The hardest part of a family vacation? Decide where to go

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Travel booking We can hear a scene from Monty Hall’s old game “Let’s Make a Deal”: You are given options, each of which promises to open a door to another world. But which door does not reveal the luxury car, but the proverbial goat?

In our new feature, Trip Quandary, three travel advisors face a common dilemma and do their best to reassure decision makers and suggest healthy solutions. For the first test, we asked three travel planners with experience in the Caribbean, Costa Rica and Belize for their recommendations. For a multigenerational, Boston-area family of 10, a winter break vacation worth $40,000 for flights, meals and comfortable plush digs for five days..

One hard and fast requirement: sunlight. “As a family, we took a cruise to Bermuda, and an all-inclusive cruise in Cancun and Aruba,” said brother Cheryl Gerson, who researched the trip. Some in her group want beach time, she added, while others prefer sightseeing. The age range is from teens to early 80s, so our planners had to factor mobility issues and teenage angst into the equation. Here are their three suggestions – which position do you take?

Option 1: Costa Rica, graduated

Irene Edwards, a Costa Rica travel specialist and founder of Seattle-based Greenspot Travel, has a plan that allows families to extend their trip by a week (within their budget) so they can comfortably explore two different regions.

A great itinerary starts (or ends) in northwestern Costa Rica in Guanacaste, known for its beaches. The group will gather at the Autograph Suite Marriott Resort Punta Islita, which has its own beach. Although not large, it allows for activities from ziplining and horseback riding to surfing and fishing.

Hotel Aguas Claras on the Caribbean side of Costa Rica.

A few days later, the group boarded a private charter to return to the Caribbean side of the country. In Puerto Viejo, in a renovated area, Hotel Aguas Clara makes a great home base and offers a variety of accommodations – houses, bungalows or rooms where you can mix and match according to family preferences.

advantageDecember is reliably sunny weather.

ConsIt’s the busiest and most expensive two weeks of the year.

Option 2: Beach, Historic Belize

“There are two places we recommend to please everyone,” said Patricia Johnson, director of Absolute Belize.

First: Ambergris Caye, the largest, most populous of the tiny islands that make up the country, sits next to the Belize Barrier Reef and its exotic outdoor sports. The family can enjoy diving, reef fishing and snorkeling with colorful fish, nurse sharks and turtles at Shark Ray Alley and Hol Chan Marine Reserve. For family members avoiding sharks, a sunset sail or a beach barbecue will suit everyone.

Kayaking tour near Naia Resort and Spa.

The second: the Placenia Peninsula, where the tribe can stay in villas at the beachside Naya Resort and Spa. You can kayak around the mangroves, go river tubing in the Cockcomb Basin Jaguar Preserve, or explore the ancient Mayan sites of Nim Lee Punit and Lubatant.

advantageDecember is outside the rainy season and temperatures are cooler.

Cons: Many of the best guides and tours are booked months in advance, so last minute choices can be limited.

Option 3: Inclusive Jamaica

“The culture in Jamaica is very different from the other islands,” says Melissa Pugh, a travel consultant with Atlanta-based JetWorld Travel, which specializes in upscale Caribbean vacations.

Beyond stunning beaches and rainforest or mountain hikes, you can book private guided food tours (jerk, seafood, universal Rastafarian and street fare) or an architectural tour of Kingston.

Hyatt Ziva Rose Hall, a family-friendly all-inclusive.

Ms. Pugh suggests booking an all-inclusive resort in Negril, Ocho Rios or Montego Bay. Among her choices: Crescent, Hyatt Ziva Rose Hall or Zotri.

Another idea is a private luxury resort that doesn’t have all-inclusives on property, like a trial club, tennis, beach club and golf. “The family can book a villa with all services and hire a chef and pay for meals,” Ms Pugh said.

advantage: You’ll see plenty of holiday lights, so the island feels festive.

Cons: As in many places, staffing in Jamaica was a challenge. The service may be useful.

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