Maui

Recommended by Amy

in response to Brigid

70th birthday family trip destinations! My dad is turning 70 at the end of March, and we want to go on a family trip. It will be my parents’ 40th anniversary a bit later, so a nice time to celebrate. There will be 7 or 8 adults and four children (6, 4, 3, and infant). We generally like getting a large VRBO/AirBnB with a good kitchen, and folks are open to international with direct flights from Chicago. Please share your favorite destinations or specific homes that can accommodate a large family. We’ve traditionally enjoyed beach vacations in Sanibel/Captiva and Watercolor, Florida or Hilton Head, but beach is not required.

Visit

It’s such a wonderful place for all ages! Great weather, beautiful beaches and sights, lovely community, and plenty of places to stay. I went with family ages 2.5-75 years old, and everyone had fun. My daughter highly recommends the butterfly farm. ❤️

Places to Go

2 months ago

Comments

Brigid

@brigidAug 21, 2026

This would be so dreamy, but a tough sell on the flight options based on a previous try to make this trip happen. I think this one might just be a me + my parents option for a future year. I keep floating Hawaii, and someday, it will take.

Maui

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