We have chartered with Moorings many times on a powerboat and have done both. The last 4 trips we have done the "Evening Start". This allows you to get everything done during the day. I send my crew off to the pool or shopping for provisioning that we like to get in person. Wife likes to look at the meat or fruit at the store to hand pick. All the other canned and bottled stuff we provision ahead of time. I go do my captain stuff prior to getting the boat. This would be getting the boat phone and confirming any accessories we reserved like scuba tanks. I meet the staff and let them know of the phone number and try to at least get the boat name so when the food delivery comes it goes to the right boat. The other advantage is you can do the boat briefing and get settled in. Not sure if this is your first time chartering but never keep your food in the cardboard boxes that they deliver in. The glue holds cockroaches and the eggs. Empty and take them straight to recycle. You will get your boat between 5 and 6 PM. You can get everyone to settle in and unpack. Then you can relax with a cocktail. This is when I will go over the boat and how do use issues with new crew. I look at the long range weather report and boat accordingly. I usually have 2 back up plans during the trip for crowds or weather. The beauty of already being onboard from the night before is you can get off the dock that next morning. This actually gives you a full day on the water. If you elect to stay at a hotel and arrive the day your charter starts you will not get off the dock until around 3 PM. It limits your choices where to go do to it being later in the day. Of course its all about your budget.