Nothing says mid winter break like a trip to the Carribean. While we haven't done any self-catering Carribean holidays we did do our first all inclusive this past winter in the Dominican Republic. All inclusives have lots of benefits for young families and we love that the Dominican has wonderful (and consistently wonderful) weather, beautiful sandy beaches and is just a quick 4 hour flight from Ottawa/Toronto. The airport in the Dominican has two great kids play spaces and a priority pass lounge with great snacks and a little outdoor sitting area (we have access through our Visa and it's a nice perk when traveling with young kids).  

We hope to get back to the Caribbean soon so hopefully we will have more to add in the near future :)