Either one you choose, I prefer to keep all of the linens, utensils, cutting board, wine opener, glassware etc in the basket rather than the food. If it is a small picnic with just a few items you picked up from the shop, one large basket should suffice for everything. However, if it is a larger picnic with a wide variety of food, I tend to use at least one basket for linens, utensils etc. and a cooler for all of the food. Assess beforehand how many baskets and coolers you need (plus hands to carry!) before you begin packing. Consider your location too because even though you may not have a large spread, the hummus and cheese you bought do need to be kept out of the heat! I will toss in a ice pack or two if one basket can hold everything and skip bringing the cooler.
Layering is key when it comes to finally packing. I find that putting the linens, towels, and any softer items at the bottom of the basket works as it acts like a protective cushion. Wrapping utensils and any servingware in tea towels or a napkin helps keep them all together. Cheese or bread knives should also be handled with care as they may jostle around; you wouldn’t want anyone to get a stray poke in the leg! Finally, all glassware and dishes should be layered on top, wrapped in a napkin, if they are breakable. (One reason why I prefer to use enamel over glass!) If you have a large serving pitcher, tuck that in first before anything as you layer the rest of the items around it.
However you choose to pack, be sure to bring a carefree “oh well” kind of attitude. “It’s starting to sprinkle! Oh well, it will be an adventure!” Stress and anxiety — leave them at the door! Picnics should alleviate them not bring on more. At the end of the day, picnics are about gathering and sharing over delicious food outside with good company, not perfection.