Jackets are no longer required for men, but you should consider wearing your Sunday best to this elegant Southampton steakhouse. Housed inside a 17th-century Bermuda cottage where merchant sailors once lived, the Waterlot Inn is the grande dame of island restaurants. You’ll sit on Windsor chairs in a romantic, candlelit dining room as teams of expertly trained servers help navigate an extensive menu of local seafood and specialty cuts of meat (like the 62-ounce ribeye tomahawk for two). Arrive early so you can enjoy a cocktail at the outdoor lounge. Located on picturesque Jews Bay, it’s the perfect spot to watch the sunset before dinner.