April 12 2025In the latest episode of the Coastal Currents Podcast, we’re diving into the heart of Cape May’s hospitality scene with brothers Tyler and Jackson Sole — the dynamic duo behind the historic Washington Inn and Cape May Winery. These two are not only keeping their family’s legacy alive but continuing to shape it for future generations.
It all began with their grandfather, Toby Craig, a gym teacher and coach from Wilmington, Delaware, who took a leap of faith and moved his family to Cape May to buy the now-iconic Washington Inn. Selling their house and leaving behind teaching careers, Toby and his wife turned a former bed-and-breakfast into a thriving restaurant. They lived upstairs with their children, creating a true family-run establishment from the ground up.
Over the years, the family’s work ethic and hands-on approach became a hallmark of their success. Whether it’s Tyler managing the Washington Inn or Jackson cultivating grapes and crafting wine at Cape May Winery, both brothers learned early on that leadership means being actively involved — bussing tables, running food, and staying connected with both staff and guests.
For Tyler, early memories include mastering the waffle iron at the family’s former Pelican Club and watching Chef Mimi, a 33-year veteran of the Washington Inn kitchen, work her magic. Chef Mimi, they both agree, has been a cornerstone of the family’s culinary legacy.
Jackson’s journey took him even further afield — to New Zealand, where he worked at a large-scale winery and absorbed invaluable lessons about wine production and regional terroir. Now back in Cape May, he applies those insights to local vineyards, nurturing 24 acres of vines and crafting wines that showcase the region's potential.
What’s clear from their stories is a deep passion for not just maintaining tradition, but evolving it thoughtfully. Whether it’s Tyler’s dedication to keeping the Washington Inn “classically cool” while adapting to modern trends, or Jackson’s careful selection of grape varietals best suited to Cape May’s climate, both are innovating while honoring their roots.
The Sole brothers also spoke about the profound impact of their late father, who, despite not being a natural behind the bar, embodied community service. A Marine Corps veteran, teacher, coach, and leader, he left an enduring legacy of integrity and involvement that continues to inspire the family today. The Sole family even awards a scholarship to local students who reflect these same community-focused values, keeping his memory alive in a meaningful way.
Tyler and Jackson’s approach to business is simple yet powerful: lead from the front and create spaces where guests feel truly welcome. At Cape May Winery, that means crafting an environment where visitors can relax, connect, and enjoy world-class wine in a setting that feels like an escape. At the Washington Inn, it’s about balancing fine dining with warmth and personality — a place where the servers have stories, the cocktails are unforgettable, and the food is consistently exceptional.
As Cape May continues to thrive as a destination, the Sole family’s contributions stand as a testament to the power of family, tradition, and community spirit. Whether you’re sipping wine among the vines or enjoying a meal at the Washington Inn, you’re experiencing a legacy of hospitality that spans generations.
Cheers to the Sole brothers, and to keeping Cape May’s traditions alive and thriving!
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