For the salad and trout: A crisp white is the best option here. Mediterranean wines from Italy, southern France, Spain or Greece would work especially well, such as pinot grigio from northern Italy, fiano or greco di Tufo from the central Italian region of Campania or an insolia or catarratto from Sicily. A dry rosé from southern France also would work admirably well with both dishes. If you prefer to match a different wine with each course, think sauvignon blanc for the Caesar and unoaked or lightly oaked chardonnay for the trout.
For the dessert: Try a Banyuls or muscat de Beaumes de Venise from France. Even a Calvados apple brandy from France or a quality dark rum would be splendid.