Beach resorts & villas
Kids’ clubs, calm water and villas with room for everyone, from Turks and Caicos to Maui.
- Best months
- Year-round
- Typical length
- 5 to 7 nights
- Best for
- All ages
Family & multigenerational
One person to call, and everyone gets a trip they’d choose.
By the Global Escapes travel team · Updated
- Typical length
- 5 to 10 days
- Best time
- School breaks, especially summer and the holidays
- Group size
- One family to 30 or more for reunions
- The pace
- Together time, plus everyone’s own adventures
- What we handle
- Rooms, flights, activities and one plan for all
- Great for
- Milestone birthdays, reunions and graduations
Trips that work for every generation
Grandparents who want a slow morning, teenagers who want a zip line, and the person organizing it all, who deserves a vacation too.
Multigenerational trips are some of the most rewarding we plan, and the most complicated. Different ages, budgets, mobility and interests all have to fit into one trip that feels easy.
That’s what we do. We find the villa or resort with the right room setup, line up activities for every age and handle the logistics, so the organizer gets to enjoy the trip too.
Where families love to go
These trips work beautifully for groups that span the generations.
Cruises
Unpack once, eat together, then split up for the day. Many luxury and river lines offer family sailings in summer.
- Best months
- Summer and holidays
- Typical length
- 7 nights
- Best for
- Ages 6 and up
National parks & ranches
Yellowstone, the Grand Canyon and Utah’s parks, with guest ranches and lodges in between.
- Best months
- June to September
- Typical length
- 6 to 9 nights
- Best for
- Active families
Costa Rica
Zip lines, hot springs, sloths and beaches, all within a few hours of each other.
- Best months
- December to April, and July
- Typical length
- 8 to 10 nights
- Best for
- Ages 6 and up
Alaska
A cruise for comfort, plus land days for wildlife and glaciers.
- Best months
- June to August
- Typical length
- 10 to 12 nights
- Best for
- All ages
Italy & villa stays
A countryside villa in Tuscany as home base, with cooking classes and day trips for everyone.
- Best months
- May to June, September
- Typical length
- 7 to 10 nights
- Best for
- Big groups, food lovers
Family safari
Family-friendly camps in South Africa and East Africa, with guides who love young explorers.
- Best months
- June to August
- Typical length
- 7 to 10 nights
- Best for
- Ages 6 and up
Ski trips
Ski-in, ski-out condos in Colorado, Utah or the Canadian Rockies, with lessons for every level.
- Best months
- December to March
- Typical length
- 5 to 7 nights
- Best for
- All ages
Theme parks
Orlando and beyond, with the right hotel, park tickets and dining reservations sorted ahead of time.
- Best months
- Fall and spring for smaller crowds
- Typical length
- 4 to 6 nights
- Best for
- Younger kids
When families travel
School calendars set the dates. Here’s where each trip shines.
DestinationJanFebMarAprMayJunJulAugSepOctNovDec
Beach resortsJan: BestFeb: BestMar: BestApr: BestMay: GoodJun: BestJul: BestAug: GoodSep: GoodOct: GoodNov: GoodDec: Best
CruisesJan: GoodFeb: GoodMar: BestApr: GoodMay: GoodJun: BestJul: BestAug: BestSep: GoodOct: GoodNov: GoodDec: Best
National parksJan: Off seasonFeb: Off seasonMar: Off seasonApr: Off seasonMay: GoodJun: BestJul: BestAug: BestSep: BestOct: GoodNov: Off seasonDec: Off season
Costa RicaJan: BestFeb: BestMar: BestApr: BestMay: GoodJun: GoodJul: BestAug: GoodSep: Off seasonOct: Off seasonNov: GoodDec: Best
AlaskaJan: Off seasonFeb: Off seasonMar: Off seasonApr: Off seasonMay: GoodJun: BestJul: BestAug: BestSep: GoodOct: Off seasonNov: Off seasonDec: Off season
ItalyJan: Off seasonFeb: Off seasonMar: GoodApr: BestMay: BestJun: BestJul: GoodAug: GoodSep: BestOct: BestNov: Off seasonDec: Off season
Family safariJan: GoodFeb: GoodMar: GoodApr: Off seasonMay: Off seasonJun: BestJul: BestAug: BestSep: BestOct: GoodNov: GoodDec: Best
Ski tripsJan: BestFeb: BestMar: BestApr: GoodMay: Off seasonJun: Off seasonJul: Off seasonAug: Off seasonSep: Off seasonOct: Off seasonNov: Off seasonDec: Best
Theme parksJan: GoodFeb: GoodMar: BestApr: GoodMay: GoodJun: GoodJul: GoodAug: GoodSep: BestOct: BestNov: BestDec: Good
Best Good Off season
Summer break
Peak time for beaches, parks, Alaska and Italian villas. Book 9 to 12 months ahead for the best rooms.
Spring break
Ski trips, Costa Rica and the Caribbean are favorites, and they fill early.
The holidays
Cruises, ski towns and warm-weather resorts are popular. Holiday weeks often book a year out.
Off-peak
If school calendars allow, late May, early June and late August bring better rates and fewer crowds.
How we make it work
The details that make a group trip feel easy for everyone.
The right rooms
A villa with a kitchen, connecting rooms or suites close together, whatever fits your group.
Something for every age
Kids’ clubs, teen activities and slower options for grandparents, with a few big moments for everyone.
Together and apart
Shared dinners and a group outing or two, with free time built in so no one is overscheduled.
Every pace welcome
Accessible rooms, private transfers and excursions chosen with every mobility level in mind.
One plan for everyone
A shared itinerary, and one person to call before and during the trip.
A day that works for everyone
- Morning
Slow start or early adventure
Grandparents linger over breakfast while the kids hit the water.
- Midday
Lunch together
One long table somewhere beautiful.
- Afternoon
Everyone chooses
A cooking class, a snorkel trip or a nap. No one has to do it all.
- Golden hour
Family photos
A local photographer captures the whole crew.
- Evening
The big dinner
A private dinner or celebration we’ve arranged for the milestone.
What we handle
- Rooms or villas that fit the whole group
- Flights and transfers for every household
- Activities and excursions for each age
- Special touches for the milestone
- One itinerary everyone can see
Nice to add
- A family photographer
- A private chef or celebration dinner
- Babysitting or kids’ club time
- Group travel insurance
- Matching welcome gifts for the crew
Destination spotlight
Costa Rica for the whole family
Zip lines for the teenagers, hot springs for the grandparents and sloths for everyone, all within a few hours of each other.
Explore Costa RicaGood to know
The small things that make a big difference.
Start early
For summer and holiday trips, 9 to 12 months ahead gives you the best choice of rooms and villas.
Pick a home base
Fewer moves means less packing and more time together. One or two stops is plenty.
Name a point person
We work with one organizer, then share updates and the itinerary with every household.
Plan for downtime
Naps, pool time and quiet evenings keep everyone happy, especially the youngest and oldest.
Check every passport
Children’s passports are valid for five years, and many countries need six months of validity left.
Insure the group
With more people, there’s more that can change. Group travel insurance protects everyone’s investment.
Questions we hear a lot
How far ahead should we plan a family reunion trip?
Nine to twelve months is ideal, and a year or more for summer and holiday trips with large groups.
Can each household pay for its own rooms?
Yes. We can set it up so each family books and pays separately, while we keep the whole trip coordinated.
What’s the best trip for three generations?
Cruises, beach villas, Alaska and Italy are favorites, because they combine comfort, easy logistics and something for every age.
Can you plan around mobility needs?
Absolutely. Tell us what everyone needs, and we’ll choose accessible rooms, transfers and activities to match.
Do you plan milestone celebrations?
Yes. Private dinners, photographers, surprise touches and special excursions are some of our favorite things to arrange.
Let’s plan the family trip
Tell us who’s coming and what you’re celebrating. An advisor will take it from there.