Colombia Gay Group Trip: Medellín to Cartagena
7 Days, 6 Nights
Dates TBD. February, 2028
About This Trip
Join SideQuests on this 7-day adventure of a lifetime from Medellín to Cartagena! This is an inclusive LGBTQ+ group trip designed for couples, solo travelers, and groups of friends alike. This trip is all about self-discovery, exploration, and making some lifelong friends and memories along the way.
-
We start in Medellín, the City of Eternal Spring, where it's 75 degrees basically every day and the whole city feels alive and energetic like nowhere else on earth. We'll spend our first four days based in the heart of the city - within the coveted tourist-district, El Poblado. We’ll tour a family-run coffee finca in the hills, where you'll taste a fresh cup of coffee at the source and learn about the process from plant to brew from start to finish. We’ll spend an evening drinking and dancing through El Poblado with private dance performances and instructors leading the way - the mix will feature a variety of reggaeton and salsa choke. Don’t worry if you’re not much of a dancer, this is fully cultural experience fun for everyone. And yes, there's an optional gay nightlife outing as well! And yes, you should absolutely come.
-
Midway through the week we take a day trip into the countryside to Guatapé, one of the most colorful towns - and water systems - in all of South America (not an exaggeration, wait until you see the zócalos). We'll bond through a small hike up the roughly 740 steps of Peñol Rock for a panoramic view over a maze of blue-green lakes that looks unbelievable from above, then spend the afternoon on our own private boat cruising the reservoir with music, drinks, and nowhere else to be. We’ll stop in the town of Guatapé with time to shop, take some photos, and grab a bite before heading back to the city.
-
Then we fly south (flight included) to Cartagena, where the Caribbean takes over. We'll check into a boutique hotel in Getsemaní, the street-art-covered neighborhood that steals everyone's heart, and kick off our coastal chapter with a sunset catamaran cruise around the Bay of Cartagena: bottomless drinks, fresh paella made onboard by a private chef, and the city lights coming alive as the sun drops. The next day we tour the 500-year-old Walled City and San Felipe fortress, offering spectacular views, a historic and cultural experience of the region, and plenty of opportunity for photos. We’ll then spend a full day at a private beach club on Isla de Tierra Bomba where we will absolutely be pool and beachside. We close it all out with a farewell dinner together at one of Cartagena’s top restaurants.
-
If Colombia has been on your list but you've been waiting for the right people to go with, the right itinerary, the right well-rounded experience. to really see it - this is the trip.
This trip balances big adventure days with real downtime: a Queer Connection and Community-Building Workshop mid-trip, and plenty of free evenings to wander, eat, and connect. It's gay adventure travel with room to breathe.
And if you've been searching for gay solo travel that doesn't actually feel solo, that’s the entire reason SideQuests exists. Most of our travelers come solo! Our local partner Out in Colombia is an LGBTQ+-owned and operated company running the best gay tours in the country, and our bilingual local guides will take excellent care of you from the moment you land in Medellín to your final morning in Cartagena.
One more thing: if your only mental reference for Colombia is a certain Netflix series based on its older history… we wrote a whole guide for you. Check out Is Colombia Safe for LGBTQ+ Travelers? before you go.
Limited Earlybird Spots! Save by being one of the first to sign up:
2028: February - dates tbd
Medellín - Guatapé - Cartagena
Limited Spots Available
What’s a Gay Group Trip in Colombia like?
Hear it straight from the travelers who came to Colombia with us. Some arrived solo, some with partners or friends, and all of them left with a new community.
-
Four days in a city that reinvented itself into one of the most exciting places in South America. A working coffee finca in the hills, included Colombian lunches, and perfect 75-degree weather doing its thing every single day.
-
A private drink-and-dance evening through El Poblado with live dance performances set to reggaeton and salsa choke (seriously - some of the most fun I’ve had abroad)! Plus a first-night outing to Medellín's best LGBTQ+ bars. Read up before you go in our Colombia LGBTQ+ guide.
-
Hike up a giant granite monolith for a panorama view over a maze of blue-green lakes, then after a luxurious lunch at one of the best restaurants in the area, cruise those same waters on our own private boat. Finish off with a visit to Guatapé town to shop, eat, drink and be merry! Bring your camera!
Tour Highlights
-
Our first night on the coast: a private catamaran cruise with bottomless drinks and fresh paella made onboard while the city lights come alive. Music, ambiance, great company, great food and drink… there’s nothing better.
-
Enjoy a guided tour through the 500-year-old UNESCO Walled City and San Felipe fortress. This city is beautiful and the architecture, stunning. Explore coffee shops, vendor stalls, dreamy Spanish streets and more. You leave with the history and the pictures to prove it.
-
A speedboat ride to a private beach club on a Caribbean island: pool, beach, lush gardens, included lunch, optional spa treatments. The exhale day the whole week builds toward.
-
Travel alongside a small group of LGBTQ+ travelers with a bilingual local guide, thoughtful logistics, and host Peter there the whole way. Optional morning meditations or journal prompts, a Queer Connection and Community-Building Workshop, and the kind of trip where the group chat outlives the trip by years.
What’s Included?
Navigation:
Tour Highlights — What’s Included — Itinerary — Your Host — FAQ — About — Hotels
-
Overview Today's the day! Your private arrival transfer will bring you from Medellín's José María Córdova Airport (MDE) to the Landmark Hotel Medellín, where you can check in any time from 3:00 PM. Then meet in the lobby at 5:30 PM to head out for our happy hour mixer and welcome dinner. Medellín makes a first impression fast... the green mountains rising on every side, the perfect spring air, the energy of a city that clearly loves being itself. Tonight is about settling in and finally meeting the group you've been chatting with on WhatsApp for months.
-
Land at MDE, and we take it from there. Your private transfer to the hotel is included, so there's no haggling with taxis on day one. Arrival details will be arranged closer to the trip.
-
We're ECSTATIC you're here! We'll gather for a drink at one of the great bars in central Medellín before dinner and cheers to the start of an amazing week together.
-
Our first meal together at a highly rated local restaurant: a 2-course set menu with shared appetizers, one alcoholic beverage, and one non-alcoholic beverage included. Relaxed, delicious, and the moment this whole thing becomes real!
-
After dinner, anyone who's up for it can join us for a couple of Medellín's best LGBTQ+ bars in buzzing Poblado, recommended by our local guides. Stay for one drink or close the place down... zero judgment either way.
-
Our home for the first three nights, right in the heart of the city.
Day 1
Welcome to Colombia!
-
We start the day the only correct way in Colombia: at the source of the world's best coffee. After breakfast we head into the hills to a working coffee finca, then return to the city for an evening of drinks and dance performances through El Poblado. Wear comfortable shoes and bring sunscreen, sunglasses, a water bottle, and a hat... today earns it.
-
Enjoy a delicious breakfast (and incredible Colombian coffee) at Landmark Hotel’s restaurants, meals made fresh to order.
-
A family-run finca near the city where you'll follow coffee from plant to cup, learn how Colombian cooperatives still produce it the traditional and fair way, and taste what might honestly be the best coffee of your life. You'll learn to brew the perfect cup at home and can buy beans straight from the source. Your suitcase has room, we checked.
-
A traditional Colombian lunch at a local restaurant: one main course with a non-alcoholic beverage included.
-
A private evening tour from Parque del Poblado to Parque Lleras with stops at local venues, drinks at each one, and live dance performances set to reggaeton, salsa choke, and the rhythms Medellín gave the world. This experience is private and tailored to our group. The rest of the evening is yours.
-
Day 2
Medellín: Coffee Farms, Drinking & Dancing
-
Today we trade the city for one of the most colorful corners of South America. After an optional morning meditation and breakfast, we take a scenic drive to Guatapé for the optional climb up Peñol Rock, an included Colombian lunch, an afternoon on our own private boat on the reservoir, and free time wandering the technicolor streets of town. Evening is yours back in Medellín... dinner solo or as a group.
-
Enjoy a delicious breakfast (and incredible Colombian coffee) at Landmark Hotel's restaurants, meals made fresh to order.
-
A giant granite monolith with roughly 740 steps to the top and a panoramic view over a maze of blue-green lakes that does not look real in photos and somehow looks even less real in person. The climb is optional, the photo op is mandatory.
-
A delicious Colombian lunch at one of Guatapé’s most coveted restaurants, including one main course, shared appetisers, and a drink of choice.
-
Our own boat on the Peñol-Guatapé Reservoir, shaped entirely around what the group wants: chill and scenic or music up and lively. There's an ice chest onboard, so grab your favorite drinks before we set sail.
-
Free time in the most photogenic town in Colombia. Every building is covered in brightly painted zócalos, and every street wants to be your camera roll. Grab a coffee, wander, soak it in.
-
Item description
Day 3
Guatapé: Peñol Rock & a Private Boat Day
-
It’s time to say goodbye to Medellín and head to the vibrant city of Cartagena! Start your day with an optional morning reflection or meditation session. After a delicious breakfast at the hotel, we’ll make our way to Medellín International Airport for our short flight to Cartagena. Once we arrive, you’ll enjoy a private transfer to the OSH Hotel Getsemaní, a charming boutique hotel that blends colonial style with modern comforts. Check into your room and get settled in, and get ready to explore the heart of Cartagena. Your evening will kick off with a spectacular sunset cruise around the Bay of Cartagena, complete with drinks, heavy hors d'oeuvres, and a delicious paella prepared onboard by our private chef. After a memorable evening on the water, you’ll return to the OSH Hotel Getsemaní for an overnight stay, resting up for more adventures ahead.
-
One last made-to-order breakfast (and one more round of that Colombian coffee) at the Landmark before we trade the mountains for the coast.
-
After breakfast, gather in the hotel lobby for checkout and board your private transfer to Medellín International Airport where we will catch our short flight to Cartagena.
We’ll then take a private transfer from Cartagena International Airport to OSH Hotel Getsemani, ready for check-in!
-
A charming boutique hotel that’s both very modern and quintessential Colombian. The OSH is perfectly positioned right at. theedge. ofthe famous Getsemaní neighborhood, with streets covered in all kinds of artwork. It steals everyone's heart. Plus, the view of the city from the rooftop pool is unbeatable… but if you’re feeling the pool on the ground level, grab a cabana! Settle in, freshen up, and get ready for the water.
-
A catamaran cruise through the Bay of Cartagena with heavy hors d'oeuvres, bottomless beverages, and a grand paella made onboard by our private chef and waitstaff. Music sets the tone as the sun drops, and the night unfolds however the group wants it to. We return to Muelle de los Pegasos, right outside the gates of the Walled City, perfectly positioned for dinner, nightlife, or a slow stroll through the Old City.
-
Day 4
Medellín & Cartagena: Sunset Bay Dinner Cruise
-
Today is for the history. After breakfast we tour Cartagena's UNESCO World Heritage Walled City with our bilingual local guide in an air-conditioned private vehicle. The afternoon offers the optional Cartagena Cooking Experience add-on, and the evening brings one of the most meaningful parts of any SideQuests trip: our Queer Connection and Community-Building Workshop.
-
Breakfast at OSH Getsemaní is made fresh to order alongside a ready buffet to peruse, and it’s all pretty fantastic. Settle in, order another coffee, and ease into the Caribbean pace.
-
We start at San Felipe de Barajas, the most formidable feat of Spanish military engineering in the Americas, begun in 1536 and 121 years in the making. Then into the Walled City itself: ramparts, plazas, and the old Dungeons, once troop storerooms and now a handicrafts market selling woven bags, woodwork, and brightly decorated cloth made by Colombia's indigenous artisans. Lunch is on your own in the Old City afterward, and your guide has recommendations for days.
-
An afternoon with local cooks preparing Cartagena's most iconic dishes in traditional cauldrons: fresh ingredients, recipes old and new, and pairings that'll have you craving more. Bookable as an add-on at checkout.
-
An open-format evening gathering, roughly 90 minutes, where we examine how our past experiences shape how we see ourselves... share your story or just listen, no expectations either way. From previous trips, this becomes a real safe space to heal, inspire, and connect, and for a lot of travelers it ends up being the moment of the whole week.
-
Day 5
Cartagena: Historic Walled City & Colombian Cooking
-
The exhale day the whole week builds toward. A speedboat carries us to a private beach club on Isla de Tierra Bomba for a full day of pool, beach, lush gardens, and turquoise water, with lunch included and optional spa treatments if you want the full send-off. Back on the mainland, we gather one last time for our farewell dinner... the most celebratory meal of the trip and the hardest one to end.
-
Breakfast at OSH Getsemaní is made fresh to order... settle in, order another coffee, and ease into the Caribbean pace.
-
Pickup from the hotel, private transport to the pier, and a quick, exhilarating speedboat ride to paradise.
-
Full day to lounge poolside or on the sand, surrounded by tropical gardens and crystal-clear Caribbean water. Service directly at your lounger. Optional spa services are available if "vacation from the vacation" is your love language.
-
Savor exquisite cuisine with a breathtaking view. Your meal will typically be 1 main course, or a set menu served family style. One non-alcoholic beverage is included with your meal.
-
This unforgettable day of luxury and wellness will come to an end with a scenic ride back to the mainland on the speedboats. Once there, your private transportation will be waiting to take you back to your hotel, giving you time to reflect on the day and the stunning beauty of the Caribbean. Don't miss the opportunity to escape to this paradise and make unforgettable memories on this ultimate day excursion.
-
A set menu with shared appetizers at a highly rated local restaurant, with one alcoholic and one non-alcoholic beverage included. One minute you're landing in Medellín wondering what the week will bring, and suddenly you're here, at the last dinner, not quite ready for it to be over.
-
Day 6
Day at the Beach Club on Isla de Tierra Bomba & Farewell Dinner
-
One last breakfast, checkout, and goodbyes... to Cartagena, to Colombia, and to the people you've spent this extraordinary week with. Your private departure transfer to Cartagena's Rafael Núñez International Airport (CTG) is included, with recommended departure times shared in the group WhatsApp. And if Colombia already has you googling your next adventure before you've even boarded, we understand completely. Peru and Japan are right there on our trips page, just saying.
-
One final breakfast at OSH Hotel Getsemaní before checkout, or before continuing your adventure onward!
-
Your private transfer from the hotel to CTG is included... one last SideQuests detail handled so your only job is making your flight. Book departures out of Cartagena, not Medellín.
-
Colombia has a way of rewriting whatever story you arrived with... the warmth of the people, the color of it all, the week that felt like a month in the best way possible. We hope this trip gave you the full taste. We'll miss you! See you on the next one!! 🇨🇴
Day 7
Farewell & Onward Travel
Frequently Asked Questions
Have questions specific to this trip? Here are some common questions about our adventure.
-
Our trips attract a diverse community, primarily LGBTQ+ travelers in their 20s-60s who are looking for meaningful connections and authentic experiences. We welcome allies and friends of all identities who share our values of inclusivity, curiosity, and openness.
-
We keep our groups intentionally small—typically 16-24 travelers—to foster genuine connections and allow for more intimate, authentic local experiences that wouldn't be possible with larger groups.
-
Each trip is slightly different, but most SideQuests include:
Boutique accommodations
Most meals (with options)
Excursions + guided activities
A bilingual local guide
Private group transportation
Your hosts (hi, that’s us!)
You can view all the trip-specific inclusions on each individual trip page. Airfare to and from the destination is not included. You'll receive a detailed packing list and itinerary before departure.
-
If your booking is still pending (meaning the trip hasn’t been confirmed yet), you’re eligible for a full refund — including your 25% deposit.
Once the trip is confirmed (after 12 travelers have booked), your deposit becomes non-refundable. If you need to cancel after confirmation, you’ll receive a Credit Voucher for the amount paid (minus a $100 cancellation fee).
After the 90-day mark before the trip, all payments become non-refundable, since hotels, transportation, and activities have already been paid for. Any exceptions at that point are at the discretion of our local partners.
We strongly recommend purchasing travel insurance — it really is worth it.
-
You can reserve your spot with a 25% deposit and pay the rest in installments through Affirm. In order to do this, you must register a virtual card through Affirm.
-
Yes! Most people do. We design our trips to foster connection from day one, and many travelers arrive solo but leave with lifelong friends (and at least one new group chat). SideQuests are specifically designed to foster connection, so coming alone is actually the perfect way to experience our trips. We create plenty of opportunities to bond with the group while also respecting everyone's need for personal space and independence.
-
Not at all! Our trips are great for all experience levels. We’ve got you. Our trips are built with support and guidance baked in, from our group chats and Zoom intros to arrival instructions and packing tips. You don’t need to be a seasoned traveler, just someone ready to say yes.
-
We offer both shared and private accommodation options. Many solo travelers choose to share rooms (with separate beds) to save on costs and enhance the community experience. If you prefer your own space, single supplements are available for an additional fee (listed during checkout).
-
Not at all! While our trips are centered around queer community and joy, allies are absolutely welcome — as long as you’re here with respect, openness, and a good sense of humor!
-
Most trips include a mix of walking, light hikes, or outdoor activities — but we always include downtime, optional excursions, and flexible pacing. You do you, with a group that gets it.
-
We strive to make our trips as accessible as possible and work with travelers on a case-by-case basis. Some destinations have inherent accessibility challenges, but we're committed to finding solutions whenever possible. Please contact us directly to discuss your specific needs.
-
Fly into Medellín's José María Córdova International (MDE), arriving February 6th or ideally a day early to settle in before our welcome dinner. The tour ends in Cartagena, so book your return flight out of Rafael Núñez International (CTG). Into Medellín, out of Cartagena... that's the seamless routing, and your private transfers on both ends are included.
-
We kick off in Medellín on February 6th, 2027 at 5:30 PM with our welcome happy hour and dinner. The tour wraps in Cartagena on February 12th, 2027 after hotel checkout, with your included private transfer to CTG from there.
-
Yes. Same-sex marriage has been legal in Colombia since 2016, discrimination based on sexual orientation is a criminal offense, and the places we visit... Medellín, Guatapé, and Cartagena... are well-policed, tourism-focused, and welcoming. We wrote a whole guide on this from our own time on the ground: Is Colombia Safe for LGBTQ+ Travelers?
-
Very. Medellín is one of the most LGBTQ+ welcoming cities in Latin America, with a dense, openly gay scene around El Poblado's Provenza, growing Pride celebrations, and a tight-knit local queer community. Many SideQuests guests call it their favorite stop.
-
Yes. Cartagena's historic walled city and Getsemaní are tourist-focused, well-patrolled, and visibly open to LGBTQ+ visitors... same-sex couples are a common sight throughout the historic center. Stick to populated areas after dark and use rideshare apps between neighborhoods, as you would in any city.
-
In gay-friendly zones like Provenza in Medellín and Getsemaní in Cartagena, holding hands is completely unremarkable. Colombia is still a fairly Catholic country, so public affection runs a little more reserved in small towns and rural plazas... that goes for straight couples too. It's a comfort call, not a safety one.
-
If you hold a U.S. passport, no. U.S. citizens (along with travelers from Canada, the UK, Australia, and most of the EU) can visit Colombia visa-free for up to 90 days. Just make sure your passport is valid for your stay. Colombia does ask travelers to complete the free Check-Mig immigration form online shortly before your flight... we'll remind everyone in the group chat when it's time.
-
No vaccines are required to enter Colombia from the US. The CDC recommends being up to date on routine vaccines, plus hepatitis A and typhoid for most travelers, and a yellow fever vaccine is recommended for some regions of Colombia... guidance can shift, so check the CDC's Colombia page and visit a travel clinic 4 to 6 weeks before departure. Good news: basic Colombian medical travel insurance is already included in this trip.
-
Medellín is the City of Eternal Spring, so pack light layers, walking shoes, and something fashionable for Provenza's nightlife. Cartagena is hot and humid year-round: breathable cotton, swimwear, and a sun hat. Both cities lean stylish; skip the athleisure. A full packing list goes out before departure.
-
Start with our guide, Is Colombia Safe for LGBTQ+ Travelers?, which covers Medellín's gay scene, Getsemaní, our favorite bars and restaurants, and the "no des papaya" safety playbook. And honestly, gay group travel is kind of our whole thing... by departure day you'll have been chatting with the whole group for months in the trip WhatsApp. Browse all our upcoming trips at sidequeststravel.com/trips.
About SideQuests Travel
-
Hi, I'm Matthew, co-founder of SideQuests Travel. I created SideQuests because I didn't want to just see the world, I wanted to make new friends and build-up my community while doing it. I wanted to see an amazing place in the world and come home feeling changed, so I started hosting trips for people who wanted the same.
-
SideQuests runs small-group adventures for LGBTQ+ travelers who want to see the world while actually connecting with others and themselves.
-
The moment you book, you're added to the trip's WhatsApp chat and invited to our monthly Zoom calls, so by the time you land, you already know a bit about each person embarking on the adventure with you. On most group tours, you finally click with the others right as everyone packs to leave,
but on our trips, that happens before anyone boards a plane.
We offer optional journal prompts and meditations for those that would like to participate, and a community workshop mid-trip where people share stories and truly get the opportunity to connect on a very real level.
-
SideQuests Travel is for everyone who wants a fun, community-focused tour that’s adventurous, welcoming, and transformative.
Every hotel, guide, and operator is vetted through an LGBTQ+ lens ensuring that travel is not only safe, but enthusiastically welcoming.
Come solo, come with a friend, or a partner, and leave with a new group of friends and strengthened sense of community. We're not just building great experiences, we're building a supportive network of people you'll literally want to plan your next trip alongside.
Where You’ll Stay
We've selected accommodations that reflect Colombia's energy while keeping comfort front and center... and we can vouch for both of these personally, because we stayed at each of them with our 2026 group.
-
In Medellín, we spend our first three nights at the Landmark Hotel Medellín, a stylish hotel in the heart of El Poblado, walking distance from the restaurants, cafés, and nightlife of Provenza. The rooftop pool and bar with panoramic views over the city is the cherry on the cake, and the staff treated our (very gay) group exactly like they treat every other guest... like family. Breakfast at the Landmark's restaurants is made fresh to order, and the Colombian coffee alone is worth setting an alarm for.
-
For our final three nights in Cartagena, we check into the OSH Hotel Getsemaní, a boutique stunner where colonial style meets modern design in the street-art-covered neighborhood that steals everyone's heart. You'll arrive to a welcome cocktail, the ground-floor pool is ringed with private cabanas, the spacious rooms feel more like private studios than hotel suites, and the rooftop bar, Ajeno, has epic views over the colonial rooftops... it became our group's default sundowner spot last trip, and we suspect it'll become yours. Breakfast here is made fresh to order too.
All accommodations feature private bathrooms and daily made-to-order breakfast. Solo travelers can choose between shared rooms (with another solo traveler, partner or friend), or a completely private room for an additional supplement. If a friend or partner is coming with you but booking separately, no need to worry... we send out a questionnaire to get your roommate of choice or rooming preferences in order ahead of the trip.
Testimonials From Our Travelers
-
![A man with tattoos and earrings standing at the beach during sunset, looking to his left.]()
“We felt like family just a day or two into the actual trip.”
David, Greece
-
![A man standing on a sandy beach during sunset, smiling and looking to his right, wearing a pink short-sleeve shirt with a white leaf pattern.]()
"It’s wild how quickly a group of queer travelers became a little family. From late-night laughs to deep conversations, this trip gave me so much more than I expected."
JJ, Costa Rica
-
![Two smiling men, one with blond hair and the other with brown hair and glasses, standing close together with their arms around each other, in front of a decorated building with colorful architecture.]()
"I’ve already signed up for three more trips! I’ve never felt more welcome in a group setting."
David, Thailand
-
![Three young men standing on the beach with ocean in the background, smiling and enjoying the moment.]()
"He made sure everyone felt included and was enjoying themselves... He checked in with everyone to make sure we were all onboard with our schedules and feeling good about the trip overall.”
Thomas, Greece
-
![A smiling man with dark, wavy hair and a beard, wearing a white shirt, standing in front of a stone wall during sunset.]()
"Matthew created an environment welcoming and safe for everyone (regardless of gender identity or sexuality) to have an amazing trip.”
Sam, Greece
-
![]()
“Michael and Matt were great at breaking down barriers and helping all feel welcome.”
Kevin, Costa Rica
