It depends on where you live and what access to the waters you have.
Check local sail clubs if becoming a member
might get you access to boats for way less than any charter
If there are many ramps or the shore is very easy, you can have a trailerable boat
Another option is renting
a rack and keeping something that you just lift
on one arm and store in between your trips. Second hand Lasers / Hats or Sunfishes should not be too expensive to buy/use and re-sell later.
At other times a part-share is a good option - esp. once you step into heavier keel
boats that require a dock/marina berth.
Last but not least - a windsurfer or a kitesurfing s/h kit can be had for next to nothing and then sold off. Zero need for ramps or racks. You can bring your kiting kit to the waterside in a rucksack.