AARP Smart Guide to Family and Group Travel

Helpful tips for booking a crowd-pleasing trip — from planning to reminiscing

Stephanie Vermillion,

AARP

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Published August 28, 2023

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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.

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PLANNING

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.

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ACCOMMODATIONS AND MEALS

18. Aim for included breakfasts

If you’re staying at a hotel, look for rates with breakfast included. This takes one daily meal out of the planning equation and ensures everyone in the group can grab a bite at their leisure. It also means the group leader won’t have to rally the troops for a set breakfast time.

19. Consider an all-inclusive venue

“There’s a time and a place for the all-inclusive, and it couldn’t be more important than when you’re traveling for the first time with small children,” Brophy says. These types of resorts make your life easy as a traveler, with on-site babysitters, entertainment and set meals you don’t have to worry about coordinating. Brophy recommends this option particularly for multigenerational trips with young kids in tow.

20. Try a vacation rental

If you’re traveling with a large group, it can be easiest to have everyone stay at one location. That’s where vacation rentals come into play. “Having the short-term stay experience feels more laid back,” says Brophy, who notes that these accommodations can also provide cost savings.

21. Collaborate on packing when possible

Instead of five travelers bringing separate hair dryers or curling irons, communicate before the trip on a shared packing list. This is especially important for staying in a vacation rental. “It makes sense to go deep into the [packing] specifics instead of having a lot of little things,” Brophy says. “Know what will be included and available, then [create] a list.”

22. If it’s a special occasion, tell the establishment

Is your group gathering for a birthday, anniversary or similar special event? If so, tell the hotel or restaurant. “Give a heads-up that the group is coming,” Brophy says. “You’ll be surprised — people really make an effort to go out of their way to make experiences special and memorable.”

23. Book meal reservations

Getting a table for a large group can sometimes be difficult. That’s why it’s important to book dinner reservations in advance, especially if your heart’s set on a particular restaurant. “Have some meals structured and organized,” Brophy says. At the same time, leave room for spontaneity or informal dining options to really soak up the area’s culture. “For others, you can explore or grab street food. Food is a brilliant way to experience a destination.” Before you book any restaurants, ask your group for allergies or dietary restrictions to ensure everyone stays healthy and happy.

24. Share cooking responsibilities

If you’re staying in a vacation rental, divvy up the meal responsibilities by having one person, couple or family prepare a meal each night. Discuss the idea and schedule ahead of time so your group can brainstorm their recipes. During your vacation rental shopping trip, each party can purchase the specific ingredients they need.

25. Prioritize private rooms

Sure, you love the family or friends you’re traveling with, but having a private room is essential for unwinding and having down and alone time. If it’s a vacation rental, ensure everyone has their own bedroom. Though some homes have extra beds tucked within the couch, if possible, it’s better for everyone to have their own separate room and space.

26. Stay put

To prevent stress and travel mishaps, consider staying in one hotel or vacation rental the entire time. The groups can venture out for activities or day trips via car, train or private guide.

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PLANNING FOR ACTIVITIES

27. Take a cruise

For access to multiple destinations without the stress of packing and unpacking and coordinating the logistics to get your group from place to place, book a cruise. “Cruises are the best of all worlds,” Stewart says. “Travelers can unpack once and eat and play together without sacrificing their own space. Plus, they eliminate the need to secure dining reservations for large parties, and activities are often geared to many different age levels.”

28. Gather group interests

If you’re dreaming of a specific itinerary with multiple can’t-miss sights and tours, you may be better off going on a solo or two-person trip. When it comes to groups, “you need to carefully weigh everybody’s interests,” Brophy says. “It’s part of the planning process. Weigh interests, keep things flexible, and balance shared experiences.”

29. Look for diverse-experience destinations

Try finding a destination where you can hit multiple types of travel in one trip. For example, “South Africa ticks all the boxes,” Brophy says of her home country, noting the mix of beaches, wildlife experiences, wine country and outdoor adventure. “It really allows a multigenerational family to experience a lot.” Other destinations with multiple experiences in one spot include British Columbia, with national park hiking, wildlife watching, wine and museums, and the U.S. Virgin Islands, with beaches, hiking, snorkeling and history.

30. Take a heritage trip

Few multigenerational trips have as much meaning or generate as many lasting memories as a heritage or “roots” trip. Zelig says many travelers book active, adventure-centered roots trips through his tours. Some tour agents specialize in or run private excursions to help you explore your heritage, including ProGenealogists, Legacy Tree Genealogists and Kensington Tours.

31. Go easy on day one

It may be tempting to cram in as much as possible on your first day, but our experts all repeated a recommendation for group travel: Go slow. This is particularly important on day one. “If there’s a time zone difference [or] if someone has to be at the airport early to make the flight, that first day shouldn’t [have you] hit the ground running,” Brophy says.

32. Allow for individual experiences

Yes, you’ll plan the trip around your group’s interests, but it’s also wise to build in time for individual activities. This will alleviate any friction and ensure each traveler can explore the destination based on their niche or activity level. “At the end of the day, everyone is investing their time and energy into [the trip],” Brophy says. “There should be an understanding that there will be set group activities, but everyone needs some breakaway [time].”

33. Hire a local guide

Go deeper into your destination with a local guide or special experience. “The shift toward private tours for groups has increased, especially after COVID-19,” Brophy says. “It’s worth investing time researching what you want to do, then finding something that’s a little more premium for your group, understanding that you can split the cost across a bigger group of people.” This could be splurging on a private boat canal tour or a private driver and guide for a day instead of the typical bus tour. If you’re staying at a vacation rental, hire a chef to come by for a private cooking lesson.

34. Try an active adventure

Depending on the activity level of your group, you could plan an active trip, such as a cycling or long-distance hiking excursion — especially if these are the kinds of things you and your friends or family do together at home. “It’s a great way to bring like-minded people together,” Zelig says. “You’re going to experience history and travel on an active tour, and immerse yourself in new experiences.” Cycling tours are becoming increasingly accessible with the boom in e-bikes, too, Zelig says.

35. For amusement parks, book a guide

If the thought of taking a multigenerational trip to an amusement park sounds chaotic, Stewart has some advice: “I highly recommend using a specialized guide in the park,” she says. Parks such as Disney World, Universal Studios and roller coaster hub Cedar Point in Ohio have special private tours. These are run by both the parks and individual companies. “A guide does all the heavy lifting from scheduling meal times and locations to planning the most effective routes to hit all the rides. They know that best viewing spot for parades and can often get behind-the-scenes access,” Stewart says.

36. Know each traveler’s preferred activity level

To ensure everyone on your trip is comfortable, gather preferred activity levels before you start planning, Al-Hazzá says. Just because something is too intense for some group members doesn’t mean a few people can’t partake. Time built in for individual activities will ensure everyone wins.

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INCORPORATING KIDS AND PETS

37. Ask the group about bringing Fido or Fifi

Before you tell your four-legged pal that they’re coming, make sure to clear it with the group. “I am a huge fan of traveling with my dog, but I am hypersensitive to how bringing her changes the dynamic of a group trip,” Stewart says. Equally important: “Make sure no one traveling with you is allergic [to pets].”

38. Follow pet rules

Though establishments are increasingly pet-friendly, many resorts, restaurants and vacation rentals still don’t allow animals. Some may allow pets but require that they aren’t left alone. “If the trip itinerary includes long days away from the accommodations and your pet cannot join you, then I recommend leaving them home with a caretaker,” Stewart says.

39. Look for pet-friendly amenities

If you are visiting a pet-friendly hotel, odds are it has some Fido- or Fifi-friendly amenities available. “It’s worth asking a resort if they offer pet sitting or pet walkers,” Stewart says. “Domestically, this is a rising trend.”

40. Don’t skimp on pet-travel preparations

Bringing your pet is about as involved as bringing your child. “They’re fur babies, so the preparation and planning is almost the same as with kids or grandkids,” Brophy says. That means making a packing list, checking accommodation rules, figuring out pet-friendly restaurants and ensuring up-to-date immunizations. Additionally, find a nearby vet in case of emergency.

41. Prepare for transit

It’s hard to know how your child will react to air travel, especially if it’s their first flight. But that’s no reason to skip your multigenerational trip or family reunion. “For little ones, book the overnight flight if you can,” Brophy says. “Travel is the most onerous with small kids. Just try to prepare the kids with activities and snacks beforehand. It makes a massive difference.”

42. Have a first aid kit

When traveling with kids, it’s critical to start your trip prepared. “Always have a kit with you full of stuff for anything that could go wrong, such as medications in case they get sick, bandages and Neosporin for the times they’re going to fall — which is bound to happen — a thermometer and a variety of foods in case they can’t tolerate the local food,” Al-Hazzá says.

43. Hire a local babysitter

Many hotels, particularly amenity-rich accommodations such as Omni Hotels, Ritz-Carlton and Beaches Resorts, either offer babysitting or day care services, or they can help you book a local babysitter. Inquire about these offerings via the concierge before you arrive to determine what works best for your itinerary.

44. Keep it simple

The simpler your trip, the less stress you’ll face — and that’s particularly important when traveling with kids, Brophy says. “Kids feed off your energy. Everyone in the group feeds off each other’s energy. If the schedule is not too rigorous, it helps everyone relax and have a good time,” she says.

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Stephanie Vermillion is a freelance travel journalist and photographer for publications like National Geographic, Outside Magazine, Travel & Leisure, and Vogue. She's the author of 100 Nights of a Lifetime: The World's Ultimate Adventures After Dark, which will be published with National Geographic and Disney Publishing in December 2024. She can be reached at StephanieVermillionStudio.com.