I'm a travel advisor who specializes in Disney destinations, cruises, girls' weekends, and custom trips in the US and abroad. If it involves a suitcase, I'm probably your person.
I do the parts of planning nobody sees: cutting thirty open tabs down to the few options that actually fit, being online the morning next year’s packages release, calling the resort to make sure the room you booked is the room you get, and re-checking your price after you've booked. (Yup, even after.)
You still decide what the trip is. You just stop being the only person who has to know everything.
A 3-minute form. I'll get back to you within about 24 hours. Zero obligation.
Est. 2018
A lot of travel advice and content right now is giving you a checklist. Go HERE, eat THIS, get the photo, prove you were there. And... I find that kind of icky, if I'm being honest.
I once watched a couple speed-walk through Versailles — selfie in every room, then on to the next — and I'd put money on the fact that if you asked them which room was their favorite, or how any of it felt, they'd go quiet.
I truly believe that the best and most memorable vacations are the ones that feel like they were made for the specific person taking them. So most of my job is taking things away: cutting the options down to the few that actually fit you, and leaving room for the stuff you didn't plan.
You get to stay the author and hero of your own trip. I'm the one behind the scenes keeping track of the details, from the day you book until the day you're home.
Most of my work happens where you'll never see it (which is sort of the whole point). Here's a little of what that looks like.
“I wanted someone I could trust to handle all of the logistics.”
I booked rooms with the accessibility features the family needed and re-routed a custom birthday cake between two resorts for his brother’s 40th.
“She even had a Figment-themed birthday cake delivered to the Rose & Crown Pub to help us celebrate.”
Midway through a split stay, Disney moved the family’s luggage from their first resort to their second. Late that evening, they realized one thing hadn’t made the trip: her daughter’s medicine.
I talked her through it, called the resorts, got confirmation that the medicine was on its way, and texted her every update until it was back in her hands.
“…you were on top of it, and we felt so taken care of in a moment that would [normally] cause panic.”
“I love to travel but I really do not like having to plan the flights, hotel, car etc.”
I cut a very long list of Aruba resorts down to the few that fit, gave them a heads up when a price jumped before I sent the invoice, and landed an oceanfront upgrade and extra resort credit at the St. Regis for their anniversary.
“She took all of that trouble and aggravation away.”
“I appreciate how I can give an idea and a few examples and you’ll provide info on the items I sent as well as additional options you think I may like.”
I found a package with a $100 credit and breakfast included, arranged a surprise birthday note and chocolates at the hotel, and sent her flight arrival and port departure details before she left.
“The hotel was fabulous. The welcome note was a wonderful touch and the location was great.”
No templates. No copy-paste itineraries. Collaborative, unhurried planning grounded in genuine knowledge of the places and people I recommend. Every confirmation, reservation, and detail handled with care.
You know exactly what you want and you want someone to take care of it on your behalf. Once the plan exists and is booked, I guard it. I monitor changes, catch problems before you do, advocate with suppliers, and stay your one stable point of contact before, during, and after travel.
A focused expert session for travelers with an existing plan they want reviewed, a destination they're researching, or a trip they're building themselves and want guidance before committing. Built especially for travelers required to book through a company's preferred vendor, or wanting to use credit card points / airline miles.
Walt Disney World, Disneyland, Aulani, Universal Orlando and Epic Universe. First visits, three-generation trips, runDisney weekends, and the reservation windows that open before you're awake.
Disney Cruise Line, Seabourn, Alaska, the Caribbean. I start with the part people worry about most — flight timing, the transfer, getting to the port — so the fun part gets to be fun.
Bookstores and baseball in Boston, a Disney trip with your best friends, whatever your group's version of a good time is. Separate invoices, one place for everyone's questions, and whoever's organizing gets to be one of the friends too.
Built piece by piece: your hotels, trains, transfers and tours, set to your pace, no tour group required. Croatia inn to inn, Paris to Lucerne to London, ten days across Japan.
I also plan luxury trips, guided tours, and weddings & honeymoons. Whatever the trip, I plan around how your family actually works — a parent who can't walk long distances, a resort chosen around a neurodivergent kid's needs, a gluten sensitivity — and if you're celebrating something, I make sure the property knows why you're there.
You decide how much you hand over at every step. Here’s what it usually looks like.
A 3-minute form. A rough idea is plenty, and “I’m not sure yet” is a real answer. I read every one myself and get back to you within about 24 hours.
I’ll email you to confirm what you’ve shared and ask a few more specific questions, so everything I put together starts from what you actually want.
A proposal with the trade-offs named plainly. Ask questions, swap things out, or tell me none of them feel right (that’s useful too). When you’re ready, you approve it right in the proposal.
Once you approve, I book the pieces you’ve handed to me. Then I keep watching: price re-checks after you book, the dates when dining and experiences open for booking, and a call to every property before you arrive to make sure the room you booked is the room you get.
Flight guidance, reminders, and the FYIs you might not think to ask about (like how early you actually need to be at the station for the Eurostar). Questions, ideas, or second-guessing a decision? Send it my way.
Closer to your trip, I’ll walk you through how to reach me while you’re traveling, and which things to handle in the moment vs. bring to me.
A 3-minute form. I’ll get back to you within about 24 hours. Zero obligation.
I'm Ashleigh Bergh. My email signature says travel advisor. My résumé says fifteen years in customer-facing and customer-success roles in tech, non-profit, and education.
But what neither of them says? I love to travel - and I absolutely hate to fly. When I visit somewhere new, the first places I research on a map aren't restaurants or museums, but book stores. I am a chronic over-packer, but no sudden shift of weather or unfortunate appearance of a blister has ever taken me down on a trip.
And I truly, wholeheartedly believe that purposely leaving white space in your itinerary is where the real magic happens - not the stuff curated for the algorithm.
All those years in customer success made me genuinely good at understanding what someone wants, needs and is hoping for, and I do my very best to make sure that everything we build together helps meet it all for them - without the stress of managing every detail themselves.
I was the travel advisor for my own destination wedding when I got married at Walt Disney World in October 2022 — approximately 3 days after Hurricane Ian hit Central Florida. That Monday through Wednesday, I worked through every guest room I'd booked, in the block and out of it, and again on Thursday, once the airport reopened and everyone knew whether their flights had changed. Every guest who could still make it had a room waiting. Every guest who couldn't got a full refund.
While on a jaunting car ride through Killarney National Park in Ireland, one of the horses threw a shoe, and our guide gifted me the horseshoe to keep! One of my favorite souvenirs, and I'm convinced it brings me a little Irish luck.
I've driven to/from Massachusetts to Los Angeles three different times and have taken three different routes. I love road trips, and I firmly believe that you see the world very differently through the windshield of a car!
Whether you're drowning in research or just need a second set of eyes on an existing plan, the first step is a conversation. Zero obligation, no hard sell.