Fairfield County (Stamford area) is always a good choice. It's the most populous area of the state and the wealthiest. You may also want to consider eastern Connecticut, where the Foxwoods / MGM Grand and Mohegan Sun casinos are located. Lots of ladies do outcalls to casino patrons. Besides the casinos, eastern Connecticut also has a huge summer tourist population along the coast. The Mystic / Stonington area is booming. The whole area (casinos and shoreline) is pretty compact with good hotel choices.
So, spend some time enjoying eastern Connecticut's great seafood, its world class casinos and its unique attractions (like me)