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Investor Spotlight: John and Lisa O’Toole

Investor Spotlight: John and Lisa O’Toole

Making Memories

For John and Lisa, the family memories they’ve made during their vacations with Equity Estates have been one of the biggest and best returns on their investment.

“From the time our kids were young to the past few years as they’ve grown up into adulthood, these trips have been like a magnet that brings us together as a family,” John says. “Traveling with our kids and having the most incredible vacations with them is an absolute precious gift. And, with Equity Estates, we have once-in-a-lifetime experiences together on every single trip.”

Though they will be empty nesters in the fall—Austin (25) and Ashley (22) have already moved away from home, and their youngest, AJ, will be heading off to college soon—John and Lisa are looking forward to this next phase in their lives, excited to take more trips just the two of them or with friends, but also happy that Equity Estates will continue to be a way for the family to connect and come together.

Stress-Free Travel

Whether it’s a quick getaway within the US or a longer trip outside of the country, John and Lisa say one of the main benefits of vacationing with Equity Estates is how easy and stress-free the entire process is, with everything taken care of before they arrive at their destination.

“All of the arrangements are handled in advance, so there’s no wait time. There’s no stress. No work to be done while you’re there because it’s all been taken care of,” says Lisa. “It’s nice to have all these things at your fingertips and not have to worry about anything.”

That includes having reservations made for meals and activities and also getting the grocery list before leaving for their trips, knowing that everything will be fully stocked when they get there. Having these things taken care of leaves time to relax and really enjoy each vacation.

John agrees. Before investing and traveling with Equity Estates, they’d sometimes feel they needed a vacation after their vacations. “But the personal travel concierges and local hosts make everything so easy, we actually come home from our trips feeling refreshed and relaxed.”

Favorite Destinations and New Experiences

Though they say it’s impossible to choose a favorite Equity Estates vacation, since all of them have been spectacular, there are a few trips that made a huge impression and several destinations that the family looks forward to visiting again and again.

Their vacation in Florence when the children were younger was especially memorable. From stunning views of the city and the Ponte Vecchio from the elegant third-floor Equity Estates apartment to the culture, food, shopping, and amazing excursions to Cinque Terra, Tuscany, Venice, and Rome, it was one of the family’s most incredible—and unforgettable—trips.

Vacations in Hawaii and the Caribbean are other long-time family favorites because they all love being on the water and spending time together boating, snorkeling and swimming.

This year, that love of the water took them back to St. John in March for more snorkeling and adventure, and where the highlight of the trip was a blissful day on the beach at the Lovango Private Beach Club, complete with a private cabana and an incredible chef buffet—an experience that Lisa describes as “heaven on earth.”

In April, they were back in the Caribbean for a first-time family vacation on the gorgeous island of Virgin Gorda, where they spent eight glorious days swimming, snorkeling, paddle boarding, and seeing the sights.

During their stay, they hiked to The Baths (a natural wonder of caverns, small caves, and secret rock pools), played on the beach, and had the opportunity to tour Richard Branson’s Necker Island. In fact, one of the family’s favorite Virgin Gorda experiences was visiting a different nearby island each day to explore and have fun and then have dinner there in the evening.

Another highlight of the trip was having a private chef come in to create two special meals for the family. Lisa explains, “We like to bring in private chefs (arranged by Equity Estates) for a welcome breakfast or dinner at the start of our trips or maybe for a goodbye dinner at the end of the vacation. On Virgin Gorda, we were able to get off the boat—all of us hungry—and go right in for a beautifully prepared meal already set out for us. Then, the next morning, I surprised everyone by having breakfast waiting as well. It was wonderful to have chef-prepared meals ready for us when we arrived and when we woke up.”

A Win-Win Investment

Both John and Lisa say that investing with Equity Estates is easily one of the best things they’ve ever done. They get to vacation in places they might never have thought to visit otherwise. They have amazing experiences in incredibly beautiful destinations. And they’ve created life-long memories and a love of travel for their children.

Best of all, after adding it up, John points out that the investment isn’t much more expensive (especially for a family of five) than what they’d spend for a nice hotel suite or extra rooms for their vacations, but they get so much more for their money, and everything is high quality.

Lisa calls it a win-win investment “because you invest with the possibility of a return on that investment, but you also get to stay in beautiful homes and have fun seeing the world in the meantime. We wish we’d invested sooner!”

Looking to the Future

The O’Tooles already have trips arranged for this year and next. Beyond that, Lisa plans to do a girls getaway for her birthday, they would like to visit some of the reciprocal properties in Europe (Puglia, Provence, Paris, and Scotland are at the top of their list), and they’re looking forward to revisiting old favorites and exploring new destinations on future family getaways.

“We’re all on our own journeys now,” says John, “so our vacations with Equity Estates will be a critical part of how we continue to come together and connect as a family. The homes are always perfect…and we know that wherever we stay, there will be enough space for everyone to spread out and have time to themselves but also have wonderful communal areas where we can spend time together.”

“Equity Estates gives us an anchor, a base, to explore more of the destinations we’re visiting and even surrounding places,” Lisa says. “And the homes are so beautiful, it’s always hard to leave.”

A Personal Connection

After nearly a decade with Equity Estates, John and Lisa are happier than ever that they made the decision to invest. Beyond the amazing destinations, amenities, and luxury homes to choose from, and on top of the family memories they’ve been able to create, it’s the personal connection that makes their relationship with Equity Estates special.

Their personal travel concierge and other members of the team have become like trusted friends to them, with their advice and trip-planning suggestions two of the things John and Lisa appreciate the most.

“Equity Estates is like family,” says Lisa. “It’s more than just a financial investment. The service feels personal.”

“The culture at Equity Estates is unique,” John adds. “There’s a kindness, and you can tell that they love what they do, which has a huge impact on our experience. Everyone is incredible, from the local hosts to the PTCs, all the way up to Philip. You know that they’re all there to help you and make you happy. And the fact that they have been able to create this internationally, in all of their destinations, is amazing.”