1. Pick the right destination
- British Virgin Islands — the classic first charter: easy line-of-sight navigation, calm anchorages, 60+ islands within 30 nm.
- Greek Ionian — gentle winds, green scenery, easy day hops.
- Bahamas (Exumas) — stunning water, more open water passages — better for week two of experience.
- Avoid for a first charter: open-ocean routes, strong-wind areas in peak season (e.g. central Cyclades in August).
2. Sort the paperwork early
- Passport valid 6+ months — check visa rules per country.
- ICC or equivalent if chartering in the Mediterranean.
- Sailing résumé / logbook if asked by the operator.
- Travel insurance covering sailing and hurricane-season weather events.
- Drone permit if you plan to fly one (many countries require one).
3. Choose bareboat or crewed
First time on a catamaran? A skippered or crewed charter is the most relaxing intro — the captain handles navigation while you learn the ropes. If you're experienced sailors doing bareboat, expect a 2–3 hour checkout sail before you leave the dock.
4. Pack smart
- ✓ Soft bags only
- ✓ Reef-safe sunscreen
- ✓ Light fleece / windbreaker
- ✓ Non-marking deck shoes
- ✓ Rash guard & snorkel gear (optional)
- ✗ Hard suitcases
- ✗ Heels / formal wear
- ✗ Irons, large appliances
- ✗ Scented sunscreens (reef damage)
5. Expect the first day to be slow
Day one is always the slowest: briefing, provisioning check, checkout sail, learning the boat. Plan a short afternoon hop and a relaxed first dinner on board or at a nearby dock. The magic really starts day two.