always you adventures

The inaugural Always You Adventure will bring five participants and five adult chaperones to Martha’s Vineyard for an experience centered on identity and the transition into adulthood.

The journey begins in Pittsburgh as the group travels together by vehicle toward the coast. Hours on the road allow conversation to begin naturally. The young women share stories, laughter, anticipation, and the quiet understanding that they are stepping into something new together.

From the mainland the group boards the ferry and crosses the water to the island. Approaching Martha’s Vineyard introduces them to a place shaped by history, where families return across generations and a strong sense of community remains visible. Many who arrive speak of a feeling that the island invites reflection and encourages people to see themselves within the life of the island.

During their time on Martha’s Vineyard the participants will move through the towns and shoreline side by side. They will spend time near the water, share meals, explore the towns, and encounter the traditions and generational presence that give the island its distinctive character. Each evening the group will return to the Always You Reflection Circle as the island grows quiet. In those gatherings the young women speak honestly about what they experienced, what stayed with them, and how those moments illuminate the adults they are growing into.

Living together in a shared home in Oak Bluffs deepens the experience. Oak Bluffs has welcomed families returning across generations and remains a place where that sense of tradition can still be felt. Days spent traveling, exploring, and reflecting together allow the participants to form friendships grounded in trust and shared experience. These relationships are intended to remain part of their lives for years to come.

Community sponsorship makes this experience possible.

Your support allows a young woman to step into this journey and experience a place that strengthens her sense of who she is becoming.

Always You Adventures is made possible through the generosity of individuals who believe that exposure to new environments strengthens confidence and expands perspective.

Five young adults will participate in this inaugural journey to Martha’s Vineyard.

We invite our community to support the Martha’s Vineyard Leadership Experience by sponsoring participants.

Full Sponsorship – $750
Supports one participant’s full participation in the retreat, including travel, lodging, and program experiences.

Half Sponsorship – $325
Contributes toward transportation and lodging expenses.

Supporter Contribution – $100
Helps provide meals, activities, and retreat materials.

Contributions of any amount are welcomed and appreciated. 

Every contribution helps create an experience that expands how these young adults see themselves and their future.

Your support makes this journey possible.

 These colorful cottages have welcomed families to Martha’s Vineyard for generations. Their presence reflects a long tradition of gathering and shared life that continues to shape the character of Oak Bluffs. 

 The Martha’s Vineyard Leadership Experience marks the beginning of Always You Adventures. 

Future journeys will introduce additional destinations where participants can encounter new environments and cultures while expanding their sense of what is possible in their lives.

Travel changes how people see the world. It also changes how they see themselves.

Always You Adventures will continue creating these journeys, and we invite you to join us in making these experiences possible for the young adults who will travel with us in the years ahead.

 Each new horizon invites us to imagine what is possible.