As I sat down to write this month’s fun HaveWind installment, I’ll admit to getting swept away in a little Halloween nostalgia, as it’s probably one of mine and Phillip’s favorite holidays. Fun fact about us: WE LOVE TO DRESS UP. While we are currently doing our proper Halloween diligence poking through thrift stores and scouring eBay to find the right—nay, the perfect!—accessories for our 2025 costumes I was inspired to share a few features from our HaveWind Halloween History. Before we dig into the fun, a little housekeeping as I know you all have been watching my new Author garden grow. Here’s what’s going down in AnnieLand.
What’s Going On Here at HaveWind:
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Now back to the HaveWind Halloween Goodness …
THE RULE: ALWAYS CARRY A COSTUME ABOARD
I think Captain Phillip—also known as Captain Stubing in this particular clip—said it best:
It’s true. You never know what you’re going to get into while cruising. Especially with us. I can’t tell you how many times Phillip and I dressed up aboard … AND goaded others into dressing up with us. We’ll get to the Boozer Cruisers, just you wait. That Love Boat is coming. But, let’s get some order going here. Start at the top.
2024: Evil Circus Ringmaster and His Naughty Tiger
Last year we had just wrapped our epic Outbound Rendezvous in Maine, and it was our first season to ever cruise in Maine as well, which was an experience so mind-blowing I shared it over several posts here (Portland, Camden/Boothbay, Bar Harbor/MDI). Maine was probably the pinnacle of our last few years cruising, the jewel in our east coast crown. It was such a lush, rich, rewarding experience shared with incredible friends with whom I know we have forged lifelong bonds. Many of the ladies I was always walking and bonding with on those gorgeous hikes in Maine are some of the very ones who encouraged me in my writing journey and were my first beta readers of Clovis. You know who you are. Thank you ladies.
After our summer in Maine came to an end, Phillip and I started making our way back down the east coast headed toward Norfolk, VA (Little Creek to be more exact) to Cobb’s Marina, where we were scheduled to have some pretty significant work done. We installed a brand new Northern Lights 6K generator last October, which I’ll be sharing here at HaveWind next. It was a sweet install. While we have celebrated Halloween in Norfolk before (it’s a fun place for it), this last year we scurried home to Pensacola for a rockin’ Halloween party with friends. You’ll probably remember our boat broker, Kevin—I toured his incredible 1982 Pearson 36 many moons ago here. He and his wife, Laura, made fabulous Halloween partners in crime. Phillip was an evil circus ringmaster and I was his naughty tiger. ROWR.
2023: I Dream of Jeannie and Major Roger Healey
Who dreams of Jeannie? We do! Phillip and I went for a pretty spot-on Jeannie and well … we had a little mishap with our costume accessories and Jeannie’s reputation suffered for it. Sorry, Jeanie. We were planning for Phillip to be Jeannie’s love interest—USAF Major Tony Nelson—but we didn’t Google it correctly or there was alcohol involved and Jeannie went off on a pretty public foray with Army Major Roger Healey. Whoops. But, fun was certainly had in Charleston. We often end a night there at the Cocktail Club—where the drinks knock even me on the floor—and were thrilled to find ourselves falling into this beautiful bouquet of Disney princesses there. Thanks for the fun ladies!
2022: Genie and a Fireman
Funny thing about that genie idea. It actually started in 2022, where we were staying on Ubi in Portsmouth, VA for about six weeks having generator work done (that’ll tie in later, trust me). They had this incredible thrift store there in Portsmouth that was stuffed with Halloween costumes. You could find that weird leather hat you need for a steam punk costume. Those red sparkle heels for a naughty nurse (or Dorothy from the Wizard of Oz—we prefer costumes, or just about anything, really, that does double duty). Even … a full length fireman’s jacket (that doubles as a mad scientist) and poofy blue genie pants (that double as M.C. Hammer). The costumes that year were pretty rag-tag, but that made them all the more fun. You’ll see the gold sparkle heels did pass the test for the genie outfit the following year. We teamed up with fellow Outbounders, Peter and Patty (featured here multiple times), in 2023 for an awesome Talking Heads cover band in Norfolk. It was incredible!
And, for even further proof we love to dress up, the four of us even did it completely outside of Halloween just to go skating in retro seventies getups with glow sticks and rave necklaces in Greenport on Shelter Island, NY when we were buddy boating then with P&P. I’m starting to think we have a little bit of a problem.
2020: Tiger King … and His Naughty Tiger (obviously)
In 2020, we had to be what everybody in the world was watching on Netflix (because everyone in the world was watching Netflix). Tiger King! Any time we put hair on Phillip, I lose it. The man rocks any wig. I’m not kidding. This mullet was a keeper. Keep an eye on that sparkly disco-style shirt. You’ll see it later, too. I mentioned the double duty.
2019: The Cast of Stranger Things
Annnnd what was everyone watching in 2019? You guessed it. Stranger Things! I made a pretty wicked Eleven—including her box of Leggo waffles (it’s all about the details), while Phillip and I roped our amazing friends Stephen and Beth into rounding out our Stranger Things crew. Jesus did we have fun that night, rocking things out in downtown Pensacola. Thank you S&B for making it a night to remember … as well as forget!
2018: Little Red Riding Hood
We call this one Phillip’s “run over dog” wig. It has actually played several roles: a wayward werewolf, that strange Wilfred character from the Daniel Radcliffe show Wilfred, and almost Joe Exotic’s mullet but we couldn’t quite stuff it right under the hat. In this one, its original purpose, it played the Big Bad Wolf grandma-style to my sexy Red Riding Hood.
Again, though, notice how Phillip really pulls off any wig. The man is a genius!
2017: The Love Boat’s Captain Stubing and Julie McCoy
Let the Boozer Cruiser portion of this Halloween tour begin! We did host two pretty epic, went-down-in-history, “Boozer Cruisers” back in Pensacola before Phillip and I really started cruising further and abroad. We would coordinate with 5-7 other boats in the anchorage where each boat would dress up and decorate their boat with a theme (including themed drinks or snacks that they served) and spend the evening dinghying around to everyone’s boats and enjoying the costumes, décor, and delicious treats. It was an epic event filled with memories, shenanigans, completed unexpected turns of events, surprise cameos, you name it. Our Boozer Cruisers were wild and something we will never regret having done. At one point we had 35 people aboard Plaintiff’s Rest. 35 folks on a 35-footer. That’s probably thirty too many, but we did it.
The videos from these crazy Halloween throwdowns pretty much speak for themselves. Several folks in the anchorage didn’t even know about the event until we settled on the hook and told them—one would be BaBaLu from the intro video—but they were able to participate in the tremendous fun. Why?? Because they followed Cruisers’ Rule #14: Always Carry a Costume Aboard. That year, 2017, Phillip and I dressed up as Captain Stubing and Julie McCoy from The Love Boat offering The Love Boat’s iconic cocktail “The Isaac” served on our “lido deck” (aka Plaintiff’s Rest topside). Only problem was, Julie kept losing pieces of her costume throughout the night until she turned into a puddle of business clothes in the cockpit the morning after. Like I said: fun was had.
2016: Baywatch’s Mitch and C.J.
This will probably be one of the most memorable Halloweens of our life, kicking off the Boozer Cruisers and introducing us to this wild cast of characters who hang out at Ft. McRee in Pensacola. Even in crazy Baywatch gear, we fit right in. We also ended the night on a total stranger’s boat. Some guy who just rolled into the anchorage and was happy to let us (and 30 of our closest friends) completely crash his boat and drink his booze. Now half the chicks were half-dressed, so that helps. But, damn did we have fun!!
2015: Pirates! Arrrgggghhh!
This is back when our cruising had just started and we were venturing around new parts of Pensacola—Pirate’s Cove being one. They hosted this kickass Halloween party that year and a fundraiser for the Point Yacht Club where little Author Annie (yes, I guess I have been doing this a while) hosted a book-signing to help with the event. Our long-time friends Brandon and Christine know how to do pirates, right — all the way down to the little ones. It doesn’t take much for any cruiser to become a pirate. Just add rum. Lol.
Again, fun was had. And, I have to admit to having a little nostalgic moment watching me way back then pursuing my writing and pushing my books. Go little books, go! If you really love to write, I guess you just never quit. For those who haven’t yet checked out Clovis, what the hell are you waiting for? Ha!
Halloween Circa 1988
Since we’re on the Clovis topic for a bit, here is a fun pic of me and my brother, John (known in the book as “Jude”) getting our Halloween on back in Clovis, New Mexico. That is one sexy little fairy and a fat hobo clown, circa 1988. Yeah baby! For anyone who knows me and my brother, though—or has read Clovis—you’ll know we should have swapped outfits. Hahahahahaa!!!
2025! Yeah Baby!
Which brings everything back full circle. While we’ve got several costumes planned this year (that’s not uncommon at all—I told you we treat this holiday like professionals), our first was a flamboyant disco duo where we teamed up with Brandon and Christine who were sexy pilots (anyone get the Capt. Striker reference Brandon sported on his name tag?) for a local Halloween bash. I’m pretty sure Phillip was assaulted by no less than six women who had to run their fingers through his incredibly tall hair. I’m telling you, the man can rock any wig. And, look, there’s that Joe Exotic sparkle shirt. You didn’t forget about it, did you? The double duty is key.
Hope you all have a fun Halloween planned yourself. What’s everyone dressing up as? Next up here at HaveWind, we’re going to share the immense list of work we did on Ubiquitous back in Cobb’s Marina in the fall of 2024–where Yours Truly stood in as project manager as Phillip was in trial. It was an interesting, arduous time and it includes the removal of our Fischer Panda generator for the install of a new Northern Lights 6K generator. Yeah baby! Stay tuned!
