Travel Advisor

Jessica Maycock
Expertise
- Off-the-Beaten-Path,
- Outdoors & Nature,
- Big Island,
- Maui,
- Wyoming,
- South Dakota
Based in
Gillette, Wyoming
Languages spoken
English
Profile details
About
An avid travel enthusiast with a passion for exploring Hawai'i and U.S. national parks, I bring my Type A planning skills to ensure every trip is meticulously crafted for an unforgettable experience.
Travel style
My travel style is rooted in authentic, off-the-beaten-path experiences, where I seek a perfect balance between relaxation and adventure. Appreciating the beauty of nature is always at the heart of my journeys.
Jessica's travel guides & trip reports

Kick Back in Kihei: Adventures in Southwest Maui

Off The Beaten Path in Hawai'i: Quiet Adventures on the Southern Coast of the Big Island
Favorite hotels
Jessica's travel photos





Jessica's reviews
Jessica was there for us every step of the way. She helped us plan a very fun adventure. Flights, vehicle and stay. She didn’t stop there. She helped us plan fun things to do and had a lot of helpful insights on ideas for our trip. We would love to use her again. Hopefully in the near future, as she made it so easy. Loved the package price as well! We had difficulties on the way home with our flight and she was there for us making sure we were taken care of. This is the best and only way to plan a trip! Thanks Jessica Maycock!
- Constance H.
Booked travel to Maui
- January 2025
Booking through Jessica was one of the best experiences I have had. I told her what I was wanting for a girls weekend and that I didn't know where to go but gave her a list of "wants" and she went above and beyond my expectations. She provided an itinerary with things to do and places to eat and every recommendation she had was fabulous. I didn't have to worry about anything. The Inn that she booked for me was cozy and accommodating and was located in a place that kept reminding me of a Hallmark setting. It was absolutely the best girls weekend I have ever had. I highly recommend using Jessica, she listens to what you want and makes it happen.
- Stacy I.
Booked travel to Colorado
- January 2025
Love this travel agent! She handled details of booking smoothly and quickly. Very helpful and provided great recommendations. Will use Jessica again!
- Janet G.
Booked travel to Florida
- January 2025
We appreciate Jessica’s recommendation and reservation at this hotel. She booked us an extra night so we could stay in our room until we flew out later on our last night. Very thoughtful!!!
- Joseph M.
Booked travel to Texas
- October 2024

Get in touch with Jessica
Reach out to customize and book your own experience. Or, just to chat about travel in general.
You can normally expect a response from Jessica within a business day or so. You’ll also be subscribed to our travel newsletter (you can unsubscribe at any time).
