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Family vacations fuel a lifetime of nostalgia, from the time we are small children through our adult lives. Island travel evokes a particularly romantic reverie, which jetsetters of all ages will appreciate. Although pulling off a multi-generational trip does take effort, the planning can be fun if you approach it with the right attitude.

First off, it's everyone's vacation, so involve everyone. Call a family meeting, and have each person announce the top three places they'd like to visit and why. Note any overlaps, and draft a list of vacation-spot finalists. Think about each family member's goals or requirements for the trip. If you and your daughter want to pick up surfing, Barbados might top your list. If your son and his grandfather love history, the Maya sites near Cancún are an ancient marvel. If you continue to research, you'll discover several places that offer both surfing and historical sites, plus a kids camp for Timmy and a nature reserve for Grandma. The most important family travel advice: Don't plan on spending every minute together. A little breathing room goes a long way toward family harmony. Instead, choose a destination with a wide range of attractions, so loungers can hit the beach while active types swim with sea turtles. Plan on meeting up at specific points throughout the day, but otherwise, keep itineraries loose. Think about all you'll have to catch up on at dinner!
When traveling with little ones, a flexible schedule is key, as Teresa Plowright, About.com's Travel with Kids column writer, advises. "Kids can so easily get their hearts set on something, and if problems arise (anything from a transportation issue to a sibling's tummy ache) then the disappointment is huge. When sightseeing with young kids, for example, I plan one morning activity and don't even mention the afternoon activity until I'm sure everyone's up for it."

Once you've chosen a location, your accommodations will play a large role in your family's overall experience. Family-focused resorts are especially appealing for groups with younger travelers in tow. Adults can savor precious one-on-one time while their little ones enjoy organized and supervised activities. The best advice is to look for resorts with programs aimed toward specific, narrow age ranges — a program for 4- to 12-year-olds will likely bore both your preschooler and your preteen. Some resorts even offer themes or "celebrity" appearances, such as your children's favorite TV characters.
All-inclusive family resorts make things even easier, especially when trying to coordinate numerous adult families. Plowright says: "Bottom line about all-inclusive vacations: All needs are provided for, fun is abundant, parents can enjoy a beautiful setting and relax. And with all-inclusive pricing, parents never need wonder 'How much will this cost?' when kids want more drinks or activities." One up-front payment means no splitting checks, and purses and wallets can stay in the room. Buffet-style meals are generally available anytime — a huge advantage when easing toddlers into new time zones. Plus, picky eaters can make their own plates, while gastronomes-in-training sample chicken luau, okra, steamed mussels or plantains.
Families seeking more space and privacy should consider vacation rentals. Justin Halloran of vacation rental network HomeAway Inc. says,
"Hands down, the best tip I can offer when traveling with kids is to stay at a vacation rental instead of a hotel." This father of three children under age 4 adds, "Plus, separate bedrooms for the adults and kids is also key for my family because no sleep means no vacation." Depending on the level of service your group desires, prices for basic rental accommodations can be quite comparable to those of resorts, especially when divided among multiple adults. Vacation rentals offer the convenience of your own kitchen, laundry, dining room, etc., so you really can feel right at home — only better. Parents don't have to fret over a crying baby at mealtime, and family members with special needs may be more easily accommodated. Plus, your party will experience a more authentic version of island living — driving or walking to local food markets, speaking with the neighbors and sightseeing off the beaten track.
For the ultimate vacation, villa rentals will have your group living like royalty. These luxurious dwellings often lie steps from the beach, with sweeping ocean views and top-notch amenities. Your personal chef prepares all meals to order, the laundress sees to the washing, a gardener keeps the grounds up to snuff, and whenever you'd like to explore the area, just consult your driver. Nannies are also available at many properties, so adults can enjoy time alone together. Debbie Moncure, owner of The Villas of Bluefields Bay in Jamaica, communicates extensively with families ahead of time to coordinate the details of their stay. "Before they depart, we send them a long list of lunch and dinner options, so they will have exactly what they want when they arrive the first day," she explains. Her all-inclusive villas come fully stocked with guests' favorite food and drink, and chefs easilyattend to dietary restrictions or special requests for children. Whether your clan chooses a Tahitian resort, a villa in Jamaica or a cruise around Hawaii, remember the true luxury of a family vacation is spending time together. As children grow up and lives get busier, our opportunities to devote an entire week or two to family bonding grow increasingly rare. So enjoy each moment – and be sure to take lots of pictures.