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Family Reunion Planning Tips: How to Organize an Unforgettable Trip

  • My Incredible Vacation
  • 5 days ago
  • 2 min read

Updated: 5 days ago

Start Planning Early

The earlier you start, the better your options. Large vacation homes, especially in popular destinations, book up fast. Ideally, begin 6 to 12 months in advance, especially if you're coordinating across multiple households and travel schedules.

  • Pro Tip: Use a survey tool like Google Forms to gather date preferences from the group.

  • Where to Stay: Look for large vacation rentals on platforms like VRBO that can accommodate your entire crew.


Pick the Right Location

Choose a destination that suits your family’s needs and travel comfort level. Consider:

  • Proximity to major airports

  • Weather during your travel window

  • Variety of activities for all ages

  • Dining options and grocery availability


Some popular family reunion spots include:

  • St. Thomas, USVI for beach lovers

  • Gatlinburg, TN for mountain getaways

  • Destin, FL for a sunny, drivable option


Divide Up Responsibilities

Don’t try to do it all yourself! Assign roles to make planning smoother:

  • Lead planner – main decision-maker

  • Activity coordinator – finds fun things to do

  • Meal planner – organizes group dinners

  • Money tracker – handles deposits and shared costs

Tip: Use a shared Google Sheet or app like Splitwise to manage expenses transparently.



private golf course at lakeside rental
The Lighthouse Lakeside Retreat in Missouri

Choose the Right Vacation Rental

Hotels can feel disconnected, but a large vacation rental keeps everyone under one roof (or nearby). When booking:

  • Filter for homes that sleep 10+ guests

  • Check for multiple bathrooms and living areas

  • Look for amenities like a pool, game room, or private beach access

Here are a few things to consider:

  • Is there enough parking?

  • Are there stairs or accessibility concerns?

  • Can you host a large group meal on-site?


Plan Group Activities—but Not Too Many

While it’s great to have a few activities planned, leave plenty of downtime. A mix of structured fun and free time keeps everyone happy.

Ideas for group-friendly activities:

  • Beach day or hike

  • Boat charter or fishing trip

  • Family talent show or game night

  • Group photo session (hire a local photographer!)

If your rental is near attractions, build an itinerary with optional outings so family members can join as they wish.


Coordinate Meals in Advance

Feeding a crowd can be chaotic. Here’s how to simplify it:

  • Assign each household a meal to prepare

  • Use Instacart or local grocery delivery

  • Plan a mix of eat-in dinners and group restaurant outings

  • Consider hiring a private chef for one special evening


Make It Memorable

Create moments you’ll talk about for years. A few fun additions:

  • Custom t-shirts or tote bags

  • Shared photo album on Google Photos

  • Family trivia night

  • A memory wall or “time capsule”

These small touches go a long way in bringing everyone together.


Final Tips for Success

  • Have a backup plan for weather or travel delays

  • Make a group packing list and share it

  • Designate a “go-to person” for questions during the trip

  • Remember—perfection isn’t the goal. Togetherness is.


Ready to Plan Your Family Reunion?

Your dream vacation starts with the perfect place to stay. Explore handpicked vacation rentals built for big groups and make this reunion your most incredible one yet.

 
 
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