Maiden Enterprises

A Legacy of Adventure and Exploration

The Maine Windjammer Association boasts a rich history, rooted in the indomitable spirit of exploration and adventure that defines the state of Maine itself. For over four decades, our fleet of traditional tall ships has whisked guests away on unforgettable journeys along the untamed beauty of the Maine Coast.

Experience the Ultimate Sailing Adventure

Our iconic windjammers offer multi-day, all-inclusive sailing adventure cruises in one of the most acclaimed cruising grounds in the world. From thrilling tacks and exhilarating ocean views to the peaceful lull of a gentle breeze, each voyage is a transformative experience.

Beyond the Adventure

But the magic of a Maine Windjammer Association cruise extends far beyond the thrilling sailing experience. It's about connecting with nature's untamed spirit, experiencing the warm hospitality of our seasoned crew, and indulging in delicious, fresh-prepared meals inspired by local traditions.

Explore the Untamed Beauty of Maine

Our itineraries take you to the heart of Maine's captivating landscape. From exploring secluded islands and pristine coves to spotting majestic eagles and playful porpoises, each day unfolds a new breathtaking panorama. You'll visit charming villages, witness the raw beauty of uninhabited islands, and savor the rich cultural heritage of the region.

Discover the Spirit of Maine

Sailing aboard a Maine Windjammer Association vessel is an immersive experience that captures the essence of Maine. Our passionate crew shares their deep connection to the land and sea, weaving tales of the region's rich history and vibrant culture.

Join the Journey

Whether you seek a romantic getaway, a family adventure, or a transformative solo voyage, a Maine Windjammer Association cruise offers an unparalleled experience. Explore our fleet and offerings to find your perfect adventure, and embark on a journey that will leave a lasting impression on your soul.