DreamTrips Celebrates 20 Years With a High-Energy Relaunch Cruise That Signals a New Era

Last week, the open waters between Miami and the Bahamas became the setting for a defining moment in the world of travel-based entrepreneurship. Aboard a special anniversary cruise, DreamTrips officially marked the relaunch of its brand, aligning the moment with its 20th anniversary and ushering in what many attendees described as the beginning of a powerful new chapter. 

Departing from Miami and sailing to the Bahamas, the cruise brought together nearly 350 attendees for several days of connection, celebration, training, and unforgettable experiences. But what made the trip stand out wasn’t just the destination—it was the community that came to life onboard, reinforced by a symbol that was impossible to miss. 

The iconic blue “YOU SHOULD BE HERE” sign—long associated with DreamTrips’ global movement—seemed to take over the entire ship. It appeared everywhere attendees looked: at events, gatherings, photo moments, and shared spaces. More than décor, it became a statement, a reminder, and a shared language for what the cruise represented. 

A Community First, A Cruise Second 

From the first day at sea, the sense of community was unmistakable. This was not a group of individuals sharing a ship—it was a connected, supportive, and welcoming community forming in real time, unified by shared experiences and a shared identity. 

For first-time DreamTrippers, the experience was especially powerful. Many arrived excited about the cruise itself, but were quickly overwhelmed—in the best possible way—by the depth of community they encountered. Seeing the “YOU SHOULD BE HERE” sign everywhere they turned reinforced what they were feeling: that they had stepped into something bigger than a vacation. 

New members spoke openly about how unexpected it was to feel so included so quickly, describing moments where complete strangers made them feel like long-lost friends. The feeling of belonging, shared purpose, and collective excitement left a lasting impression and turned first-time travelers into lifelong members of the DreamTrips community. 

Veteran DreamTrippers felt it too. For those who had been part of the brand’s journey for years, the cruise served as confirmation that the heart of DreamTrips—its community—was not only intact, but stronger than ever. Many shared that seeing the iconic blue sign reappear throughout the ship felt symbolic: a familiar reminder that DreamTrips hadn’t lost its soul, and that the brand’s culture was alive and thriving. 

Training, Recognition, and Vision 

The cruise also featured a dedicated training and recognition session that brought the community together with purpose and clarity. Members, leaders, and families gathered for recognition moments and powerful speeches and trainings from company leadership. 

The message was consistent and grounded in what attendees were already experiencing onboard. DreamTrips is built around real people, real relationships, and real shared experiences—not hype. 

“DreamTrips has always been about community,”

said Mark Smith, Owner and CEO of DreamTrips.

“When you see that blue ‘YOU SHOULD BE HERE’ sign everywhere on this ship, it’s not marketing—it’s a reminder of who we are. This cruise wasn’t just about celebrating 20 years. It was about showing what’s possible when people come together with a shared vision.”

Celebration, Connection, and Shared Experiences 

Outside of training, the cruise delivered nonstop moments that strengthened community bonds. A vibrant white party brought nearly everyone together in celebration, while karaoke nights created laughter, vulnerability, and shared memories. Informal gatherings throughout the ship turned meals, sunsets, and late-night conversations into meaningful points of connection. 

A highlight for many was the stop at CocoCay in the Bahamas, where members experienced one of the region’s most sought-after island destinations together. Throughout the cruise, attendees enjoyed exceptional dining experiences and an abundance of food, adding to the sense of comfort, enjoyment, and shared experience at sea. 

A Global Community With a Shared Vision 

The anniversary cruise also reflected the global reach of DreamTrips. Attendees traveled from all over the world including the United States, Australia, Norway, Israel, and Hungary, creating a diverse international community united by a shared travel lifestyle. 

Different cultures and backgrounds blended effortlessly, reinforced by a common message seen everywhere onboard: YOU SHOULD BE HERE. 

One Question Going Forward 

As the ship returned to Miami, attendees—both first-time travelers and long-time members—were left with a single, shared question: Where are we going next? 

With DreamTrips, the answer is simple. 

 Anywhere they want. 

YOU SHOULD BE HERE. 

SOURCE: DreamTrips