
Captain Carrie Found Her Dream Job at 12
I met Carrie when I was working for Trilogy Excursions in Hawaii last year. Carrie was a senior employee who had a reputation for being extremely organized and a little tough. I was slightly intimidated before our first day of work together, but I quickly realized that her work ethic matched my style.
Carrie has a routine for everything. Every single item on the boat has a home; each task that needs to be completed has a ritual. She takes pride in delivering the best possible service to the guests onboard, so she definitely doesn’t want to waste any time looking around for things or wondering if a task has been completed. My first job working on a boat instilled these same values in me, so I really enjoyed the system.

The thing that I remember most about working with Carrie is her passion for getting to know guests on a personal level. She and I would work a crazy schedule that sometimes included a full day tour with two snorkel stops and lunch, followed by a whale watching tour and then a sunset sail. In one day we could meet as many as 100 people and Carrie would learn and remember 95% of their names. Her talent sometimes seemed supernatural, but when you account for her serious passion for people and for her job – it actually makes sense. Here it is, my interview with Captain Carrie:

1. Where are you from?
Jacksonville, FL
2. When and where did you first learn about sailing?
The first time I was on a sailboat was on a Trilogy excursion (as a tourist) in 1987 (I was twelve). I sailed with Trilogy again when I was 20 and just about to start my senior year in college. I knew I wanted to move to Maui when I graduated from college. Six weeks after my graduation, I moved to Maui to work for Trilogy. Mostly, I was just so excited to work on a sailboat! I was not ready to enter the “real world” of corporate America right after college, so moving to Maui to work on a sailboat seemed like an incredible option.
3. What is your current position, and how long have you worked for that company?
I am currently a training captain/first mate for Trilogy Excursions and have worked for Trilogy for almost 9 years total (1997-1999 and since 2009).
4. Describe the best workdays:
I love working with others (captain and crew) that have the same passion for having a fun, safe, and smooth day on the water! I love days where our guests have the best day of their vacation! Most times, these are whale-watching days when we see a lot of action and have amazing guests and crew. Sometimes it all just comes together perfectly!
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5. Favorite boat snack?
Fresh avocado and chips! Fresh coconut & mango are great, too!
6. What’s the best part about working on a sailboat?
The times when we get to turn off the engines and let the wind take us. That feeling of the boat gliding through the water is the best.
7. What are some of the struggles?
Since I work for a sailing charter boat company, the biggest struggle is managing guests and their expectations, especially regarding the weather.
8. What are some of your hobbies outside of work, and how (if in any way) has your job helped you to develop these interests?
I love the ocean and want to share that love with guests so that our oceans and everything in them can be healthy in the future. I like learning about our Humpback Whales, too!! Sharing this information while on the job is a highlight of my job!
9. What’s the best advice you could give to people (specifically women) interested in getting a job in this field?
That it is not all “glitz and glamour.” Working hard & getting the job done correctly/right the first time will make your work easier all around (and your crew will appreciate it and have your back).
Carrie will be getting married this month, send her your love in the comments below!
Inspired by Carrie’s interview? Pin it for later!
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Allison on April 5, 2016 at 17:55
This makes me want to go to Maui and take a trip with Carrie!! Let the planning begin…
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Do it! You definitely won’t regret it. I recommend going between Jan – March to catch the peak whale watching season!
We are so proud of you 2!!!!
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🙂 Carrie is the best!
I’m so excited to have Capt Carrie as my sister in law! So proud of her and wish her and my brother all the best! Great interview, thanks!!
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I also met your brother while in Maui, two wonderful people! 🙂