How to Book the Festive Season

Jumby Bay’s Harbour Villas afford stunning views of the Caribbean Sea, providing a private retreat for holiday travelers.

Jumby Bay’s Harbour Villas afford stunning views of the Caribbean Sea, providing a private retreat for holiday travelers.


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Have you had clients who want to travel during the December holidays but get frozen out because they didn’t plan ahead? These insider tips from top luxury travel advisors will give you the tools you need to get into the booking team in a timely manner and to handle large family groups with grace and aplomb.

Planning at least a year out is imperative, all of our advisors agreed. But there’s more to it. Clients who have stayed repeatedly at a resort are often given first choice for reservations. So how do you break the cycle?

Managing expectations is key. Bob Romano, a partner at Fugazi Travel Agency in San Francisco, recommends that advisors warn clients that getting a good room at a resort in a warm weather destination is very competitive during festive season, since prior guests are approached first. “They need to get into any place decent first so that they can be part of the rebooking process,” he tells Luxury Travel Advisor. “It goes without saying that it is almost imperative for clients to work with a top travel consultant in a top agency as we are the ones with the relationships and resources to assist with confirmation.”

London is among those European capitals that many people are learning to discover for holiday travel.Pictured: London is among those European capitals that many people are learning to discover for holiday travel.

Jody Bear, owner of Bear & Bear Travel in New York, advises that repeat clients who spend the holidays at a hotel can rebook for the following year. “For ‘festive,’ they have until September or October before the hotels open the books to new clients, so it can be a waiting game, which is sometimes frustrating for the client. That being said, the earlier you put in a request, the more likely you will be confirmed,” says Bear.

Booking a beloved resort year after year not only gives the client priority, it helps the resort to know their preferences, says Meg North, executive vice president of Brownell Travel in Birmingham, AL. It also helps the resort to exceed the clients’ expectations as they get to know them better, she says. 

“We have many clients who return to the same spot year after year, such as the villas at the Four Seasons Nevis; Cayo Espanto in Belize and and The Four Seasons Hualalai,” says North.

Judy Nidetz, an advisor with Travel Experts, is based in Chicago so her clients tend to head to warmer climes during the holidays. Since many hotels sell out ahead of time, planning early is her first piece of advice. Her best tip, however, is to check each hotel’s cancellation policy to see when space that has been held by previous guests will be released into general inventory. “That’s a good time to obtain space that might otherwise never be available. This is usually in early fall,” she tells Luxury Travel Advisor. “The other issue is getting air space, which is another reason to book early. Many tour operators offer ‘Best Price Guarantees’ if you purchase their insurance. This is a great selling point to try to lock in when space is more readily available and no wondering if they can get a better deal later.”

For large families, Susan Weissberg, president of Wylly’s Professional Travel in Coral Gables, FL, requests interconnecting, adjacent and special needs rooms as early on as possible, but advises that booking blocks of airline seats is equally important and should be done as soon as flights become available in the computer systems. Weissberg is currently requesting confirmations for the 2014 peak season and is basing them on the current rates and advising clients that rates are subject to change. 

Amanda Klimak, co-owner and president of Largay Travel, in Waterbury, CT, actually advises to start planning 12 to 18 months in advance for holiday periods. She notes, like Weissberg, that the catch is that many resorts will not have final pricing on the specific room types you want to reserve at that time. “They will often reserve it at the rate that was in existence last holiday season and then when rates are published, modify that rate. The irony is that often when you reserve far in advance you can get the room but are subject to more onerous minimum-stay requirements than somebody who does it closer to arrival; it’s all about supply and demand.”

As for handling large family reservations, reserving bedding and room preferences very early on is vital, but so are the other details. “It’s important to assist with activities such as dinner reservations and spa [bookings] in order to avoid disappointment during this very busy time of year,” says North of Brownell Travel.

At Four Seasons Punta Mita’s beachfront casita one can breathe in the fresh ocean air and gaze upon the white-sand beach of Bahía de Banderas.Pictured: At Four Seasons Punta Mita’s beachfront casita one can breathe in the fresh ocean air and gaze upon the white-sand beach of Bahía de Banderas.

Sometimes bedding configuration isn’t just about a hotel room.“Some families also prefer villas, so I always ask their preference,” says Bear of Bear & Bear Travel. “Since the ages of large families vary and, therefore, the focus of the trip might vary, I always discuss what they are looking for; the travelers sometimes prefer educational or sightseeing trips rather than going to a beach, for instance. Taking out insurance is always important and, with large families, the cost of the trip can be expensive and the cancellation policies over festive are extremely strict, so I always recommend insurance,” she says.

Since working with an entire family can be a challenge, Cassie McMillion, a luxury travel advisor with Betty Maclean Travel in Naples, FL, prefers to have one family member be the spokesperson for the whole group. She also sends out a questionnaire that asks for preferences regarding room categories, connecting rooms and dietary restrictions, as well as any other questions that will help to personalize the experience. 

Romano of Fugazi Travel vehemently agrees that with large family reservations it is extremely important to understand who the decision maker will be, along with who is acting as spokesperson. “Many best efforts can get off track by having too many people involved. At my company we really like to take a personal approach and have a serious in-person or over-the-phone discussion so the family is aware of the complexity of their request and what is required to manage and confirm it with the attention and accuracy it deserves.”

For large families, it’s important to know the dynamics. Who doesn’t want to room with another family member? Who wants connecting rooms? Are adjoining rooms okay? “It’s also important to ask if the family has traveled together before [and] what the highlights and the lowlights were,” says Klimak of Largay Travel.

Where to Send Seasoned Holiday Travelers?

Mexico is still a large part of Nidetz’s holiday bookings, specifically all-inclusive luxury resorts in Playa del Carmen and Puerto Vallarta. “Having an all-inclusive venue makes it very easy to dine and have activities planned without having the stress of worrying about where to eat and how to make reservations for large parties. For multiple families it also makes the worry of splitting the dinner check non-existent.” For that reason, cruising also remains popular with her clients. Nidetz has also been booking all-inclusive properties in the Dominican Republic and says that Hawaii is still a popular destination for the holidays.

Bear’s clients travel broadly over the holidays, from Africa for a safari to a sightseeing/active trip to South America to a beach resort in the Caribbean.

Vail Village has the top ski schools and a lot of distractions such as shopping, restaurants and bars for the less extreme skiers.Pictured: Vail Village has the top ski schools and a lot of distractions such as shopping, restaurants and bars for the less extreme skiers.

McMillion of Betty Maclean Travel also sees South Africa and Hawaii trending as favorite holiday destinations; her newest find is the Four Seasons Punta Mita. “It has everything from surf schools to tequila tastings. The Marietas Islands are very close and the options for adults and children are great. They also have up to five- bedroom villas for families,” she says. 

Hawaii, Mexico, the Caribbean, Costa Rica and Belize are popular with Fugazi Travel’s clients, but more and more family groups are choosing Argentina, Brazil, Chile and Uruguay along with Thailand, Cambodia, and Vietnam for their holiday vacations, says Romano. “People are becoming very disenchanted with paying exorbitant airfares for five-hour flights and receiving very poor customer service. They realize they can fly a world-class airline long haul for sometime less money and receive a vastly superior travel experience,” he says, adding that many people are also learning to discover European capitals for holiday travel, such as London, Paris, Vienna, Rome and Florence.

Of course, it all comes down to geography. “We have clients in the Midwest who are very happy to spend the holidays in Arizona or Palm Springs, while our California clients are more interested in roaming around a bit. They enjoy the cultural events offered in Europe at Christmas and New Year’s while people from snowy environments feel warm in California and Arizona.”

For cold weather, Largay’s clients prefer Vail and Aspen, even for non-skiers. “They have the best ski schools anywhere and there are lots of distractions, such as shopping, restaurants and bars for the less extreme skiers. Big Sky, Montana and Jackson Hole are wonderful for hard-core skiers that are almost exclusively looking for the skiing.

For warm weather destinations such as the Caribbean, it’s Round Hill Hotel and Villas in Jamaica for villas and private home-based stays. “In Antigua, Curtain Bluff has an old-fashioned environment with great food. In Turks and Caicos, Grace Bay and the Regent Palms are both incredible,” says Klimak. As for Caribbean cruises, she feels that Royal Caribbean “does families very well. They have a great spectrum of age-appropriate entertainment. And NCL’s the Haven area always pleases,” she adds. Walt Disney World is another favorite, though Klimak advises “it is both one of most expensive times to visit and without a doubt the most crowded, but clients go in droves. The key is to be prepared since the weather may be cold,” she warns.

Weissberg of Wylly’s Professional Travel, who is an expert on travel to Israel, says that one of the most popular destinations for family travel this year is the Holyland. “Celebrating Bar and Bat Mitzvahs and following in the footsteps of Jesus in Israel are increasing in popularity.” Multigenerational groups are seeking the Caribbean, South America, Hawaii, the South Pacific, Tahiti and some of the Far East. There’s also a great demand for South African safaris, she tells Luxury Travel Advisor.

North of Brownell Travel says that her clients book Mustique, Cayo Espanto in Belize; the villas at Four Seasons Nevis; Jumby Bay and Jumby Bay’s Estate Homes; Four Seasons Bora Bora; and Dorado Beach a Ritz-Carlton Reserve. “Australia and New Zealand are great for family trip over the holidays and many folks enjoy a Caribbean cruise on a luxury cruise line like Seabourn,” says North. 

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