White catamaran cruising on turquoise water with islands in the distance—your dream sailing adventure checklist starts here.


⛵ Sailing Roadmap

Follow and track progress as my daughter and I work towards our dream of swapping Hobbies for 45ft catamaran sailing adventures in the Bahamas and Mediterranean.
Published by Joseph McGurkin

📍 Foundation

  • [ ] Take ASA 101 (Basic Keelboat) or US Sailing Basic Keelboat
  • [ ] Take ASA 103 (Coastal Cruising)
  • [ ] Practice docking, reefing, and sail trim on 25-35 ft boats
  • [ ] Learn basic navigation (charts, chartplotter, COLREGs, tides/currents)
  • [ ] Do a weekend liveaboard trip on a keelboat

📍 Cruising Skills

  • [ ] Take ASA 104 (Bareboat Cruising) - multi-day liveaboard
  • [ ] Take ASA 114 (Cruising Catamaran)
  • [ ] Charter with a skippered catamaran (BVIs or Bahamas)
  • [ ] Do your first short bareboat charter (3-5 days) in easy waters
  • [ ] Practice anchoring, mooring, and docking cats

📍 Bareboat Confidence

  • [ ] Log at least 50+ days on 30-50 ft cruising boats
  • [ ] Do a 7-10 day bareboat charter in BVIs, Bahamas, or Grenadines
  • [ ] Handle night sailing & watch rotations
  • [ ] Try sailing in areas with tides & currents (e.g., New England, Keys)
  • [ ] Learn med-mooring techniques (for the Med)

📍 Ready for Bahamas & Mediterranean

  • [ ] Charter a 40 to 50 ft catamaran in the Bahamas (Abacos, Exumas)
  • [ ] Charter a catamaran in the Mediterranean (Croatia or Greece first)
  • [ ] Complete a marine first aid & safety course
  • [ ] Keep building miles and updating your sailing resume

⭐ Stretch / Advanced (Optional but valuable)

  • [ ] ASA 106 (Advanced Coastal Cruising)
  • [ ] Offshore passage or delivery trip (multi-day open ocean)
  • [ ] Weather-routing or advanced seamanship course