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Boston is a prime location to spend your Valentine’s weekend with that special someone. There are many intimate, trendy venues to sip and savor a scrumptious meal accompanied by tasty cocktails. The Boston Waterfront and Public Garden are both perfectly romantic settings to spend time together. With our creative and fun guide to this special weekend in Beantown, your Valentine will most certainly be feeling the love…and you’ll be looking wicked impressive!
Take it to The Charles

Walk along the Charles River before sunset with a picnic basket filled with chocolate strawberries and a bottle of bubbly champagne to pop open. Pack up a couple of cozy wool blankets, snuggle up and enjoy your treats on one of the many docks right on the Charles. Be adventurous and rent Hubway bikes during the day and ride along the water, enjoying the scenic paths and romance of the Charles…set against a backdrop of bright blue, city solace and colorful sailboats.
Ice Skating and Hot Chocolate

The Boston Commons is a fun place to go ice-skating and enjoy a creamy cup of hot chocolate in the afternoon, starting your Valentine’s Day off on a perfect note. The Frog Pond is frozen over throughout the winter season, creating the ultimate setting for an ice rink, where each and every skater can do spins and glides surrounded by Boston’s skyscrapers.
Little Italy: The North End

Beantown’s very own Little Italy is the epitome of romance Valentine’s weekend (well, any weekend for that matter). Do as the Italian’s do and take your honey out for a romantic Italian dinner and sweets in the North End. The quaint and charming eateries, intimate lighting and native Italian accordion players lining the bustling Hanover and Salem Streets is certainly a treat that you don’t want to miss. The North Square is a hidden gem within Little Italy; tucked away from the hectic crowds between beautiful brownstones, picnic tables and cobblestone.
Where to get that unparalleled Italian dinner:
* Nico – 417 Hanover St, Boston, MA 02113
* L’Osteria – 104 Salem Street, Boston, MA 02113
* Mare Oyster Bar – 135 Richmond Street, Boston, MA 02116
* Mamma Maria – 3 North Square, Boston, MA 02113
* Gennaro’s – 5 North Square, Boston, MA 02113

A taste of many of the North End’s sweet indulgences:
* Lulu’s Sweet Shop – “Boston’s 1st Gourmet Cupcake Shop” will definitely not disappoint with mouthwatering flavors such as Chocolate Peanut Butter and Red Velvet Cheesecake to soothe your sugary fantasies. Lulu’s is located at 57 Salem Street, Boston, MA 02113.
* Caffe Vittoria – A decadent selection of “Pasticceria Tradizionale,” including a Joonbug favorite, Napoletane (layered pastry and fresh cream cake), accompanied by an intimate yet upbeat interior setting. Caffe Vittoria is located at 290 Hanover Street, Boston, MA 02113.
Back Deck

This year-round venue is the perfect spot to relish a professional backyard grilling feast…creating an ambiance of the awesome summertime season with charcoal-grilled delicacies, teak tables and all! Each guest is invited for a super casual (yet trendy) old-fashioned charcoal cookout on Valentine’s Day. Includes a juicy Porterhouse Pork Chop, which is fixed medium well with brown sugar and spice brined, braised red cabbage, polenta and coated in a heavenly balsamic-fig glaze. Or maybe you’re in the mood for the Deck’s Pernil Cubano en Calabaza, where the pulled pork is first grilled then roasted, prepared uniquely in a roasted half acorn squash with cilantro cream, spicy tomato salsa, rice and black beans. And for dessert…you can definitely not turn down the Irish Bread Pudding lathered in a Caramel Whiskey Sauce! Although, you may want to end your meal on a more traditional note with the Creamy Risotto Rice Pudding, made with golden raisins and toasted almonds. How about ending this cookout with traditional gooey S’mores for the table? The Back Deck makes the best homemade S’mores ever incorporating your choice of peanut butter or espresso marshmallow, how original is that for snack?
Back Deck is located at 2 West Street, Boston, MA (corner of West & Washington).
Romantic and Luxurious Overnight Packages to Treat Your Valentine:
Some of these luxurious amenities include chocolate-covered fruit, Godiva chocolates, restaurant gift certificates and a fine bottle of wine. Make this Valentine’s Day a memorable one with one of these sentimental packages of your choice…

* Ames Hotel – “Valentine’s Day Package”
* Boston Harbor Hotel – “Valentine’s Escape” and “Romance Getaway”
* The Boxer – “Valentines Day West End Rendezvous” Package
* Fairmont Copley Plaza – “Be My Valentine” Package
* Liberty Hotel – “Guilty Pleasures Romance” Package
* The Marriott Long Wharf – “Honeymoon Bliss” Package. Savor this perfect location, in walking distance to Faneuil Hall and the North End (right on the breathtaking waterfront).
* Mandarin Oriental – “Month of Romance”
Click here for more details on these hotel packages.
Say How Much You Love Your Valentine…in Chocolate

Boston Wine School presents its very own “In Love with Wine and Chocolate” specialty class this Valentine’s Day. This awesome event includes a delectable dinner, five divine chocolates and splendid “wine pairings.” What better day to delight in your three favorite, yet culpable, indulgences than Valentine’s day?
The class takes place on Friday, February 14, 6:30-9:30pm at Boston Wine School (1354 Commonwealth Avenue, Allston, MA). For more details, click here.
Dine Through Your Senses…Blindfolded.

Beacon Hill’s elegantly breathtaking Hampshire House hosts its unique “Dining in the Dark” on February 14th, taking all lucky guests on a sensuous journey. The Hampshire House itself is an antique mansion decked out in gold chandeliers, beautiful fireplaces, tall bookshelves and grand foyers. Each and every diner is blindfolded, leading to an exciting play with the senses where “the idea is a show, the food is the main character, the music is the supporting role and the Hampshire House is the set.” This is a fun, spontaneous and creative way to spend this special evening with your Valentine.
The event takes place at 6:00pm – 10:00pm. Hampshire House is located at 84 Beacon Street, Boston, MA 02108. Click here for more information.