What we’re about
This group is for people who want to get out and explore Chicago and beyond. If you don't want to wait on their 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 and the world is too big!
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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🏛️🕰️ Strolling Through Kenwood: Mansions, Myths & Megastars 🚶♀️🎩
Blackstone Branch, Chicago Public Library, 4904 South Lake Park Avenue, Chicago, IL, US🏛️🕰️ Strolling Through Kenwood: Mansions, Myths & Megastars 🚶♀️🎩
🏠📜Kenwood Treasures: A Walk Through Chicago’s Historic South Side
Step into one of Chicago’s most elegant and storied neighborhoods! From Gilded Age mansions and Prairie School gems to Civil Rights icons and President Obama’s former home, this walking tour reveals the rich legacy of Kenwood through architecture, activism, and culture.
📅 Saturday, October 25, 2025
🕛 1:00 PM – approx. 3:15 PM
📍 Start: Blackstone Branch Library, 4904 S. Lake Park Ave
🎯 End: Isidore Heller House, 5132 S. Woodlawn Ave (approx. 6 blocks from start)
💰 Cost: $20 (cash preferred; Zelle, Venmo, PayPal accepted)
🚶♀️ Distance: About 2.3 miles outdoors
⚠️ Tip: Walk Ends about 6 blocks from the start — if driving, consider parking at midway point so less walking back to the car
***🔎 What You’ll See & Learn:
✅ Stately Gilded Age homes & early Prairie-style architecture
✅ Sites tied to Barack Obama, Muhammad Ali, and Julius Rosenwald
✅ Hidden gems by Frank Lloyd Wright, Shaw, and other local legends
✅ Historic houses of worship, activists, educators & entrepreneurs
✅ Insightful storytelling and great company across multiple meetup groups!📸 It’s not a photo walk but trust us—you’ll want your camera!
🎤 Led by a passionate, knowledgeable guide (that’s me!), this walk is perfect for architecture buffs, history lovers, and curious Chicagoans.
***🏛️ Featured Stops & Highlights Include:
🏛️ Blackstone Branch Library
🧱 George Blossom House (FLW)
🧱 Warren McArthur House (FLW)
🏠 Former Elijah Muhammad House
🏡 Howard Van Doren Shaw House
🥊 Former Muhammad Ali Residence
🏠 Charles Adams Goodyear House
🏠 Ezra S. Brainerd House
🏢 Rainbow PUSH Coalition HQ
🏛️ Julius Rosenwald House
🧱 Gustavus F. Swift Mansion
🧱 Moses Born Residence
🏛️ Martin A. Ryerson House
🧱 McGill House
🦅🏛️Former Obama Family Home
🕍 KAM Isaiah Israel Congregation
🏠 Isidore Heller House (FLW)
***🍽️ Optional Lunch After the Tour
Stick around and grab a bite at one of these local favorites:- 🥗 Can’t Believe It’s Not Meat (vegan)
- 🥪 Cafe 53
- 🍕 The Sit-Down Cafe
💵 Bring cash for lunch—some spots don’t split checks!
***👟 What to Bring:
• Comfortable walking shoes
• Water bottle
• Weather-appropriate attire
• $20 tour fee (exact change appreciated; cash preferred but Zelle, Venmo, PayPal accepted)🚗 Transit & Parking Tips:
• Free & metered street parking available on Lake Park, Woodlawn & side streets—watch signs
• Park midway if you’d like to be close to both start & end
• CTA-accessible – use the CTA Trip Planner for the best route
***📌 RSVP & No-Show Policy
✔️ Please keep your RSVP current
🚫 No-shows make future planning tough
🕛 RSVP updates close at the tour start time
***✨ Discover Kenwood — where elegance, activism, and architectural beauty converge. Come explore the stories behind the stones on this engaging neighborhood walk! 🏛️🌳👟
2 attendees
Karaoke at Randall's Pub!
Randall's Pub, 6341 N. Clark Street, CHICAGO, IL, USLet's sing some karaoke!
Spooky season is upon us, folks! It's a perfect time to get out, see your friends at Randall's and sing your heart (and soul) out ❤️👻
Our last karaoke show this month is on HALLOWEEN NIGHT! So wear your best costume and come party with your pals at Randall's Pub!🎃
Randall's is a fun and friendly environment where you can be comfortable to sing your heart out to a supportive crowd. Lisa Lenny runs a good vibes only room with a 2-drink minimum to participate in karaoke (drinks include non-alcoholic beverages).
🌟Songs start at 9PM and karaoke runs until midnight🌟
If you'd like to check out our karaoke song list ahead of time, follow the link below:
https://www.karafun.com/karaoke-song-list.htmlSee you at Randall's!
1 attendee
Thailand Trip! - Jan 2026
Location not specified yet• Dates: January 5 - 19, 2025 (15 days / 14 nights)
• Cost: $5200 (per person, excluding international flights)
• Single supplement: $876
• 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 yet• 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
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