Gay Men and the Art of Aging Gracefully

DATES: 02/12/2025 - 02/20/2025
LOCATION: Merida, Mexico
PRICE: $2,795.00
ABOUT THE INSTRUCTOR:
VISIT WEBSITE

Don Shewey is a writer, therapist, and pleasure activist in New York City. As a journalist and critic, he has published three books about theater and written hundreds of articles for the New York Times, the Village Voice, Esquire, Rolling Stone, and other publications. His writings on gay sexuality include the books The Paradox of Porn: Notes on Gay Male Sexual Culture and Daddy Lover God: a sacred intimate journey. He has chronicled his psycho-sexual-spiritual adventures in essays that have been included in numerous anthologies, including The Politics of Manhood, Best of the Best Gay Erotica, The Queerest Art: Essays on Gay and Lesbian Theater, and Men Like Us: the GMHC Guide to Gay Men’s Sexual, Physical, and Emotional Well-Being.

He is a New York state-licensed psychotherapist whose private practice specializes in sex and intimacy coaching (bodyandsoulwork.com). In 2018 he completed training at California Institute for Integral Studies in psychedelics- assisted psychotherapy. His work as a teacher and community health activist revolves around healing through pleasure, adult sex education, and grounded daily spiritual practice.

He is active on social media and maintains two blogs, Another Eye Opens (cultural commentary) and Food for the Joy Body (smart thinking about sex, intimacy, and life in a body). An archive of his writing is available online at donshewey.com.

Don Shewey is a writer, therapist, and pleasure activist in New York City. As a journalist and critic, he has published three books about theater and written hundreds of articles for the New York Times, the Village Voice, Esquire, Rolling Stone, and other publications. His writings on gay sexuality include the books The Paradox of Porn: Notes on Gay Male Sexual Culture and Daddy Lover God: a sacred intimate journey. He has chronicled his psycho-sexual-spiritual adventures in essays that have been included in numerous anthologies, including The Politics of Manhood, Best of the Best Gay Erotica, The Queerest Art: Essays on Gay and Lesbian Theater, and Men Like Us: the GMHC Guide to Gay Men’s Sexual, Physical, and Emotional Well-Being.

He is a New York state-licensed psychotherapist whose private practice specializes in sex and intimacy coaching (bodyandsoulwork.com). In 2018 he completed training at California Institute for Integral Studies in psychedelics- assisted psychotherapy. His work as a teacher and community health activist revolves around healing through pleasure, adult sex education, and grounded daily spiritual practice.

He is active on social media and maintains two blogs, Another Eye Opens (cultural commentary) and Food for the Joy Body (smart thinking about sex, intimacy, and life in a body). An archive of his writing is available online at donshewey.com.

Together let’s explore what we are all feeling!

How often do you find yourself saying, aloud or to yourself, “I’m too old to (fill in the blank)”? How often do you find yourself saying or thinking, “I’m NOT too old to (fill in the blank)”? Whether we face the subject with defiance or dread, grief or gratitude, cringing or curiosity, aging happens to all of us, if we’re lucky. What tools have we gathered, individually and collectively, to equip ourselves for the challenge and the opportunity of aging gracefully?

2024 group in front to Merida sign

The intention of this pilot program for Il Chiostro is to re-write the book on aging as gay men. Our tribe doesn’t necessarily have a lot of role models for navigating this season of life. Some of us have family structures to provide continuity as we age. Others of us rely on peers and partners for support, camaraderie, and a sense of belonging. How do these things change over time? What sustains our capacity for growing in mind, body, and soul? In the lovely atmosphere of a mid-winter getaway to sunny Mérida in Mexico’s Yucatan peninsula, we will gather for a week-long adventure with other soulful gay men, exploring best practices for not only surviving but thriving in our golden years.

For me, “Gay Men and the Art of Aging Gracefully” was both deeply meaningful and lots of fun.  I learned much from our group’s frank “Salon-style” discussions and put it all into practice in our excursions in beautiful Merida and other parts of the Yucatan.  
My thanks to Don and Michael for planning and leading this adventure.  ~ Kurt, 2024

Program Structure

In daily group sessions, we will investigate a number of pertinent topics from our perspective as older gay men. Sex, of course, and money and health and travel. But also retirement, relocation/housing, finding and nurturing community, grooming, exercise, diet, loneliness, intergenerational contact, touch, intimacy, keeping up, and letting go. You will come away nourished by sharing communal wisdom about aging and life with other seasoned fellows and reviewing old assumptions about aging. You will leave invigorated from celebrating triumphs and envisioning the possibilities that later life holds.

The sessions will be guided by what feels right to the group.  Although we will propose topics for discussion, we expect each day will evolve according to the themes and emotions most present in the minds of the participants.

Come join us and let’s all see where this exploration takes us as we warm ourselves together in the winter sunshine of a city packed with experiences to discover.


Meals and our “Home”  Our home for the week will be a private residence called El Pueblo, recently renovated by an industrious gay couple.  There are 7 rooms each with king beds and private bathrooms.  All rooms will be singles unless you specify who you would like to share with. [Click tab above for a full description with photos.]


Other Activities

Cooking class with Wilson in the country

An important element of aging gracefully and happily is to have fun! Throughout the week, we encourage participants to explore the cultural, historical, culinary and gay friendly events independently. All of our hosts will be happy to help you plan special experiences, including a trip to the beach, an excursion to see the stunning pink flamingoes in Celestun, etc.  As part of the program, however, we will organize at least one extra activity or excursion each day.  For our week together we propose…

  • A Yucatan cooking class with renowned local Chef Wilson and his staff.  We’ll travel to his rural village, about 1 hour from Mérida, to Wilson’s outdoor kitchen where guests help prepare a traditional Yucatecan meal — including a pig buried in the ground and roasted in the embers for hours.
  • The Mayan temple at Uxmal

    Guided tour of the Uxmal Mayan temple – an ancient Mayan city, founded around 500 AD and considered the most representative of this region’s dominant architectural style.  Soon after the Spanish conquest in the 1500’s, Uxmal was mysteriously and inexplicably abandoned.

  • Visit to a magical cenote with guide.  Includes swimming through several  open and enclosed ancient freshwater swimming holes, some with stalactites and stalagmites.
  • A magical cenote

    A house tour of a magnificent, preserved mansion along the grand Paseo de Montejo;  gain insights into the vast wealth and importance of Mérida during the height of the henequén boom.

  • Excursion to Celestun to see the fantastic array of pink flamingoes feeding in the gulf.
  • Cocktail party hosted at a home attended by local and expat gay men of Mérida
  • Mezcal tasting, optional
  • Optional in-room massage (priced separately)

Participating in the Il Chiostro “Gay Men and the Art of Aging Gracefully” program was an energizing and exhilarating experience. The men in the group were perfect examples of active aging. Sharing our fears, desires and feelings about growing older with each other was enlightening as well as inspiring. It was my third Il Chiostro experience and they never fail to provide intellectually stimulating and fun excursions, wonderful dining and culinary delights and lodgings that make you want to pinch yourself to make sure you are awake and really there. It is no surprise that I already have my fourth Il Chiostro trip booked!  ~ Gianni

Read this article about Merida as the new, up-and-coming destinations for gay men.

Flamingos at Celestun


Price: $2,795 p/p

Discounts:  $200 p/p for shared room with king bed (for couples or close friends)

A non-refundable $500 deposit due upon registration.

Balance due by December 15, 2025 (we’ll send you an invoice).

All participants should arrange their own flights to Mérida and ground transportation between the airport and El Pueblo (see Getting There tab above).

On the beach with Ricardo

Price Includes:

  • 8 nights in a single, private room with bathroom at the residence El Pueblo with free access to all common areas, pool, library, etc.
  • Daily buffet breakfast prepared by our chef
  • 6 dinners with the group featuring a variety of Mexican and cultural experiences
  • Daily discussion “salons” with group leader, Don Shewey
  • Excursions to introduce you to Mexican culture of the area
  • Transportation for all organized excursions

Does Not Include:

  • Airfare
  • Lunch
  • Car fares for independent activities (Uber is cheap and ubiquitous, but there are also taxis to hail or private drivers to hire for longer excursions.)
  • Independent meals and sight-seeing

To Register:  just click on the Sign Up Now button.  A non-refundable deposit of $500 is required to secure your spot in the workshop.  Payment can be made on line with a credit card, or you can follow the instructions to send in your registration and payment by mail.  Once we receive your deposit we will send you a formal Registration Confirmation with further information about the program.  You will receive 2-3 other correspondences by email prior to the workshop with information about the program, a suggested reading list and an electronic invoice for the balance.  Final Balance is due by December 15th.  Any time prior to your arrival, if you have questions about anything regarding the trip or the program, you can contact us by email or phone and we’ll be happy to assist you.

Mansion tour with Maruja, the owner who grew up there.

For one glorious week, we will be the exclusive guests of a unique, new venue called El Pueblo.  A spacious residence created especially with men in mind, El Pueblo is owned and operated by a multi-national gay couple. The compound has 7 large bedrooms, each with a king bed and a private, modern bathroom.  These rooms are distributed over 2 floors encircling a common indoor/outdoor area of lush gardens, a library, 2 dining rooms, 2 kitchens, numerous terraces and a stunning 25 meter, 2-lane lap pool.

The complex was designed and built from 4 existing properties expertly crafted into one fully-functioning “home” with ample space for gathering together as a group or for spending quiet time alone.

The street facade of El Pueblo

The interior courtyard of El Pueblo

El Pueblo’s location is ideal of our group – literally right in the center of Merida Centro.  It sits at the base of the cosmopolitan avenue Paseo di Montejo (some refer to it as the Champs-Elysées of Merida) – a wide boulevard lined with trees, boutiques, international restaurants, hotels, historic mansions, art galleries and cafes.  The Paseo is closed to traffic on Sunday mornings when bicycles dominate the avenue.

This lovely area is very convenient, within walking distance (or a short Uber ride) of most attractions such as the main Plaza Grande, Parque Santa Lucía, where on any night you will find locals enjoying music or dance,  the buzzing Santiago market with plenty of outdoor tables for lunch and the neighborhood of Santiago with colorful homes, small cafes, local restaurants and respectful renovations preserving the authentic setting.

Rooms are available for singles, couples or friends who are willing to share a king bed.  Click on this link for a look at the rooms…

Dining area and kitchen #1

From the balcony

The library

Covered terrace, downstairs

Upstairs lounge

Clothing optional, 2-man lap pool

 

Merida, with its international airport, is an accessible destination.  There are many direct flights into the city from Miami, Houston or Mexico City.

From the airport, it is a short taxi ride to El Pueblo.  After exiting customs,  walk to the Transport Desk to reserve – and pay for – a taxi to the center.  With a voucher in hand, your car will be waiting for you just outside the arrivals terminal.

Note:  Uber is used extensively throughout the city, but not at the airport.  Uber divers are not allowed to pick up passengers in front of the terminal. These pre-booked airport taxis are totally safe as no money is exchanged with the driver.

Money:  unlike many towns in Resort México, visitors to Mérida will not be able to spend American dollars anywhere.  We suggest using your US debit card in one of the many ATM machines in town to draw Mexican pesos from a bank.  As always when drawing money in a foreign location, obtaining pesos will incur small fees bank.

Merida is one of the fastest growing and safest  warm-weather destinations in the world and with a rich mix of culture, cuisine, architecture and openness it is especially attractive for gay men.  If you are tired of the scene in PV (Puerta Vallerta) or the tourist crush of Playa (del Carmen) or Cancun, then Merida might be the place for you.

Merida is the vibrant capital of the Yucatan state, far to the east in Mexico (directly underneath New Orleans!) with a rich Mayan and Spanish colonial history. It offers a much older, deeper, substantial history — in a word, it is Authentic México — than some of the popular vacation destinations.

The city has a population of nearly 1 million, but the quaint Centro area is concentrated with varied neighborhoods of homes and businesses of locals who have lived there for generations, expats, architects, artists, families from Mexico City and, of course, gay couples.  One intriguing aspect of this city-scape is that you can never tell what lies behind a door until it is opened to you.

Folk dancers in the plaza

One the joys of Merida is how expats and locals comfortably intermingle. Yucatecans are deeply proud of their history and heritage and so as the city of Merida finds a new audience, the local government has taken pains to preserve long-held traditions. Thursday nights in Parque Santa Lucia are reserved for regional dancing performances; Saturday nights, Noche Mexicana on the remate of Paseo de Montejo (right around the corner from El Pueblo!) or the ancient Mayan ball game pok ta’ pok which is recreated in an elaborate ceremony culminating in an actual game played by local men in loin cloths using flaming balls! Wednesday nights, the challenging history of the Mayan state is recreated in front of — and projected onto the facade of — the Merida Cathedral.  These fascinating weekly events are attended as much by locals as visitors, creating a delightful mash of culture, family and friends.

During any season there are music festivals, parades, outdoor performances, marathons, garden tours, artisanal fairs, fresh markets and food festivals.  In Merida people love to gather outdoors for any possible reason.

Renowned as the White City, Merida has been honored as the Americas Capital of Culture numerous times.  The city has a distinctive blend of ancient Mayan and Spanish cultures.  Once, it was deemed the wealthiest city in the Americas due to its mass production of henequén – derived from the abundant agave plant and used to make rope products for the global marketplace.

Example of architecture preserved in Merida

One of the many 19th century mansions built along the Paseo

Mayan temple at Chichen Itzá

For the archeologist in you, Merida is encircled by Mayan temple ruins like one of the seven wonders of the world, Chichen Itza, Uxmal and many less-travelled but no less fascinating Mayan ruins.  The city sports elaborate examples of original colonial architecture, and is fast becoming the artistic center of the Yucatan. Merida features several impressive art museums as well as The Cúpula, a privately-owned historic series of structures featuring galleries, a video room, large gardens with indoor and outdoor performance spaces, a production workshop and two artists residences.

Mayan cuisine is not at all the stereotypical tacos, enchiladas and rice and beans you might know from the Tex-Mex restaurants in your neighborhood.  Many Yucatan dishes are famously slow-cooked, such as their pork specialty Cochinita pibil, wrapped in banana leaves, buried and roasted underground for hours on end until served fall-apart tender.

The Yucatan grows over 50 different varieties of peppers, exotic fruits such as pitahaya (or Dragon Fruit), nance and guanábana.  Merida is packed with diverse opportunities to sample the local cuisine —  from lively, music-filled open markets with fresh catches from the nearby Caribbean Sea, to homemade Italian pasta and wood-fired pizza eateries, to impressive high-end tasting restaurants like K’u’uk or  Huniik. And there is a wide selection of local Mexican wines — not widely distributed in the United States — a whole new world of varietal discoveries!

Cenote with stalactites, blue water and light streaming in from above

One of the most unique attractions in the area are its magical water hole formations —  more than 7,000 cenotes – naturally-formed freshwater sinkholes embedded in the soft limestone. They were formed over 66 million years ago from the impact of a gigantic meteor that created a huge shock wave — the evidence of which is seen today as a ring of hundreds of cenotes around Mérida. To the Mayans, cenotes were a critical water source representing the gateway to the world of the dead. To the Spaniards colonialist, cenotes provided the essential waters that helped build the henequén trade and allowed their Haciendas to thrive. Some cenotes are deep water-filled shafts with strictly vertical walls, while some are shallow but wide. Other cenotes are semi-open with part of the water surface hidden from view in a cavern. But all cenotes make for an entrancing swimming experience, with lush warm, blue-hued fresh waters and dramatic tree roots hanging down from their semi-open ceilings.