Romantic Northern Wisconsin Getaways: Sailing on Lake Superior

Three wind-blown vessels sailing on Lake Superior.We’ve all seen it on television and movies, a strapping young man with his gorgeous female counterpart leisurely navigating the coastline without a care in the world. The romanticized notion of sailing conjures visions of beach houses, expensive bottles of bubbly, and a jet-set lifestyle. But what if someone told you that you don’t need to be a high-rolling hotshot to enjoy sailing on Lake Superior? With its quaint lakeside communities, turquoise waters, and rugged ridgelines, the Chequamegon Bay offers the ideal setting for any romantic Northern Wisconsin getaway, and Old Rittenhouse is the perfect complement. Adding to the allure, we’ve partnered with Dreamcatcher Sailing to provide unrivaled and affordable sailing trips focused on the Chequamegon Bay and the Apostle Islands. From casual cruises to multi-day excursions, Bayfield, WI, is your epicenter for sailing on Lake Superior.

The Best Lake Superior Sailing Charter in Bayfield, WI

Just down the road from Old Rittenhouse Inn, Dreamcatcher Sailing offers day trips ranging from two to 12 hours and multi-day trips from two to four days. With an impressive fleet consisting of a 36’ Catalina, 33’ Pearson, a 38.5’ Pearson with a center cockpit, and a 37’ Tartan, you’ll staddle onto the lap of luxury. Led by a team of experienced boat captains, you’ll be in good hands when voyaging the Chequamegon Bay and beyond. What’s more, Dreamcatcher also provides an exemplary sailing school that instills a broad understanding of meeting the inevitable challenges associated with sailboat navigation, maintenance, and terminology. The two-part training course will impart a great deal of priceless knowledge that you’ll cherish for a lifetime. Whether you need a refreshing review of the basics or a deep dive into sailing on Lake Superior, Dreamcatcher has you covered. 

A Romantic Hotel in Wisconsin for Sailing on Lake Superior

Champagne with TrufflesSailing on Lake Superior should be considered anytime you plan a romantic Wisconsin getaway to Bayfield. With a bevy of enhancements, scenic vistas, and luxurious accommodations, it’s no wonder that Old Rittenhouse Inn remains at the top of the list of places to stay for unparalleled romance. For more information or to reserve your stay, please visit our website or give us a call at 715-779-5111.