My favorite trips to plan are highly customized itineraries that speak to your tastes and interests. For example, this summer, I planned a day-by-day, three-week journey through Portugal and Spain for a couple who were very into food and wine. They wanted reservations at Michelin starred restaurants every evening. You can hardly go wrong with Michelin-star restaurants, but I found some unusual places that they wouldn’t have found on their own. While they were traveling, I kept an eye on their flights so I would know if there were delays along the way. I also checked in a few times to be sure everything was going well. Everything went great, but I never want to leave anything to chance! 

A great option for a family or friend group of eight to 12 people is a villa stay. Villas are a very special way of vacationing and can be less expensive than hotels. Often, everything—meals, private sightseeing, even the transfer from the local train station, is included. More important, you can truly experience life from a local’s point of view. There are two I especially recommend. Both have fun gay owners with whom you can feel totally comfortable in being yourself. And they’ll show you both the touristy sites and the off-the-beaten-track ones, depending on your interests.  

One is in the scenic Loire Valley of France, just two hours by train from the airport in Paris. This is the region where French aristocrats built their summer homes as monuments to themselves; today, many former palaces are museums that are open to the public. While not a fancy chateau itself, the villa I most love has five elegant suites, each decorated with fine art and antique furniture of the region. Barbra Streisand has stayed there, and everyone I have sent has said that they have never had a vacation like that. 

The people who own the villa will take you everywhere. One day, you may find yourself walking up to someone’s house in a tiny village and getting to know them over a glass of wine. And on a Saturday you can visit the flea market; if you need someone to speak French, your hosts are there to help you. 

In Italy, I often send clients to a stylish villa in the Tuscany region that is run by an English and Italian gay couple. It overlooks Cortona, of “Under the Tuscan Sun” fame, and affords amazing panoramic views of the valley. It is an incredibly beautiful place to relax, but also makes a great home base for exploring nearby towns and cities such as Siena, Montepulciano, and Assisi. With concierge service and luxurious styling, it is ideal for the discerning gay traveler.  

I also arrange a lot of free-wheeling trips through Australia and New Zealand as well as romantic getaways to Hawaii, Fiji, Tahiti, and just about anywhere else in the world.