Dining Delights: Top Dinner Hotspots in Annapolis

We know that sometimes, planning where to go for dinner can feel like work. Since we want you to relax as much as possible on your stay, we went ahead and put together the definitive list of the best places to eat dinner in Annapolis. In a town that is home to some of the best restaurants on the East Coast and plenty of hidden gems, it’s good to know where to go.

Image courtesy of Visit Annapolis

1. Vin 909 Winecafé FLOHOM’s favorite

From its charming setting in a remodeled cottage to its ever-rotating farm-to-table menu and inventive brick-oven pizzas, we love everything about Vin 909 Winecafé. This modern twist on old favorites has the look of a charming summer home and the taste of a Parisian cafe. Their exhibition kitchen offers a glimpse into the culinary artistry, adding to the overall experience. (Insider tip: get there early – Vin 909 does not take reservations)

Favorite food: Any of their award-winning pizzas, but we love Chapel Country Flambe and The Chef Moore (and a special mention to the butterscotch pudding!)

Favorite drink: Château de Marjolet Côtes du Rhône (or anything else from their robust wine selection)

909 Bay Ridge Ave.
Open Tue: 5p–9p | Wed & Thur: 12p–2:30p & 5p–9p | Sat: 12p–2:30p & 5p–10p | Sun: 5p–9p

Image courtesy of Lewnes Steakhouse

2. Lewnes’ Steak House

Trust us when we tell you that Lewnes’ has some of the absolute best steaks you have ever tried. A classic steak house that makes ordinary dishes seem anything but, Lewnes’ has been operating in some capacity since the 1920s. The sides are all served family style and everything is cooked with butter, so it’s extra delicious and always to order. For the feel of an upscale Manhattan eatery with a cozy touch of home, try Lewnes’ Steak House.

Favorite food: 13 oz filet mignon; creamed spinach

Favorite drink: Server’s recommended wine pairing (their sommelier skills are high quality)

401 Fourth St.
Open: 4p–9p, 7 days a week

Image courtesy of Vida Taco Bar

3. Vida Taco Bar

Vida has the best tacos downtown! With a passion for offering a distinctively delicious fusion experience, Vida uses locally sourced “Farm to Taco” ingredients whenever possible. Their line up of margaritas and other seriously-yummy cocktails are always made with freshly squeezed juice, and are the perfect addition to a hot summer day.

Favorite food: Buffalo cauliflower tacos; house-made guacamole

Favorite drink: Smokey & spicy margarita with #3 organic tequila

200 Main St.
Open Tue – Thur: 5p–9p | Fri: 5p–10p | Sat: 12p–10p | Sun: 12p–8p

Image courtesy of Preserve

4. Preserve

Preserve is the perfect combination of craft and comfort, brought to Annapolis by a husband and wife duo who both graduated from the Culinary Institute of America. Their dishes are as locally sourced as possible and always inventive, typically adding a twist to an old favorite. The chef’s choice menu is an excellent option for tasting the best of what they offer.

Favorite food: Crispy kale; mushroom cheesesteak

Favorite drink: Bartender’s beer recommendation from the specialty Maryland brews

164 Main St
Open Wed – Fri: 11a–9p

Image courtesy of Osteria 177

5. Osteria 177

One of Annapolis’ premier dining experiences, Osteria’s menu offers a modern take on classic Northern Italian cuisine. For the best Italian food in Annapolis (and some of the best we’ve ever tried!) look no further than this inviting bistro in the heart of downtown. Be prepared for a cozy dining room with knowledgeable wait staff who will expertly guide you through their exquisite dishes.

Favorite food: Gnocchi; chilean sea bass

Favorite drink: Server’s recommended wine pairing

177 Main St.
Open Mon – Sat: 5p-10p | Sun: 5p-9p

6. Fox’s Den

Fox’s Den is the gastropub in Annapolis. If inventive, hearty dishes paired with local craft brews and specialty cocktails is your thing, you’ll feel right at home at Fox’s Den. With a speakeasy style entrance and a warm, wooden interior, this is a great restaurant to get comfortable and dig in. Owned by two brothers and a nephew with tons of experience in keeping Annapolis well fed, their brick oven pizzas are a go-to for many locals.

Favorite food: Fig & pig pizza; pig wings

Favorite drink: For Fox Sake

179B Main St.
Open Mon: 5p-10p | Wed & Thur: 5p-10p | Fri: 5p-12a | Sat: 4p-12a | Sun: 12:30p-8:30p

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