GWLT offers thoughtfully curated group trips designed by and for women who love to explore both iconic landmarks and off-the-beaten-path local gems. Our adventures blend must-see destinations with hidden treasures, creating unique and unforgettable experiences for women who crave authentic travel.
Some of our most popular trips fill up fast, so be sure to sign up to be the first to know when our trips go live!
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Lake Geneva Winterfest weekend
January 31st - February 2nd, 2025
This January, join us for a fun-filled weekend getaway to Lake Geneva! Escape the city and enjoy two nights of winter activities, including Winterfest, featuring a national snow sculpture competition, ice sculptures, live music, and more. We will explore the park’s stunning snow and ice sculptures, have free time to browse boutique shops, and a creative wood project session at Board and Brush Creative Studio. Wrap up the weekend with an optional morning of snow tubing! The best part is this is just a two hour drive from Chicago so no PTO needed!
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mEXICO CITY
February 20th - 25th, 2025
Join us for an unforgettable women's group adventure in the lively heart of Mexico City! Immerse yourself in the vibrant culture and tantalizing flavors as we explore this incredible destination together. Highlights of our journey include a hands-on cooking class where you'll master authentic Mexican recipes, a beautiful day trip to stunning hot springs, and so much more. Packed with exciting experiences, this trip offers the perfect mix of adventure, culture, and connection—designed to create lasting memories and new friendships!
After a fun but busy 5 days in Mexico City, join us in the Mayan Riviera to relax at the beach. Our Mexico City & Mayan Riviera trips will be run back to back so you can opt to join us on both and save $175 on the combined trip.
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MAYAN riviera
February 25th - March 1st, 2025
Join us for a rejuvenating 4-night escape by the beach, where relaxation is the name of the game. This trip is all about unwinding, soaking up the sun, and leaving the daily grind behind. While we’ll spend most of our time enjoying the resort’s many fun activities, we’ll also venture out for a day trip to Tulum to explore its breathtaking beachside ruins, followed by a refreshing swim in a nearby cenote—an unforgettable natural wonder.
Craving more of Mexico’s rich history and culture? Extend your adventure by joining us in Mexico City to experience its vibrant energy. Our Mexico City & Mayan Riviera trips are scheduled back-to-back, so you can choose to embark on both and save $175 on the combined experience!
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Portugal
May 24th - June 1st, 2025
Join us for an unforgettable 8-night adventure in Portugal, where we’ll split our time between the vibrant city of Lisbon and the stunning beaches of the Algarve. Spend the first 4 nights in Lisbon exploring its charming streets, tasting local cuisine, and discovering hidden gems. Then, we’ll head south to the Algarve for 4 nights of pure relaxation along the coast. Imagine days spent lounging on sun-soaked beaches, indulging in the region’s renowned seafood, and unwinding with new friends. To top it off, we’ll be taking part in plenty of activities on the water including boating along the coast enjoying in the Algarve’s iconic caves and cliffs.
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SOUTH AFRICA
October 1st - 13th, 2025
Join us in South Africa for an unforgettable adventure that combines breathtaking landscapes, vibrant culture, and thrilling wildlife encounters. Begin your journey in Cape Town, a city where stunning coastal scenery meets rich history. You’ll hike iconic mountains, savor world-class wines in the Cape Winelands, and explore charming seaside towns along the Garden Route.
The adventure continues with a luxury safari, where you’ll experience the thrill of spotting the Big Five in their natural habitat. Enjoy daily game drives, gourmet meals, and time to unwind by the river or pool at a stunning safari lodge. With the perfect blend of relaxation, exploration, and unforgettable experiences, this journey promises memories that will last a lifetime. Whether you’re a seasoned traveler or embarking on your first African adventure, this trip is not to be missed.
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*We currently have local communities in Chicagoland Area, Wisconsin and New York City. If you are not in one of those locations, please still include your city as we are looking to add more in the future!
