Armchair Travels Tips & Tricks

Small Business Spotlight: Happily Ever Expeditions with Abigail Chiaravalle

This is part of my summer series spotlighting some of the awesome entrepreneurs I know and their small remote businesses. If you know someone who should be featured or if you have a small business that you’d like to promote, get in touch with me!

Meet Abigail Chiaravalle. She lives in the historic Southside of downtown Chattanooga, the perfect spot for a brunch-loving city dweller with a soft spot for nature. I’ve had the pleasure of knowing Abigail for a few years now, as her brother is married to my best friend making us basically family. We share a love of Sutton Foster, board games, and travel.

When Abigail decided to create Happily Ever Expeditions, a fully accredited travel agency specializing in Disney destinations, I was intrigued. I’m a huge Disney fan and theme park junkie, so I needed to know more about her passion project. Combining her love of Disney and travel with her organization and planning skills, Abigail has created a travel agency to help make family’s Disney trip dreams come true, with one very special feature: her services are FREE to her clients.

She helps her customers choose the perfect resort, makes all of their dining reservations, secures necessary Fast Passes, and builds a customized itinerary just for them allowing them to pay the same amount of money they would have, had they gone directly through Disney, but with far less worrying or work on their part. Additionally, different from other agencies, Happily Ever Expeditions does not charge extra fees for quoting or planning. You can’t get much more magical than that!

Let’s move on to the interview to learn more about what she’s learned from building her own business, how Covid has affected the travel industry, and what advice she has for fellow entrepreneurs. If you have follow up questions, please find her Facebook, and Instagram, and visit her website.

Be patient! It takes time to build a business.

Abigail, travel agent and Disney expert, on what she’s learn running her own business

What have you learned about running a small business since you began? What piece of advice would you give yourself if you could go back in time?

Be patient! It takes time to build a business. My travel agency is my passion project / side hustle. Someday it might be my only job, but for now I just enjoy having a legitimate reason for people to let me plan their Disney vacations.

How has the Covid crisis affected your work/business?

As I’m sure you can predict the pandemic has crushed the travel industry. Walt Disney World just recently opened back up and Disneyland is still closed. That being said, I believe Disney made the right decision in closing. I’m glad they’re taking steps to slow the spread of COVID-19. I am grateful to still have my day job, but look forward to the day when we can all start safely adventuring again.

Biggest challenge you’ve faced running a small business and how you’ve overcome it?

Credibility. As a small individually owned travel agency specializing in Disney, a large well known company, it can be tough to walk the line of local and credible. As an agent I do not work specifically for Disney; I choose to specialize in their destinations. It can be tough to advertise free services and convince people they’re valuable at the same time. What people don’t realize is they pay the exact same amount they would normally, including when Disney has special promotions or deals, then Disney pays me a commission. You’re really paying for a travel agent whether you use one or not, so you might as well take advantage of the services we offer.

The best achievement was completing my first client itinerary. Creating a customized plan for each day to maximize magic is my all time favorite!

Abigail, on her biggest professional win

How long have you worked from home? What has changed from when you first starting working from home to now? What have you learned? What tips can you pass on to others who may be working from home for the first time?

My travel agency has always been work I do from home. However, during the pandemic I have been working from home for my day job as well. My advice is to have a good working area. A Quality desk, chair, and monitor can make a big difference.In a zoom meeting someone commented about how my bed is always made. I joked had I known I was going to be doing so many video call meetings at my desk I may not have put it in the bedroom.

How do you separate your personal and work lives?

Take a break! I often get the song from Hamilton stuck in my head when Angelia and Eliza are trying to convince Hamilton to take a break. Sometimes you just have to step away and do something for yourself, then come back with fresh eyes.

As cities reopen, what local establishment/attraction/site would you encourage people to seek out in your town?

We love our local brewery, Hutton and Smith. They are an all around good business started by passionate people. It also helps that is just a brisk walk from our apartment, so we walk away with beer and exercise.

What’s your travel style?

I’m the type of person who puts a lot of thought and planning into vacations. I put value on new experiences and often forget to actually rest. I can, however, be spontaneous. Once when a beach trip got ruined by a hurricane we took last minute flights to Colorado instead.

What’s your favorite travel destination that you’ve been?

Catalina Island. My now husband and I went out to Catalina Island last year while in California. It was the most romantic trip we’ve done together so far. We haven’t had a honeymoon yet, but hopefully post pandemic we can change that.

Remain hopeful! It’s a tough time right now for those of us who really like to get out and explore but I have hope that we’ll be able to be back out there soon!

Abigail’s words of wisdom to fellow entrepreneurs, remote workers, and travelers

Thank you, Abigail, for sharing some of your experiences and earned wisdom with us today! I encourage everyone to follow her on Facebook and Instagram to stay abreast of Disney Resort news and updates.

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