Where's Boundless? Setting a trip date is always step one in reserving your sailing adventure with us.  Securing your adventure six months to a year ahead of time is highly recommended, although we will try to make your trip happen on less notice if possible. Should your ideal trip dates already be taken, contact us anyway as often groups are able to adjust their dates to accommodate other groups. 

  • Chesapeake Bay and Washington DC trips: All groups, MS/HS, Scouts, AHG, family and friends trips: April/May/early June/September/October

  • Virginia to New York City extended voyage: June

  • New York City to Maine extended voyage: June 

  • Maine Summer Sailing Adventures: MS/HS, Scouts, AHG, family and friends trips: July/August/September.

  • Return Maine to NYC to Virginia extended trip: August/September.

  • Bahamas Sailing Adventures: All groups. November thru April/May including most school breaks and intersessions.