A Shared Wanderlust
Equity Estates Fund V Investors, Holly and Craig Wood, have always loved to travel and explore new places. Both grew up in the Midwest — Holly in Chicago and Craig in Kansas City — before meeting in Tampa where they were both working their first jobs.
“After we started dating, it was Holly’s mom that highlighted that her name would be Holly Wood if we married,” says Craig. “And the rest is history.”
The couple have now been happily married for 31 years and have two adult daughters who share their parents’ love of travel. The oldest is currently living overseas and the youngest is in Boston, working as a fundraising consultant.
“We’ve always had wanderlust, from our early days as a couple,” Holly shares. “After moving to over nine states between us, once we had kids, we stayed put in Chapel Hill, NC to raise them before moving again to DC and then to Chicago where we’ve been for the last six years.”
During that time, they’ve traveled for family vacations, trips with friends, alone, and together. They also spend about four months each year living and enjoying the community in Marco Island, Florida.
Typical Year of Travel
Though their travel plans may vary from year to year, the Woods always make time to visit new destinations and familiar favorites whenever they can.
“Travel is our love language, and we do as much of it as we can, schedules permitting,” Craig says. “We usually use the Equity Estate days to take trips with friends and then do a non-Equity Estates trip with our girls since we usually meet them somewhere in Europe while our oldest is overseas.”
“When our overseas daughter is in the states, we make a point to use Equity Estates with both girls, including recent trips to San Diego and Montana,” Holly adds.
Holly is now retired, and Craig is CEO of a private equity-backed technology company, which allows for more freedom and flexibility in making travel plans. The investment in Equity Estates has also helped.
“We are traveling more now since investing with Equity Estates,” says Craig. “The convenience of planning the location, activities, and meals is just so much easier working with the EE team. And knowing that you need to use your days really takes the pressure off the whole decision.”
The Decision to Invest
The Woods say they discovered Equity Estates a few years before deciding to invest. They were invited by a friend (who was already an investor) to vacation at one of the residences, and that trip piqued their interest. After hearing how happy their friend was with his investment, they decided to do more research into the company.
“The business model behind Equity Estates resonated strongly with us,” Craig recalls. “The chance to explore so many different destinations with luxury accommodations and service — all while investing in a fund that would provide meaningful returns over its life. It was exactly the solution for our collective wanderlust and investment priorities. So, we decided to take the plunge. Needless to say, we are so happy that we did.”
When asked what they like best about their investment and traveling with Equity Estates, they have a hard time choosing just one thing. “We love it all!” says Holly. “The convenience, the locations, the service, the 21-day out spontaneity, all of it.”
Craig agrees. “The personalized activities are truly amazing. You just don’t get that everywhere. The houses are absolutely gorgeous; You always know that they will be up to a certain standard. We like to say that Equity Estate is affordable, approachable luxury, and you can make it what you want.”
Spa Treatments and Private Chefs
Now that they’re traveling with Equity Estates, Holly and Craig say they always make time for the in-house spa treatments wherever they go.
“It’s such a luxury and really makes us feel like we’re on vacation,” says Holly.
They also like to take advantage of the private chef services in every destination, enjoying the fact that they can stay in for a relaxing night and know they’ll have a nice dinner at each of the homes they visit.
While they say that all of the chef experiences have been memorable, there are a few that stand out.
“Holly usually likes to have the private chef drop off a pre-made meal for us on the night we arrive,” says Craig. “But in Cabo, the chef was there waiting with margaritas to welcome us and then cooked dinner. It was such a great experience, we had another private dinner in the home during that stay, and that time, a guitar player came and played while we dined.”
“The meal in St. Johns also felt extra special,” Holly says, “with the amuse-bouche served on the terrace as the sun set. And there were small, extra things we weren’t expecting. The private chef services really feel like we’re pampering ourselves.”
Special Memories
Every vacation brings its own special memories, and the family’s trip to St. John — the first they took after becoming investors — is no exception.
“I had never been to the Caribbean,” Craig says. “What an introduction. The house and entire experience blew us away. The spa treatments, the chef, and we did a private boat one day. Everything was so perfect. The sunset from that house is one of my special memories.”
Another memorable trip was the one their two daughters organized for Big Sky to celebrate Craig and Holly’s 30th wedding anniversary.
“They worked with our concierge to plan a very special long weekend as a family — we just had to show up and enjoy being pampered,” says Craig. “Creating family memories like this is the intangible benefit of an Equity Estates investment — a benefit that extends well beyond the life of the fund.”
Recently, the couple vacationed in Virgin Gorda and had an amazing time exploring, relaxing, and making new memories.
“I always say the last destination and last Equity Estates home we stayed in is my favorite,” says Craig, “But seriously, Virgin Gorda really might be the favorite.”
“I love that we were on an island, but the restaurants still had amazing food, our beach was amazing, and I even spotted several turtles while snorkeling right off our beach,” says Holly. “The concierge service with William was the best, and going to Necker Island and getting to see and touch the animals was a highlight.”
Future Trips and Bucket-List Vacations
Though the tropical paradise of Virgin Gorda was a first-time destination for Holly and Craig, the trip planned after that to Snowmass was one they were looking forward to for a different reason.
“Snowmass is a special place for us because we grew up going there,” says Holly. “But this will be our first time going with Equity Estates. We’re looking forward to that experience and another amazing adventure.”
The couple both say they’d like to take a safari with Equity Estates one day, as the itinerary “always looks amazing.” Other properties on their bucket list include Paris, Belize, and Costa Rica.
“We haven’t explored the international locations as much as we’d like,” they say. “But that’s definitely to come!”
