• With over 35 years of combined experience in travel and events, we bring precision, creativity, and care to everything we design. Our approach balances thoughtful planning with flexibility, ensuring each experience feels seamless without ever feeling overproduced.

    We focus on small group experiences that encourage connection, comfort, and shared discovery. From the flow of each day to the details guests rarely see, we handle the logistics so our travelers can stay present and engaged. We believe the best experiences are those that feel effortless while being anything but accidental.

  • Project Pineapple’s foundation is built on corporate incentive travel and experiences. This is our core work and where our expertise runs deepest. For years, we have partnered with companies to design incentive programs that reward, inspire, and connect teams through thoughtfully curated travel and live experiences.

    Our leisure journeys grew from that same foundation. Over time, guests, clients, and colleagues began asking to join the trips we planned for ourselves. The experiences, the pacing, and the care behind them sparked curiosity and demand. In response, we created a way for individuals to access the same level of intention, hospitality, and design that defines our corporate work.

    Across both incentive and leisure travel, we specialize in culturally rich, small group experiences that blend food, place, and human connection. Our itineraries often include immersive local experiences, regional cuisine, time outdoors, and moments of gathering that feel natural and unforced.

    We do not plan party trips, rushed itineraries, weddings, or checkbox tourism. Our experiences are designed for those who value depth over volume, quality over quantity, and connection over spectacle. While joy, celebration, and fun are always part of the experience, our focus remains on creating travel that feels grounded, enriching, and genuinely memorable.

  • The pineapple has long been a symbol of hospitality, generosity, and welcome. In the fifteenth and sixteenth centuries, European explorers encountered the pineapple in the Americas and brought it back as a rare and prized offering. Displayed at grand gatherings, it signaled care, intention, and a deep respect for guests.

    That symbolism endures today. The pineapple continues to represent warmth, thoughtfulness, and the idea that no detail has been overlooked. At Project Pineapple, this philosophy guides everything we do. From the way we host to the way we design experiences, our goal is always to create an environment where guests feel welcomed, considered, and genuinely cared for.

  • The pineapple has long been a symbol of hospitality, generosity, and welcome. In the fifteenth and sixteenth centuries, European explorers encountered the pineapple in the Americas and brought it back as a rare and prized offering. Displayed at grand gatherings, it signaled care, intention, and a deep respect for guests.

    That symbolism endures today. The pineapple continues to represent warmth, thoughtfulness, and the idea that no detail has been overlooked. At Project Pineapple, this philosophy guides everything we do. From the way we host to the way we design experiences, our goal is always to create an environment where guests feel welcomed, considered, and genuinely cared for.

  • At our core, we exist to reignite the joy of exploration and the art of authentic hospitality. We design experiences that help people slow down, engage deeply, and connect more meaningfully with the places they visit and the people they travel alongside.

    Through personalized, well crafted journeys, Project Pineapple aims to create experiences that feel both inspiring and grounding. Our goal is simple. To help our guests experience the world with curiosity, comfort, and a sense of belonging.

Designed Experiences. Meaningful Connection.

We create corporate incentive programs and small group travel experiences rooted in hospitality, culture, and thoughtful execution.

Our Founders

Project Pineapple was founded by Ashley Glade and Michelle Elliott, whose shared background in corporate incentive travel and live experiences forms the foundation of the brand. With decades of combined experience, they bring a thoughtful, guest-first approach to every experience they design.

Their partnership grew from a shared belief that great travel is rooted in hospitality, intention, and care. Whether designing incentive programs for organizations or immersive leisure journeys, Ashley and Michelle remain hands-on in every detail, ensuring each experience reflects the values and standards that define Project Pineapple.

Chief Experience Officer

Ashley Glade

When she’s not designing experiences or bringing plans to life, Ashley is usually splitting her time between Florida’s beaches and Montana’s mountains. Powered by good coffee and an appreciation for quality tequila, she’s happiest when she’s off-grid in her built-out 4Runner, camping remotely to recharge after being “on.” When she’s home, you’ll likely find her with a crochet project (or five) in progress and prioritizing time with the people who matter most, her family, her grounding force, and her constant inspiration.

Chief Event Officer

Michelle Elliott

When she is not onsite bringing events to life, Michelle is usually outside, ideally near the water. She loves hiking, biking, scuba diving, van adventures, and chasing sunrise and sunset whenever she can. If she is not outdoors, she is likely curled up with a good book, enjoying good tequila, and planning her next adventure.