Tawny Port
The very character of these ports is dried fruit, nuttiness and caramel meaning they are a natural partner to dessert. For tawny I like something like a sticky toffee pudding and custard - the dates in the pudding go hand in hand with tawny flavours
Colheita Port
Similar to tawny, the colheita also works well with crème brulee or nut based desserts, like hazelnut praline
Late Bottled Vintage
For chocolate-based desserts try Late Bottled Vintage port or Ruby Reserve port, something robust enough to cut through the chocolate