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Free Vacation: How I'm Helping Families in Need to Get a Deserved Break

October 3, 2021 | by David Fine

Changing the world, one vacation at a time.

“What a terrible idea! Who is going to fund that?”

This was the response I initially received for my Free Vacation idea. Now finishing its second year, this project indeed has the potential to help fix the world.

Humble Beginnings

I eagerly devoured the biography of Rabbi Noah Weinberg, of blessed memory, founder of Aish HaTorah. I was eager to learn the secrets of his success. After all, being an alumnus of his college and someone who bought into his vision, I felt a connection with him.

Even though we never met, I watched his videos and made my decision to leave a successful sales career to go to his yeshiva in Jerusalem. After reading the book three times, I was passionately committed to do something concrete to make a difference. But what could I do? I wasn’t rich, I wasn’t a CEO and I didn’t hold a PhD. But these terms didn’t characterize Rabbi Weinberg either. I cared. I was passionate. I was struck by Rabbi Weinberg’s concept of taking responsibility for fixing the world. It is a value that my wife and I instill in our children.

I needed to take the first step and make the effort.

Charlie Harary has said that most people are waiting for the “ability” before they take on the responsibility. The Jewish approach is that you take on the responsibility first and then God provides you with the ability.

I came up with the idea of Free Vacation when a friend was telling me about his wonderful cottage. I felt very jealous. This was the beginning of Covid and we were all in lockdown. How many of us could afford to get out of our houses? How many families were stuck in the city? How many people lost their jobs and were struggling with mental health issues? How many couples were feeling tension and experiencing marital problems or worse?

My wife and I realized how badly people who were going through exceptionally difficult circumstances could use a break. We wanted to help those who were often forgotten about or got left behind. We would send families who couldn’t afford to get away to a small resort located a short drive away in the country for a 4-day vacation.

We were inspired in part by a story we read about the Rabbi Shlomo Zalman Auerbach, of blessed memory. The Rabbi once sent his assistant to deliver envelopes to needy families right before the Jewish holidays, containing money and tickets to the zoo. "Those children are going to feel terrible hearing everyone talk about their vacations. I want them to have something to talk about, and that is why I am sending them to the zoo.”

Free Vacation is Born

So, Free Vacation was born with a whopping $500. A pipe dream. But the Almighty leads a person in the way he wants to go. We decided to persevere with our idea even though it wasn’t an initial success. Hearing peoples’ problems and struggles was heartbreaking.

Three weeks later, donations ranging from $18-$1000 poured in from the community to fund our initiative.

I approached a dear friend, Mark Halpern, also an Aish alumnus and CEO of, who had an extensive philanthropic background, to partner in our vision. He helped us get a charitable status to be able to accept donations in order to issue tax receipts and then helped us raise even more money than we expected. We soon reached our goal. We partnered with a local resort who bought into our vision, and negotiated a discount rental rate for 17 low income needy local families ranging from widows, families with special needs or disabilities, single mothers, and people who were without work.

While many of us get to go on vacation to relieve our stress, build nice memories, bond with our families, and get a mental break, these families don’t.

One very special woman, a middle-aged widow, had been stuck at home during the entire pandemic. She had no car and very little family. She felt so alone and life was feeling very monotonous. We were able to send her to the resort and upon her return, her entire countenance changed. She was more relaxed and felt a renewed sense of energy.

Another woman we sent was a young widow with 3 children. She hardly had the money to pay rent, let alone send her kids to camp. She was up early in the morning with her children until late at night when they went to bed, spending all day at home. Life was challenging. This woman and her children desperately needed a break and a way to recharge. Spending time by the lake breathing in the fresh country air – it was exactly what they needed.

We implemented a system wherein people could nominate themselves or nominate someone else to receive a free vacation. We would look into their situation and determine the level of need. If they met our criteria, then we would call them with the big news – they were going away for a few nights to a local resort – for free! People were ecstatic – they felt as if they had won the lottery!

Incredible Feedback

Here is some of the feedback we received from participants who attended this year:

“This was the first vacation our family has taken in over a year. It has been a year full of stress of school closures, decreased finances, isolation. And the list continues. This year more than ever we needed a vacation, and you turned that into a reality for us. My husband commented more than once after we got back that he felt physically more relaxed as well as how much calmer and more relaxed I was!! It was a really beautiful vacation for our family.”

“Words cannot begin to express our family’s gratitude and appreciation for the week we spent at the cottage. It was such a pleasure to get away from the hustle and bustle of the city and be enveloped in the serenity of nature. My kids really enjoyed the swimming they did, the hikes we took, and the many games of hide and go seek that kept them busy for hours. The cottage itself was wonderful. It was very clean and was a perfect fit for our family. Most importantly, the time at the cottage afforded us the chance to spend quality family time together. Whether it was playing a board game, or swimming together in the water or even just sitting together eating dinner, we left that week at the cottage feeling with such an overwhelming feeling of togetherness and love.”

“It has been a difficult year financially, as my husband was out of a job. We would not have gone on a family vacation if not for this wonderful opportunity. Now my children can proudly report back to their friends that they also went to a cottage, something which they have only wistfully dreamed of in the past. Though it is over a week since we returned to the city, my kids are still talking about it and asking to return next year! You have given us a priceless gift of a wonderful time spent with family in a beautiful setting and we will cherish the memories forever.”

With Year 2 ending and another 17 families later, I now have a bigger vision. My dream is to build Free Vacation into a full time global online operation, for vacations in the summer, and Holiday breaks. I want to partner with personal support groups, mental health professionals, and other organizations (single parents, widows, handicapped, couples experiencing infertility), and fund their seminars and getaways. Free Vacation would handle all the logistics and bookings. Every time someone takes a vacation, they would donate to Free Vacation to give a needy person a vacation. We get vacations, these people don’t.

If you are interested in joining me in building a revolution email me at

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