The next morning, we board an early train to moody and magical Sintra. A resort town nestled in the foothills of the Sintra Mountains. Itโs a Portugal highlight, and Iโm so glad Michael has convinced me to make the hour trek each way with him.
The cityโs highlights are numerous, but it may as well be required of all tourists to visit the UNESCO World Heritage Site Pena Palace, a hilltop castle created in the Romanticist mold and painted in bright yellow, red, and purple. Tourists are given free reign over much of the palace, and mostly everyone clamorsย for the ultimate Instagram photo with the sea and sky behind them.
Quinta da Regaleira in Sintra by Jason Heidemann
Iโve never seen a hole quite like the one at Quinta da Regaleira, the walkable Initiation Well that spirals down multiple stories into the earth, and is often described by tourists as akin to falling down the rabbit hole. The well was never used for water, but rather built for secret Masonic rituals. Itโs part of a labyrinthine network of enchanting gardens and paved trails that slope downward toward a menacing castle, which mixes Gothic, Moorish, Renaissance, and Egyptian architecture.
Of course, a full day in Sintra means that weโre left with just a few hours in the city. We arrive back in Lisbon right at the hour when all the boys areย drifting off to the sauna for the European version of Sunday Funday. After scarfing down burgers, we hit up the bars that are predictably sleepy tonight.
Weโre told that Bar 106 might have a crowd and that might be an overstatement, but underneath the smoky haze it appears to be at least mildly hopping. Here I meet Igor, a handsome youngster whose much older boyfriend Pablo is reluctantly allowing him to sow some wild oats tonight. As charming and adorable as he is, I decline his puppy dog overtures, but I do agree to join the couple and their lesbian friend at a mixed queer bar for one last drink. First, we swing through the Principe Real Garden, famous for its Cyprus trees (which are hundreds of years old) and as a nighttime cruising ground. I leave Michael to his own devices here and am not even a little surprised to learn the next morning that he plopped himself down on a park bench and found himself in the company of a willing Portuguese gentleman. What you think happened next is exactly what happened next.
Meanwhile, Igor, Pablo, their lady friend, and I make our way to Purex, a hipstery dive bar with a lesbian following. Igor is insistent that we go home together, but the lad is more than 20 years my junior. I decline, but Iโve imbibed enough Portuguese spirits to at least take a romantic stroll that ends with a kiss. Besides, I donโt really have time for tomfoolery. The next morning Michael and I have to pack our bags, pick up our car, and make a beeline for the coast!
The Author at Cape St. Vincent in the Algarve Coast. Photo by Michael O’Rourke
The water along the Algarve Coast is a piercing blue. When it laps up against the regionโs famous jutting rocks, Iโm reminded of the ubiquitous swirls that appear so frequently in Van Goghโs work. A holiday makerโs paradise, the Algarve is a confounding mixture of charming small towns and cookie cutter condos, family-run eateries, fast food chains, and, most importantly, beaches thronged by the masses and secret nudist coves frequented by gay men. Our fewdays here are a blurโa heady mix of beachy days, boozy nights, and the continuous application of SPF-50.
We are fortunate to stay off the beaten path at gay and clothing-optional Casa Risa in a small village called Mexhilhoeira Grande about 30 minutes from the coast. Because itโs the middle of the afternoon when we arrive (and a Monday no less), most guests have drifted off to the beach, but we do meet the staff including Ron, the fun and frisky owner; Alex, a bronzed and straight Aussie whoโs always walking around shirtless (and who does my laundry, but canโt fold jock straps worth a damn); and Paul, a thirtysomething Canadian bartender. When I approach him for a glass of water heโs Snapchatting X pics. โYoung people only want nude pics,โ he says without looking up from his device. โSo do the old ones.โ
Thereโs no reason not to fall in love with Casa Risa. Itโs a lush and romantic work-in-progress that manages to be both elegant (a pristine swimming pool, lavish breakfasts) and shabby chic at the same time.
One night, owner Ron gathers about 15 of us guests together, and along with his black lab Sasha we all amble down to A Curva, one of just several restaurants in town where we are treated to a multi-course meal consisting of bread, olives, prosciutto, cheese, salad, and more courses unfoldingย over many hours. We make friends with Chuck and DP from D.C., Kelan and Mattieu from Paris, and others, who will become our besties for the week. The sum cost of our amazing meal is $30 each.
Pool at Casa Risa by Jason Heidemann
There really is no expectation in the Algarve other than to sunbathe, but on our first morning, we do decide to make the hour trek out to Cape St. Vincent, a dramatic, if touristy, headland area offering a pretty lighthouse and a frightening drop off into the choppy Atlantic below. We hang here just long enough to make it worth our while and then head east toward the dayโs main prizeโthe beach.
Signs with phrases โPrai Naturistaโ and โPlage Naturistaโ are posted everywhere, and in English they all mean the same thing: Nude Beach. There are many scattered across the Algarve Coast and sunbathers are truly spoiled for choice. Some of the larger and perhaps better-known nude beaches include Praia de Manta Rota and Praia Grande, but we keep coming back to Praia do Submarino (Submarine Beach), a secluded and cove-like gem so named for an off-shore rock formation that resembles a partially submerged submarine.
Low-key, romantic, and off the beaten path, we canโt get enough of this beach and spend much time here swimming to nearby caves, chatting with fellow travelers, and letting the warm Portuguese sun sting our bare cheeks. We actually run into Casa Risa bartender Paul here and I swim off to a secluded cove with him where we are entirely alone and where I peel off my swimsuit, expectantly hoping heโll do the same; He doesnโt, but I am not wrong in thinking the cove is an idyllic setting for a hookup.
Celebrating Pride in Lisbon
We return here several days later with Casa Risa owner Ron whoassembles a group sailing excursion. As we kayak in and around the bays and inlets we spot a couple of guys canoodling in the buff at that very same cove (they patiently wait for us to pass so they can continue their good times).
Nights in the Algarve are spent at local restaurants guzzling jugs of red wine with fellow travelers from our hotel and tearing into local fare. There is Cacto, where one of us orders the lamb shoulder, and literally receives an entire shoulder, and Salerdo, where four euros gets each of us unlimited glasses of vino. Afterward, all of us staying at Casa Risa invariably wind up at the hotelโs bar where everybody drinks and skinnydips until either passing out or hooking up.
As I emerge naked from the swimming pool on our last night, a fellow American who Iโve become quite chummy with insists I let him try on one of the jockstraps I left out on my terrace to dry. I know exactly where this is going, and Iโm happy to play along. Soon weโre in his room with his French boyfriend and bartender Paul. Sufficed to say, it was a night to remember. (I find out the next morning that Michaelโs was no less forgettable.)
After a full week sampling the best booze, beaches, and boys that Portugal has to offer, we are dragged kicking and screaming to Lisbon International Airport. Fortunately, our gaycation isnโt quite yet over. We have a full weekend of hijinks ahead in Sitges, Spain. But thatโs another story.
