Saturday morning
Start downtown with coffee at Atticus Bookstore Cafe, 1082 Chapel St, or Willoughby's Coffee & Tea, 258 Church St.
Saturday afternoon
If your weekend plan is really just an excuse to eat New Haven pizza, Wooster Square is the obvious move. Frank Pepe Pizzeria Napoletana, 157 Wooster St, and Sally's Apizza, 237 Wooster St, are both there. Zeneli Pizzeria, 138 Wooster St, is another verified option in the same neighborhood.
If you want to compare styles instead of picking one lane, Modern Apizza at 874 State St and Bar at 254 Crown St keep the pizza itinerary going without much effort.
Saturday night
For dinner that isn't pizza, downtown has a few solid verified choices. Union League Cafe, 1032 Chapel St, is a French bistro in a Beaux-Arts building. Olea, 39 High St, focuses on Spanish and Mediterranean tapas. Heirloom, 1157 Chapel St, is a farm-to-table American restaurant.
If the night continues, drinks are easy nearby: Ordinary New Haven at 990 Chapel St, 116 Crown at 116 Crown St, or Anchor Spa at 272 College St.
Sunday
Sunday can be lighter. Olmo, 93 Whitney Ave, works for breakfast or lunch, and Claire's Corner Copia, 1000 Chapel St, is a longtime Chapel Street standby for vegetarian, vegan, and kosher comfort food.
That's enough for one weekend. New Haven does not need a hyper-optimized itinerary.