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
15
🎄✨ Jingle & Mingle: Chicago Holiday Hotel Lobby Tour — Take 3! ❄️🏨
Millennium Knickerbocker Hotel Chicago, 163 E Walton St Chicago, IL 60611, Chicago, IL, US🎄✨ Jingle & Mingle: Chicago Holiday Hotel Lobby Tour — Take 3! ❄️🏨
🌆 A Festive Guided Stroll Through Chicago’s Most Beautiful Holiday Lobbies ✨
Christmas isn’t over just yet! 🎁✨ Back by popular demand! If you missed the first two—or simply want more holiday magic—join us for another sparkling edition of my beloved Holiday Hotel Lobby Tour. 🌟
We’ll wander through Chicago’s most beautifully decorated hotel lobbies, soaking in twinkling trees, towering wreaths, glittering ornaments, elegant floral displays, and all the cozy glamour that makes the season unforgettable. 🎄📸
Dress warm, festive, and comfy for a leisurely downtown stroll with plenty of time to warm up, sip festive cocktails, take photos, and enjoy the décor.
This is one of my most popular annual traditions—blending Chicago history, architecture, holiday décor, and seasonal storytelling into one magical afternoon.
***
### 🕰️ Schedule, Meeting Info & Cost
📅 Friday, December 26, 2025
🕚 12:00 PM – 3:30 PM
📍 Start: Millennium Hotel Knickerbocker 163 E Walton St
🏁 End: Palmer House Hotel 17 E Monroe St
🚶♀️ Distance: ~2.5 miles | Easy pace | Indoor + outdoor | Rain or shine
💰 Cost: $20 (cash preferred; Zelle/Venmo/PayPal accepted)
⚠️ Important: We begin at the Millennium Hotel Knickerbocker and officially end at the Palmer House. This walk does NOT end where we start — please plan your transportation accordingly.
This walk is longer than my usual tours because we stop inside many hotels, enjoy festive cocktails, warm up between lobbies, take group photos, and soak up as much décor as possible! 🎄✨
📸 Not a dedicated photo walk — but trust us, you’ll absolutely want your camera!
🎤 Led by your passionate, ever-curious guide — this festive experience is perfect for longtime locals, out-of-town guests, architecture lovers, history buffs, holiday décor fanatics, photography lovers, and anyone who enjoys exploring the city’s holiday sparkle.
***
🌟 Route & Highlights
(Stops Subject to change based on group size or timing)
- 🏨 Millennium Hotel Knickerbocker – Classic 1920s elegance with vintage holiday charm 🎄
- 🏰 The Drake – Grand Palm Court tree, garlands, and old-school Chicago holiday magic 🍬
- 🏨 Waldorf Astoria – Refined luxury and elegant seasonal décor
- 🛍️ 900 N Michigan Ave Shops – One of Chicago’s largest multi-story indoor Christmas trees ✨
- 🌟 Four Seasons Hotel Chicago – Lavish lobby tree and festive flair
- 🏨 Ritz-Carlton Chicago – Sophisticated seasonal style
- 🏨 InterContinental Chicago – Grand lobby décor, Nutcracker touches, and twinkling lights
- 🎅 The Langham Chicago – Gold-and-silver shimmer, elegant tree, festive details 🎁
- 🌊 Radisson Blu Aqua Hotel – Modern holiday installations and bold seasonal design
- ⛷️ Fairmont Chicago – Chic winter-lodge vibes near Millennium Park ❄️
- 🏛️ Chicago Cultural Center – Tiffany domes and a stunning holiday tree 💎
- 🏙️ Millennium Park / Cloud Gate – Chicago’s official Christmas tree and skyline views
- 🏨 Palmer House Hotel – Towering lobby tree, opulent ceilings, and holiday cocktails 🍸
End time: approx. 3:30 PM at the Palmer House
***
🎄 Holiday Magic on the Magnificent Mile ✨ North Michigan Avenue: Chicago’s Grand Hotels & Shopping Destination
North Michigan Avenue — the world-famous Magnificent Mile — has been Chicago’s luxury corridor for more than a century. Lined with grand hotels like The Drake, The Peninsula, The Langham, InterContinental, and Palmer House, this iconic stretch has long attracted socialites, celebrities, and travelers seeking elegance.
Between these historic hotels, you’ll find world-class shopping, glamorous restaurants, and some of the most beautiful architecture in the city. During the holiday season, the avenue transforms into a glittering winter escape — lobby trees, twinkling lights, shimmering installations, and classic Chicago holiday cheer at every stop.
***
🎁 Christmas on North Michigan Avenue — A Beloved Chicago Tradition
Since the 1920s, North Michigan Avenue has been the heart of Chicago’s holiday celebrations. Grand hotels competed to outdo one another with lavish trees, sparkling garlands, festive window displays, and elaborate seasonal scenes. Department stores soon joined in, turning the area into Chicago’s premier holiday shopping corridor.
Families from across the city flocked to the Magnificent Mile to see the animated windows, gather around towering lobby trees, and stroll through festive displays — a tradition that continues today.
The Magnificent Mile remains synonymous with holiday glamour, seasonal magic, and unforgettable décor, making it a must-visit destination this time of year.
***
🚇 Getting There
Public transit highly recommended.
CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Parking
Limited and can be expensive.
SpotHero / ParkWhiz recommended.
Side streets vary — check signage carefully.
***
📝 RSVP & No-Show Policy
✔️ Please keep your RSVP updated
✔️ Cancel if you can’t attend
❌ Repeat no-shows may be removed from future events
***
🎄✨ Join us for a heartwarming, glittering, joy-filled holiday stroll through Chicago’s most magical lobbies — complete with stories, architecture, seasonal cheer, and tons of festive fun!
***
🚇 Getting There
Public transit highly recommended.
CTA Trip Planner: https://www.transitchicago.com/planatrip/
🚗 Parking
Limited and can be expensive.
SpotHero / ParkWhiz recommended.
Side streets vary — check signage carefully.
***
📝 RSVP & No-Show Policy
✔️ Please keep your RSVP updated
✔️ Cancel if you can’t attend
❌ Repeat no-shows may be removed from future events
***
🎄✨ Join us for a heartwarming, glittering, joy-filled holiday stroll through Chicago’s most magical lobbies — complete with stories, architecture, seasonal cheer, and tons of festive fun!13 attendees
🎄✨ Jingle & Glow: South Loop to Riverwalk Holiday Lobby Stroll ❄️🏨
Hilton Chicago, 720 South Michigan Avenue, Chicago, IL, US🎄✨ Jingle & Glow: South Loop to Riverwalk Holiday Lobby Stroll ❄️🏨
🌆 A Sparkling South Loop–to–Riverwalk Holiday Adventure ✨
✨ Christmas isn’t over just yet! If you missed my walk last Sunday, we’re doing it again — and this time with a brand-new route showcasing the festive beauty of the South Loop, Grant Park, the Cultural Center, Millennium Park, and the Chicago Riverfront 🎄🌊
If you joined the Magnificent Mile version, expect a completely different experience. This edition highlights the historic South Loop hotel corridor, where early-20th-century architectural gems glow with vintage holiday charm, then leads 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 makes this one of my most popular annual traditions.
***
### 🕰️ Schedule, Meeting Info & Cost
📅 Saturday, December 27, 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: This walk does not end where it starts — please plan transportation accordingly.
This tour runs a bit longer than my usual walks 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.
👢 Dress warm, festive, and comfy for a leisurely downtown stroll.
***
🌟 Route & Highlights
(Stops may shift slightly depending on timing or group size)
- 🏨 Hilton Chicago — Towering trees, nutcrackers, and the famous giant gingerbread hotel
- 🖼️ The Blackstone — Boutique elegance with chic wreaths and warm lighting
- 🏛️ Congress Plaza Hotel — Classic red-and-gold décor and old-world holiday vibes
- 🎨 Fine Arts Building — Artistic seasonal touches and handmade ornaments
- 🏨 Palmer House — Massive tree beneath the iconic painted ceiling
- 🎄 Chicago Athletic Association Hotel — Cozy lodge-style holiday décor
- ❄️ Cloud Gate (The Bean) — Holiday reflections and skyline sparkle
- 🏛️ Chicago Cultural Center — Tiffany domes dressed in elegant seasonal décor
- 🏨 Fairmont Chicago — Rustic winter-lodge warmth
- 🌊 Radisson Blu Aqua Hotel — Modern holiday installations
- 🇨🇭 Swissôtel Chicago — Bright, festive displays with river views
- 🏨 Hyatt Regency Chicago — Oversized trees and dramatic garlands
- 🚤 Sheraton Grand Chicago Riverwalk — Riverfront glow and seasonal Sleigh Bar
End time: approx. 2:30 PM at the Sheraton Grand.
***
🎄 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.
***
🚇 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.
***
📝 RSVP & No-Show Policy
✔️ Please keep your RSVP updated
✔️ Cancel if you can’t attend
❌ Repeat no-shows may be removed from future events
***
🎄✨ 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! ✨
***1 attendee
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
Past events
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