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I've stayed at the Equator several times, there's always a mix of younger and older, as well as singles/couples. We've also met international travelers every time we've been there. They just added a new upstairs sundeck, very roomy and somewhat secluded. I love the deck around the pool during the day. They also have a covered area near the pool too. It's very quiet at night, it's right across from Coconut Grove/Oasis, and Coral Tree is next door. I believe the crowd at those 3 (they're run by the same management) is a little older. The one thing about Island House is it's about twice as far from Duval (6 blocks vs 3), usually not a problem unless you're wandering back somewhat tipsy late at night.

The "back bar" across from Bourbon Street is the One Saloon, in the back of 801 Bourbon, where they have drag shows upstairs. First, the drag shows are HILARIOUS, but the last time we were there the sound was so loud it was distorting and detracted from the festivities. On Fridays, the One Saloon (where clothing is always optional, but is rarely done), has the Cock Shock- basically a 'whose dick is the biggest' contest. It's fun, lots of audience participation- frequently includes a "sword fight" to determine the final winner. It seems the most interesting characters always hang out at the One Saloon rather than at the other gay bars. We've done a sunset cruise on the Blue Q catamaran, they cater to gay guys. Fun, relaxing, wine and champagne are provided. You can find discount tickets at the bars and at the gay guesthouses. The one thing everyone at the guesthouses tells us we *must* do is a day trip to Fort Jefferson in the Dry Tortugas. We've never made it yet, you have to get to the boat between 7:30 and 8:30 am (um, ok). No drinking the night before, then- so far we've not been able to adhere to that suggestion. You can also rent an electric car or a scooter for a day. You have to keep the electric cars in Old Town due to range. With a scooter, you can go anywhere- I'd visit the beach on the south side of the island, Smathers Beach, tons of room and not so many people. Or go to Fort Zachary Taylor State Park- there's a great beach, and the fort is very cool. Go up on top and see the view. Well worth a few bucks for admission. Or cruise over to the other side of the island, New Town, or farther to Cow Key. Not exactly an adventure, but something different than just strolling up and down Duval. One thing I would also do is visit the light house. You can see the whole island, and the views are of course great.

Ok, hold on. Andersonville is fun, there are more lesbians than gay guys there, but you'll still find a younger crowd because the area has some less upscale real estate than Boystown. Boystown tends to have a mix of older residents (owners) and younger renters. Totally agree that Andersonville has great shops (especially home/decor) and lots of great restaurants. Andersonville is smaller than Boystown so tends to be more mixed gay/straight. When visiting Crew- which is fun- be careful late at night. Just don't get too far off of Broadway or Lawrence, and DON'T walk around alone after 11-ish. Bucktown/Wicker Park has some gay spots, mostly bars, but they cater to the hipster crowd, so (being older) I don't get over there much. It's on the Blue Line Damen el stop. If I was trying to get out and about, I'd go to Wells Street in Old Town, Lincoln Square- visit the @Hofbrau House, take the Brown Line el to Western Ave. I'd also make it a point to get to @JackHammer, which is just north of Devon on Clark (Edgewater neighborhood). Dancing upstairs, for something more interesting try their downstairs room on weekends, the crowd gets better after midnight. Next door is a classic leather bar, @Touche- interesting back room on weekends.

I'd try Jackhammer first, visit their downstairs room. It's open on weekends, but sometimes they have club parties and it's closed. The theme nights- leather, underwear- are pretty fun. They get a good crowd, pretty diverse- age-wise and ethnic-wise. Touche's back room is also good on weekends. Cell Block isn't very popular anymore, there's usually very few guys there even on weekends. They do have cheap drinks though.