Join the SideQuests community 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.

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 and Greet

We're 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 (optional)

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 Landmark Hotel Medellín

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.

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

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, savor an included traditional Colombian lunch. Afterwards, set sail on a private Guatapé Boat Tour, where you can relax, and enjoy the stunning scenery. After a great boating experience, 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.

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.

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 - 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.

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. Feel free to find a bite to eat as a group or on your own while exploring beautiful Guatapé.

Overnight Accommodation at Landmark Hotel Medellín

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.

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. This is not a rigid cruise, but an experience shaped around how you want the night to unfold. You’re welcome to bring your own food and drinks on board, or we can arrange everything in advance—from curated beverages to light bites or a more elaborate onboard dining setup. Music sets the tone as the city lights come alive, with the option to keep things relaxed or turn up the energy as the evening progresses. As the experience winds down, you’ll return by boat to Muelle de los Pegasos, located just outside the main gates of Cartagena Walled City—placing you directly into the buzz of the historic center and perfectly positioned for dinner, nightlife, or a relaxed stroll through the Old City.

Overnight Accommodation at OSH Hotel Getsemani

Overview

Get ready for a full day exploring Cartagena! After breakfast, delight yourself with the enchantment of the historic walled city. This is an amazing opportunity to experience the uniquely magnificent city of Cartagena , a UNESCO World heritage site, in an air conditioned private vehicle with a local bilingual qualified guide. 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. Then in the evening, 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. Afterwards, relax and recharge for the next day’s adventures or continue exploring the old historic center of Cartagena and find a great spot to eat, with recommendations from our guides.

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 4hrs - Historic Walled City Tour

The tour starts with a visit San Felipe de Barajas, which is situated outside the walled city. This monumental fort is considered to be the most outstanding feat of Spanish military engineering in the New World with its construction beginning in 1536 and lasting for 121 years. There are opportunities to visit additional museums and historical sites, like the Convento de la Popa that sits on the highest point of Cartagena, a 30 minutes hike. Visit to the Dungeons within the walled city ramparts. Originally built to store provisions for the troops they are now home to a high quality handicrafts market selling brightly decorated cloth, woodwork & woven bags made by some of the indigenous peoples of Colombia

Optional 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.

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 OSH Hotel Getsemani

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.

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

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!