The foursome were the picture of happiness as they strolled through the sunny Manhattan streets, and even their pet dog looked to be enjoying the ride!
It was indeed 'a dog's life' as their tiny pooch sat peering out from the bottom of the boys' stroller.
Being pushed along by his Hollywood A-lister owner, the family pet could not have looked more pleased with himself as he stayed cool in the shaded stroller, out of the midday sun.
Dressed in a cute yellow sun dress and stylish straw hat, Naomi, 42, enjoyed an iced coffee as she walked beside her son Samuel, who happily pushed himself along on his toy scooter.
But all eyes were on the boys' father, Liev, 43, as he was treated to a relaxing day with his family in advance of the bigger Father's Day celebrations, today.
And it would seem Naomi may have had her work cut out this year, as she revealed Liev had pulled out all the stops for her on Mother's Day.
Speaking to People magazine this week, Naomi confessed: 'He’s really set the bar high [with Mother’s Day] the last few years.
But it would seem she had yet to decide on exactly how she was intending to spoil Liev, admitting: 'So I’m going to keep thinking.'
One thing Liev can be sure of this year is a long Summer of relaxing, family fun.
Naomi explained that they are looking forward to staying home this year, telling People: 'We’re fortunate to have the summer off this year, but when you’re travelling so much, it just makes you want to not go on anywhere and just stay where you live.'