BOSTON – Valentine’s Day Date Guide 2025

We’ve made plenty of different Valentine’s Day guides over the years, and this year we’re giving you options for all kinds of budgets.

From high-end to middle tier and even college students, we have something in this guide for everyone.

High End:

Woods Hill Pier 4 (Seaport)

If you are looking to drop some cash on Valentine’s Day, there are no shortage of options in Seaport– but not all options are considered equal. Although you won’t be eating outside in the middle of February, Woods Hill Pier 4 is right on the water with beautiful views of the harbor. Its elegant and romantic ambiance is perfect for the occasion.

We love that it offers small plates to share– which seems fitting for Valentine’s Day. Most of the food is farm-to-table, coming from a 360-acre farm in New Hampshire where they raise livestock, harvest vegetables, and source a majority of the menu ingredients. There are so many tantalizing items on the menu, and since it’s small plates, you can try a bunch of them.

Here are a few of our favorites:

• The grass fed hanger steak is our top choice on the menu. The hanger steak is also known as the “butcher’s cut” because its the cut they used to keep for themselves (that’s how you know its good). A tender and flavorful cut, Woods Hill does it the right way. The grass-fed nature of the steak creates a beefier taste than your average supermarket cuts.

• Dry-aged duck breast: We’ve had plenty of dry-aged beef, but this dry-aged duck was a first for us. Cooked on the rarer side, the gaminess of the duck is amplified by the funkiness brought in by the dry aging process. In typical fashion, there is a bigarade sauce (orange sauce) served alongside it. A great combination of sweet, savory and tart.

• Grass-fed beef tartare: Like many of the dishes here, Woods Hill elevates this classic dish. Topped with a rosemary tallow aioli, crispy shallots, and a quail egg, it’s quite an indulgent experience. Just like the hanger steak, the grass-fed beef used for the tartare is impeccable.

Middle Tier:

Mida (East Boston, Fenway, South End, Newton)

While all the Mida locations are beautiful, the East Boston location is right on the waterfront with breathtaking views of the city. This is one of the most romantic restaurants in all of Boston. Known for their homemade pasta and New Haven-style pizza, Mida can go toe to toe with any Italian restaurant in the North End. Their cocktail menu is extensive with a great espresso martini and tequila drinks. We love the crispy thin crust pizza, and the high quality cheese and meats shine through.

If you’re looking for your “The Fox and The Hound” moment these are the pasta dishes we recommend here:

• Our go-to is the braised short rib tagliatelle. As any good short rib should be, it is melt-in-your-mouth tender. The chili pepper and grana padano add a depth of flavor to this rich dish. The tagliatelle has that chewiness you only get from freshly made pasta.

• Cacio e Pepe is a classic Italian dish, Mida combines this with ricotta gnocchi. The gnocchi is light and fluffy yet chewy at the same time.

Balling on a Budget:

Lone Star (Allston, Cambridge)

Lone Star will always have a fond place in our hearts. For late night food after the bar, to pre-gaming a show, or even having it be the highlight of the night– Lone Star is always there, and it’s always good.

This American-style taqueria was featured on Diners, Drive-Ins, and Dives for good reason. With great cocktails and a lively atmosphere this is an ideal spot for someone looking to celebrate V-Day on a budget. When it comes to tequila and mezcal drinks they have a full list. With freshly-squeezed citrus, their drinks are crisp and refreshing. You can’t go wrong with the house marg, but if you like a little spice in your life the el diablo is the way to go. We also enjoy the Oaxana dead which is essentially a Mexican-style tiki drink.

In our opinion, there is one item at Lone Star that’s a step above the rest– the El Cruncho Supremo (a.k.a. a classy version of the Crunch Wrap Supreme). Instead of cheap nacho cheese, this one has a spicy chili con queso, and the meat is a homemade Texas chili. On top of that, there is an avocado crema and fuego sauce. It’s a true masterpiece of a dish.

As you can imagine they also have great tacos.The beef barbacoa has spicy brisket which is tender as can be. Their two fish tacos are also class. The veracruz is lighter, cooked on the stove top in a mild spice rub, while the baja is deep-fried to perfection with a mango habanero aioli and fresh cabbage complimenting the fried aspect nicely.