McCool Travel interview with Kelly Stilwell. Article by Charles McCool.

5 Minutes With Kelly Stilwell

For McCool Travel’s 146th travel interview, I am thrilled to present Kelly Stilwell. Anyone with “Fun” in their brand name (hers is Food, Fun & Faraway Places) is OK with me. And Kelly is. She is from Annapolis, like my prior travel interview subject, Travis Pastrana. Will the next one be three in a row? Stay tuned!

Kelly Stilwell‘s bio:

Kelly Stilwell is the content creator and social media influencer at Food, Fun & Faraway Places. She lives in Florida with her husband, two daughters (when they aren’t away at college), a very grumpy cat and an escape artist bird. A former stockbroker, Kelly finally took the plunge into writing when her girls were little. Once she discovered her passion for travel, her writing took on a whole new meaning, and she knew her life would never be the same.

McCool Travel interview with Kelly Stilwell. Article by Charles McCool.

Kelly Stilwell

Kelly Stilwell

HOMETOWN …

Washington, DC

ALWAYS IN MY LUGGAGE …

DSLR and external battery for charging phone

3 FAVORITE HOME-AWAY-FROM-HOME PLACES …

  1. Anna Maria Island, FL. My favorite Florida beach (even better than Siesta Key, the #1 beach in the country this year.)
  2. Ocean City, MD. Where I grew up going to the beach. Love Fager’s Island Restaurant!
  3. Annapolis, MD. My sister lives there on the water and it’s so peaceful.

A FAVORITE TRAVEL MEMORY …

Spending the day in Portofino, Italy, about ten years ago. Can’t wait to go back.

McCool Travel interview with Kelly Stilwell. Article by Charles McCool.

Kelly Stilwell

3 FAVORITE TRAVEL BRANDS …

  1. Rocky Mountaineer
  2. Travelocity
  3. Viking River Cruises

3 MONEY-SAVING TRAVEL TACTICS I USE …

  1. Use an Airline credit card for everything to save up miles
  2. Check bags free with Airline card
  3. Take my Food, Fun & Faraway Place Tervis Tumbler with me so I don’t have to pay crazy prices for bottled water. More and more airports have filling fountains.

3 WAYS THAT I HAVE FUN WHILE TRAVELING …

  1. Meeting new people. It’s one of my favorite things about traveling.
  2. Photographing everything, especially the food!
  3. Finding the Must-Eats in each destination (I’m a foodie!)

8 WORD (OR LESS) TRAVEL MANTRA …

“Enjoy food, have fun, and see faraway places.”

McCool Travel interview with Kelly Stilwell. Article by Charles McCool.

Kelly Stilwell

FAVORITE NON-TRAVEL WEBSITE …

The Weather Channel

MOST MEMORABLE SOUVENIR …

A black and white hanging paper mache clown from Mexico.

FAVORITE CHEAP EAT …

Skinny’s Burgers on Anna Maria Island

RECENT DISCOVERY …

I have only been to Canada a few times, but now that my oldest daughter is in school there, I’m trying to explore it more. I got to see Vancouver to Banff on the Rocky Mountaineer and it was heavenly. Banff National Park is unbelievably gorgeous.

I AM FORTUNATE TO HAVE MET …

Cacinda Maloney of Points and Travel. She’s become one of my closest friends.

I WOULD LIKE TO MEET …

Glen Gilmore and John Discala (Johnny Jet!)

McCool Travel interview with Kelly Stilwell. Article by Charles McCool.

Kelly Stilwell


Thank you so much, Kelly, for sharing your travel inspiration and tips.

Follow Kelly Stilwell on FacebookTwitterInstagram, Pinterest, and KellyStilwell.com.


McCool Travel presents tips from travel experts in our 5 Minutes travel interview series—featuring travel industry giants, super frequent travelers, and adventurous persons. Check out McCool Travel’s previous travel interviews. Previous 5 Minutes travel interview: Travis Pastrana.


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3 Responses to “5 Minutes With Kelly Stilwell”

  1. shankar banjara August 22, 2017 at 9:10 am #

    Hello Kelly Stilwell i invite you to visit Nepal, Himalayas amazing place to see, capture Mount Everest, any way love to read this post with photo.

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    […] McCool Travel presents tips from travel experts in our 5 Minutes travel interview series—featuring travel industry giants, super frequent travelers, and adventurous persons. Check out McCool Travel’s previous travel interviews. Previous 5 Minutes travel interview: Kelly Stilwell. […]

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