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TRAVEL SPECIALTIES
All-Inclusive Caribbean
All-Inclusive Caribbean
All-Inclusive Caribbean
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!
Cruises
All-Inclusive Caribbean
All-Inclusive Caribbean
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!
Europe
All-Inclusive Caribbean
Central & South America
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.
Central & South America
Customized Trip Planning
Central & South America
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.
Domestic Discoveries
Customized Trip Planning
Customized Trip Planning
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.
Customized Trip Planning
Customized Trip Planning
Customized Trip Planning
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.
why "TRY SHY?"
Our Philosophy
We believe travel should be more than just a getaway—it should be a celebration of your time, your hard work, energy, and style. Life is too short for cookie-cutter trips or stressful planning, which is why TryShy Travel creates experiences that let you fully embrace every moment without worrying about the details. Our focus on curating all-inclusive adventures that balance relaxation, excitement, and connection allow you to recharge, explore, and shine! Your time is valuable, and your vacations should reflect that, too.
Our Expertise
Thoughtfully designed, effortlessly executed, and unapologetically unique, we aim to ensure every moment is designed to leave you feeling like you just unlocked a secret level of travel. Many of the destinations you’ve been daydreaming about? We’ve explored them (some, more than once). And if you ask us, real-world experience beats endless Google searches every time, and we use that knowledge to reveal insider knowledge, VIP perks, and experiences that sometimes rarely make it to the public travel sites.
Our Destinations
We don’t just plan vacations, we create brag-worthy escapes you’ll still be talking about years from now. A large part of our travel planning success comes from taking the time to understand you, your style, your priorities, and your “must-haves,” then delivering a trip that feels tailor-made. Whether you’re crafting a custom getaway or joining one of our carefully curated group adventures, the kind of trip people wish they’d booked is the kind you’ll soon be enjoying.
Our Flexible Payment Plans & Cancellation Policies
Unlike other agencies that trap you with no refunds, no credits, and zero flexibility, we believe in taking a different approach. At TryShy Travel, we get it—life happens! That’s why we give you options: pay your balance on your schedule—monthly, bi-monthly, or quarterly—hold your spot for 3 days, cancel within 7 days for a partial refund, or transfer your investment to another group trip if plans change. Travel should feel exciting, not scary—and that's why we’ve got your back every step of the way with flexible trip change and cancellation policies.
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