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Planning Your Best Family Vacation

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Our family of four has traveled widely together. We tend to take both summer and winter vacations of a week or more plus several trips over long weekends. Our longer trips are usually by air and our shorter trips are by car. When asked about planning your best family vacation, each of us will give different examples but we all agree that travel brings us closer together as a family. It has created lasting family memories of fun, of wonder and of curiosity fulfilled.

Follow my tips for planning your best family vacation and you can turn dreams into reality.  The keys are family involvement and good research.

When to Start Planning

We start planning our next trip on the way back from our current vacation. By talking over the highs and lows of a trip, we learn more about each individual’s likes and dislikes. We compromise on what we do so that each of us enjoys our time. When visiting Paris, we toured museums, went shopping and even visited Disneyland Paris at the request of our 12 year old.

Our conversations about travel are ongoing. Detailed planning starts two to six months out for our longer trips and one to eight weeks out for our weekend breaks. Starting early gives us more travel and accommodation options.

While our daughters are good travelers, we try to avoid excessive time in transit. If we are away for one night, we limit our drive to about four hours. With two or more nights we will drive up to twelve hours, but we try to include brief breaks in that trip. For our vacations of a week or more, we usually fly. Direct flights are less tiring than connecting flights and there is no risk of missing a connection. For long flights of over six hours, we try to stay more than a week at our destination.

Key Questions

When planning our next family vacation, we begin by defining our objectives.

  • Are we visiting family and friends or exploring a destination?
  • Is this an action-oriented trip or rest and relaxation at a beach?
  • Is this a trip for a weekend or a week?
  • What is our rough budget?

We like to alternate the types of vacations we take and these questions give us a specific focus.


Deciding where to go requires inspiration. We find that almost everywhere. School has prompted a visit to Gettysburg and another visit to Ben and Jerry’s ice cream factory in Vermont. The film Out of Africa led my mother and me to take a safari in Kenya. Television, books, magazines and web sites all have encouraged us to visit one location or another.If you are unsure of your next vacation, just ask two friends what their best vacations were for a weekend and for a week and then browse through Hilton Mom Voyage for a third opinion.

One fun approach is to start with a globe or a map and play “what if.” Kayak’s Dream Map shows you airfares from your home while AAA shows driving times. Google Earth lets you actually look at locations at street level. Hilton’s interactive map shows you where you can stay at Hilton hotels all across the world. These tools can give you a set of possibilities to consider. We then challenge each of our family members to investigate the choices.

10 Great Travel Research Resources

Following are my 10 favorite sources of travel information (besides Hilton Mom Voyage):

Great trips start with great research

Great trips start with great research.

The Final Details

When our family finishes our research, we have a guided discussion to decide on our next vacation destination and on the things that each family member would like to do there. Our choice is by consensus. A runner up destination is not discarded but simply deferred until next time.

The final planning then narrows down how we get to the destination and where we stay. Tourism and Convention sites now can offer good local advice. We book air travel early to get the best fares and better times or we map out an interesting driving route. We insist on safe, clean, family friendly accommodation, something that Hilton has reliably offered our family. We look for a variety of activities for all ages. We do not schedule every day but we know our options and we pre-book those attractions that fill up quickly. For tips on saving money see my other article, 20 Best Ways to Save on Travel.

If you keep the whole family involved and you do good research, you too will succeed in planning your best family vacation ever.

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Our Hilton Mom Voyage team members live throughout the U.S. and have traveled by air and car all over the world with their families!

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