Experience trawler cruising at its best in beautiful Chesapeake Bay by boarding Adirondack at the Anchorage Marina in Baltimore this fall and heading out to Rock Hall, Annapolis, Chestertown, Havre de Grace, Georgetown or any of the many great anchorages in between. Or join us as we head south on the IntraCoastal Waterway to Florida in October. These are all-inclusive custom cruises designed to give you exactly what you want in choices of location, menu, beverages and pace.

Cruise – without owning, insuring, maintaining, cleaning, worrying, provisioning

Learn – before buying or increase your skills and confidence with your own boat. 

All-inclusive (food, beverages, docking, everything except expenses you incure ashore) We give you a menu to select from before you board.

Trawler Time is a very different concept in chartering.

  • We wake up, have coffee and breakfast and check the weather. Then we make some sort of plan for the day and rarely stick to it. Sometimes we anchor, sometimes we stay at a marina. We may eat on the boat or at a restaurant. This is a real taste of the cruising lifestyle.
  • ADIRONDACK follows idyllic cruising weather south in the winter, north in summer. Imagine cruising with us from Chesapeake Bay to Florida. Meet us at a port somewhere along the Intracoastal waterway and travel along the coast, stopping at a new spot every day.
  • Capt. Jeff Janacek is a USCG 100T Licensed Master of the Great Lakes, Near Coastal and Inland Lakes and chartered for almost ten years on Lake Superior. He has cruised over 45,000 miles, including the Great Loop, DownEast Circle Loop, Intracoastal Waterway, Alaska’s Inside Passage, the Caribbean Sea, the BVI and USVI  the Bahamas and is a seasoned powerboat instructor. Check out the family blog at messinginboats.com.
  • Capt. Jeff will teach you all the tricks of the trawlering trade, including different kinds of trawlers, trawlering etiquette, rules of the road, docking, anchoring, maintenance, knots, navigation, cruising tips, meal planning, everything you need to know about handling, acquiring and keeping up a trawler. Or you can just come along for the ride, and leave the driving to him, although help with boat duties is greatly appreciated.