The Hardest Part of a Family Vacation? Deciding Where to Go

One hard and fast requirement: sunshine. “As a family, we’ve done a cruise to Bermuda, and all-inclusives in Cancún and Aruba,” said Cheryl Gerson, the sibling researching the trip. Some in her group seek beach time, she added, while others prefer to sightsee. The age range is preteen to early 80s, so our planners had to factor mobility issues and teen angst into the equation. Here are their three suggestions—which would you book?

OPTION 1: Costa Rica, Curated

Irene Edwards, a Costa Rica travel specialist and co-founder of Seattle-based GreenSpot Travel, has a plan that lets the family extend their trip to a week (without exceeding their budget) so they can comfortably explore two different regions.

One great itinerary starts (or ends) in northwest Costa Rica in Guanacaste, an area known for its beaches. The group would bunk at Punta Islita, an Autograph Collection Marriott resort with its own beach. While not huge, it still allows for activities from ziplines and horseback riding to surfing and fishing.

After a few days, the group would board a private charter to buzz them over to the country’s Caribbean side. In Puerto Viejo, a revitalized area, Hotel Aguas Clara makes a good home base and offers varied accommodations—house, bungalows or rooms to mix and match depending on the family’s preferences.

Pros: December is reliably sunny weather.

Cons: It’s the busiest and priciest two weeks of the year.

OPTION 2: Beachy, Historical Belize

“There are two areas we would suggest to keep everyone happy,” said Absolute Belize director Patricia Johnson.

The first: Ambergris Caye, the biggest, most bustling of the tiny islands making up the country, sits close to the Belize Barrier Reef and all the outdoor sports it promises. The family could enjoy diving, reef fishing and snorkeling alongside colorful fish, nurse sharks and turtles at Shark Ray Alley and the Hol Chan Marine Reserve. For family members who shun sharks, a sunset sail or beach barbecue will suit pretty much everyone.

The second: Placenia Peninsula, where the clan could stay in villas at the beachfront Naia Resort and Spa. They could kayak around the mangroves, go river tubing at Cockscomb Basin Jaguar Preserve or explore the ancient Mayan sites of Nim Li Punit and Lubaantun.

Pros: December 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: All-Inclusive Jamaica

”The culture on Jamaica is so different than other islands,” said Melissa Pugh, a travel adviser for Atlanta-based Jetset World Travel who specializes in high-end Caribbean holidays.

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

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

Another idea is a private luxury rental resort that isn’t an all-inclusive, like the Tryall Club, with access to tennis, a beach club and golf right on the property. “The family could book one villa, all services included, and hire a chef and pay for food,” said Ms. Pugh.

Pros: You’ll see holiday lights galore, so the island feels festive.

Cons: As in many places, staffing in Jamaica has been a challenge. Service may be iffy.