Utrippin Stories
Groups Travel Guide for 2025–2026
Utrippin Team••2 min read
From Florida beach houses and Smoky cabins to Virgin Islands villas, Puerto Rico, Mexico, Tuscany and Colorado ski—how to plan easy group trips.
Great group trips hinge on space, location and simple plans. We combine big shared homes or well-located hotels with smart logistics so everyone has a blast.
🇺🇸 USA Crowd-Pleasers
- Florida Panhandle (30A/Destin) — Huge beach houses, walk to sands.
- Smoky Mountains — Mega-cabins with game rooms and hot tubs.
- Colorado — Ski chalets near lifts plus non-skier options in town.
- Nashville/Austin — Music, food halls and rooftop nights.
🏝️ Virgin Islands & Puerto Rico
- St. Thomas/St. John — Villas with views + private boat days.
- St. Croix — Relaxed island pace, rum history and snorkeling.
- Puerto Rico — Old San Juan culture, El Yunque hikes, bioluminescent bays.
🌍 International Staples
- Riviera Maya/Tulum — Villas, cenotes and beach clubs.
- Tuscany — Farmhouse stays with chef dinners and wine towns.
- Costa Rica — Jungle lodges, zip-lines and surf lessons.
🧰 Logistics That Matter
- Split payments and clear rooming lists.
- Airport transfers sized to your group + grocery drop.
- Core daily plan + optional tracks so everyone's happy.
📅 When to Go
Spring: Austin & Puerto Rico. Summer: Florida + Virgin Islands. Autumn: Smokies & Tuscany harvest. Winter: Colorado ski and city NYE.
💡 Final Thought
Pick a home base that fits the crew, book the big stuff early, and leave white space for spontaneity—the secret sauce for unforgettable group trips.