire us anyway and be done with all this nonsense already. Besides, you’re probably reading this at work, and I’d hate for you to get caught planning your wedding when you’re supposed to be working – so get back to work! But contact me to book your appointment first, of course!


How many events do you guys plan each year?

That varies from year to year but we typically only offer full service destination wedding planning services to 10 or less couples each year. By keeping with such a small number of events we’re much more able to give you our complete and undivided attention. 

We work with approximately 25 – 35 wedding groups per year for destination wedding travel planning only services, where the couple is working with either the resort or another event planner for their wedding planning.


Do we really need a Full Service Destination Wedding Planner?

That depends! For destination weddings where the guest list is small (under 40 guests) and you will be choosing just the resort’s offered wedding package and not a lot of extras, you’re probably fine without a full service destination wedding planner. Especially if you’re working with a destination wedding travel planner, since they coordinate so much of your guests travel details.

However, if any one of these (or possibly more) apply:

  • You are a working professional that works a lot of hours each week, making it difficult for you to stay on top of the wedding planning details
  • You may want more specific details for your destination wedding that are not part of the standard wedding package offered by the resort
  • You’ll have more than 50 guests
  • You really care about the small details and decor vignettes
  • You’re planning multiple days of events and excursions
  • You know that you’re the kind of person that needs someone else leading the event (as in, you tend to procrastinate or put off making decisions)
  • Or you just generally do not want to be the “point person” for your destination wedding and the weekend’s activities

You should really consider a full service destination planner, in addition to your destination travel planner.


What’s the best resort for a destination wedding?

That is a fantastic question but, unfortunately, there is not one catch all resort that is perfect for every wedding. The best resort for you and your guests will depend on many factors – location, guest count, time of year, overall wedding and resort experience you prefer, spending plan, and much more – and we’ll ask you a ton of questions on your discovery call to help determine the best destination wedding resort for you and your guests.

Ready to get Started?

“Calm, thoughtful, creative, flexible–all words that describe Cheryl Bailey of Yellow Umbrella Events. My daughter had a dream, a vision and Cheryl made it a reality. She transformed Brazos Hall into a wonderland, keeping to our budget and orchestrating all the parts to make the entire planning process stress-free. Highly recommend, Outstanding, Wonderful to work with.” – Christine Draths