[1] Let’s start with the assumption you are looking for a power boat, not a sailboat as then a whole different set of criteria and choices would come into play.
Everything really comes down to how you will use the boat and your budget, of course. First, ask yourself how you will be operating the boat. Are you planning to be an owner-operator (operate the boat yourself without crew)[2], or will you have crew? This will mainly determine the size of boat you should consider and will limit the length you can comfortably and safely operate with just two people. Realistically, the length for an owner-operator boat will rarely exceed 70’, and even that is a lot of boat to handle with just two people.
Indeed, modern technologies make driving and operating the boat easy enough. For the second person, though, taking care of the boat will become more cumbersome with length. It will become more difficult to tie the boat up quickly, especially in less than ideal conditions, the lines will become longer and heavier to deal with, and every service that gets charged per foot (such as dockage and detailing) becomes more expensive. The number of people you expect to generally have onboard will also be a factor in size, which obviously plays a role in how many guests you can comfortably accommodate (seating, staterooms and heads)[3], especially in the case of overnight trips.
The next questions relate to how you imagine you will be using the boat in practice. Will you go out on longer trips, shorter trips, or just day trips? Will you have many and/or frequent guests, will you want to do a lot of entertaining? Do you care more about being underway, or is it more about the destination (and getting there quickly)? Is the speed at which you travel important? If speed is not of the essence, and you are planning on spending longer periods of time on board, a trawler style boat is likely to better suit your needs. For faster speeds, and relatively shorter trips (time and distance), a cruiser style boat is probably a better fit. If you are planning to just do day trips, without overnight stays on board, picnic style boats are worth considering, as are (relatively smaller) day boats, such as smaller cruisers, open boats, bow riders, wake boats, and center consoles. Important factors to consider for day boats include the need for shade and/or protection from weather, whether you have a head (bathroom), cold storage (for food and drinks), and cooking facilities such as a grill or other, and whether you want to, and can, tow toys such as tubes, wakeboards or water skis.
If you are planning to overnight on board, do you plan to mostly spend nights at a dock in a marina, or will you be spending a lot of time at anchor? Storage is important if you are planning to spend more time onboard. Not only storage for things such as clothes and toys, but also food and cold storage, as well as cooking facilities (stove, oven, microwave, grill). Away from services provided by marinas (notably power, water, and pump-outs), factors such as the fuel capacity (range), fresh water capacity (unless you have a water maker and boat in an area where you can use a water maker), holding tank capacity, and the capacity of the generator will become important factors in determining your independence, and how long you will be able to stay away from shore side services. Trawler style boats will generally be better equipped for spending longer periods of time away from a dock, both underway and at anchor. Nonetheless, most cruisers – and smart use of water (if you don’t have a water maker) – should allow you to stay let’s say up to a week at a time at anchor.
Other factors to consider include the climate in which you boat, as well as personal lifestyle choices, which are important factors in determining how much outdoor vs indoor space you would need on your boat. The need for speed, the desire for water toys (carrying them on board, and/or being able to tow toys) are other relevant factors. Are you planning to fish a lot (sportfish type boats, center consoles rigged for fishing), a little or not at all (pretty much any other style boat – you can always choose to have a couple of fishing rods on board and attempt to catch your lunch and dinner)?
These are just some of the questions that will help you determine the factors that are important to you in how you are planning to use the boat that you will be shopping for. Finding the boat that best suits your needs will provide the greatest enjoyment once you take delivery.
Whatever you decide is best for you, get out on the water have fun!
[2] See https://www.yachtcreators.com/blog/yacht-owner-operator/ and https://www.yachtcreators.com/blog/long-boat-trip/
[3] Boat speak for bedrooms and bath rooms.
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