My wife and I travel to Monterey every year for Car Week. I thought it would be OK if I shared a few impressions with you:
Everyone needs a "goto" watering hole. For me, that spot is Crown and Anchor. It's as authentic an English pub as you'll find in California. I've met the owners, I know the staff. I can order a fine ale/stout/porter and so on. The wine selection is serviceable. The barkeeps will build you a drink and will work with you to improve it. That's an impressive trait. As a pub in good standing, they also have food. Pub grub, by definition, is pedestrian and the offerings at the Crown and Anchor, for the most part, don't dazzle. Still, there are some gems if you dig for them. The sanddabs here are, in my opinion, the best in town. Pair them with garden-fresh peas and carrot slices. Use the hideous mashed potatoes to plug the leaks in your adobe. Service is polite and capable (the owners insist). Eat at the bar or in in the bar area so you can chat with others. They draw an impressive crowd.
Car week, at the end of the day, is all about cars and the folk who drive them so drop the top on your convertible and head south on Highway 1 to Big Sur. Try to pull into the parking lot at Nepenthe around 10:30 a.m.. Climb the steps to the cafe, order a syrah and take in the views of California mountains, rocky outcroppings, chilly fog and the Pacific. It's intoxicating, it's the gift of forgetfulness. Don't bother taking the steps to the restaurant at the next level. The food there is crap. Leave before 11:30 a.m. or face the tourist crush. It's not pretty.
Fisherman's Wharf gets a bad rap. Deservedly so. Still, there are a few dishes at a few places worth exploring. Cafe Fina has decent abalone (properly pounded), OK Oysters Rockefeller, and a very good Pizza Margherita from their wood-fired oven. Wine list is decent and service is friendly and accommodating.
Wharf 2 is the nearby commercial pier. Sandbar is a tiny place that's been feeding locals and tourists for years. They're on the water (just barely above the water). Wine list is decent, service is friendly and competent. You come here for the calamari. Quite simply, it is the best in Northern California. The calamari is ridiculously fresh, pounded thin, lightly breaded and seasoned before being gently fried. Pair it with a bottle of California sparkling wine. Do not share your order. Make your partner get her own. Ignore the rest of the menu.
1833 has its fans and detractors. I go there for the small plates, apps and wine. I like the grilled octopus and the sweetbreads. I like to ask for help in selecting a good bottle of wine. I understand the barkeep can build a good cocktail but I haven't been able to schedule serious bar time. Maybe next year.
Carmel during Car Week is a zoo. It has gotten progressively worse over the years. Best to avoid.