A fantastic menu of elegant small plates complements the list of largely natural old-world wines at Spoke Wine Bar in Somerville’s Davis Square, making this an ideal first-date choice for wine lovers. Travel from the Loire to Wachau and back again, sipping on some of the best small-production wines available on the Boston market. The seasonal menu and oft-refreshed wine list ensure there’s always something new to discover.

Porter Square’s Dear Annie has become a national sensation since opening in late 2021, and for good reason — whether you opt for a by-the-glass pour or take a bottle home with you, you’ll encounter nothing but fun, fresh finds at this walk-ins-only hot spot. The veggie- and seafood-based menu offers a casual but delicious counterpart to the wine selection, enhanced by the romantic, dimly lit space filled with communal seating, not totally dissimilar to sibling Rebel Rebel (see below).

Natural-wine lovers should make their way to Lauren Friel’s Rebel Rebel to experience a list of progressive producers and new by-the-glass pours on a regular basis. The wine-lined walls and soft neon lighting of this small but bustling bar let you know you’re in for a treat before you even order. This is a cornerstone of trendy Bow Market, a restaurant and retail hub in Somerville’s Union Square, so if you can’t find a seat inside, you can always sit in the year-round shared courtyard and order food from other vendors at the same time. On the market’s second floor, you’ll also find sibling Wild Child, a hip bookstore and wine shop.

Is it a grocery store? Is it a snack bar? Yes, and — it’s Super Bien, an impossibly cool “grocerybar” with an incredible selection of South American natural wines. Melissa Stefanini brings her famous empanadas from Buenas in Bow Market to Brighton’s Charles River Speedway (also home to celebrated sake bar the Koji Club). Maia Fleming, former wine director at Rebel Rebel, curates a wine list studded with eco-conscious and forward-thinking producers from Chile, Argentina, and beyond. All this plus bright neon colors and a buoyant neighborhood vibe are a recipe for a good time.

In Downtown Crossing, you’ll find Nathálie’s sibling, Haley Henry, which puts tinned fish — along with an incredible wine list — in the spotlight. The small, elegant space feels quite intimate but also keeps things light and lively with a sense of humor and nostalgic ’90s tunes blasting from the speakers. This makes it the perfect place to branch out and try a small producer you’ve never experienced before — the knowledgeable staff is happy to chat about the bottles they have open and can help find something that pairs well with the tin of pungent sardines they’ll pop open for you.

French reds steal the show at Troquet on South, a Leather District restaurant that also specializes in modern French cuisine, but starting with a Champagne by the glass is always a smart move if you’re partial to bubbly. Owner and sommelier Chris Campbell is happy to guide you through the extensive list, helping you select a bottle everyone at the table will love. This is a white-tablecloth spot that’s anything but stuffy, refined yet still creative. For a nightcap, pop by Offsuit, a speakeasy-style cocktail bar tucked into a back corner (if you can get a seat, that is).

Step down a side staircase at Ken Oringer’s newest restaurant, Faccia a Faccia, to get to the underground wine bar, Bar Pallino. Here, you’ll find an eclectic wine list that focuses on natural, biodynamic, and organic options, sourced from Oregon to Austria, curated by beverage director Jodie Battles. And, for non-wine-drinking friends, there are cocktails including Negronis on draft, beer, cider, an in-depth mezcal list, and more.

Greek wines are chronically overlooked, but Back Bay’s Krasi is trying to change that. Wine director Evan Turner has constructed an astoundingly deep list that ranges from classic, approachable Assyrtiko to complex, muscular Mavrodaphne grown in pre-phylloxera vineyards. The menu of Greek meze focuses on light, refreshing Mediterranean flavors that allow the wine to shine. Polished and fashionable, the space provides an ideal backdrop for a first date and a business dinner alike.

Tucked into a corner of sports-bar-dominated Fenway is Nathálie, which offers a constantly changing wine list brimming with natural wines and female producers, plus a refined but casual vibe that feels both relaxing and upscale. Like sibling bar Haley Henry (see above), Nathálie will open anything on the long but focused wine list for you if you commit to half a bottle. Make sure you also check out the seasonal small plates, familiar yet creative, from black bass crudo with salsa macha to sauteed calamari.

Artsy bistro Gray’s Hall is the place to be if you’re looking to open some bottles in South Boston. Next door to sibling market American Provisions, the bar’s wine list leans natural with a worldwide reach, even offering some fortified Spanish numbers. Select from an array of reasonably priced small plates like swordfish skewers and pretzel baguettes, then ask the friendly staff for help choosing the right wine, from Alto-Adige oranges to acid-driven Zweigelt.