Grand Cypress Resort in Orlando, Florida

Nearly 15 years ago I started a tradition that has been a great deal of fun and very rewarding – a “Buddies Golf Trip” with classmates from high school. After a few years with the high school guys I started a second golf group for my college friends with equal success. A few of the faces (and bodies) have changed over the years, but for the most part each group has stabilized into a really close-knit bunch. I just came back from my 7th annual trip with the college group, and many participants told me that it “gets better each year.”

Objectives: Social interaction, fun, good golf experience

My original thinking on the trip was to emphasize the social aspects. Opportunities to get together with old friends, great experiences at quality golf resorts, and lots of unprogrammed time. I wanted to keep the costs reasonable, so as not to scare anyone away, and the first couple of trips were really low cost. In fact, the first trip involved only 4 golfers, so we were able to share a timeshare week I donated, and we enjoyed a homemade Italian meal one night in the villa that my mother prepared and sent up with me. We had other meals, of course, but with a few groceries for coffee, fruit, and cereal, and we only needed to worry about transportation and a few meals. The golf itself was the biggest expense.

I lived in Florida (land of thousands of golf courses), and I chose Orlando as our first destination. Easy to get to, lots to do in the area, and reasonable prices for golf groups. For the first trip all of us were working, so the plan was to arrive on a Thursday night, play Friday, Saturday, and Sunday – and depart Sunday evening. That worked for everyone, requiring a Friday off work and a late Thursday flight. As the years went on, the group grew from 4 to 12, the distances traveled grew, and more of the group retired or partly retired. That opened up many more possibilities for us, but the biggest change was to switch to a Monday arrival and a Friday departure, with golf on Tuesday, Wednesday, and Thursday.

Nature of the Group

We were in our 60’s when we started, and now we’re in our 70’s. We’ve got some good golfers (7-12 handicappers,) but most men shoot in the 90’s. Looking at both groups….guys seem in pretty good shape. They’ve kept their weight down, they lead active lives, they try to eat properly, but Father Time is still undefeated. In recent years we’ve had hips replaced, knee surgeries, even open-heart surgery. Amazingly, they keep coming back and participating. (This year one guy called me to say he was getting a knee replaced a month before the golf trip, and he was afraid he might just have to follow us along in a golf cart. Another told me he had a serious blockage in his heart and was scheduled for triple bypass surgery ONE WEEK after golf! Both men showed up and played every round. But we all were watching the heart patient carefully – ready to call 911 if he should sneeze.)

I should add that he wasn’t completely reckless- he carried a thumb drive with all his medical records and a CD of his recent scans everywhere he went, just in case!

Finishing hole at Grand Cypress Resort in Orlando, Florida

My point here is that adjustments or accommodations need to be made to keep the outing relaxed and fun. We’ve moved up from the blue (and the white) tees. Most resort courses now offer different sets of tees, so you can choose a suitable distance for your group. In the early years I was looking for 6500-7000 yards; then the goal became 6000; now I think 5500 is about right for us. Also, I think three consecutive days of golf is just right for us. In the beginning three days was driven more by our need to get back home and back to work. Now it’s to keep it from becoming an endurance test. Sore backs and aching shoulders need a rest after three straight days of competition.

The other important rule we’ve adopted is to employ “2-man scramble” competition. In case you don’t already know, this means a 2-man team uses the better shot of their team on every shot. That is, each player tees off, and the better result is chosen. Both men hit the next shot from there, and play continues that way – to include putts. This usually speeds things up, since you don’t waste time playing shots from drop areas or assessing penalties for shots out-of-bounds.

“New Course” at the Grand Cypress Resort

I do my best to mix the foursome up and to maximize the number of partners. Mixing 12 players over three rounds is not a trivial exercise. In fact, the mathematics of it are pretty interesting. After struggling with that problem for a few years I discovered a free pairings tool offered by Golf Genius which can make this task easy. But ultimately, in three rounds the most you can achieve is playing with 9 different players in your foursomes (out of 12 people.) And you can only have 3 partners out of 12.

To increase the mix, we came up with the idea of switching playing partners (within the foursome) after 9 holes. You get more combinations that way, but it is mathematically impossible to arrange complete mixing of all players in three days of golf.

Time to visit, relax

The schedule that we’ve settled into looks like this: arrive Monday, get settled, BYOB reception in a large common area about 5 pm, then on to dinner (Orlando restaurants have no problem with separate checks which simplifies things.). On Tuesday included breakfast is early then golf starts around 8-9:00 am. After golf is free time. Sometimes we linger around the clubhouse grill getting some lunch and drinks. Some guys need to make calls, check messages, or shower and nap. Our accommodations normally offer pools and hot tubs which is a favorite afternoon activity.

Nothing is “mandatory,” but we always get 12 for dinner together. I usually select a mid-range restaurant that offers a wide selection of food choices and call for a reservation. One night might be seafood, one night a steakhouse, or Italian, or Pizza. I avoid fast food places or franchises, and instead look for good local spots that get high marks. After dinner it’s back to the villa for sports on tv, war stories, political debates, or calls home. For years I’ve joked about going “clubbing” after dinner, but nobody has taken that bait.

Good Golf, good food & drink

The key to success, I believe, is the social interaction of the group. Having lots of time to visit - hang together over a cup of coffee or a beer - has made our trips memorable. In both groups, even though we graduated together, we might not really know the golfer we’re playing with today. Four to five hours in a golf cart together gives you a unique opportunity to learn about someone.

As you would imagine, I’ve developed a “template” for all aspects of the trip. But after planning 5 or 6 trips I’ve hired an agent to help me. We tend to move around trying different courses each year, and my agent can do far better than I in finding good deals for golf packages. The agent I’m referring to is TeeTimesUSA.com, and I’ve been using them for at least 10 years. They give me quotes for lodging and golf packages for 12 golfers with three days of golf at a variety of resorts. We normally choose 4-BR villas for 4 nights lodging, and three different golf courses. I have actually tried to beat their prices myself by going directly to the hotels and courses, but I haven’t beaten them yet. As a big golf consolidator, they can offer some terrific deals. And their fee is just rolled into our package cost; it’s not an extra cost for me. (One recent example is a promotion offered by the Waldorf Astoria and the Ritz Carlton. Playing both courses produced a big savings over the ala carte prices.)

My college group has a different story. We discovered the Grand Cypress Resort on year 1, and we’ve been there ever since. Our package there is 4 nights lodging, 4 days of golf (although we normally only play 3,) and a full breakfast for 4 days. We have double rooms (2 men sharing,) large living rooms, a casual dining room, full kitchen, and we can walk to the clubhouse and breakfast. That eliminates driving to golf, and really allows you to relax and enjoy the beautiful grounds. They currently have 54 holes of Jack Nicklaus-designed golf, although recently they announced a huge construction job there to expand the resort. So for the next two years they will be closed to visitors. Next year we’ll be looking for another home. (UPDATE: in Nov 2024 we will go back to this location, now called Evermore Resort. It has had a huge renovation - new accommodations, restaurants, shops, golf, etc. We are hopeful we will like it as much as the original Grand Cypress Resort.)

54 holes of golf at Grand Cypress Resort

Not too serious

I learned over the years that guys really don’t come for the golf competition; it’s the reunion nature of the trip that brings them. Early on I had too much emphasis on the games; points, ranking, leaderboards, etc., and aside from being too much work for me, it was unnecessary. One year I even set up two fairly equal teams, and we played a Ryder Cup format. A fun change, but too much structure, and too complicated. Now I suggest that each foursome decide on their own game. Maybe winning teams wins lunch that day. If we switch partners after 9 holes, you’ve got other possibilities.

I still try to keep track of winners and losers, and I have some gag awards to give out at the last night’s dinner, like the “Best Jokes Award.” (This year I told the group that the “Stupidity Award” had been renamed to the “Courage Award” – given to the golfer who showed up to play despite the entire medical community advising him not to go.)

Photos and shirts, competition

There are a few things we’ve done that improved the trip or added to everyone’s enjoyment. For example, one year we decided to buy golf shirts in our school colors with our class year and a golfer’s image. When we split into two teams, we wore different colors. Another task, which fell to me, was to create a Trip Book. For us this became a photo book with the best photos from the trip. Obviously, this requires people to take some photos, and that often gets forgotten. I try to take photos throughout the trip, but it is easy to forget. One mandatory photo, however, is the “Group Photo” which normally happens on the first tee of the first day. Starters are used to this, and anyone with a cellphone can provide the camera. After the trip I collect all the photos I can, edit them down to the best ones, crop and color correct, and put together a Trip Book in pdf format. With each of my groups the book has gotten bigger each year. I put the newest photos on top over previous years, and the first photo in each year’s trip is the Group Photo. Before the next trip I print out the new pages, give them a 3-hole punch, and add it to the previous Trip Book. In the same binder I add the pairings for the three days of golf, and I bring the Trip Book to the resort. (The golf resorts will often print golf cart signs and annotated score cards if you provide the pairings. This helps them get the carts organized, and it helps the golfers find the right carts and partners.)

Some Lessons Learned

Set a firm date for next year

I always let the guys know the exact dates for next year before we break up. In addition, after I assemble the new Trip Book I send that out by email to the group with a reminder of next year’s dates. This is not 100% foolproof; some fool normally forgets the dates anyway, but it minimizes problems. I tried to keep to a reliable calendar event to help us all remember. With the HS group we picked one week before the Super Bowl; with my college group we picked the week of Veterans’ Day.

Have replacement golfers in mind

I was sure I was going to need a last-minute replacement this year, but it never happened. It has happened to me before, though, and I’ve learned to at least mentally select some guys to fill in at the 11th hour. Usually we’ve been able to find another classmate, but one year it was a neighbor. Not a classmate, but he fit in really well, and it gave us a even number for teaming.

Keep the event fun

As I mentioned, I was guilty of trying to build too much into the three days of golf. Fundamentally it’s social interaction that makes the trip – along with top-notch golf courses. I haven’t said too much about the courses, but I believe everyone wants to play outstanding golf courses. We can all find mediocre municipal courses back home. In Orlando we’ve played the Disney courses, the Waldorf, the Ritz Carlton, and the Grand Cypress, and there are many we haven’t played. Next year we are looking at the Reunion Resort, with courses designed by Palmer, Nicklaus, and Watson.

Good food is a must

Guys want to eat well, and although there may be different preferences, quality food is essential. The only real “complaints” I’ve gotten have been when the restaurant failed us.

Get help with the trip

I’ve mentioned the trip planning company which can take on part of the load in finding and booking the right lodging and golf arrangements. And I know there are firms that specialize in Arizona golf, or Carribean golf, etc. Some of your team can help out with the golf games or meals. I had a buddy who seemed to have more than a few suggestions as to how I could do the golf better – so I asked him to be the Commissioner of Golf the next year. He continues to do it, and he does a great job. Helps me a lot. A couple of times a few guys fixed dinner in the villa – either cooked by themselves or brought it in, and the results were great. Lots of work for a few guys, though, including a clean-up and getting enough china and silverware.

TAKE HOME MESSAGE

If you’re a golfer, you should arrange a buddy trip or take part in somebody else’s. It’s tremendous fun, and it’s wonderful to rekindle friendships from years ago. All of us look forward to this trip every year; some even put off heart surgery to take part!

PS: He did have triple bypass open heart surgery a few weeks after the this golf trip. He is doing fine today.