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Four Important Milestones to Hit When Planning a Family Vacation

Posted on Thursday, July 6th, 2023

Story by: Molly Waldstein | Travel Writer


Thinking about taking an active vacation with family, but not sure where to start? This handy checklist can help you pick a destination, book your tour—and prepare your family to bond, have fun, and create memories to last a lifetime.

Four Important Milestones to Hit When Planning a Family Vacation

Thinking about taking an active vacation with family, but not sure where to start? With a wealth of fantastic destinations, it can be hard to narrow down the field. To give you the inside edge, VBT put together this handy checklist. It can help you pick a destination, book your tour—and prepare your family to bond, have fun, and create memories to last a lifetime.

Milestone 1 (18 Months before Travel): Find Your Family’s Dream Destination

If you’re having a hard time picking the perfect destination for your next family adventure, here are a few questions to help you build your shortlist:

  • What makes your family feel good? Maybe you love the feeling of pedaling side by side under a lush canopy of leaves, or maybe it’s the tantalizing aroma of haute cuisine that bonds you together. Start by talking about sharing the most delicious, mouth-watering meal you can imagine—then pick a destination that puts that meal on the table in front of you.
  • What makes you feel whole? Wholeness comes from something that supports both body and soul. Start by thinking of a favorite novel or film that your family has loved over the years. Now picture it—including the sights, the sounds, the smells, the stories. Pick a destination that lets you walk in the footsteps of your favorite characters.
  • What makes you grow as a family? Family travel is about deepening connections and creating memories to last a lifetime. Think about the family photos you’d like to bring home from your adventure—and picture yourself showing them to your grandchildren or great-grandchildren as they get older. Ask yourself what you want those photos to look like, then pick a destination that delivers that perfect snapshot.

Milestone 2 (12 Months before Travel): Narrow It Down with a Few Practical Questions

Once you have a short list of destinations, our experienced team of VBT Tour Consultants can help you and your family narrow it down. These travel experts have the most up-to-date information about tour dates and availability, plus details that aren’t on the VBT website. If there’s a tour you have questions about, chances are a VBT Tour Consultant has been there! Here are a few questions to consider before you call:

  • Are your travel dates flexible? If you have a specific travel window, VBT Tour Consultants can quickly find every available option for your chosen dates.
  • Do family members have dietary restrictions? Although gluten-free and vegetarian options are available on every tour, not all tours are created equal when it comes to variety. Our Tour Consultants can point you towards destinations with the best cuisine for your family’s dietary needs.
  • What activity level works best for your family? Families come in all shapes and sizes—with different interests and abilities. VBT cycling adventures are a great way to give everyone the pace they need—so the laid-back adventurers have time to shop or chill by the pool while the avid cyclists are free to challenge themselves with some extra miles. Whatever your family’s pleasure, VBT Tour Consultants will give you the inside scoop on road and trail conditions, level of effort, sightseeing, and optional activities.

Milestone 3 (10 Months before Travel): Call a VBT Tour Consultant to Get the Inside Scoop

Once you’re on the phone with a VBT Tour Consultant, here are a few questions to ask:

  • How many spaces are left on the tours you like best? If you have your heart set on a departure that’s nearly booked, be sure to reserve your space before it sells out!
  • Has your VBT Tour Consultant been on this tour? If not, they probably have a colleague who has! They can give you the real inside scoop from first-hand experience.
  • Are E-bikes available? E-bikes are available on many tours—but they’re popular and sell out fast. If E-bikes are on your family’s list of must-haves, a VBT Tour Consultant can let you know where and when you can snag some.

Milestone 4: Manage Your To-Do List by Breaking It Down

Congratulations! You’ve picked a tour and booked your reservation—this is going to be a lot of fun! As the big day approaches, this final checklist will help you prepare:

3 to 6 Months before Departing

  • Let the adventure begin—learn all about your destination through books, films, and language-learning apps.
  • For international trips, check your passport and renew if it expires within six months of your planned return date.
  • If necessary, apply for a visa on your destination’s embassy website.
  • Consider a Travel Protection Plan, like Redpoint Travel Assistance, to protect you and your trip investment.
  • Begin training for your trip. It’s a great reason to enjoy fresh air and exercise.

1 to 2 Months before Departing

  • Go shopping! Purchase gear for your trip and test it out.
  • Let bank and credit card companies know you’ll be traveling. Ask about international fees and card security.
  • Want to text friends about a delicious seafood dish you had on tour? Check with your mobile service provider about an international data plan.
  • Stock up on prescriptions, contact lens, spare glasses etc. Contact your health insurance company about coverage for international emergencies.
  • Ensure your pets and your home are in good hands in your absence. Arrange for animal care, house sitting, and yard maintenance.

1 Week before Departing

  • Get excited: it’s the final countdown!
  • Begin packing. Check your airline’s carry-on restrictions and latest TSA security measures at to avoid hassle at the airport.
  • Download audio books, games for the flight, translators, maps, and secure calling and messaging apps like WhatsApp.
  • Make copies of important travel documents.
  • List the valuables you’re bringing and photograph each one.
  • Leave a copy of your itinerary with family or friends.

1 Day before Departing

  • Check into your flight online.
  • No one wants to come home to a smelly kitchen—use your trip as an excuse to purge the fridge, take out the garbage, and give the counters and sink a quick clean.
  • Power up! Remember to charge your electronics and batteries.
  • Set out-of-office messages.
  • Check destination forecast and adjust your packed items if needed.
  • Water your houseplants… because they need love too.

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