5 Key Lessons from Our Maryland @ Sea Community Cruise
Have you ever wondered what happens when you bring Maryland and the greater Mid-Atlantic community together in the middle of the ocean? Last week, our team had the incredible opportunity to host "Maryland at Sea," our first-ever community cruise on Virgin Voyages Scarlet Lady, bringing together folks from across the Old Line State and neighboring regions.
Beyond the gorgeous sunsets, amazing entertainment, and delicious food, what truly stood out were the valuable lessons we learned about building regional connections in a unique setting. The experience of watching our neighbors form bonds while sailing the Western Caribbean offered insights that went far beyond what we expected.
Lesson 1: Start Small, But Think Big
When we first announced "Maryland at Sea," we worried about numbers. Would enough people from our Mid-Atlantic community sign up to make it worthwhile? Should we wait until we had a larger regional following?
We ultimately decided to move forward with a smaller, more intimate group of Maryland and neighboring state residents, and that decision turned out to be one of our smartest moves.
Starting with a manageable size allowed us to provide personalized attention to each participant. We learned everyone's names long before we sailed, remembered their preferences (including favorite Maryland sports teams!), and could quickly adapt activities based on the group's energy.
This approach gave us a perfect testing ground for community-building techniques without the pressure of managing dozens of people. The enthusiasm generated by this smaller group of neighbors was just as powerful as what we might have experienced with a larger crowd, and perhaps even more so because of the close connections formed.
Best of all, this "beta test" cruise has already created significant buzz throughout Maryland and beyond. Our email list has grown substantially as people who missed out are signing up to be notified about the next voyage. Sometimes, starting small is the fastest path to thinking big.
Lesson 2: Be Decisive With Choices
Prior to the cruise, we imagined offering maximum flexibility would be appreciated. "What would everyone like to do tomorrow?" and “Which Shore Things should we sign up for?” seemed like community-centered approaches.
We quickly discovered this created more anxiety than freedom. When faced with too many options in an unfamiliar environment, our sailors became overwhelmed rather than empowered.
Our solution? We shifted to presenting clear, curated choices: "Tomorrow we’d love to play group bingo. Who's in?" This approach still gave people agency but within a framework that felt manageable and well-considered.
Quickly, we noticed participants were more relaxed and engaged when given bounded choices rather than unlimited possibilities. And this lesson applies well beyond cruises. In any community setting, thoughtful curation of options often creates more satisfaction than unlimited freedom.
Lesson 3: Over-Communicate, Always
If there's one lesson that stood out above all others, it's that we simply cannot over-communicate important information. What seems repetitive to us as organizers is often just adequate for participants who are processing many new experiences simultaneously.
We shared key meetup times and locations and other updates through:
Weekly email notifications
Frequent text messages
Verbal reminders at each gathering
The Virgin Voyages messaging app
Did people find this annoying? Quite the opposite! Our sailors appreciated the clear, consistent communication. In settings with spotty WiFi and countless distractions, this redundancy ensured everyone felt informed and included.
As one sailor said, “Working with [Untethered Voyages] was amazing. [They] communicated so well, made sure I meet all the deadlines and I had everything I needed to board the ship with no issues.”
Lesson 4: Balance "Me vs. We" Time
One of our biggest reminders was about the importance of respecting different social needs. Our Maryland at Sea group included a wonderful mix of introverts and extroverts, each with their own preferences for how much group time felt energizing versus draining.
Rather than forcing everyone into the same schedule, we made all group activities entirely optional with no judgment for those who needed more personal time. We were clear that participants could join in as much or as little as felt right for them.
Some cruisers thrived by attending every single event, while others preferred to dip in and out, enjoying solitary moments on deck between social gatherings. Both approaches were equally valued and respected. We provided a clear schedule of options but emphasized that everyone should listen to their own needs and energy levels.
This judgment-free approach to participation created a remarkable level of comfort. By removing any pressure to "show up for everything," we actually found people participated more authentically when they did join in, arriving refreshed and genuinely wanting to be there.
Lesson 5: Simplicity Often Wins
In planning the Maryland at Sea cruise, we worried about whether our community-building efforts would feel substantial enough alongside all the impressive entertainment that Virgin Voyages provides. Would our simple gathering spaces and casual meetups feel valuable compared to the ship's elaborate productions and professionally designed experiences?
What we discovered surprised us. Some of our most memorable community moments came from simple activities—an impromptu UNO game in a bar created deeper connections than the ship's spectacular PJ Party and Scarlet Night. A casual conversation circle during a group meal led to more meaningful exchanges about life than any of the high-production entertainment options.
On the last night of our Maryland at Sea journey, we gathered for what was supposed to be a quick trivia game. Someone pulled out a deck of cards, and before we knew it, our planned activity had transformed into something beautifully unstructured. Only dinner reservations eventually broke up the gathering—and even then, warm hugs and excited talk about "next year" dominated the farewells. The most powerful connections didn't happen during our carefully planned activities, but in these organic, unscripted moments of simply being together.
These simple, low-pressure environments allowed authentic relationships to form naturally between neighbors who might never have connected back home. While Virgin Voyages offered plenty of impressive, professionally produced entertainment options that we all enjoyed, our sailors often gravitated toward the simpler settings where genuine conversation could flourish.
Building the Maryland Community at Sea and Beyond
What struck us most about our Western Caribbean Charm experience wasn't the destinations we visited, but the journey we took together as a community. The lessons we learned aren't limited to cruise ships—they apply to any regional community-building effort, whether online or in person.
Building meaningful community isn't about grand gestures or perfect planning. It's about creating spaces for authentic connection among neighbors, remaining responsive to the group's needs, and recognizing that sometimes the simplest approaches create the strongest bonds between people who share a regional identity.
As we disembarked and said our goodbyes (many with genuine tears in their eyes), we were struck by how quickly a group of relative strangers from across Maryland and the Mid-Atlantic had become a tight-knit community. The shared experience of being at sea together—disconnected from everyday distractions and connected through intentional gatherings—accelerated relationships in ways that would have taken months or years in other contexts.
We're already planning our next Maryland at Sea cruise, this time with the benefit of these five key lessons. We can't wait to see how these insights will help us create an even more meaningful experience for both returning participants and new community members joining the adventure from across our beautiful region.
If you’re in the Maryland / greater Mid-Atlantic US and are interested in joining us in 2026, share your feedback via our interest form. We can’t wait to hear from you!
What community-building tactics have worked for you in bringing together regional communities, whether at sea or on land? We'd love to hear your experiences in the comments below!
