Gather equipment and chill an insulated lunch box with an ice pack for 10 minutes while prepping ingredients.
Slice cheeses: cut brie into four 2 oz wedges, slice cheddar into 4 equal 2 oz portions, and break manchego into 4 small shards.
Prep fruit: halve grapes if large, core and slice apples into 8 wedges per apple and toss apple slices with 1 teaspoon lemon juice immediately to slow browning.
Portion items into 4 compartment boxes: place cheeses in the largest section (soft nearest the ice pack side), fruit in two separate sections (berries and grapes/apples), and crackers in a sealed compartment to avoid moisture contact.
Add 1 tablespoon honey into each small sealed jar and place jar in its own compartment; add 1 oz roasted almonds and a rosemary sprig to each box as garnish.
Close boxes, place in chilled insulated lunch box with ice pack separated by cloth, and transport within 2 hours for optimal texture; refrigerate if not served within that time.