I have chartered one way,
St Martin to Tortolla with VPM Bestsail twice. It is a nice downhill run, and was quite enjoyable. Flying into SXM and out of STT was also reasonable. However, other airports may be quite a bit more expensive to fly into one and out another. Another consideration with an uphill run is that you will use a lot more
fuel. Some companies charge a
cleaning fee and others do not. So, I have found the only way to really compare
bareboat charters is to make a spreadsheet with all expenses, including travel.