Leo

Choose Leo if the next Annapolis meal should be casual rather than formal. The basics are direct: Leo is a Mid-Atlantic/Southern restaurant in Annapolis from Chef Matt, with a price of about $40 per person and a casual dress code. It works well to judge it on that clear information rather than on claims about a broader dining or drinks program.

The dishes to know are the fried tofu “chicken” with vegan basil ranch and the mushroom ragout with mezzi rigatoni. Those two items give the most concrete read on the kitchen from the available information: Mid-Atlantic/Southern cooking and a couple of named choices that can anchor an order.

Plan around the basics

There is not enough information here to build Leo around a specific bar program, cocktail list, wine selection, or seating strategy. The safer read is simpler: Leo is a casual Annapolis restaurant where the appeal is the Mid-Atlantic/Southern lane, the $40-per-person price point, its published hours.

For planning, dinner is listed Tuesday through Sunday from 4pm to 10pm, with Monday closed. Saturday and Sunday also include lunch from 11am to 3pm. For broader local planning, use the full Annapolis restaurants guide rather than treating one meal as the whole night.

What to order

The strongest ordering guidance is to start with the named dishes: fried tofu “chicken” with vegan basil ranch and mushroom ragout with mezzi rigatoni. Beyond that, keep the order within the restaurant’s Mid-Atlantic/Southern identity and check the current menu before going.

Who should make this their Annapolis regular

Leo is a fit for diners who want a casual Annapolis meal in a Mid-Atlantic/Southern lane at about $40 per person. It is also practical for people who want dinner Tuesday through Sunday, or a weekend lunch option on Saturday or Sunday. If the goal depends on a specific tasting format, beverage program, seating style, or special-diet accommodation, confirm those details with the restaurant first.