Gregory Kiep

Marketing Blog

Gregory Kiep is the premier marketer and promoter for gay events, gay travel, and promotion. Based in Provincetown, he has travelled around numerous markets making connections and talking about his travels to places like Provincetown, NYC, Los Angeles, Fort Lauderdale, Mykonos, South America, Europe, Nice, and more.


Greg's Gaycations: Provincetown

Provincetown has long been a popular vacation destination for LGBT travelers, and the best-known gay spot on the East Coast. For over 100 years, “P-town” (as it has been nicknamed over the years) has been home to an exciting artist’s colony as well as experimental theatre with Drag Queens on stage as early as the 1940’s. In 1916, the Boston Globe acknowledged Provincetown’s status in the art community with its front page article titled, “Biggest Art Colony in the World in Provincetown.” This helped encourage the gay and lesbian presence to flourish in the 1920’s and 1930’s as artists, actors, novelists, poets, and radicals all began to summer in town.

The ability to experiment with varied art forms without fear of judgement led to the prosperous art community and paved the way for the sense of acceptance for which Provincetown has come to be known. By the 1970’s, the gay population in Provincetown was significant and a variety of restaurants, bars, and boutiques were opened to cater to the community. When gay marriage became legal in 2004, Provincetown quickly became one of the top destinations for gay weddings. Today, it offers the perfect mix of relaxation with all the fabulousness one would expect in a gay vacation destination.

When To Go

The Provincetown season runs from the beginning of May until Halloween each year, with July and August being the busiest months. There are a variety of festivals and celebrations all season long, with barely a weekend going by where there is not a theme of some sort. The majority of these are geared towards LGBT travellers who come from all over to attend major celebrations such as Fourth of July and Carnival in August. Other popular events include the Portuguese Festival which highlights the town’s heritage, the International Film Festival, Bear Week and Family Week which is a celebration for LGBT families.

Where To Stay

During peak times, it can be difficult to get a reservation at the limited number of hotels and guest houses but there are typically last minute options available at There are also many private homes and condos that are rented weekly during the season, typically from Saturday to Saturday. You can find out about these on Homeaway, Airbnb, or

The Brass Key Guesthouse is considered to be the pinnacle of luxury accommodations with a gorgeous pool area and popular bar on-site. If you want to be “in the thick of the action,” consider Boatslip Resort (where the daily tea dance takes place) or The Crown & Anchor which is part of the complex where a chunk of the nightlife and shows take place. Another favorite is the recently remodeled Cape Colony Inn which offers outstanding rates and one of the most comfortable beds in town. They also have a great pool area that is great for families.

What To Do

One of the appeals to P-town is that there, truly, is something for everyone. Race Point Beach is consistently recognized as one of the top beach destinations in the United States and is a quick bike ride away from the town center. For those that enjoy the water, whale watching and deep sea fishing are extremely popular activities and easily to find.

Provincetown has long been known for its art scene, with galleries lining the main streets of Bradford and Commercial. Sprinkled among these are great boutiques that offer everything from home furnishings to luxury resort-type fashion. The vast majority of these are “mom-and-pop” establishments, although Marc Jacobs runs a successful presence in town.

For those who are more inclined to relax with a cocktail, the LGBT bar scene is considerable for the size of the town. Each day during the summer, there is “Tea Dance” at the Boatslip, which is one of the biggest traditions of the Ptown scene. (Make sure you try a Planter’s Punch!) At night, there are options for everyone starting with A-House, which is the oldest in Ptown and contender for the oldest gay bar in the United States. If you want to dance the night away, check out Wave or Paramount, both part of the Crown & Anchor complex. Want more of a “sip a martini” type of night? Shipwreck Lounge, Monkey Bar, and Aqua Bar are all great options. For the ladies, Pied Bar is the self proclaimed “longest running woman-owned club in the universe!”

A trip to Provincetown is not complete without taking in one of the shows at Crown & Anchor, The Post Office, or one of the other theatre spaces in town. Each year, “gaylebrities” from all over the world are flown in to delight audiences and share their talents with the Ptown scene. There are also the beloved Ptown constants that are back each year such as Miss Richfield 1981 and Varla Jean Merman.

How To Get There

From Boston, it is an easy jump to Provincetown, making it popular for East-coasters especially. There are two fast ferry companies that make the trek across the water in about 90 minutes. Another option is Cape Air which has quick flights to the Provincetown Municipal Airport. The drive from Boston’s Logan airport takes about 2.5 hours but winds its way all the way through gorgeous Cape Cod towns.

About Greg

Gregory grew up in Cincinnati, Ohio and lived in Hyde Park and Downtown during his 24 years there. Upon receiving his MBA from Xavier University, he launched a marketing firm specializing in LGBT lifestyle services and products. He has travelled all over the world to over 60 countries independently and in conjunction with Atlantis Events. When he is not on an adventure, he calls Boston home.


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