Your Guide To Exhilarating Group Travels.

From Parisian picnics beneath the Eiffel Tower to energetic NYC strolls, the tranquil allure of gondola rides in Venice, and samba dancing at Rio's festive carnivals— TrippyMates is your passport to iconic destinations tailored for memories made in unity.

Share sunlit laughs, twilight tales, and everything in between as you all dive into a world where every adventure is better together.

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Experience Unparalleled Group Travel Adventures Worldwide.

Explore our curated group travel journals highlighting the best activities and tours in prime destinations, nocturnal adventures, top-tier accommodations. and more.

As long as it involves group travel and designed to create worthwhile experiences, we have the perfect guides to make your dream getaways treasured and unique for everyone joining the ride.

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Find the Most Preferred Accommodations Tailored To Your Discerning Tastes.

Choose from a wide array of luxury hotels, spacious yet cozy holiday homes, cottages with group accommodations, or well-appointed multi-room villas from anywhere in the world— TrippyMates features thousands of properties so your group can surely find a worthy home away from home.

Start with these three featured destinations.

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The Caves West End Hotel in Negril, JamaicaThe Caves West End Hotel in Negril, Jamaica

Sun-kissed beaches, rhythmic reggae beats, and the legendary Seven Mile stretch of pristine sands—Negril is the embodiment of Caribbean dreams. Whether you're diving into turquoise lagoons, toasting the sunset at Rick's Café, or dancing under the moonlight, Negril's vibrant spirit is best enjoyed in the company of friends and family.

Tryall, Sandy Bay, Jamaica villa with pool
Tryall, Sandy Bay, Jamaica villa with pool


Providenciales luxury villa in Turks and CaicosProvidenciales luxury villa in Turks and Caicos

Step into a realm where nature's splendors meet vibrant island nightlife. During the day, immerse your group in the serene beauty of secluded coves, explore the rich tapestry of underwater coral reefs, and embark on eco-adventures that unveil the islands' hidden gems. As dusk falls, Turks & Caicos transforms: lively beach bonfires, rhythmic island beats, and waterfront bars come alive, inviting your crew to dance, laugh, and celebrate.

Emara East villa in Turks and Caicos at nightEmara East villa in Turks and Caicos at night


Palm Cay 4-bedroom villa beachfront in NassauPalm Cay 4-bedroom villa beachfront in Nassau

Crystal-clear waters, a mosaic of colorful colonial architecture, and the contagious rhythms of Junkanoo beats—Nassau is a symphony of island wonders. Dive into vibrant coral reefs, barter at bustling Straw Market, or relish a beachside barbecue. In Nassau, the essence of The Bahamas comes alive, best savored with laughter, stories, and shared moments. Where Your Tribe Finds Its Vibe.