Preheat the oven to 400 degrees F.
Poke the outside of your squash with a fork on all sides a few times.
Then microwave on medium high for about 3 minutes to soften the squash enough to easily cut in half.
Cut your squash in half-lengthwise and carefully scoop the pulp and seeds out. Make sure not to scoop too deep, we don’t want to remove the yummy spaghetti strings!
Rub the outside and top of squash with olive oil and place the 2 halves on a large rimmed baking sheet with inside facing up. You can use rolled tin foil to hold the boats in place so they stay flat and don’t move around when filled.
Sprinkle each squash boat with salt and pepper, then fill each with half of the cheeses, minced garlic, and herbs.
Carefully pour 1/4 cup of heavy cream into each boat to fill to the top.
Place the squash in to the oven and bake for about 45 minutes- until the squash is nice and golden brown and cheese is bubbly.
Remove from the oven and let cool for a few minutes, then carefully mix up the insides of each squash boat with a fork to pull all of the stringy squash from the outer shell.
Sprinkle with a little more cracked pepper and chives if you desire and serve warm.
Enjoy!