We brought a cooler to Antigua in November as we were also renting a condo for two weeks. I had contacted the Tourism Board to ask about bringing in food and they assured me this was not a problem as long as it was for your own consumption. When we were going through customs and they saw the food they said you have to pay duty on this. We just stood there and finally he let us go through. I read somewhere that the best way to get through without a problem is to get one of the baggage folks in the airport. We did that (50 cents per bag). Since we always rent a condo and go for two weeks, we always travel with food. We have done this on several islands. The only time we had an issue was in Grand Cayman. You must bring meats in their original packaging. Someone traveling with us had homemade sauce and meatballs as well as sausage confisticated. Sometimes we get critical comments from people about cooking on vacation and dragging food with us. We always have several meals out - we just don't always feel like getting dressed for dinner after a relaxing day on the beach. Some places where the grills are in a common area, we have heard people say they wish they had thought of bringing food. We do not pack dairy in our cooler - mostly meats or frozen entrees. We buy our perishables, fruits and breads on the island. Enjoy Antigua.