Bring a 4-quart pot to medium high heat.
Add olive oil, and then add the fennel, onion, ginger, and cinnamon stick.
Cook vegetables until soft, stirring occasionally. Stir in the strawberries.
Continue to cook down until strawberries have softened, about 5-10 minutes.
Add all liquids, tarragon, and a pinch of salt.
Cook until everything is hot and slightly reduced (about 5-10 minutes).
Remove cinnamon stick.
Remove from heat and allow to cool slightly. Use an immersion blender to puree until smooth (alternative: puree in batches in a tabletop blender).
Allow soup to sit for about 20-30 minutes. Pour soup into sealed containers then chill for at least 24 hours to allow the flavors to develop overnight.
Serve chilled with more fresh strawberries and tarragon.