Celebrating 4 years in business! Thank you for supporting our small business!
Celebrating 4 years in business! Thank you for supporting our small business!
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When you’re deciding who to travel with, trust is everything. That’s why we showcase real reviews, past trip highlights, and transparent details about destinations upfront. Your safety, trust, and peace of mind are always our top priorities. You’ll know exactly what you’re signing up for and can feel confident your vacation is in reliable hands.
Our curated group trips come with low deposits and flexible payment plans so it’s easier than ever to secure your spot and lock in your dream getaway without stretching your budget.
Our itineraries aren’t copy-and-paste packages—they’re uniquely designed to deliver jaw-dropping moments; and no two trips are ever alike. Even if you’ve joined us on two group trips to Napa Valley already, you can expect something completely fresh and different the third time.
When you choose a hosted group trip, you'll have on-the-ground support and a consistent point of contact from start to finish.
We cap our hosted group sizes at 25 guests on purpose to give you personalized attention and VIP-level vibes each time. Groups share similar energy and respect for shared experiences. To ensure the group feels cohesive, participants are encouraged to adhere to our Group Code of Conduct.
Our group trips feature private events, curated excursions, and elevated touches that go beyond the typical. We aim to create unique experiences you won't find anywhere else.
Destinations are selected with care and respect for the local people, food, and heritage. We believe in connecting with communities in ways that celebrate their culture.
Enjoy thoughtful extras like group themes, private photo shoots, welcome gifts, and custom surprises.
While the itinerary might be curated, you're always free to opt out of group activities and make the trip your own, with no judgements.
We've built in options for our curated trips that give you room to breathe, change your mind, and keep your travel dreams alive.
Need a few days to think it over because you're not ready to commit? Lock in your spot for 3 days on any eligible trip while you confirm details, request PTO, or convince your bestie to join. Once you decide you’re in, pay your deposit and let the countdown to good times begin!
Over here, we like to keep it flexible. Choose the payment method that works best for you at checkout—and if life shifts, no worries. You can always update your payment method later.
Paid your deposit, but changed your mind a few days later? No worries! Cancel within 7 days of booking and get a partial refund, no questions asked.
At TryShy Travel, we like to keep your deposits low and your expectations high. From all-inclusive resorts to tailored luxury experiences, we make it easy to have it all—without breaking the bank upfront. We also know plans can change. If you need to cancel more than 180 days before a trip begins, your deposit (less a small admin fee) is converted into a Future Travel Credit that can be applied toward another TryShy Travel group trip. Cheers to trips that hit different!
Please reach contact us if you do not find an answer to your question.
The trip's custom group booking page is where you can find a list of all inclusions (and exclusions) for a trip. Find this by clicking on the group trip you're interested in on the group trips page.
No, there is no fee to travel with us. Any extra cost or fee required is explained on the trip's booking page, where applicable, and is usually for a service or optional tour outside of the agency.
Yes, we offer optional travel insurance for all of our curated group trips. You can add it to your package during the booking process, or reach out if you'd like alternative quotes.
Absolutely! We offer adequate free time on our trips to allow you a chance to explore at your own pace, add personal experiences, or simply soak in the vibes your way. You're also at liberty to skip any portion of an itinerary you don't wish to participate in.
We do our best to vet accommodations, excursions, and local partners thoroughly, and we’re hands-on hosts—so you can relax, enjoy, and focus on the memories.
We keep the connection alive from day one! And at about 60 days before a trip, you’ll have access to a private group chat to meet fellow travelers, get updates, and ask questions. Once you’re on the trip, your hosts will keep everyone in the loop so you never miss a moment or a memory-making opportunity.
All of our trips are designed for travelers who love culture, connection, and a touch of luxury with a fun twist. If you enjoy curated experiences, meeting new people, and making unforgettable memories while keeping things stress-free and stylish—this trip is always for you!
We plan our trips in advance to offer our clients the most flexibility and peace of mind when booking. We offer a 7-day cancellation window after your deposit is paid and a future travel credit option in the event of a cancellation 180 days+ before the trip's start date. Travel protection is always strongly recommended to protect your investment.
Respect the vibe, respect each other, and get ready for a trip you won’t forget—because we don’t do basic, and we don’t do drama.
941-557-9757
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FL Seller of Travel # ST38545,CA Seller of Travel # 2071045-50
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