- 1. Trying to cover too much ground
- 2. Ignoring the weather window
- 3. Underestimating docking
- 4. Overpacking — and bringing hard luggage
- 5. Provisioning badly
- 6. Rushing the boat checkout
- 7. Anchoring without enough scope
- 8. Not assigning crew roles
- 9. Forgetting the on-the-ground costs
- 10. Leaving the paperwork to the last minute
1. Trying to cover too much ground
The single most common mistake is planning an itinerary like a road trip — racing to tick off as many islands as possible. Sailing is slow. A comfortable day is 20–30 nautical miles, or 3–5 hours of actual sailing, and that's before you account for weather, late starts, and the simple pleasure of staying put. Plan half the distance you think you can manage. The best charters leave time to swim, linger over lunch, and explore ashore.
2. Ignoring the weather window
New charterers often fixate on the planned route and sail into conditions they should have waited out. The wind dictates everything. Check the forecast every morning, build flexibility into your plan, and never be afraid to stay an extra night in a sheltered bay. A good skipper changes the plan to suit the weather — not the other way around.
3. Underestimating docking
Most charter mishaps happen in the marina, not at sea. Med-mooring stern-to, picking up a lazy line, or backing into a tight berth in crosswind takes practice. Arrive at anchorages and marinas early, while berths are plentiful and you're not rushed. Brief your crew on roles before you approach, and go slowly — you can always make a second pass.
4. Overpacking — and bringing hard luggage
Yachts have limited stowage and no room for rigid suitcases. Pack light, in soft duffel bags that squash flat. You need far less than you think: swimwear, a couple of changes, a warm layer, and good non-slip deck shoes. Leave the hard shell at home.
5. Provisioning badly
Either way too much or way too little. Plan your meals before you shop, remember you'll eat ashore some nights, and don't forget plenty of water and the small things — coffee, snacks for night watches, seasickness tablets. We cover this in detail in our yacht provisioning guide.
6. Rushing the boat checkout
At handover you'll be eager to cast off — but the checkout is where you learn the boat and catch existing damage. Take your time. Test the engine, electronics, heads, and anchor windlass. Photograph any existing scratches or dings so you're not charged for them later. Ask where everything is before the base staff leave.
7. Anchoring without enough scope
A dragging anchor at 2am is a rite of passage you can skip. Use enough chain — a 5:1 scope ratio is a good starting point — set the anchor properly by reversing onto it, and take a transit on shore to check you're holding. When in doubt, let out more chain.
8. Not assigning crew roles
A boat where everyone does everything is a boat where nothing gets done. Assign roles — helm, lines, fenders, anchor — before each maneuver. It removes the frantic shouting and makes docking and sail handling calm and predictable, even with a green crew.
9. Forgetting the on-the-ground costs
The charter fee is only part of the cost. Budget for fuel, marina fees, the end-of-charter clean, a security deposit, and dining ashore. Our charter cost guide breaks down exactly what to expect so there are no surprises.
10. Leaving the paperwork to the last minute
Different countries accept different qualifications, and some require an ICC or a second competent crew member. Confirm what your charter company and destination require well before you travel — see our license requirements guide. Bring originals, not photocopies.