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Wine connoisseurs, get your tickets to Chef Daniel Bruce's Boston Wine Festival, one of the nation's longest-running wine events. This isn't your typical, two-day festival; the festival spans three and a half months and hosts a few events each week. The 23-year-old event features wine tastings, paired with signature dishes created by Chef Bruce. Throughout the history of the Boston Wine Festival, the menu has never been repeated.

There's not much that could be more romantic than a date on the water. Plan your next date night with a Spirit of Boston sunset dinner cruise on the beautiful Boston Harbor. As you dine on a buffet of sumptuous foods you'll enjoy taking in the view of the city from the luxury ship; after dinner you'll have plenty of opportunities to get close with drinks and dancing. For an extra romantic moment, toast to your love while experiencing the view from the ship's outdoor deck.

For a day outdoors, the Rose F. Kennedy Greenway is the perfect place to hang out. The greenway is comprised of 1.5 miles of park space, meaning there's plenty of opportunity for recreational fun in nature. Public art, gardens and fountains can be found throughout the greenway. This incredible stretch of land is also surrounded by some of the city's most important neighborhoods, including the Wharf District and Chinatown.