Save up to $400 on air + land vacation packages! Offer expires April 9th!
We curate trips that break the mold & offer service that sets the standard
We curate trips that break the mold & offer service that sets the standard
TryShy Travel is a premium, full-service travel agency specializing in all-inclusive vacations for those who tour and travel as hard as they work. We craft elevated experiences for families, couples, and solo explorers, with carefully tailored itineraries that highlight the exceptional. Our dedication to personalized service ensures every element of your journey is refined, seamless, and handled with the utmost care. Founded and led by Shyla Bryant, a passionate travel enthusiast and dedicated professional, the company has been creating memorable trips for customers since 2021.
Why stress over planning when we’ve already mapped out the magic? Our curated group trips are designed with the perfect balance of fun, freedom, and unforgettable vibes. Most trips are hosted, and every trip is infused with local culture and curated to make you feel like a VIP from touchdown to takeoff.
We plan the details, set the scene, and match the mood to the destination. All you have to do is choose your vibe and pack your bag: your new travel fam will be waiting. You’ll laugh harder, explore deeper, and come home with stories you’ll be telling long after the tan lines fade.
From the turquoise waters of Aruba to the lush hills of St. Lucia, the Caribbean is our favorite playground! We love building all-inclusive vacations that take you from tropical shores to worldwide adventures. Whether you're looking for an exciting island hopping vacation in Antigua or wanting to travel to an all-inclusive party resort in Jamaica, we’re here to get you there!
Our agency is certified with the Cruise Lines International Association (CLIA), meaning we have the insider knowledge, training, and connections to craft flawless cruise experiences just for you. Your dreams of sailing the turquoise waters of the Caribbean, exploring Europe’s legendary river cruises, or taking a luxury voyage across the globe, have met their match with our cruise planning expertise!
While the Caribbean is our sweet spot, TryShy Travel's planning expertise doesn’t stop there. Our passion for crafting unforgettable European getaways stem from personal journeys and insider knowledge to connect you with iconic cities, hidden gems, and authentic cultural experiences that’s both picture-perfect and uniquely yours.
From the serene beauty of Lake Atitlán to the breathtaking sunrise atop the famous Indian Nose Mountain, Guatemala is a perfect glimpse of the magic Central America offers. South America boasts vibrant cultures, lush landscapes, and ancient traditions that come alive at every turn. We'll guide you to destinations boasting with color and brimming with adventure—all while making sure your journey is seamless from takeoff to touchdown.
We’ve crossed the U.S.A. on multiple road trips and explored more than 38 states. From the sweeping vistas of the Grand Canyon to the thundering beauty of Niagara Falls. As Hawaii destination experts, we also design escapes that feel exotic. Our domestic travel planning delivers curated, bucket-list worthy itineraries, local experiences, and seamless logistics so you can focus on making memories.
Your travel style isn’t one-size-fits-all, and neither are our itineraries. Whether you’re craving a luxurious Caribbean escape, a whirlwind European adventure, or a weekend getaway close to home, we design trips that match your vibe, budget, and bucket list. From handpicked accommodations and curated excursions to smooth transfers and 24/7 support, every detail is exclusively tailored for you. All you have to do is pack, and we’ll handle the rest.
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