What we’re about
This group is for people who want to get out and explore Chicago and beyond, make new friends, and have some fun! If you don't want to wait on friends to finally say “yes” to get out to enjoy all that Chicago has to offer and to see the world. Life is too short!
The local events in this group are member-driven so if you’d like to host a Meetup in your area (i.e. walk, museum, coffee, play pickleball, concerts, etc), feel free to let me know and I'll help you get it set up in the group!
The trips in this group are usually 90% solo travelers but everyone is welcome, female/male, solo/couple/friends, straight/LGBTQIA+! So let’s travel together with fun, like-minded travelers! If you have an open mind and are kind to fellow travelers, you will fit in perfectly on these trips!
NOTE: The people on these trips are from all over the States but you’ll always be connected with people from the same city on a trip so you can meet up face to face and get to know your future travel buddies prior to the trip. You’ll also be connected to the whole group via email prior to the trip so you can virtually get to know those that are from different areas. On average, the people on each trip are 90% solo travelers but it’s hard to predict the exact demographic for each trip so please keep this in mind.
Feel free to join the Facebook group to connect with past travelers on these trips, see pictures, ask questions, funny travel memes, travel-related articles, etc: https://www.facebook.com/groups/613025845523107
The trips in this group are put on by a tour company called Globe Drifters and they focus on small group trips geared towards solo travelers with the mission of giving new meaning to travel by putting the human experience at the heart of their trips. The groups are small, usually with 12 people maximum per trip and about 90% of everyone on each trip are solo travelers so you’re not stuck being the odd man out on trips with mostly couples. You’ll have the best of both worlds, solo travel with the security of a small group of other solo travelers for some company on your adventure! To contact Globe Drifters directly, you can email [info@globe-drifters.com](mailto:info@globe-drifters.com).
Upcoming events
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🎄✨ Merry & Bright: South Loop to Riverwalk Holiday Lobby Stroll ❄️🏨
Hilton Chicago, 720 South Michigan Avenue, Chicago, IL, US🎄✨ Merry & Bright: South Loop to Riverwalk Holiday Lobby Stroll ❄️🏨
🌆 A Sparkling South Loop–to–Riverwalk Holiday Adventure ✨
Our holiday magic continues — this time with a brand-new route showcasing the festive beauty of the South Loop, Grant Park, the Cultural Center, Millennium Park, and the sparkling Chicago Riverfront. 🎄🌊✨
If you joined the Magnificent Mile version, get ready for a completely different experience. This edition highlights the historic hotel corridor of the South Loop, where early-20th-century architectural gems glow with vintage holiday charm, and then guides you north through Chicago’s cultural heart before ending among the modern glass towers of the Riverwalk — glittering with seasonal lights.
Expect twinkling lobby trees, elegant historic décor, grand architecture, creative seasonal displays, and waterfront holiday ambiance — all wrapped into one joyful winter stroll. 🎁✨
This is a fresh route, new lineup of hotels, and a whole new festive vibe… but with the same beloved holiday spirit that keeps this tour one of my most popular annual traditions.
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🕰️ Schedule, Meeting Info & Cost
📅 Sunday, December 13th, 2025
🕥 11:00 AM – 2:30 PM
📍 Start: Hilton Chicago — 720 S Michigan Ave
🏁 End: Sheraton Grand Chicago Riverwalk — 301 E North Water St
🚶♀️ Distance: ~2.4 miles | Easy pace | Indoor + outdoor | Rain or shine
💰 Cost: $20 (cash preferred; Zelle/Venmo/PayPal accepted)
⚠️ Important: We begin at the Hilton Chicago and officially end at the Sheraton Grand Chicago Riverwalk. This walk does NOT end where we start — please plan your transportation accordingly.
This tour is slightly longer than my usual events because we stop inside many hotels, warm up between lobbies, enjoy festive cocktails, take group photos, and soak up as much décor as possible! 🎄✨
📸 Not a dedicated photo walk, but you’ll definitely want your camera.
🎤 Led by your ever-curious, history-loving, architecture-obsessed Chicago guide — perfect for locals, visitors, and anyone who loves the city’s holiday sparkle.
Wear something warm, festive, and comfy for our leisurely downtown stroll. 🎁✨
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🌟 Route & Highlights
(Stops may shift slightly depending on timing or group size)
- 🏨 Hilton Chicago — Historic holiday grandeur with towering Christmas trees, nutcrackers, and its famous giant gingerbread hotel.
- 🖼️ The Blackstone — Boutique South Loop elegance featuring chic modern wreaths, warm lighting, and a stylish lobby tree.
- 🏛️ Congress Plaza Hotel — Vintage Chicago charm with classic red-and-gold decorations, garland-lined halls, and old-world holiday vibes.
- 🎨 Fine Arts Building — A Victorian treasure decorated with handmade ornaments, greenery, and artistic seasonal touches.
- 🏨 Palmer House — Opulent holiday magic with a massive lobby tree glittering beneath the hotel’s iconic painted ceiling.
- 🎄 Chicago Athletic Association Hotel — Cozy lodge-style décor with rustic wreaths, fireplaces, and warm winter ambiance.
- ❄️ Cloud Gate (The Bean) — Millennium Park sparkle with stunning reflections of the city’s Christmas tree and holiday lights.
- 🏛️ Chicago Cultural Center — Tiffany domes and marble staircases dressed in elegant garlands and shimmering seasonal décor.
- 🏨 Fairmont Chicago — Sleek holiday warmth featuring the Fairmont Lodge’s rustic winter décor and cozy cabin-style accents.
- 🌊 Radisson Blu Aqua Hotel — Modern holiday installations and glowing contemporary décor inside the iconic Aqua Tower.
- 🇨🇭 Swissôtel Chicago — Bright, cheerful, Swiss-inspired holiday displays with festive colors and river views.
- 🏨 Hyatt Regency Chicago — A lively, bustling lobby filled with oversized trees, sparkling lights, and dramatic garland displays.
- 🚤 Sheraton Grand Chicago Riverwalk — Festive riverfront glow with a stunning lobby tree, twinkle lights, and the seasonal Sleigh Bar.
End time: approx. 2:30 PM at the Sheraton Grand.
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🎄 Holiday Magic in the South Loop, Grant Park & the Chicago River District ✨
South Loop Historic Hotel Corridor
South Michigan Avenue, part of Chicago’s historic Central Business District expansion in the early 1900s, became home to grand hotels catering to travelers, socialites, and performers visiting nearby theaters. During the holidays, these hotels have long competed to dazzle guests with lavish Christmas trees, twinkling lights, and festive displays, creating a tradition that stretches back nearly a century. Many buildings retain their original Beaux-Arts and Renaissance Revival architecture, making the holiday décor even more striking against their historic facades.
Cultural & Civic Chicago
As we move north, we pass through Chicago’s cultural heart — the Fine Arts Building, the Chicago Cultural Center, and Millennium Park. These areas have historically been centerpieces of the city’s civic and artistic life, and during the holiday season, the combination of public art, illuminated fountains, and seasonal décor transforms them into magical winter wonderlands.
Chicago Riverfront
The Riverwalk, a relatively modern addition completed in the 2010s, connects historic commercial architecture with contemporary urban design. During the holidays, the riverfront glows with festive lights, tree-lined promenades, and seasonal installations, creating a reflective, sparkling scene that perfectly complements the grand hotel lobbies along our route. The Riverwalk has become a holiday destination in its own right, drawing locals and visitors to stroll along the water, sip warm drinks, and admire the city’s winter magic.
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🚇 Getting There
Public transit highly recommended.
CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Parking
Limited and can be expensive.
SpotHero / ParkWhiz recommended.
Street parking varies — always check signs carefully.
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📝 RSVP & No-Show Policy
✔️ Please keep your RSVP updated
✔️ Cancel if you can’t attend
❌ Repeat no-shows may be removed from future events
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🎄✨ Join us for a heartwarming stroll through the South Loop, Grant Park, Millennium Park & the Chicago River — filled with stories, architecture, history, and magical holiday sparkle! ✨
***10 attendees
Thailand Trip! - Jan 2026
Bangkok, THTHAILAND TRIP!
• Dates: January 5 - 19, 2026 (15 days / 14 nights)
• Cost: $5200 (per person, excluding international flights)
• Single supplement: $875
• Trip details: https://globe-drifters.com/trip/thailand/
See who goes on these trips and what we do & see: THAILAND TRIP PHOTOS!
If you have questions, email info@globe-drifters.com.
Travel around Thailand on a small group, 15-day trip and explore its temples, jungle, and beautiful beaches! From island hopping on a long-tail boat to jungle trekking in one of the oldest rainforests in the world, you won’t be disappointed in the Land of Smiles. Thailand’s stunning landscapes and laid-back vibe make it the perfect getaway! Thailand’s breathtaking landscape, mouth-watering food, relaxing massages, and laid-back vibe make it the perfect travel destination. Did we mention a massage is only $8?! No matter your style, Thailand has something for everyone.
Shop like a local: Visit Bangkok’s largest and most authentic fresh market, where locals buy their daily ingredients—from fresh fruits and vegetables to creepy-crawly delicacies—before learning to cook authentic Thai dishes with a local chef.
Picture perfect beaches: Visit the laid-back town of Railay, accessible only by boat and pedestrians. The beaches here are straight from a postcard!
Sleep in a treehouse!: Stay the night in a teak forest in treehouse bungalows. This is a one-of-a-kind experience that not many tourists get to see.1 attendee
Cuba Trip! - Mar 2026
Location not specified yetCUBA TRIP!
• Dates: March 14 - 22, 2026 (9 days / 8 nights)
• Cost: $2700 (per person, excluding flights)
• Single supplement: $450
• Detailed itinerary, visa info, FAQ, etc: https://globe-drifters.com/trip/cuba-march/
See photos from previous trips here: CUBA TRIP PHOTOS
For more information or if you have questions, please email info@globe-drifters.com
Cuba travel, legal and local… Thanks to the small group size, we avoid the big, government-run establishments, most of which US travelers aren’t allowed to patronize. As a small group, we can also dine at privately owned restaurants to support everyday citizens. Our groups of 12 travelers or less can visit smaller, more off-the-beaten-path places for more meaningful interaction with locals. Below are some of the things that make our small group trips to Cuba unique:
Authentic, local interaction: Your own dedicated Cuban trip leader throughout the trip will be your friend and show you Cuba through the eyes of a local.
Playa Larga: A sleepy beach town on the Bay of Pigs to escape the hordes of travelers at the major tourist hotspots. It’s a great place to witness everyday Cuban life in a typical Cuban town.
FAC: The Fábrica de Arte Cubano is a great place to mingle with Cubans over a drink while listening to live music and admiring works of art by local artists.1 attendee
Portugal Slowcation! - Apr 2026
Location not specified yetPORTUGAL SLOWCATION!
• Dates: April 9 - 19, 2026 (11 days / 10 nights)
• Cost: $4450 (per person, excluding flights)
• Single supplement: NONE!
*Room upgrades available for premium rooms.
• Details: https://globe-drifters.com/trip/portugalslowcation/
Check out pictures from previous trips to see what we do, where we go and who goes on the trips: PORTUGAL PHOTOS!
If you have any questions, please email info@globe-drifters.com.
What is a slowcation? Click here to find out: https://globe-drifters.com/slowcations/
Experience the magic of Portugal at your leisure on our slowcation… Explore Sintra’s fairytale castles, verdant hills, and charming cobblestone streets returning each day to a dreamy 19th-century estate. Then, head to Porto for wine tasting, golden sunsets aboard private sailboats, and strolls through colorful, lively neighborhoods. With hands-on experiences, unforgettable meals, and time to truly connect with each place; this is Portugal at your pace!
Portugal like a local: Step off the tourist trail into authentic Portuguese traditions. Learn the art of cheese making at a family-run dairy farm, paint your own azulejo (traditional tile), and wander through the unique landscapes of a working cork plantation.
Fairytale castles: Roam through Sintra, where enchanting palaces, lush gardens, and picturesque streets reveal centuries-old legends and hidden gems at every turn.
Douro Valley delights: Sail in style down the Douro River and indulge in the finest wines at exclusive quintas nestled in the scenic, rolling hills of Portugal’s award-winning wine country.1 attendee
Past events
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