Upcoming Group Trips

Travel together, experience more and leave the planning to us.

2027 Trips
2027 Trips
2028 Trips
2028 Trips
Why Travel With TryShy?

Travel Together &

EXPERIENCE MORE

TryShy Travel curates hosted small group trips for travelers who want to explore incredible destinations, enjoy thoughtfully planned experiences and connect with others without figuring out every detail themselves. We offer a limited number of hosted trips each year and intentionally keep our groups small to create a more personalized travel experience.

Six women from a TryShy Travel group trip posing beneath the iconic Welcome to Napa Valley sign in California.

2027 Group Trips

  • Aerial view of a beach resort with sandy beach, lounge chairs under umbrellas, a hotel complex with pools, and a coastal landscape with hills and ocean in the background.

    St. Kitts | Soca & Sunsets | February 5 - 9

    Join TryShy Travel for a curated four-night Caribbean getaway to St. Kitts filled with sunshine, island culture and unforgettable experiences. Your trip includes beachfront resort accommodations, daily breakfast, roundtrip airport transfers and a day trip to Nevis.

    Explore This Trip
  • Aerial view of a tropical resort in Grand Bahama with pools, palm trees, colorful cabanas, and a large cruise ship docked at a pier by the ocean.

    Carnival | Spring Break | March 15 - 19

    Trade the usual spring break crowds for ocean views, island stops and grown-up fun aboard Carnival. This Bahamas cruise is for travelers who prefer cocktails over chaos, bikinis over books and a vacation that is already planned.

    Explore This Trip
  • Palm trees framing a white-sand beach with turquoise water, lush coastal hills, and a bright blue sky.

    Jamaica | Degrees, Daquiris & Dancehall | July 15 - 19

    Hard work deserves a little island time! Celebrate a new degree, a personal milestone, or simply because those vacation days won't request themselves off.

    Explore This Trip
  • Aerial view of Sydney Harbour Bridge and Sydney Opera House with city skyline in the background.

    Australia | Classic Down Under | October 5 - 17

    Experience Australia through a thoughtfully planned itinerary featuring Sydney, Uluru, Melbourne and the Great Barrier Reef region. From cosmopolitan cities and Aboriginal culture to a sunset dinner near Uluru and a Great Barrier Reef experience, this signature hosted trip brings several bucket-list moments together in one journey.

    Explore This Trip

2028 Group Trips

  • Tropical resort pool at sunset with silhouetted palm trees, lounge chairs, and cabanas reflected in calm water beneath a pink and purple sky.

    Secret Destination | February 17-21, 2028

    Dare to be surprised? For the first time ever, TryShy Travel is taking you on a thoughtfully curated, 4-night escape where the destination stays a secret until the end, but the experience is anything but ordinary. Sign up for updates!

    Keep Me Informed
  • Amalfi Coast, Italy, with colorful cliffside villages overlooking the Mediterranean Sea.

    Virgin Voyages | Bonjour, Bellissima | May 28-June 4, 2028

    Join us on this hosted, seven-night Mediterranean escape aboard Virgin Voyages’ Valiant Lady. Sailing from Barcelona, Spain along the French Riviera and through Italy, consider this your invitation to trade the everyday routine for something bellissima.

    Explore This Trip

What Travelers Say About TryShy

“Can you imagine a stress free vacation that included booking, payment, departure and return? Shyla makes the entire experience one that is not only seamless but STRESS and HASSLE FREE!”

Woman with tattoos wearing sunglasses and a white dress sitting on rocks near the ocean with turquoise water and sailboats in the background. 
— Emily Z.

“You can expect a white glove experience when traveling with Shyla. She creates a comfortable vacation. If you’re the kind of person who can only afford one vacation a year and needs affordable budgeting, you can work with her to make your travel dreams come true!”

A group of six women and one man inside a car, smiling and making peace signs. The woman in the front is taking a selfie, wearing glasses and a floral top. The others are seated behind her, some wearing sunglasses, and one woman is wearing a hat. They appear cheerful and enjoying their time together. 
— Brittney B.

“This week was great!!!! Tryshy Travel made sure we got to our destination in Miami to board the beautiful ship Carnival Celebration. We had a very great trip. I will book over and over with TryShyTravel.”

Two people standing inside a red amusement park ride with a wooden roof. The woman on the left is wearing a wide-brimmed straw hat, sunglasses, a gray T-shirt, and a red lanyard. The man on the right is wearing a white hat, sunglasses, a light blue T-shirt, and a blue lanyard. They are smiling and holding onto a control lever or handle. In the background, there is a spiral staircase and a woman standing at the top of the ride with trees and a cloudy sky visible behind. 
— Sandy W.

See What Traveling With TryShy Looks Like

Good trips create memories. Great group trips create stories you will still be talking about years later. Take a look at some of the destinations, experiences and connections our hosted group travelers have enjoyed.

Group of people sitting around a table in a restaurant, smiling for a photo, with pizza and drinks on the table.
Woman leaning on a large, rust-colored metal sculpture resembling a letter W, outdoors with trees in the background.
A group of six women standing in front of a display with shelves of black bottles, books, and gift bags. The background features a blue wall with the word 'BROWN' on it, and three bright ceiling lights.
Two women smiling and standing close together in a lively outdoor shopping area under colorful umbrellas. One woman is wearing patterned pants, a green crop top, and sunglasses. The other woman is wearing a floral orange and pink dress, a hat, and su
A woman with blonde hair in a bun, wearing a black jacket, is leaning forward to kiss a bronze sculpture of a camel's head in a lobby area with elevators in the background.
Group of people celebrating on a cruise, all wearing matching red shirts, inside a decorated tropical-themed room.
View More TryShy Group Trip Memories
Icon of three people with a speech bubble, representing a group discussion or crowd.

Why Travel with Us?

Curated, Not Crowded

Blue outline icon of a travel checklist with an airplane icon, featuring a checklist with four checked items and a folded corner.

Small group experiences with intentional itineraries and exclusive touches.

The Details are Handled

Outline of a suitcase with a handle, drawn in blue lines on a black background.

We take care of planning so you can spend less time figuring it out and more time enjoying it all.

Travel Your Way

Blue line drawing of a camera on a black background.

Come solo, bring your partner, or invite your crew—everyone is welcome.

More Than a Vacation

Our trips are designed around experiences you’ll actually remember and talk about years from now.

Hosted Group Trip FAQs

  • Absolutely. Many TryShy hosted group trips welcome solo travelers, couples and friends. You can enjoy the comfort of traveling with an organized group without needing to bring your own crew. Travelers booking a room alone will pay the applicable single-occupancy rate, which may be higher than the per-person double-occupancy rate.

  • Inclusions vary by trip and may include accommodations, airport transfers, group transportation, tours, activities, select meals, special events and travel protection. Every trip page provides a detailed list of what is and is not included, so you can review the full experience before reserving your spot. Payoff Perks are included on every hosted group trip.

  • Flights are not included unless the individual trip page specifically states otherwise. When available, TryShy Travel may offer assistance with arranging flights based on your departure city and travel preferences. Always review the trip inclusions before booking, and do not purchase airfare until your trip has been confirmed.

  • Yes. All TryShy hosted group trips offer payment plans after the required deposit is paid. Your booking page will provide the deposit amount, payment schedule and final payment deadline. All reservations must be paid in full by the stated deadline to remain confirmed.

  • No. We want you to enjoy the destination at a pace that feels comfortable for you. Some activities may be optional, while others are included as part of the hosted itinerary. If you choose to skip an included activity, its cost may not be refundable, and you will be responsible for arranging any alternative transportation or plans.

  • Join the TryShy Travel email community to receive announcements about new hosted group trips, early booking opportunities and important registration deadlines. You can also follow TryShy Travel on Facebook, Instagram and TikTok and check the Upcoming Hosted Group Trips page for the latest experiences.