Your Multi-Gen Family Travel Planning Timeline

Planning multi-generational travel? Learn why booking 10-12 months ahead makes family reunion travel easier and more affordable. Melissa shares real examples from traveling with grandparents including Mexico resorts, cruises, and Hawaii trips. Discover the ideal timeline for coordinating flights, hotels, and activities when multiple families travel together.

What You'll Learn:

• Why early booking matters for multi-generational trips
• Real examples: Mexico resort (3 months out vs. cruise booked 11 months ahead)
• Securing multiple hotel rooms on points during peak seasons
• Coordinating PTO requests, flights, and rental cars across families
• When to book excursions for popular destinations
• Timeline checklist: 12-15 months discussion to 2 weeks pre-trip info share

00:00 Welcome to Quick Tip Tuesday

00:25 Listener Question: When to Start Planning?

00:47 Examples from Our Trips

01:43 Booking Early vs. Last Minute

03:10 Detailed Timeline Recommendations

05:00 Final Tips and Conclusion

Don't miss this inspiring, practical travel with kids podcast hosted by family travel expert Melissa Conn, founder of The Family Voyage, certified Child Passenger Safety Technician, and mom of two who proves family travel is achievable for everyone.

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Transcript

[00:00:00] Hey there and welcome back to Family Travel Unpacked. I'm Melissa and you're listening to Quick Tip Tuesday. In case you're new here, you can always find detailed destination guides, travel tips, hacks, and more on my website, thefamilyvoyage.com.

 So on the previous episode, we talked all about multi-generational travel, the logistics, the compromises, all of it. If you haven't had a chance, be sure to go back and check it out. I got a message from a listener asking about timing, like more details on when she should actually start planning these kinds of trips. Honestly, it's such an important piece of the puzzle that I wanna do a quick follow up episode just on that timeline issue because the thing is, planning a trip for four people is already a juggling act.

Planning for eight or 10 or more is a different ball game, and that timeline can really impact things. Let me give you some examples from our own trips so you can see what I mean. Now, if you're just talking about bringing the grandparents on a weekend getaway that your immediate family's planning, which we've done, you probably don't need a ton more lead time than what you would normally [00:01:00] have. One time grandma even invited herself along for a weekend getaway that was starting the next day because she had so much fomo when we were telling her about it. It took a couple phone calls to Hyatt to sort everything out on such short notice, but I got it done . 

But let's talk about the family reunion type trips that are really about bringing all the branches of the tree back together. Our first big multi-gen trip was to Mexico. We did a resort getaway with my husband's side of the family, and we planned just three months out now. It was fine and we had a great time, but our options were pretty limited at that point. We were scrambling to find enough rooms that fit our budget, and some of the properties that we were interested in had already sold out.

There was also less time for everyone to coordinate. Some people needed to get their PTO approved and those short notice flights were really expensive because we were traveling over New Year's.

Now contrast that with the cruise that we have upcoming, we booked it 11 months in advance. And yes, it wasn't the absolute rock bottom price. Cruises do sometimes have last minute deals, but I was able to secure three cabins in a row.

That might not sound like a big deal, but trust me, it is for us. It means we can shuffle [00:02:00] kids between the rooms. If our son wants to stay up late hanging with his uncle, it's no problem 'cause they're right next door. When we need to get everyone ready to go somewhere, we're not running up and down the hallways or to a different deck completely trying to wrangle everybody. And here's a bonus. I was actually able to get the cruise repriced a few times when rates dropped. So we got all the upside of booking early, meaning enough rooms in the location we wanted, without worrying too much that we were missing out on a huge sale. It was the best of both worlds.

Then there was Hawaii last year. We went over winter break, so I booked about 10 months out to lock in three rooms on points at the Hyatt Regency Waikiki. And if you know anything about Waikiki over the holidays, you know that getting three standard rooms on points is no small feat.

If I'd waited, I might have snagged one, maybe two... but three? That's a lot harder. Booking early also meant that my husband could put in his PTO request well in advance, which matters because plenty of people at his organization wanna take time off over New Year's as well. The early bird gets the worm! And we had plenty of time to look at flights and find something sort of affordable with [00:03:00] times that worked out close enough to each other. Since we were hopping between Oahu and Maui, there was also an extra layer of logistics that I had to deal with.

So what's my actual recommendation for your timeline? Obviously, shorter timelines can work if you're super flexible or you're not worried about budget, or you're going somewhere with massive capacity, but if you want options and you wanna keep your costs reasonable, here's what I'd suggest.

Start talking about destinations and looking at the calendar 12 or even 15 months in advance. I know that sounds crazy far out, but remember, you're coordinating multiple family schedules. You've gotta work around sleepaway camps, gymnastics meets band concerts, and school plays. When you're multiplying that by two or three families, you need that lead time and it gives you plenty of time to weigh different options and have conversations with everyone to see what they want to do. You can also figure out what the budget's gonna look like with different options. A lot of times we'll start talking about the following winter break when we're all together for Thanksgiving.

So 10 to 12 months out, that's when you actually start the booking process. You request PTO, get your cruise or hotel lined up and [00:04:00] start looking at flights. If you're not all picking up your own rental cars, you wanna land around the same time, or at least close enough that nobody's sitting at the airport for four hours waiting. Make sure to send everyone the cancellation timelines on penalties so that they know what they're committing to.

Flights get confirmed and rental cars booked somewhere in that three to six month window. By that point, everyone should know exactly when they're arriving and leaving.

Then one to three months out, you're booking excursions and activities. How far in advance depends on the destination. For our Maui trip, I actually booked the luau about 10 months in advance because they give priority seating based on when you book. I wanted us all to be able to sit together and have a great view, but for lots of activities, a month or two ahead is plenty.

Then about two weeks before the trip, do a final info share. Send everyone's flight details, hotel confirmation numbers, and all that stuff in one email or a group chat. It's also a great time to make sure everyone's signed up for the loyalty programs. Like if you're staying at a Hyatt, make sure grandma has a Hyatt account and that it's linked to her reservation so that she gets benefits too.[00:05:00] 

Now, I'll say this timeline's ideal, but life doesn't always work that way. Sometimes an opportunity comes up last minute and you just go for it. That Mexico trip I mentioned? Three months was tight, but we made it work. We just had fewer options.

The key thing is this: the more people you're coordinating, the more lead time you need. It reduces stress, gives you more options, and honestly, it gives everyone something to look forward to longer. There's something nice about having that trip on the calendar, you know, it's like future joy.

 Alright, that's it for today's quick tip. If you found this helpful, definitely go back and listen to the last full episode on multi-generational travel if you haven't already.

Be sure to follow along and leave a five star review wherever you're listening. And as always, you can find more detailed guides and tips on my website, thefamilyvoyage.com. Happy travels.