The main square in Borgo di Gaiole  will offer you a choice between cafes for a breakfast of pastry and cappuccino, and various restaurants to enjoy traditional cuisine. Since Gaiole hosts a residential community, you can find all amenities necessary for your stay. These include: restaurants, pizzeria, grocery stores, butcher, chemist, banks, post office, and much more. In the summer months Gaiole comes alive with local festivals in the evening and into the night, with music, games, wine tasting, and every year new festivities are added.

There are a handful of supermarkets in Gaiole di Chianti within the locality, which are perfect for all your shopping needs. You will need a car to travel to the larger supermarkets, which are only up to 15km away, but a handy way to stock up on all your larger holiday items. There are also some wonderful studios and boutiques that specialize in handmade glass and ceramics etc. These can be found in the surrounding villages and towns, and are well worth a visit.