These days, dining is all about the experience and the dish. With the experience and the dish comes the cost to dine. Where some restaurants can be on the pricier side, these 8 great places are worth the price of admission.


Located in Boston’s Back Bay, Ostra is a Mediterranean inspired restaurant that is definitely worth your dining dollar. This luxurious seafood spot has high ceilings, bright colors and dark floors with a menu that combines simplicity with extravagance. The Japanese hamachi tuna, outstanding oysters and an over the top, three pound lobster are worth shelling out some bucks for. The lobster is a splurge and a delicacy of its own. Dressed simply with a little bit of garlic, butter and herbs, and is twice cooked, adding a nice roasting flavor last.

Photo by Ostra

Make your trip to Back Bay in to an overnight stay. The newly renovated Hilton Boston Back Bay hotel is located is less than a mile from the decadent Ostra.

 Top of the Hub

Come for the views, but stay for the seafood. Soaring 52 floors above Boston is Top of the Hub. A restaurant that provides exquisite food and 360 degree views of Boston and the surrounding area. With seafood options from salmon to lobster, towers of shrimp to satisfyingly decadent oyster selections, this high flying gem is a seafood lover’s haven.

Take your experience at Top of the Hub to new heights with pre-fixe options for brunch, lunch and dinner. These three, four and five course, chef selected meals come with the option to pair each course with wine for the ultimate elegant dining event.

Looking for a room with a view to stay the night in? DoubleTree Suites by Hilton Boston – Cambridge all-suite hotel offers sweeping cityscape views of Boston and Cambridge that are bound to compliment the views you experience at Top of the Hub.


Menton in Boston’s Fort Point neighborhood is the spot you should go if you are looking to REALLY impress someone. This elegant space has a luxuriously modern décor, so the focus stays on the interesting and artistic offerings from world renowned Chef Barbara Lynch. Chef Lynch likes to work with what’s in season, so her menu palette changes frequently but never disappoints. If you really want to go big at Menton, order the ‘Chef’s Whim’ where you experience an elaborate multi-course meal with the option to pair wine as a toasting shot.

Continue your evening of whimsy in the city. Check in to the Hilton Boston Downtown/Faneuil Hall hotel, that is but a short distance from beautiful Fort Point Channel, completing your night of romance.

Strega Prime

Steakhouses don’t get any bigger, flashier, or more fantastic than Strega Prime in Woburn. It’s an intoxicating maze of fountains, private dining rooms, high-tech media walls, eye-catching artwork, a state of the art bar and lounge, and a mind-boggling wine list.  When it comes to the food, Strega Prime is worth the splurge with everything from a giant seafood tower to irresistible sides like cider and pancetta brussels sprouts and truffle parmesan fries, to the insanely tender fourteen ounce bone-in filet mignon.

Photo by Strega Prime

With Strega Prime located 10 minutes from Hilton Boston Woburn, you can enjoy a night out satisfying your appetite and satisfying your REM cycle.

Da Vinci Ristorante

Da Vinci Ristorante on Columbus Ave in Boston is a romantic, refined restaurant decked out with fine artwork and eye-catching candelabras, with a focus is on modern Italian cuisine. There’s a satisfying beef tenderloin served in a red wine demi glaze reduction, and PEI Mussels sautéed and served in a fragrant broth of lemon, white wine, butter, and cherry tomatoes. If you really want to spoil yourself, you need to order the Bolognese.

Photo by Da Vinci Ristorante

A lot of restaurants use regular old ground beef in their Bolognese, but Chef Peppino uses real sirloin steak that he ground himself, adds the fresh homemade fusilli pasta, some red wine in there, it’s slow-cooked for hours, creating a sauce that is so rich, it should buy its own yacht.

Fill up on bolognese and settle down for a long winter’s nap at the DoubleTree by Hilton Boston Downtown hotel, that is but a short distance from beautiful Back Bay.


Tosca in Hingham is a big, romantic restaurant with low lighting, exposed brick walls, mahogany beams, and lofty ceilings. While this place certainly looks fancy, the menu is great for a variety of meals. Offering something casual like pizza, fired up in a wood burning oven, or something more upscale with a variety of steak and chops options that would give any Boston steakhouse a run for its money.

Fill up on delicious eats at Tosca and digest in comfort at Hampton Inn Boston/Braintree. This hotel that is just a half hour away, offers a free hot breakfast and complimentary Wi-Fi to all Hampton Inn guests.

Smith and Wollensky

Smith and Wollensky is one of the premiere high-end steakhouses in Boston, with an elegant dining room, a state of the art dry-aging room, and an open kitchen where the finest aged cuts are grilled just right. If you really feel like indulging, nothing finishes off a meal here, like devouring their signature dessert, the Gigantic Chocolate Cake. This 6 inch tall slab of satiable sweetness is an eye catching table topper that turns heads as it makes its way to your table from the kitchen.

Make a weekend of your retreat to Smith and Wollensky by capping it off with a stay at Ames Boston Hotel, Curio Collection by Hilton that is less than a mile from your new favorite steakhouse.


Sorellina in Copley Square is a special occasion kind of place, but if you’re looking for an unbelievable meal, this is THE reservation you must make. The soaring urban space is strikingly modern and the menu is mouthwatering. Opulent ways to start your meal include pillowy potato gnocchi topped with Maine lobster or super juicy American Wagyu beef meatballs.  Splurge worthy entrees include the Bone in Veal Chop with soft polenta and an 8 ounce filet mignon with whipped potatoes.



Previous Article

Chelsea Roy Weekends Like a Local in Boston

Next Article

Experience the Phantom Gourmet Phantasy Suite at a Boston Hilton

Related Guides