Toss cauliflower with ½ tablespoon of olive oil. Spread out on a parchment lined baking sheet. Roast for 20 minutes without turning. Flip and roast 5 more minutes.
Meanwhile, combine remaining olive oil and onion in a small dutch oven or soup pot. Saute 5 minutes or until soft.
Add garlic through salt. Saute 1 minute to let the spices toast.
Stir in wine and let simmer for 2-3 minutes or until greatly reduced.
Stir in broth and water. Simmer until cauliflower is done. Set aside 1 cup of roasted cauliflower and add the rest to the pan. Simmer for 5 minutes and transfer to a blender. Blend until smooth.
Return the soup to the pan and add Gouda. Bring to a boil, stirring frequently to melt the Gouda. Stir in half and half. Remove from heat and pour into 2 bowls. Garnish with ½ cup of roasted cauliflower each.
Serve with soup crackers.
Notes
Use less half and half if you want a lighter, more brothy soup.