Traveling with an entourage is no longer reserved for the likes of the Jolie-Pitt brood and their handlers. Travel with friends can create some of your most memorable experiences, as long as the logistics, group dynamics and, of course, the place is right. Admittedly, there was a time when I looked at vacation as a pure couple's sport. But with 150 days on the road running my travel company, a major benefit is the over 20 trips I've taken with friends.
One of the success factors to traveling with entourage is knowing how to manage logistics, so that there's no stress or conflict due to lack of planning. That means investing in the more comfortable car with GPS (or splurging on a driver in certain regions of the world), having staff to manage domestic tasks and picking a hotel or villa where everyone will be comfortable. When in doubt, upgrade your accommodations. Also, be up front with costs before the trip. Everyone should be on the same page with the type of restaurants and places where you'll be spending money.
Speaking of people, who you bring is as important as where you go. Leave the drama queens, high-maintenance friends, and control freaks at home. You want companions who can roll with it, and who are enjoyable to be around.
As for where to travel, the possibilities are endless. Here are a few favorites, which are part of a blowout list, not for the price-sensitive faint of heart. A private island in the Caribbean? A villa with 18-karat-gold floor-to-ceiling bathrooms? Just bring the entourage, and it's yours.
Mustique, Petit St. Vincent, and the Grenadines
Why: A private island where the likes of Mick Jagger (and Mick's litter of kids) get away, this is one of the best-kept secrets in the Caribbean. With only one restaurant and two bars on the island, you might think there's not enough to keep you entertained for the week. That is until you realize that each of the villas is your own five-star hotel, with a five-star private chef. The perk of renting a villa on Mustique besides its surprising affordability? Being treated by the billionaire next door like you belong.
Stay: Villas are the way to go, which all come with a full staff, including gourmet chef. If the walls of Villa Hibiscus could talk, they would tell stories about a certain partying prince, who stayed there with his brother, William, and said-brother's then-girlfriend, a commoner named Kate. Other standout villas are the Moroccan-inspired Toucan Hill and the massive, seven-room Hummingbird.
Entourage Activities: The Tuesday cocktail party hosted by the island's only hotel, the Cotton House, which is the best people-watching -- ever. It also introduces you to other vacationers, and almost certainly invitations to dinners and cocktail parties.
St. Barth's, French West Indies
Why: This is the St. Tropez of the Caribbean, where along with your beach you get a high dose of French culture and the best selection of restaurants and shopping in the region.
Stay: Eden Rock's Villa Rockstar, which defines rock star. With 18-karat-gold floor-to-ceiling bathrooms, it's the most over-the-top villa on the most over-the-top island in the world. For a more chill option, check into Le Sereno at Grand Cul de Sac Beach, with gorgeous beachfront suites and a Miami-style pool scene.
Entourage Activities: Chilling on the beach at Isle de France over drinks and lunch, afternoon table dancing at Nikki Beach, dining on the truffle spaghetti at Le Gaiac, then more table dancing at Le Ti St. Barth. Repeat.
Why: One of the few places where it's acceptable to be on a two pastas a day and bottle of Brunello diet.
Stay: Arguably the most beautiful private villa in all of Tuscany, Borgo Finoccchieto is where CEOs and political royalty get away from it all. Or, like a certain president, move their command headquarters for a "life is good" moment. Don't have the serious coin it costs to rent the entire property? Head to nearby Castiglion del Bosco near Montalcino, where your crew can take over a villa or settle into the beyond-gorgeous guest rooms that are larger than most apartments in New York City.
Entourage Activities: Brunello, Brunello, Brunello. The basics here are drinking and eating with friends. Those looking to expand their horizons should discover the dessert wine Vin Santo at Pizzicheria de Miccoli in Siena, where the owner will give you samples of everything from boar's meat to cheeses to wine, which you can purchase with reckless abandon. Serious wine aficionados should meet up with the Tuscan Auteur, who is the unofficial Brunello Babe of the region. She'll get you past the vineyard rope for entrée to Stella Di Campalto's wine harvest dinner and tastings at Colleoni, which sells out far before the general population even has a chance to say Brunello.
Cabo San Lucas, Mexico
Why: There are few things in life that are a sure thing, and this is one of them. You are guaranteed a good time with sun, beach and margaritas. With frequent flights and minimal logistical challenges, this is also an easy group trip to plan.
Stay: Resorts like Capella Pedregal and One & Only Palmilla allow for your entourage to have their own space, while coming together for dinners and beachside margaritas.
Entourage Activities: Gorging on a big steak dinner at the new outpost of Mastro's, which pairs quite nicely with high-end tequila. Poolside people-watching, where Hollywood starlets seem to congregate like common folk on any given afternoon.
Why: It's ski season, and the back bowls of Vail are calling you. The definition of ski trip should include "bring the entourage," because skiing is no fun alone. Neither is hot-tubbing after a long day on the slopes. No need to chase powder in Colorado; there's a good chance you'll get lots of it from January into late March.
Stay: Four Seasons Vail which, while not on the slopes, creates a ski-in, ski-out experience for its guests. It doesn't get better than this for ski accommodations in Colorado; this is the much-needed dose of five star that Vail needed. For groups, splurge on renting one of the condos in the Four Seasons residences.
Entourage Activities: That would be skiing, of course, at China Bowl and Blue Sky Basin with your crew and après-ski at the Red Lion. For the single ladies, they don't call Vail "Mail" for nothing. The other benefit of skiing is working up that appetite, for big group dinners in cozy ski sweaters at Sweet Basil and La Bottega.