In a 3- to 4-quart pan over high heat, bring wine and 1/3 cup sugar to a boil. Boil until reduced to 1 cup, about 5 minutes. Remove from heat and stir in vanilla and sliced strawberries. Let cool about 1 hour, stirring occasionally.
Cut cake into 1/2-inch-thick slices, then into 1 1/2- by 2-inch pieces.
In a bowl, with a mixer on high, beat cream and remaining sugar until soft peaks form.
Arrange a third of the cake in the bottom of a 2 1/2- to 3-quart straight-sided glass dish. Spoon a third of the sliced berries and wine over the top. Spread about a third of the whipped cream over berries. Repeat layers twice, ending with cream.
Cover trifle loosely and chill at least 2 hours or up to 1 day. Garnish with whole berries. Scoop down into layers to serve.