Traveling Jack’s Top 3 Places for a Pride Vacation

A vacation is reason to get away, but a celebration is a reason to travel! As June rapidly approaches I realize I am not only thankful of the fact that I can live in a city where I am proud to be a gay man and to be lucky enough to be able to visit places all around the world where I can be myself. When thinking about how I plan to spend my Pride Month….I think about the cities I love, but more over the cities I love to visit.

I rattled my brain to determine what my top three destinations would be for Pride festivities. What I discovered is, with Pittsburgh being my undeniable number one favorite city and home, I would be better off naming the two cities that are celebrating pride before and after Pittsburgh that I must stop by to celebrate!

Key West

Key West Pride (keywestpride.org) takes place June 5-9. Otherwise known as The Conch Republic, Key West is a true fusion of everything that I love about getting away; a beautiful setting, terrific weather, a laid back but exciting way of life and sensational dinning. The island is primarily comprised of guest houses, small restaurants, cafes and bars filled with the most fabulous people. The best part about Key West is that anything your little heart desires is at your fingertips. When the quiet, casual way of life starts to give you the itch to find a party….take a few steps onto Duval Street and you are already in the party! There are three MUSTS when in Key West. Number one, go to a show at 801 Bourbon Bar (801bourbon.com). The best songs, the best gals and the strongest drinks! You will be sure to have the night of your life. Number two, enjoy the best meal on the island at Café Marquesa (marquesa.com). The setting rivals the food and neither will disappoint! The environment is slightly more upscale, but still has that quintessential Key West feel. Last but not least The White Tarpon at 700 Front St promises to knock your socks off with their signature Key Lime Martini. It will please anyone’s palate making you believe you are drinking a piece of key lime pie! Key West is a MUST to kick off the beginning of Pride Month!


Obviously there is no where else I would rather be than home for Pittsburgh Pride, but after Pride wraps up here, I will be off to my other favorite place….Chicago! Chicago Pride (chicagopride.com) takes place June 22-23 and choosing a favorite place in Chicago is virtually impossible for me. Shopping, food and cocktails are everywhere you turn. Boystown is the obvious destination for everything Pride, but the beauty of Chicago is the true diversity that each neighborhood has to offer. An absolute must for a bite is Mercat a la Planxa (mercatchicago.com) on Michigan Ave in the Southloop. Hands down one of the BEST tapas restaurants I have ever been. Atmosphere, food and cocktails certain to thrill even the most demanding guest. The end all and be all though of my Chicago Pride trip will be attempting to get a reservation at The Aviary (theaviary.com). This modern, trendy spot is all anyone is talking about. The Aviary is in such demand that all reservations are randomly selected day of. I rarely recommend anything without having been myself, but with all of the buzz surrounding The Aviary, it is somewhere I need to be.

Pride is almost here! It will be a fun filled month packed with friends, parties, but most importantly everyone celebrating who they are….wherever they are!

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Jack Bellas is Partner of Revive Marketing Group and resides in Pittsburgh’s South Side. Jack’s love of the city is rooted in its culture, growing restaurant scene, and continuously evolving nightlife.