Gay San Juan by Day and Night

Of all the islands in the Caribbean, Puerto Rico has the well-deserved reputation as one of the most gay-friendly, with San Juan offering more nightlife than I could explore over a four-day/three-night visit.

The perfect mix of modern and historic, Puerto Rico's capital is warm all year, but more comfortable during the high season, which runs from November through early spring.

Historic Old San Juan is a can't-miss daytime destination, but probably shouldn't be your focus after sunset. Its narrow Colonial streets feature a number of charming bars and restaurants. After a nice walk, relax with a watermelon mojito at the nymph-themed La Madre (351 Calle San Francisco).

Discovering Condado

Most gay nightlife can be found in the adjacent Condado and Santurce neighborhoods of modern San Juan; you'll know love is all around when you spot the green-faced mascot of Ashford Avenue's Condom World, (a few blocks from Condado's hottest hotels.)

All of Condado's major hotels are LGBT-friendly, with many actively marketing to the community. Better still, the city's gay beach, located at the foot of Calle Vendig (Vendig Street), is a short walk. It's strategically positioned in front of the Atlantic Beach Hotel (1 Vendig Street), and the currently hot, gay-owned Oceano (2 Cll Vendig).

La Concha Resort's LGBT liaison JC Cappas stays connected to the hotel's diverse clientele and says a number of couples have become regulars. It's also a popular destination for weddings, honeymoons and mixed groups. La Concha's lobby bar is a great spot to start -- or top off -- an evening.

Santurce

The heart of gay nightlife is a pleasant walk or short cab ride away in Santurce -- a charmingly gritty (but not dangerous) neighborhood. I especially liked that San Juan's gayborhood lacks the stereotypical "gay ghetto-feel," so common in many American cities.

Santurce is packed with small bars where gay, straight, tourist and local crowds mix, pouring out into the crowded streets on weekend nights. Nights are humid and "hot" -- literally and figuratively. So while the guidebooks may recommend dressing up to go out, don't believe them. Dress for comfort: shorts and polos, linen shirts or even a cute T-shirt should be fine.

Santurce offers lots of smaller bars to end your day and start your night, including El Patio De Lila (Calle Robert #1360). Packed with locals, it features a great karaoke list and strong, affordable cocktails.

For "no nights off" partiers, there's Tia Maria Liquor Store (Ave. de Diego 326) -- fun, relaxed, affordable, and the only bar in Santurce that's open seven nights a week. Like many of the smaller bars, it's often standing-room-only. Known for its "heavy pour" drinks, cocktails include the intriguingly named "Obama Shot."

After Midnight

San Juan moves slowly until around midnight. So don't be surprised to find dance mecca Circo Bar (650 Calle Condado) empty if you show up around 11:30. But don't fret. Expore! Check out the pool table and bartenders in the side rooms before high tide hits the dance floor and the drag show starts around 1 a.m.

Almost all the clubs and bars cater to a mixed, straight-friendly crowd, except for SX (1204 Avenida Juan Ponce de Le�n), known as the city's best stripper bar.

"San Juan is different from the mainland. Most of our clubs and bars are very mixed. However, SX is probably the one place where you'll find more men. It has VIP rooms with gogo boys," says La Concha's Cappas. Warning: Unless you're under 30 and hit the gym daily, the beautiful young men are probably being nice for a reason. Enjoy the attention, but use caution.

If you're planning ahead, 2017's San Juan Pride overlaps at least one other local festival. So June 2017 might be the perfect time to visit. Pride Weekend is June 23-25 and Condado is party central and home to the city's energetic parade.