Dominican Republic, Puerto Rico, Cayman Islands
4. Dominican Republic
You get a lot of value for your money. "Competition keeps airfare and resort rates down, so many families end up saving $500 or more by coming here," says McCarthy. Stick with the La Romana or Punta Cana areas, which have family-friendly beaches.
Sand Sanctuaries The all-inclusive Club Med Punta Cana offers drop-off children's programs for babies to teens, a circus school, tennis instruction, music lessons with Dominican-inspired instruments, cooking classes, and an art studio. While the kids are busy, you can fly on the trapeze, learn to windsurf, or hang out on the wide white-sand beach. (Spring rates for a room with two beds start at $147 per night per adult, $74 per child ages 4 to 12, free for younger kids. Summer rates start at $123 per night per adult, $62 per child ages 4 to 12; clubmed.us.) The newly renovated, all-inclusive Grand Palladium Bàvaro Suites Resort & Spa, in Punta Cana, has the largest club in the Caribbean for kids ages 1 to 12, babysitting, meet-and-greets from Raggs (of PBS fame), and plenty for you to do such as beach volleyball, sailing, or water aerobics. (Late-spring and early-summer rates start at $135 per adult, $68 per kids ages 3 to 12 for a room with two beds, free for younger kids; palladiumhotelgroup.com.)
Side Trips Book a tour from your resort to the historic capital of Santo Domingo -- it'll take about two-and-a-half hours each way, so it's best for older kids. Punta Cana Tours offers a trip that stops at The Three Eyes National Park (with underground caves and lagoons) and a lighthouse, Faro a Col?n ($92 per adult, $52 per child under age 12; puntacanatours.com). Next: San Francisco, New York City, and San Antonio
5. Puerto Rico
If you don't have passports and you want to spare the expense of getting them (nearly $500 for two adults and two children), Puerto Rico is a great option. "Your kids can be immersed in the unique culture," says Schretter. Fly into San Juan and stay there or in the northeastern part of the island, or split your stay between both.
Sand Sanctuaries Located on Condado Beach, the San Juan Marriott Resort & Stellaris Casino offers a large oceanfront pool with a slide, a toddler pool, spa treatments, and babysitting. (Spring and summer rates start at $169 per night for a room with two beds; marriott.com.) Or stay at Las Casitas Village -- even though it's a Waldorf Astoria Resort, it's not terribly expensive considering it boasts an expansive family water park with a kids' pool, several slides, and a lazy river; a supervised camp for children ages 4 to 12; and babysitting services. You'll also be able to take a short ferry ride to Palomino Island, a private oasis for resort guests. All rooms are villas with a kitchen, so you can easily store snacks and cook some of your own meals. Plus, you'll be able to hang out in the bedroom while the kids go to sleep on the pullout in the living area. (Spring rates start at $299 per night for a one-bedroom villa. Summer rates start at $269 per night; lascasitasvillage.com.)
Side Trips "Two must-sees are the historic forts in Old San Juan and the El Yunque rain forest," says Schretter. Take public transportation or a shuttle, if your resort has one, to Castillo San Cristóbal, a huge stone fortress built in 1783; kids ages 5 and up will be able to earn a badge if they take the ranger-led tour ($3; nps.gov/saju). At El Yunque, in Eastern Puerto Rico, your family will be able to walk on any of the 13 trails (including several stroller-friendly paved ones) to spot parrots, tree frogs, and lots of unusual flowers.
6. Cayman Islands
This financial hub offers a pristine beach, a low crime rate, and modern roads so you can explore on your own.
Sand Sanctuaries Stay on Seven-Mile Beach, particularly to the north, or in the more secluded area of Rum Point, where the water is so shallow that kids can walk out 25 feet. "Most of the lodgings on the island are condos," says Stallings. To find one, he suggests going to wimco.com. One-bedroom beachfront rentals in the spring and summer start at $1,400 per week.
Side Trips Visit Cayman Turtle Farm, where kids can gently pick up turtles from the touch tanks or swim with them in the turtle lagoon. Its free-flight aviary was designed by consultants from Disney's Animal Kingdom ($45 for adults, $25 for kids 5 to 12, free for younger kids).