All-Inclusive Vacations, Cruises & Group Trips

Caribbean, U.S. & European Vacations Designed Around You

Your next best vacation deserves more than a quick online search.

TryShy Travel is a premium, full-service travel agency specializing in Caribbean all-inclusive vacations, cruises, custom U.S. and European getaways, and curated group trips. With more than 20 years of travel expertise, we provide personalized recommendations, expert guidance, and seamless coordination for couples, families, solo travelers, and groups who want more from their time away.

Husband and wife smiling as they cruise along the river in a gondola ride in Venice, Italy.

“Shyla was exceptional from the very beginning. She is highly knowledgeable, and all the information she provided was clear and easy to follow. Whenever we had questions, she responded promptly and thoroughly.” — Betsy W.

Scenic lake surrounded by towering mountains covered with dense green trees, with several boats and people on the water and along the shore under a blue sky.

You Pick the Destination. We'll Handle the Rest.

Stress-Free Group Travel Planning

Join one of our small, curated group trips or let our group travel experts plan your family reunion or birthday getaway. Whatever you choose, we’ll take the pressure of group planning off your hands.

Cruise Vacations

As a CLIA-certified travel agency, we specialize in booking Caribbean, Alaskan, and European cruises with confidence.

All-Inclusive Vacations

Two blue hands holding a blue infinity symbol on a yellow background.

We provide expert planning for Caribbean, Mexico, and luxury all-inclusive resorts.

Vacation Packages

Illustration of a globe with an airplane flying around it, on a yellow background.

Book a vacation package with handpicked stays, experiences, and travel options tailored to your style, budget, and destination.

Work With Us

Rated 5.0 on Google by 70+ Happy Travelers

20+ years of travel expertise backed by CLIA and IATAN industry credentials.

“From start to finish, Shyla went above and beyond anything we could have imagined! If you’re looking for someone who genuinely goes the extra mile and treats your vacation like it’s her own, I cannot recommend her enough.”

— Alayna B.

“Shyla handled ALL the arrangements for our trip to Jamaica and couldn’t have gone any smoother…NOT AN ISSUE WAS HAD 👍Thanks Shy, you provided us some of the BEST customer service we ever received from a travel agent. Would we use her again… WITHOUT A DOUBT!.”

— Scott D.

“Each step of the way Shyla was there helping me and my group. There were 12 of us and it went very smooth!!!! Definitely would use again and would refer her to everyone!!! Thank you!”

— Yunia I.