PRIVATE Local Sunset Sail by a Certified Captain

As we cruise through the historic waters of Baltimore, Maryland, you’ll experience one of America’s oldest and most storied port cities from a unique perspective. Depending on our route and weather conditions, you may catch a glimpse of the iconic Domino Sugar sign, the towering cranes of the working port, Fort McHenry—birthplace of the national anthem—or the shimmering skyline of downtown Baltimore. Keep an eye out for historic ships, playful harbor wildlife, and the vibrant neighborhoods that line the waterfront. While views may vary, every trip through Baltimore offers a blend of history, industry, and charm that’s distinctly local.

From the water, you’ll have the rare chance to view Fort McHenry just as ships did during the War of 1812. This star-shaped fortress famously defended Baltimore from British attack in 1814 and inspired Francis Scott Key to write “The Star-Spangled Banner.” As you sail past, imagine the cannon fire, the smoke, and that enormous American flag flying overhead. The fort remains a national symbol of resilience and patriotism, and seeing it from the harbor offers a powerful connection to the city’s historic roots.

Nestled along the waterfront in the Port Covington area, Sagamore Spirit Distillery is a modern whiskey destination with deep Maryland roots. From the sailboat, you can spot its sleek, glass-fronted buildings and copper stills glinting through the windows — a nod to the region’s rich rye whiskey heritage. The distillery sits on a five-acre campus designed to reflect Baltimore’s spirit of craftsmanship and innovation. While you may not smell the mash from the water, seeing the facility from the harbor offers a unique perspective on how Baltimore continues to blend tradition with modern flavor. It’s one of the harbor’s most impressive new landmarks and a reminder that the city’s story is still being written — barrel by barrel.

Baltimore’s skyline offers a striking blend of old and new, and from the sailboat, you’ll have one of the best panoramic views in the city. You’ll see the World Trade Center (the tallest pentagonal building in the world), the historic Federal Hill, and the glass pyramids of the National Aquarium — all framed by the charm of rowhomes and bustling piers. As the sun sets, the buildings light up, making for unforgettable photos and a true appreciation of the city’s unique vibe.

Located in Port Covington, Under Armour’s Global Headquarters represents the new wave of innovation and redevelopment along Baltimore’s waterfront. As you sail past, you’ll see sleek modern architecture, athletic fields, and company buildings set against the backdrop of a historic working harbor. This site connects the old with the new — where industrial piers once stood, a global athletic brand now thrives, all while keeping its Baltimore roots strong.

Sailing along Key Highway and into Locust Point, you’ll pass neighborhoods steeped in maritime history. These shores once welcomed thousands of immigrants arriving by ship and served as the launch point for wartime supply vessels. Today, historic rowhomes and red-brick warehouses sit beside new waterfront condos, breweries, and parks. From the deck of the sailboat, you’ll witness how Baltimore’s harbor remains alive — always evolving, but never forgetting its roots.