Assaggio's in Kailua is our go to place for a reasonably priced special night out on the Windward side of O'ahu. We've gone with larger groups at times but it seems the smallish space works best for couples or groups of four to six-- that is if ya really wanna enjoy the atmosphere. If you're just there for the amazing heavy on the pasta foods well, by all means pack 'em in. And although the space is small it's set up so that the vibe is not ever one of being too crowded so much as it is intimate, so check plus on atmosphere. The service is always excellent from the minute the host greets you at the front door to their bidding you and your very full tummy adieu. Go hungry and be prepared to devour more of the hot bread and butter than you thought possible-- it's that good.
My fave here has always been their house salad with just the sweetest cubes of Asiago cheese and delicately pickled carrots followed by the Chicken Assaggio. My husband is far more adventurous and tends to go with the nightly special and I have to tell ya he's yet to be disappointed.
It's best, although not necessary, to make a reservation.
Parking upstairs is limited so go a bit early as you may have to look for street parking but it won't be too far and Kailua is such a sweet town for strolling through.