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I'm suggesting using plastic buckets because they are cheap (I get them for a buck apiece at a local doughnut shop) and sturdy. There are lots of different planters and pots and even ready-made self-watering models available at you local garden supplier, even plastic-free models. Choose one that holds about 5 gallons; a round 5-gallon flower pot is about 12 inches tall and 12 inches across at the top. If you don't have space, but still want to give cherry tomatoes a try, you can plant them in the Nickel Pincher's $1 Upside-Down Tomato Planter, made from a reusable grocery bag.
For the uninitiated, a tomato cage is just what you would guess: wire mesh you place around a plant to support it as it grows. Depending on the variety, cherry tomatoes can grow as tall as 10 feet. Avoid any that look as though they're covered in plastic. That's usually vinyl, a toxic plastic that can expose your plants to lead and other undesirable substances.
1. If your container doesn't already have them, drill ¼- to ½-inch holes every few inches around the bottom edge, plus another few in the center bottom so excess water can drain.
2. For best fruiting, pick a location where the plant will get at least 8 hours of direct sun each day. You can skip the tomato cage—and save a little cash—if you have a spot close to a balcony or railing, which you can use to support the tomato vines.
3. If you do go with a cage, insert the pointy end into the planter, and then fill the planter with potting mix.
4. Water until the potting mix is evenly moist. Top it off with a little more potting mix, adding enough so it comes to about ½ inch below the rim of the planter and making sure the soil surface is level.
5. Dig a small hole in the center of the planting mix. Carefully remove your tomato plant from its original pot (unless the pot is designed to dissolve), and slide it into the hole, planting it deep enough so only the top four to six leaves show once you cover it back up with potting mix.
6. Water every two or three days to keep the soil evenly moist (in hot, dry weather you may need to water every day). Feed your plant organic fertilizer once a week, according to directions.
7. As the plant grows, the branches will start to poke through the holes in your tomato cage. Push them back inside so the plant doesn't droop.
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Most cherry tomato plants will start flowering in about a month. Flowers will be followed by tiny green fruits. After a few weeks, those turn into full-blown cherry tomatoes you can harvest. A really ripe cherry tomato will come off its stem very easily and is well worth waiting an extra day for, so hold off on picking them until they're ripe. Pluck individual fruits every day for best results. With luck, your plant will continue to produce right up until frost. If the weather turns unseasonably cool or an early frost threatens, tuck an old sheet over and around the plant to extend your harvest season.
My absolute favorite cherry tomatoes are Sweet Million, which bear long clusters of sweet yet tomatoey red fruit; SunSugar, which produces super-sweet, richly flavored golden fruit; and an heirloom called, rather unimaginatively, Black Cherry, whose tomatoes have a complex, rich, sweet flavor. All three are what are called "indeterminate" varieties, meaning they will continue to grow taller and produce more until the plants are killed by frost, which—if they really like where they are—means the plants may grow to six, eight, or even 10 feet tall. If you don't want to deal with that much plant, see if your garden center has any dwarf or patio varieties of cherry tomatoes for sale.
Red or yellow pear tomatoes are fun because of their shape (they have necks just like their namesakes), though their skins tend to be a little thicker than your average cherry tomato. You can also often find grape tomato plants, which bear very sweet oblong fruits similar to those sold in supermarkets.