Where to stay?
For a weekend, I would suggest a downtown hotel. There are lots to choose from to fit most budgets. If it were me, and only a weekend, I'd splurge on something like the Ritz Carlton at the Avenue or the Renaissance right off Public Square. (My husband gasps!) Then there's the Wyndam at Playhouse Square or for more conventional budgets, there is also a Holiday Inn Express and a Hampton Inn among others. Check out Tripadvisor to learn more about pricing and what others thought of the hotels.
Assuming you arrive in the late afternoon plan on a nice dinner at one of our finer restaurants. Some suggestions: Cibreo's (Italian and right across from theaters. Reservations!!), Cowell & Hubbard (French/American), or District (American, Mediterranean, Seafood). All of these are right in the theater district and walking distance to your evening entertainment--a musical or play.
Playhouse Square on Euclid Ave between 14th and 17th Streets is in my opinion Cleveland's gem. It is the nation's second largest theater complex only surpassed by Lincoln Center in NYC and is the world's largest theater restoration project. Five majestic theaters built in the 1920s have all been restored to their grandeur and have created a wonderful entertainment center. A couple of years ago, The Cleveland Playhouse also moved to this area so there are lots of entertainment options to choose from. [FYI George Burns and Gracie Allen were married in the Palace Theater in 1926]
The theaters usually empty out around 10 and if you are still up for some more entertainment or a little after-the-show snacking, there is the Horseshoe Casino located on Public Square or perhaps a visit to the East Fourth Street neighborhood which is a pedestrian area with all sorts of coffee shops, bars, restaurants, comedy entertainment, and live music. This is a great spot during the day too especially if weather permits sitting outside.
If this is the first Saturday of the month, head to Playhouse Square again after breakfast. From 10 a.m. to 11:30 a.m. tours depart from the State Theater lobby and you will get a look at all the beautiful theaters plus a peek behind the scenes. The tour lasts for 1 1/2 hours, the memories a lifetime. If you don't mind the cost, a private tour can be arranged for any day of the week for $90.
Now you're probably hungry. Head over to another Cleveland gem, the West Side Market on West 25th Street. Here is your chance to sample and see a huge collection of vendors, many of whose families have been there for generations, who sell all sorts of meats, vegetables, pastries, delicacies, ethnic foods, etc. and etc. Sample your way through or get a sandwich or a pastry to try.
From the market, find your way to the Nautica Complex not too far from there along the Cuyahoga River. In the old powerhouse, you will find Cleveland's new aquarium. It takes about an hour to go through the aquarium if you like and you could do that either before or after your Lolly the Trolley City Sight-Seeing tour. The Trolley tour is either a one hour or two and a half hour tour. The longer makes one stop at the Rockefeller Greenhouse. They offer several specialty tours including one that centers around one of our more colorful Cleveland characters, Elliot Ness.
Another option for the evening is to check what is going on at the Nautica Entertainment Complex or book your evening at the Hilarities 4th Street Theater or the House of Blues. Want something a little more classical and elegant? Check to see what the Cleveland Orchestra has to offer at Severance Hall or out a little south of the city in the open air concerts at Blossom Music Center.
Choose to sleep in or answer the call to worship at either historical St. John's Cathedral that dates back to 1848 or the Old Stone Church near Public Square which dates back to 1838.
Rock N roll Hall of Fame and Museum. Then, if it's baseball season, do my favorite thing: take in a ballgame at Progressive Field. It's a great ballpark and the Indians are showing lots of promise.
Maps are available at the Positively Cleveland website and there is an information center in Cleveland's landmark building, the Terminal Tower right on Public Square. There is so much more tucked into nooks and crannies in the city: the Arcade, the Police Museum, the Soldier's Memorial on the Square, Voinivich Park, the Flats, the Warehouse District, First Energy Stadium (Browns), Quicken Loans Arena (Cavaliers), Ohio City. It would take several weekends to cover it all. But if you have more time and want to get out of the downtown area, there is lots more to explore. Stay tuned.