Travel is full of unforgettable moments, and sharing the merriment and mishaps with friends and family can make your adventures even more special. “You have shared memories you’ll bond over for the rest of your life,” says Tami Al-Hazzá, cofounder of boutique travel company Femscape Sojourns. Multigenerational trips can also deepen family ties. “It allows kids to see parents or grandparents in different roles,” she says.
Planning a trip with multiple parties does present some challenges: agreeing on budget, aligning on activities and navigating travel from points A to B. This AARP Smart Guide to Family and Group Travel will help you tackle the planning essentials to ensure a smooth family or friend-group getaway that’s full of memories — and free of stress.
1. Start a group chat
In the beginning stages of trip planning, Selene Brophy, travel experiences business reporter for the industry news outlet Skift, recommends kicking off a group message thread. “WhatsApp seems to be the most seamless,” she says, although other options include iMessage and Facebook Messenger. In addition to preplanning, a group message ensures you and your companions are all on the same page once you’ve landed. It helps you stay connected, and you can share links to potential activities and restaurants.
2. Assign trip-planning roles
Planning a group trip can have a “too many cooks in the kitchen” feel. To avoid the congestion, divvy up planning roles and responsibilities. Most group trips have an overarching leader to sort details, monitor booking and keep everyone in the loop. Group members can assist with more focused roles, such as the hotel researcher and booker or the flight-route scouter. Discuss roles and confirm who’s doing what via email, text or shared documents for easy reference.
3. Discuss budget early
“A budget must be agreed to before planning begins,” says Katie Stewart, senior travel adviser for Ciao Bambino, a travel agency that specializes in family getaways. To start the conversation, ask the group to share rough estimates of what they hope to pay, either by family, couple or per person. “Just remember to account for all items [when budgeting], like flights, rental cars, accommodations and activities.” Keep a spreadsheet or shared document with final costs and booking confirmations, so everything is in one place.
4. Plan well in advance
Travel is booming, and that means things book up quickly. “Generally, planning at least a year out gives groups the greatest flexibility and choice,” Stewart says. “Not all locations will have pricing or availability open that far in advance, but groups can get the foundational details set so travelers can schedule time off and start looking at transportation options.”
5. Be flexible
Planning a trip around multiple schedules can be tricky. If your lifestyle allows it, be flexible with dates. “If you’re planning with families, I recommend making decisions on dates as soon as school schedules are available,” Stewart says. “I also like to gently remind the lead planner that no matter how important the trip is to them, they must be understanding when invited travelers cannot flex around school, sports or work.”
6. Hire a travel agent
Planning a vacation for two people can be all-consuming. Adding multiple families or couples to the mix only increases the complexities, so Brophy suggests hiring a travel agent from the start. “It’s a trend we’re seeing more and more,” she says. She notes that having an around-the-clock support team is worth the investment, particularly for flight delays or cancellations. Stewart adds that travel agents can review the group budget and traveler interest information and offer plans to meet everyone’s needs — a benefit that can take the stress off group planning leads.
7. Get insurance
Transit hiccups abound. That’s why Stan Sandberg, cofounder of insurance comparison site TravelInsurance.com, says travel insurance is critical. “When you’re talking about a family reunion or family travel where you have more than eight people, you could use a group plan. It may simplify some of the steps,” he says. Typically, though, “standard travel insurance requires each household to be covered under their own policy.” That’s because travel insurance is regulated on a state level. Though you could get group insurance, it may be easier to have each household acquire their own so they can sort issues as they arise, especially if groups are traveling on separate flight paths.
8. Choose an easy-to-reach spot
Just because you want to go to a bucket-list destination doesn’t mean it’s the best option for the group. “Multigenerational and group travel is about the people first,” Stewart says. “Make it as easy as possible for friends and family to say yes to the plan by considering not only a location that offers something for all age groups and interests but is also easy for all travelers to reach.”
9. Factor in an inheritance alternative
As you weigh the budget for a family trip, consider reframing how you think about inheritances, suggests John Zelig, group tour manager for VBT Bicycling Vacations. “I’ve had a grandmother that put together a whole trip instead of [leaving] an inheritance,” he says. “‘Your inheritance is to go on the trip with us,’ she told her family.” The family took three separate bike tours across Europe, from the Netherlands to Italy.
10. Ask about group perks and discounts
It’s always fun to snag a deal, and memberships, including AARP’s, come with cost savings that will trim prices for you and your group, such as discounts on hotels, cruises and rental cars. Booking with a travel agent could unlock savings you wouldn’t think of, says Stewart, a member of Virtuoso, a global network of luxury travel advisers. “As a Virtuoso agent, I can extend Virtuoso amenities to clients,” she says. This includes perks such as free breakfast or resort credits. “Some hotel partners offer a second room at 50 percent off for families, discounts on spa or resort activities or special amenities.” When booking a hotel, always ask if there’s a group rate or discount.
11. Locations to avoid
Al-Hazzá says there are certain types of vacations to avoid, including “destinations where no one knows the language, or any destinations that have a number of safety regulations,” she says. Take into account the health and fitness of your fellow travelers. For example, if mobility is an issue, ditch the hill town and opt for a place with easy public transportation or flat surfaces.
12. Split payments via apps
There are several ways to go about splitting up your vacation costs. You could have each family or household tally their costs, then combine and split them at the end. Or use apps such as Splitwise, Divvy or Billr to organize and split your travel costs during or at the end of your trip, Al-Hazzá says.
13. Do a run-through
Communication is key when you’re planning a group trip. According to Al-Hazzá, to avoid friction, plan a group meeting to run through the rough itinerary and gather opinions and preferences. While you have everyone gathered, remind your companions about travel must-haves, such as immunizations, passports, visas or travel gear.
14. Set an airport meeting time
If your group is flying together, set an agreed-upon airport meetup time for flight day based on airport recommendations for your type of travel, be it domestic or international. “I feel like checking in early and checking your bags early is a safer bet for your bags getting onto your flight,” Sandberg says. Early arrivals will ensure everyone can get through security and to the gate well before boarding time.
15. Confirm passport status for all travelers
For international trips, it’s important to check that every traveler has documentation — and do the check early, given renewals are currently taking months to complete. Ask your trip members if they have TSA Precheck or Global Entry. Sure, it’s not required, but it’s important to make everyone aware of the option to ease transit, especially if you plan to use these tools to skip the line yourself.
16. Be ready to improvise
Just like flexibility, being open to improvisation is critical. Have your itinerary set, but know that things may change in the moment, especially based on the group dynamic. Spend your evening vacation meals discussing the next day’s plan to gauge how your companions are feeling. Sometimes the schedule calls for a long museum day, but you and your fellow travelers crave a chill-by-the-beach afternoon. If that’s the case, improvise, and embrace plan B.
17. If things go well, plan a reunion
If you and your fellow travelers mesh well, get the conversation started for your next group trip. You can use your existing message thread to get the ball rolling for round two.