There are lots of ways to see the world. You could backpack and hostel your way around the globe. You could join the Navy if you haven’t hit 42 yet. Or you could just stay home and watch a lot of Netflix.
But if you have the means and you’re not a big planner — and you’re looking to meet new friends along the way — then an all-inclusive group tour might be your ticket to a worry-free holiday.
Make no mistake: handing off all the arrangements for a group vacation comes with a price, but also some bonuses, including camaraderie, ease of travel, and peace of mind.
Following are some recommendations for travel companies that cater to queer travelers 50+, focusing on culture, history, and natural beauty.
Oscar Wilde Tours
Professor Andrew Lear is an American author, Classicist, and historian of gender and sexuality. He is considered one of the foremost experts on same-sex love in the ancient world. With his company Oscar Wilde Tours, he shares his expertise in that period and fin-de-siècle England, Renaissance Italy, Weimar-era Berlin, medieval Japan, and more. “LGBTQ+ people can take pride in forebears like Sappho and Socrates, Michelangelo and Leonardo da Vinci, Shakespeare, Tchaikovsky, and Virginia Woolf, the genius dancer Nijinsky, the literary revolutionary Thomas Mann, and of course, the sublime Oscar Wilde himself,” says Lear. The famous historian and Harvard professor shares the art, stories, and heritage of community forbears throughout Europe, with packages like “Gay Gods and Heroes” in a super-sized tour of Greece and Italy.
Out Adventures offers a variety of packages for lots of tastes, but their small group gay cruises hit the spot of travelers 50+. Tours are limited to a few dozen — their largest excursion caters to just 40 passengers. This is an upscale outfit and features travel on high-end yachts and riverboats docking at small but notable ports of call, including village wharves and hidden bays inaccessible to larger vessels. On-board meals and service are four-star, and last-minute itinerary changes based on passenger preferences are not uncommon with tours to Tahiti, the Galapagos, Greece, Croatia, Egypt, and Italy.
San Francisco–based Olivia is the most popular travel company for lesbians and LGBTQ+ women, celebrating their 50th anniversary in 2023 with a blowout in Cabo and a Caribbean cruise on Holland America’s ms Nieuw Amsterdam. The company prides itself on a mission of inclusivity, focusing on OWLs, or “older, wiser lesbians” that they say are “a vital part of Olivia’s community.” Olivia packages feature special meetups on cruises and at resorts to help women 60+ connect, share stories, and forge new friendships. “Grab breakfast with the OWLs or pop into one of our special OWLs cocktail hours and share your unique experiences among Olivia family.” OWL meetups are typically for women 60 and over, but all are welcome, especially those supporting or traveling with an OWL. Look for Early-Bird pricing.
When you think of a gay group vacation, this cruising outfit probably comes to mind. Founded in 1985, RSVP pioneered the all-gay cruise. Last year, competitor Atlantis Events bought the company, and now RSVP markets to adults age 50+. The company says their Exotic Caribbean All-Gay Cruise 2023 is the “first fully all-inclusive big ship gay cruise designed for exploration, friendship, and endless adventures.” The ten-day trip aboard the NCL Norwegian Pearl starts in Miami in March and hits six countries, including Panama and Colombia, plus Grand Cayman and a first stop down the Overseas Highway in Key West. The all-inclusive price starts at $1499.
Detours Gay Adventure Travel
Detours was built on the premise that not all gay travelers want to party — like, a lot — on their vacation, so they’ve filled the gap with relaxed adventure tours. They call it “a laid-back, no-strings-attached approach to gay group travel that feels more like exploring the world with old friends than anything else.” On tour to Israel and Jordan, “you may find yourself on camelback riding through the desert, reading a newspaper while you float weightlessly in the Dead Sea, sprawled out under the sun at the gay beach full of locals, exploring one of countless world-class museums, or taking in the unique culture and traditions on display through the streets of this Middle Eastern region.” As relaxed as it is, this outfit is definitely a more active choice among options. The British Columbia-based company spans every continent but their own and Antarctica.
Gay travel outfit HE Travel — the HE stands for Hanns Ebensten — calls itself the King of Gay Travel, with a 40-year track record of providing “the finest in gay travel tours”; Ebensten ran the first exclusively gay adventure tour down the Grand Canyon in 1973. Today, many of the company’s offerings are focused on more leisurely pursuits, like “soft adventure” bike tours through French and Italian vineyards and culinary expeditions (a handy “physical challenge” scale ranks the tours; most don’t top 2 or 3 out of 5). HE Travel spans the globe with small-group travel to every continent.
The name Toto Tours is derived from the Latin word meaning “inclusive,” or colloquially, “in toto.” That’s the philosophy of owner Dan Ware and his outfit, around since 1990 and catering to a predominantly 50+ clientele. Toto boasts a repeat customer rate on any given tour as high as 70%, attesting to the quality of service and friendships formed among travelers. Tours run the gamut from “Roman Holiday: Christmas in the Eternal City” to “Jungle Book: Wildlife of India.”
“We go to places most people will never see.” So says Puckett Expeditions founder Chris Puckett of his slow travel, small tour outfit; groups top out at 12. Puckett calls it “deep exploration group travel” with Iceland, Patagonia, Thailand, Mont Blanc, New Zealand, Vietnam, South Africa, Turkey, and Croatia all on his itinerary over the last two years. Puckett’s custom excursions incorporate both natural adventure and lots of cultures, “forest, water, and rock,” plus “the best restaurants and little villages.” The guide’s goal “is not only to connect you to the places we visit, but also to one another, to meet like-minded travelers and make long-lasting friendships along the way.” Says Puckett: “Every year, our guests have become some of our closest and most treasured friends.”