Colombia:
Colors & Culure
From Medellín to Cartagena – A Journey Through Colombia's Heart
7 Days 6 Nights
Jan 17 - 23, 2026
About This Trip
Join me on a 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!
Immerse yourself in Medellín and Cartagena, two of Colombia's most beautiful cities! Famous for its exotic flora, innovative coffee culture, and thriving nightlife scene, we'll explore Medellín's trendy cafes, shops, and restaurants that line its picturesque streets. After four days in the City of Eternal Spring, hop on your included flight to Cartagena, where the allure of the Caribbean meets vibrant Colombian culture. We'll continue the adventure Caribbean-side as we experience a spectacular sunset cruise around the Bay of Cartagena, explore the dazzling Getsemani neighborhood with our very own professional photographer, and hit the beaches from a private beach club on Isla de Tierra Bomba. There's even more in the itinerary below, amongst some amazing morning meditations, group discussions, and evening outings!
Come and experience the things I love most in life — travel, exploration, photography, and community. I want to see an incredible part of the world with you, dive into growth-centered discussions, make great new friends, and take home some unforgettable memories.
$3,299
For the first 8 bookings
Regular Price: $3,499
25% Deposit: $825
2026: Jan 17 - Jan 23
Medellín - Cartagena
Limited Spots Available
Trip Overview — Trip Activities — Trip Inclusions — Trip Itinerary — About Your Host
Trip Overview
Your Trip Includes:
DURATION
7 days
GROUP SIZE
8-24 spots
MEALS
6 Breakfasts, 3 Lunches, 3 Dinners
PLACES
2 cities
ACTIVITIES
9 included
TEAM
Local Experienced Guide, Host
Included in Your Trip:
✅ All accommodations (7 days, 6 nights in carefully selected 4 and 5-star boutique hotels)
✅ All in-country transportation including domestic flight from Medellín to Cartagena
✅ 12 meals: including daily breakfast, 3 lunches, and 3 dinners (some alcohol)
✅ 9 premium excursions including all entrance fees, and local guides
✅ Bilingual local guide & SideQuests Trip Host throughout entirety of the trip
✅ Community and connection: A chill, welcoming, LGBTQ+ group of fellow 16-24 travelers
✅ Host-led gatherings (meditations, reflections, workshops, and nightlife outings)
✅ Colombian domestic travel insurance: covers medical throughout the country, expatriation, and some luggage issues
Not Included:
❌ Flights (except as noted)
❌ Meals and alcohol not specified in the itinerary
❌ Optional activities and personal expenses
❌ Airport transfers
❌ Tips for guides and staff (recommended at your discretion)
Trip Itinerary:
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Welcome to Medellín!
Overview
Today is where the adventure begins! Please check-in at the Landmark Hotel Medellín any time from 3pm. Plan to meet in the lobby at 5:30 P.M. to head out for our happy hour mixer and welcome dinner. We’ll finalize the exact happy hour location and dinner reservation time as your trip date approaches. If you’re arriving today, we recommend flying into MDE. Looking forward to seeing you!Welcome Happy Hour Meet & Greet
I'm ECSTATIC you're here! What better way to start an epic trip than with a social gathering and drink prior to dinner? Let's gather for happy hour at one of the amazing bars in central Medellín close to the hotel or dinner location and cheers to the start of an amazing week together.Dinner — Included Meal
The welcome dinner will take place at a highly-rated local restaurant and is included in your itinerary. You'll enjoy a 2-course set menu, plus shared appetizers, one alcoholic beverage, and one non alcoholic beverage.LGBTQ+ Medellín Nightlife Outing
Explore Medellín's thriving LGBTQ+ scene in bustling Poblano. We'll depart from our group dinner location to enjoy a couple highly rated LGBTQ+ bars, recommended by our guides. Stay for as little, or as long as you'd like! Have a drink, and take on the night!Overnight Accommodation at the Landmark Hotel
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Medellín: Coffee Farms, Drinking, and Dancing
Overview
This morning you’ll enjoy breakfast before venturing out to experience a traditional coffee finca. Enjoy a tour of a local coffee farm from the fields to production. After your farm tour, you'll have the opportunity to taste the coffee yourself. Then, enjoy an included traditional Colombian lunch. Returning back to Medellín, you'll have a little time to freshen up before an exciting evening of drinking and dancing through Medellín's iconic Poblado neighborhood. Enjoy private dance presentations set to the rhythms of Medellín’s urban and Latin music scene—Reggaeton, Salsa Choke, and more. After the full experience, the evening is free for you to enjoy. Today you’ll want to wear comfortable walking shoes and bring sunscreen, sunglasses, a water bottle, and a hat.Morning Coffee & Reflection 1
A completely optional way to start your day. One of the great things about these group trips is the space and opportunity to write and reflect on so many aspects of our lives. I love to journal, get my thoughts down on paper, and reflect on how I’m feeling here in this moment. I'll provide a journal, prompts, and we'll take a little time before breakfast to gather in a nearby square or indoor public space and put pen to paper. Some mornings will consist of a simple guided meditation, other mornings will be focused on the journal prompts and reflections. We'll also have the opportunity to expand on these topics during our group community-building workshop.Breakfast — Included Meal
Breakfast at the hotel is included. Enjoy the typical full/American or buffet style breakfast prior to the start of today's excursions.Activity - Approx 4hrs - Medellín Coffee Farm Excursion
Our excursion begins with a pick-up from your hotel, and we’ll head to a working coffee finca located near the city. At the finca, you’ll get a chance to learn the entire process of making coffee – from the plant to the cup. You’ll also get an understanding of the daily life of Colombian coffee cooperatives, who still produce coffee in a traditional and fair way. The coffee finca you’ll visit is a typical small family-run business in Colombia that produces exclusive coffee. You’ll get to taste this coffee and appreciate its unique flavor. More importantly, you’ll learn how to brew the perfect cup at home and even have a chance to purchase coffee straight from the source. The coffee farm excursion is the perfect way to appreciate Colombian culture, learn about coffee, and taste the best coffee you’ve ever had.Lunch — Included Meal
Lunch at a local restaurant is included. Your meal will typically be 1 main course with a non-alcoholic beverage, subject to change.Activity - Approx 3hrs - Drink & Dance through Poblado
Discover Medellín’s vibrant culture at your own pace on this exclusive, private tour. Explore the Poblado neighborhood, starting at Parque del Poblado and making your way to Parque Lleras, with personalized stops at local venues showcasing the city’s lively nightlife. Enjoy private dance presentations set to the rhythms of Medellín’s urban and Latin music scene—Reggaeton, Salsa Choke, and more. At each stop, savor drinks that perfectly complement the beats while enjoying live musical and dance group presentations. This private experience is tailored to your group, ensuring an unforgettable evening.Overnight Accommodation at Landmark Hotel Medellín
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Medellín: Guatape Boat & City Tour
Overview
After an optional morning meditation, enjoy a hearty breakfast at the hotel to fuel up for a day of adventure. Our first excursion takes us on a scenic drive to Guatapé, where you'll have the option to climb Peñol Rock for breathtaking panoramic views—perfect for a photo op! Then, set sail on a private Guatapé Boat Tour, where you can relax, and enjoy the stunning scenery. After a great boating experience, savor an included traditional Colombian lunch. Afterwards, take time to explore the colorful streets of Guatapé at your own pace, soaking in the charm of this picturesque town. You'll have some free time in the evening to explore on your own and grab dinner solo or as a group, then as the day wraps up you have the choice of joining a Queer Connection and Community-Building Workshop, focused as an intimate and safe space to reflect on personal growth, build confidence, and connect with fellow travelers. Finally, you'll return to the Landmark Hotel, where you can relax and recharge for the next day’s adventures.Morning Coffee & Reflection 2 (Optional)
A completely optional way to start your day. I love to journal, get my thoughts down on paper, and reflect on what I'm thinking about/experiencing on trips like this. We'll either do a morning guided meditation, or a journal session/reflection in a public square or nearby indoor location. I'll provide a journal, prompts, and we'll take a little time before breakfast to gather and connect.Breakfast - Included Meal
Breakfast at the hotel is included. Enjoy the typical full/American or buffet style breakfast prior to the start of today's excursions.Activity - Approx 2hrs - Climb up Peñol Rock
Your day begins with a scenic drive from Medellín to Guatapé, with an optional climb up Peñol Rock for stunning views. This is one of the most epic views in the area and is a perfect photo opportunity.Activity - Approx 4hrs - Gay Guatapé Boat Tour
Experience the beauty of Guatapé your way with a Private Guatapé Boat Tour. Whether you’re looking for a chill, relaxed day or a lively celebration with friends, this private tour is tailored to your group’s desires. Bring your favorite drinks—an ice chest will be on board—or pick up some beverages before we set sail. Once on the boat, the choice is yours: relax, take in the scenery, or turn up the music and enjoy a lively cruise on the Peñol-Guatapé Reservoir.Lunch - Included Meal
Midway through the day, savor a traditional Colombian lunch, which is included on your itinerary. Your meal will typically be 1 main course, or a set menu served family style. One non-alcoholic beverage is included with your meal.Activity - Approx 2hrs - Guatapé City Exploration
Explore the colorful streets of Guatapé at your own pace before heading back to Medellín. Stop for a coffee, take in the sights, and soak up the photo opportunities throughout this picturesque town.Queer Connection and Community-Building Workshop (Optional)
In this workshop we’ll examine how our past experiences influence how we see ourselves. We’ll get to know each other on a deeper level, discuss our backstories, and explore solutions as we see how we can learn to love ourselves better through several mindfulness and confidence-building techniques. This is an open discussion format, where everyone can come as they are with no expectations — feel free to listen and/or share. This approximately 1.5 hour workshop will take place after dinner at a cozy location on or near the accommodation grounds. (From previous group trip experiences, this can truly be an amazing safe space meant to heal, inspire, and cultivate meaningful connections) Topics and timing of this gathering will be announced closer to the trip dates, and are subject to change.Overnight Accommodation at Landmark Hotel Medellín
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Medellín & Cartagena: Sunset Bay Cruise
Overview
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.Morning Reflection/Meditation 4 (Optional)
A completely optional way to start your day. We'll be expanding on our last couple days of journaling and meditation, particularly on the topics from the previous night's workshop. I'll provide a journal prompt or simple guided meditation, and we'll take in the sights of Medellín for one last morning before we head to breakfast and Cartagena.Breakfast - Included Meal
Breakfast at the hotel is included. Enjoy a typical full/American or buffet-style breakfast prior to the start of today's activities.Transfer - Approx 2.5hrs - Medellín to Cartagena
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.Transfer - Approx 1hr - CTG to OSH Hotel Getsemani
Take a private transfer from Cartagena International Airport to OSH Hotel Getsemani.Check In at OSH Hotel Getsemani
Discover the essence of Cartagena at this boutique hotel in Getsemaní, where colonial charm meets contemporary design. Immerse yourself in our rooms, blending modernity with local elements, for an authentic experience. Explore the city from our prime location and indulge in exceptional gastronomy at our restaurant. In this Getsemaní hotel, every moment is an unforgettable adventure in the heart of Cartagena. The great thing about being a minimalist. Everything you want in a room, in the perfect amount. Our Essential rooms feature a king size bed, closet, desk, rain shower, and amenities.Activity - Approx 3hrs - Sunset Bay Cruise
Enjoy dinner and drinks aboard a sunset cruise on a catamaran through the Bay of Cartagena. Enjoy heavy h'ors d'oeuvres, bottomless beverages, and a grand paella made onboard by our private chef and waitstaff.Overnight Accommodation at OSH Hotel Getsemani
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Cartagena: Getsemani Street Art & Colombian Cooking
Overview
Get ready for a full day exploring Cartagena! After breakfast, delight yourself with Getsemani enchantment and its urban art accompanied by a certified bilingual guide and professional Photographer. We'll explore this iconic neighborhood together while relaxing and leaving the photography to our own personal photo crew. Afterwards, enjoy lunch on your own. In the afternoon, for those who add-on the Colombian cooking experience, get ready to make something special and enjoy an afternoon of delicious recipes. Continue exploring the old historic center of Cartagena, and find a great spot, with recommendations from our guides, to enjoy dinner.Morning Coffee & Reflection/Meditation 5
A completely optional way to start your day. We'll be expanding on our last few days together journaling. If you’ve missed any sessions, don’t worry! All of these are completely independent from each other and you can join any time. I'll provide a journal prompt or short meditation, and we'll enjoy a little time soaking up the beauty of Cartagena before breakfast.Breakfast - Included Meal
Breakfast at the hotel is included. Enjoy a typical full/American or buffet-style breakfast prior to the start of today's activities.Activity - Approx 2hrs - Getsemani Street Art Paparazzi Tour
Get ready, choose your best outfit and enjoy the charm of the coolest neighborhood of the city. You will have natural, spontaneous and candid photos during your tour. Our photographer will look for the best angle and light, working hand in hand with our guide. If you have a special photo idea, let our photographer know. On this tour you will learn about the stories and legends of this mythical neighborhood captured in its murals and graffiti. While you explore and know more about Cartagena, our professional photographer will capture your best momentsOptional Add-On Activity - Approx 3hrs - Cartagena Cooking Experience
The warmth and tastiness of Cartagena’s cuisine come right from the generosity of the local cooks who celebrate their culture with joy and passion with fresh ingredients, recipes and defined flavors old and new, all with the care and dedication served in their traditional cauldrons every single day. How can you choose between so many delicious treats everywhere you look? We took it upon ourselves to curate the must-try flavors for you to know by preparing some of the most authentic dishes from Cartagena’s recipe books and creating such pairings that'll have you craving for more.Overnight Accommodation at OSH Hotel Getsemani
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Cartagena: Beach Club & Isla de Tierra Bomba
Overview
Today is all about relaxation and indulgence as we take a day trip to a secluded island paradise just off the coast of Cartagena. Start your morning with an optional reflection or meditation session, where we’ll reflect on the highlights of the past week. After breakfast at the hotel, we’ll embark on a private transfer to the pier, followed by an exhilarating speedboat ride to Isla de Tierra Bomba, where your tropical escape awaits. Spend the day lounging by the pool or on the beach at a private beach club, surrounded by lush gardens and crystal-clear waters. Enjoy a delicious lunch with breathtaking views, followed by more beach-time before we head back to the mainland in the afternoon. After returning to the hotel, we’ll gather for a memorable farewell dinner at a highly-rated local restaurant, savoring a special set menu together. A perfect end to a day of relaxation, reflection, and unforgettable memories in paradise.Morning Coffee & Reflection/Meditation 6 (Optional)
A completely optional way to start your day. What have been the highlights from this last week? What have you loved most? We'll take this time in the morning before breakfast to come together, connect, and partake in a simple meditation, or discuss what we've learned for our final reflection session together.Breakfast - Included Meal
Breakfast at the hotel is included. Enjoy the typical full/American or buffet style breakfast prior to the start of today's excursions.Transfer - Approx 1hr - Private Transfer and Speedboat
Begin your adventure with convenient pickup from your hotel in private transportation and head to the pier. From there, board a speedy boat for a short and exhilarating ride to your private beach club.Activity - Approx 8hrs - Beach Club on Isla de Tierra Bomba
Upon arrival, bask in the splendor of a natural setting surrounded by tropical gardens and the sounds of turquoise waters. Relax poolside or on the beach. You can also indulge in booking a spa service, where you'll receive a five-star treatment that will leave you feeling rejuvenated and refreshed.Lunch - Included Meal
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.Transfer - 1hr - Speedboat and Private Transfer
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.Dinner - Included Meal
Our farewell dinner at a local highly-rated restaurant is included. Your meal will typically be a set menu with shared appetizers, with one alcoholic and one non-alcoholic beverage included.Overnight Accommodation at OSH Hotel Getsemani
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Cartagena: Departures
Overview
After an incredible week together, all good things must come to an end. Savor the memories made as you enjoy one last breakfast, checkout, and head home. If you are departing from Cartagena, we recommend flying out from CTG.Breakfast - Included Meal
Breakfast at the hotel is included. Enjoy the typical full/American or buffet style breakfast prior to checking-out, or continuing your adventure onward!
Frequently Asked Questions
Have questions specific to this trip? Here are some common questions about our adventure.
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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.
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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.
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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.
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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.
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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.
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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).
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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.
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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 10 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.
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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!
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Yes! Our booking partner (TrovaTrip) offers payment plans through Affirm — you can reserve your spot with a 25% deposit and pay the rest in installments.
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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.
Where You’ll Stay
On this journey, we've selected accommodations that reflect Colombia's character while providing comfort and authentic experiences. In Medellín, we stay at a locally-owned boutique Landmark Hotel in the vibrant El Poblado neighborhood.
In Cartagena, our accommodation, OSH Hotel Cartagena is located within the historic walled city, offering colonial charm with modern amenities. All accommodations feature private bathrooms, and solo travelers can choose between shared rooms (with another solo traveler of the same gender) or private rooms for an additional supplement.
















Stories From The Journey