Matt Construction

For the greatest night ever, the choice destination would be The Greatest Bar Boston. Seems kind of conceited to refer to itself as the greatest, but you'll find out how this nightlife spot lives up to its name in no time. Part restaurant, part sports bar, part nightclub, The Greatest Bar offers something for everyone, especially you.

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.

If you're hungry, head to the South Street Diner to appease your appetite. No matter what time of day or night, this eatery stays open 24 hours a day, 7 days a week, so it's perfect for late in the day breakfasts or that necessary fourth meal after a night at the bar. This diner has been a part of city culture since 1947 and it's definitely a Boston destination that you have to experience.