Any time is great to hire a boat for cruising, snorkeling, fishing, whale watching, diving, etc.
But it is likely to be best if you are able to choose a time that is in-season and offers the right weather for the activity you are planning.
Boat Season
A typical boat season is likely to run from April to October each year in many countries, such as those bordering the Mediterranean and in the United States and likely to experience a significant amount of bright sunlight throughout this period. A sailing vacation is likely to be more enjoyable if you are able to avoid the busiest time of the year when many of the locals are taking their holidays, so you might want to avoid July and August.
Best time to charter
In reality, a sailing adventure is likely to be best enjoyed at the start of the season (mid-May to mid-July) or at the end of the season (early-September to mid-October) when the crowds are much more manageable and sea water is still warm. A further benefit is that the prices quoted by the rental companies are certain to be that much more affordable if you are to stay outside of the busiest parts of the season.
Plan early
If you are looking for more flexibility in the available dates for the sailing holiday and selection of yachts, you might want to look at making the arrangements early and booking the holiday well ahead of time. For a high season charter (July & August), an early booking is likely to be highly desirable. Although, if you are looking to charter a yacht throughout the mid to low-season, more flexibility is likely to be available and even possible to book the last minute charters.
Obviously there is a far-sight more sunlight throughout the main boating season, but if you would like a bit more tranquility and peace, a winter cruise might be highly desirable.
Charting in the Bahamas
Before planning to charter a yacht it benefits so look at the likely temperatures and conditions related to the preferred destination. A charter in the Bahamas for instance is most favored throughout the summer months with the temperature kept at a constant 80-90 degrees with cooling wind and sunny skies. Plus, it is possible to experience these pristine waters throughout the winter (December to February) with temperature falling to about 60-65 degrees. While this is a lot cooler it is still more pleasant than certain areas of the United States.
Certain times
Certain times of the year are significantly more popular than others for charting a yacht in the Caribbean or similar popular destinations. Christmas and New Year will need advanced booking to ensure a yacht is available for the preferred dates. Plus, in regions of the Mediterranean the availability of ports or marinas can be limited, so planning ahead is needed to make sure a preferred dockage is reserved for the time of the voyage.