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Growing up in the Philippines, Jamaica wanted to be a teacher, flight attendant, nurse or a chef. She was able to realize her dream of working as a flight attendant and she says it helped her be open-minded, more understanding, humble and grateful. As a bartender for Chicago's First Lady Cruises, those skills still come in handy. Learn more about Jamaica, including what her future travel plans are.
Why did you become a bartender?
Bartending is fun and a great part-time job. It’s fast-paced and it’s pretty cool running into different people all the time.
What is your favorite building on the tour and why?
Carbide & Carbon building! It’s not your typical straight, tall or simple black or white building. It has black granite, dark green terra cotta with gold accents that look like a champagne bottle. I think it’s pretty clever and it definitely makes me think of the prohibition period!
Tell us about a memorable experience on the job at Chicago’s First Lady Cruises.
My fave would be working a charter for a 60th birthday on Little. The song 1,2,3,4 by Plain White T’s came on and the kid who was getting a drink from me said his dad sang the song! I thought he was kidding, but our deckhand, Robert Hartley, confirmed it! I couldn’t believe it then next thing you know Tom Higgenson came down with his son to get a drink! I’ve also worked pretty good charters having Chase Elliot (NASCAR driver) on the boat and my fave brewery, Revolution!
What has been your most interesting guest interaction?
I forgot which charter it was, but it was for Instagram popular travelers or something. I met this super sweet and lovely lady Ms. Sarah G, who got so excited when she found out my name is Jamaica. She immediately told me she’s Jamaican and would love to give me recommendations if I ever go there! She gave me her card, took a photo of my name tag which she posted on Instagram including the rest of her weekend in Chicago!
Where in Chicago are your favorite places to….
● Unwind – Museum Skyline
● Experience the great outdoors – Lake Michigan/Starved Rock
● Grab a great cup of coffee/tea – Sawada Coffee in the West Loop!
● Enjoy a delicious dinner – my best friend and I enjoy trying out new spots so I can’t say we’ve dined at the same place twice. I would say anything on the West Loop or River North then Roka Akor for dessert! Try “ube pot de crème”! They don’t always put it on the menu, but you can always ask the server!
● Play tourist for a day (besides the cruise of course!) – The Bean! Or London House
What’s something about Chicago that is a “hidden gem” of yours?
There’s a quiet beach up north. I don’t even know what it’s called, but it’s off of Willow Road straight down to the lakeside.
When you have visitors to Chicago, where is one of the first places you take them (besides the cruise)?
Skyline and Signature Lounge on 95th!
What is the most adventurous thing you've ever done?
I would say my first time traveling internationally. I was supposed to go to Amsterdam, but I didn’t get on the flight so, I booked a flight to Copenhagen without any plans and just figured it out when I got there and had the best 3 days ever with a maximum 5 hrs of sleep!
Where is your favorite place you’ve traveled to?
Besides Copenhagen, I like Dublin and Korea!
Where is the next destination on your travel wish list?
JAMAICA!!! and Greece
What’s the last book you read or are currently reading?
Crazy Rich Asians!
If you had to eat just one meal for the rest of your life, what would it be?
Any pasta really
What is something people are surprised to learn about you?
One thing people are surprised to know about me is for being well-traveled so young and having experience in a variety of industries.