By David Barclay | July 10, 2024

Multi-generational trips can be a great vacation option to bring together grandparents, parents and grandchildren, especially if family members are scattered around the country (or world) and don’t see each other frequently.
Planning a Multi-Generational Trip
While planning a multi-generational trip may seem straightforward, these trips generally require more thought and upfront planning. Multi-gen vacations typically involve a large number of travelers, spanning many ages, interests, and physical abilities. To ensure everyone enjoys the trip, it should be designed to provide flexibility and multiple optional activities to meet everyone’s needs.
A few considerations for a multi-generational trip:
- Plan well in advance: While you should start planning at least 6 months in advance, starting 12+ months out is even better. Generally, vacationers will want to reserve larger accommodations to host the entire family. These accommodations are more limited in number and tend to book up sooner. Also, with more travelers comes more input on where to go and what to do, and gaining alignment among family members on the trip vision can also take time.
- Consider trip costs & cost sharing: Who is paying for the trip and what they wish to spend on a trip should be decided up front, before the planning begins. If the grandparents/senior generation are paying for everyone, they may not want to spend the same $$/traveler that they might spend on their usual trips. If other family members will pick up part or all of their trip costs, it’s important to know what everyone wants to spend and plan a trip that works for all family members. If budget isn’t discussed and agreed to in advance, either some family members may opt-out when the final trip itinerary and budget is shared, or go on the trip but remain resentful of the cost.
- Make sure trip provides something for everyone: A good multi-generational trip provides lots of options for family members to pursue their interests. While the full family will want to participate in some activities together, it’s important to also provide opportunities for the family to break up into smaller groups, allowing them to explore their shared interests and spend quality time with a subset of the full family. A good trip will provide options across a variety of interests and activities (e.g. sightseeing, museum/historical site visits, cooking/foodie experiences, outdoor activities, kid activities & adult activities). In a typical day, the grandchildren might want to swim at the pool/water park or visit a children’s museum, while adult family members might want to visit an art museum, take a cooking class or learn the local dancing tradition. However, don’t forget about multi-generational experiences, maybe the grandparents will want to schedule a special activity with their grandchildren.
- Don’t over plan the trip: A good multi-generational trip has a combination of full group activities, sub-family group activities and free time/downtime. Unplanned time is as important or more important for large multi-gen trips than for couple/family trips. Planning nonstop activities is likely to wear out the family members (especially the oldest and youngest family members) and limits flexibility for family members to pursue their interest. With well-spaced blocks of free time, younger family members can catch needed naps or good old playtime, while the adults can explore on their own or recharge with a good book and a cold beverage.
Where To Go For A Multi-Generational Trip
There are many great options for multi-generational trips. The ideal location should be determined by the size of the travel group, the interests of the group, and what they want to get out of the travel experience (e.g. exploration of a new part of the world, or relaxation and more time to connect with family members). A well-developed trip vision to which all travelers have aligned will help guide the decision process on where to travel.
Resort Vacations

Resorts can be a great option for multi-gen travel. Depending on the size of the family, it may be possible to get a large suite or villa so everyone can stay together. Resorts are also great for larger families, with a plethora of rooms available to accommodate almost any size family. Resorts are a good option for multi-gen trips when family members have different travel budgets. Good resort options exist across a multitude of price ranges, and at a particular resort some family members can choose entry-level garden view rooms while others can opt for higher priced ocean view rooms or suites.
Which resort is the best option depends on the family members and the focus of the trip. If the family has many kids and teenagers, a resort with large pools and/or a water park can be a great fit. Families may wish to consider a resort like Baha Mar with its large waterpark, or the Beaches Turks and Caicos, which provides multiple pools and is all-inclusive, so family members don’t need to worry about dividing up the food bills.
Multi-generational families with children may also want to consider resorts with good kids’ clubs. The Four Seasons provides excellent experiences for younger family members with its Kids For All Seasons program. Some Four Seasons resorts offer expanded kid focused experiences. For example, the Four Seasons Jackson Hole offers the Kids Ranch for family members from 3-17 years old. Ritz-Carlton is also a great option for groups with many children, offering the Ritz-Kids program for family members from 4-12 years old.
Moderate-sized families (8-20 family members) looking to stay together in a shared multi-room accommodation might consider resorts that have many multi-room suites and villas. Garza Blanca near Cancun can offer up to 4-bedroom suites (including some penthouses with private rooftop decks) that can accommodate up to 10 family members. Casa de Campo has numerous villas ranging from 3-12 bedrooms to fit a variety of travel budgets, and with over 7,000 acres of resort property, it offers a variety of activities and opportunities for family members to pursue their individual interests.
Families looking for incredible food and elevated service might consider a higher-end luxury resort. Rosewood resorts (for example the Rosewood Mayakoba near Cancun or Rosewood Little Dix Bay in the British Virgin Islands) offer great on-property restaurants, many activities, a high staff-to-guest ratio, and butler service. Grand Velas Riviera Maya offers one of the best all-inclusive experiences in Mexico and is very family friendly. Jumby Bay, off the coast of Antigua, offers an exclusive private island all-inclusive experience, with many on-island activities and multiple themed dinners each week.
Big City Vacations

For multi-generational families looking for history, culture, and a plethora of diverse experiences, nothing beats a trip to a large city. Paris, London, Barcelona, and Berlin are just a few great options, with many non-stop flights from the U.S., for those looking to travel to Europe. Large cities can offer something for everyone, allowing sub-family groups to brand off and explore separate interests. They also provide flexibility for more traditional touring and exploring combined with opportunities to go off the beaten path for more adventurous family members. Within a large city, there will be many options for luxury hotels that cater to family and multi-gen family guests, including special programs and gifts for the younger family members.
Villa Rentals

Those families wishing to explore outside of a major city might consider renting a villa. While Italy and the Tuscan countryside is well known for villa rentals, villas are generally available in most parts of the world. Greece, Spain, France, and Switzerland are just a few options for countries with great villas and beautiful regions to explore. Villas are a great option for multi-generational families that want the flexibility to branch out and explore on their own. If the family rents a few rental vehicles, they will have the option to break up and explore in smaller groups. Many villas management companies can arrange for a private chef, daily cleaning, and pre-stocked refrigerators. However, villas also provide the flexibility for families to cook for themselves, with branches of the full family signing up for specific meals.
Luxury Cruise

The luxury cruise lines offer many great options for multi-generation families that want to travel well and enjoy a great vacation together. Similar to a luxury resort stay, a cruise provides families multiple opportunities to explore, since the resort travels with them. A few options that work well for multi-generational family trips.
- Ship with a Ship: Offered by a few premium lines including Celebrity Cruises and Norwegian cruise line, this cruising option provides many of the amenities of larger ships, but with the luxury of smaller boutique ships. The Retreat on Celebrity and the Haven on Norwegian offer private suites areas with a private pool, sundeck and restaurant. Guests are also able to access all other areas of the ships, offering more activity options for younger travelers and great dining variety at the multiple specialty restaurants. These lines can also be a good option for multi-gen families with varying travel budgets among the family members. Some family members can book the suites area while others can book standard staterooms. However, one watchout is that while guests of the suites areas are able to visit the rest of the ship, those staying in staterooms in the main part of the ship are not allowed entrance to the suites areas.
- Luxury Cruise Ships: Luxury ships offer a more refined experience that everyone can enjoy. Some luxury lines, while not focusing on kids/multi-gen families, are still able to provide a great experience across multiple generations of guests. Explora Journeys offers a kids’ club with activities for guests age 6-17. Its ships also offer numerous connecting suites, perfect for parents and children looking for a multi-suite option. Regent Seven Seas offers the Club Mariner Youth Program on select voyages (typically during school breaks) with one or more program counselors to manage the kid focused activities. Ritz Carlton Yacht Collection brings the Ritz-Kids program to the seas, designed for guests 12 & under.
- Expedition Cruises: Expedition cruises on a luxury cruise line can be a great option for multi-generational trips, assuming no family members have any meaningful mobility issues. Guests on expedition cruises tend to be significantly younger than on classic cruises and children are more common. Lindblad can be a great option for multi-gen family trips, as it is very family focused and has special kid programs/activities, including a few separate excursions designed for young cruisers. Other luxury lines are also very accommodating of kids since expedition cruise guests tend to skew younger and attract families (read about my family’s expedition cruise in the Galapagos on the Silver Origin). An Alaskan cruise can also be a great option, as it’s a popular cruising region for families during the summer months and most lines are accustomed to seeing to the needs of all ages of guests.
Chartered Crewed Boat or Yacht

A variation of a multi-generational cruise is to charter a crewed boat or yacht. Ideal for families with up to 12 family members (typically the limit for a chartered boat), a charter is completely customizable for your family’s unique interests. For larger multi-generational families, multiple boats/yachts can be chartered and sail together. There are many locations to sail, including the Virgin Islands, the Caribbean, The Bahamas, the Dalmatian Coast (Croatia), Greece (though summer winds may limit where you can sail), and Turkey.

David Barclay
Owner, Barclay & Company Travel
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