We keep hearing (and writing) that “travel is back,” and the popular themes are wellness, workations, and especially long overdue, rescheduled destination weddings. For some people, the reason never matters, but others occasionally need a little nudge like, “It’s National Margarita Day, so don’t you deserve a few days at the JW Marriott Cancun’s lobby bar?” If anything, it helps us treat every vacation like a holiday.
This came up earlier this summer in a conversation with 11 old friends as we debated dates for our fantasy football draft. As we enter year 21 of our league, I pointed out that we hadn’t had a real, in-person draft party in quite some time, so wouldn’t it be fun if we picked a cool destination so we can all catch up?
Turns out that’s a little tougher than we’d have thought. After all, most of us have families and careers, so it’s difficult to plan these kinds of trips for just a one- or two-day escape. “So, let’s make a thing of it,” I insisted. Eyebrows were raised and more questions followed. “Let’s pick a resort in the Caribbean so spouses or entire families can come, fun can be had, and vacation days can be used. Let’s put the party back in draft party!”
Well, it’s still a work in progress. This year’s draft was yet another Zoom call, but if I could head somewhere tropical to waste the 10th overall pick on Alvin Kamara, these are the resorts I’d highly recommend.
Sandals Royal Curaçao
The freshest resort in my mind, the newest property on Curaçao is a great choice for all the best reasons. For starters, the all-inclusive Sandals Royal Curaçao feels like it was designed to entertain groups (adults-only, sorry kids), with dining options and amenities that encourage variety and ensure the word boredom has no meaning.
Want to go big and have a draft that will possibly go viral but certainly be unforgettable? Book multiple Awa Seaside Butler Bungalows and make your selections in one of the private pools as the waves crash nearby. Or grab a few of the tables at the food truck pavilion so everyone can enjoy a variety of food options and the must-have mango margaritas while you laugh at that one guy who always picks the injured player.
And perhaps best of all, Old Quarry’s first hole tee box is just steps from those trucks, so everyone can grab a rental set and keep the fun going on one of the Caribbean’s most beautiful (and challenging) courses.
(Bonus idea: Draft off-site at Bklyn, a bar inspired by New York City’s rap and hip hop culture that also serves some awesome cocktails and snacks—just don’t be loud or you’ll miss the great music.)
W Punta de Mita
We all know that villas are immensely popular right now because they allow families and small groups to feel like they’re staying in a home away from home. (Also, they’re typically just flat out cool.) Now, if we’re talking about 10-14 adults, chances are it’s going to be tough to find something that large at a resort. Instead, I’d suggest finding the coolest villa from which to draft, and perhaps allowing the league champion to stay there. (That will probably earn some boos.)
A perfect example is the Extreme Wow (or E-wow) Oceanfront Oasis Suite at W Punta de Mita. This two-bedroom suite is one of the coolest accommodations in this popular Mexican destination, with a plunge pool and jacuzzi, as well as large windows that open to make this feel like a wide-open palace. It is truly fit for royalty… or at least a trophy holder.
Sonesta Maho Beach Resort
When friends ask me for Caribbean travel recommendations right now, my first pick is St. Maarten. Often overlooked as “that place you land” when visiting her neighboring islands, this Dutch slice of paradise has overcome serious adversity in recent years and deserves a spotlight for its emerging creativity. And with its size, style, and family-friendly atmosphere, Sonesta Maho Beach Resort makes for an ideal base camp, especially if kids are coming.
That’s because the Aqua Park, with its three slides, is simply awesome, but adults will also be thrilled with the resort’s massive Oasis pool, which will be the best place to relax the brain before all those difficult decisions are made. The draft, however, would take place off property at the Dutch Blonde Beach Bar, home of the Caribbean’s best beer.
Leagues that draw draft order on the night of the event could even use this bar’s escape rooms, with the fastest times earning the earliest picks.
Perhaps most recognizable to fans of The Bachelor, this resort is a St. Croix institution. Arriving here feels like you’re checking in to a really fun summer camp, as the spacious property includes a variety of outdoor amenities and activities that will make any group entirely pleased with the choice.
What makes The Buccaneer Beach and Golf Resort (now a part of the Trademark Collection by Wyndham) so enticing is easy—the beaches. Want to relax and catch some rays? Grotto Beach. Want to grab a snorkel or kayak and explore the water? Mermaid Beach. Want nothing but seclusion? That’s Whistle Beach, which is also home to the thing that makes this resort such a good choice: The Beach House. This six-bedroom accommodation is as cool as it gets in the U.S. Virgin Islands, and the pool is simply begging to be a draft party location.
After the last pick is made, everyone can tee off from the 18-hole course that boasts magnificent ocean views, and also has some very forgiving holes that will make players of all experience levels feel great about their games.
Aruba Marriott Resort and Stellaris Casino
Those of us who have played fantasy football for a long time tend to think about it a lot. Like, sometimes more than anything else. That’s why it wasn’t that unusual that as I enjoyed the incredible Atardi beach dining experience at Aruba Marriott Resort and Stellaris Casino, I found myself thinking, “Man, this would be quite a draft spot.” To be fair, though, that goes for a lot of spots on this property, which is why it’s such a good choice.
But, again, if this is the destination, I’m tempted to take the draft festivities off-property, because once you’ve had the Passion-Rita and Long Island-Rita at The West Deck, you’re going to want to live there. That’s not to say the food and drink aren’t terrific at Aruba Marriott—definitely among the best on the island—but it’s fun to explore and find those special places.
Plus, once the shuttle arrives back at the resort, the entire crew can hit the casino for some post-draft gaming.
Marriott Cancun Resort
I know a lot of people just want to keep things simple and head to a sports bar for wings and beers while they roast their buddies who chose Kamara over Saquon Barkley and Davante Adams, but you can still do that in a resort setting. Case in point: Marriott Cancun Resort’s Champions Sports Bar, which has TVs in the bar and dining area—ideal for those players who need hints from sports shows while everyone enjoys wings and burgers.
And the bonus is that you’re in Mexico, at one of the most entertaining resorts, so when you’re not drafting, the whole league can eat some of the best quesadillas and guacamole I’ve ever had at the SacBé Beach Shack, or everyone can meet up the final evening for a truly informative and delicious mezcal tasting.
(Yet another bonus is that this hotel is connected to the JW Marriott Cancun, which is home to the lobby bar with 150 margaritas. Even the guy who always finishes in last place can’t complain about that.)
Quivira Los Cabos
If your league mates are bringing families and/or golf clubs, you’ll want to head to the Pacific coast of Mexico and a resort community that is getting better and more exciting by the day. Not only is Quivira Los Cabos home to a course that recently landed on the World’s 100 Greatest Golf Courses—it should be top 10, in my opinion—but it boasts an ideal range of accommodations and phenomenal dining options.
Couples who leave the kids at home will want to book rooms at the adults-only Pueblo Bonito Pacifica, which looks like a luxurious sandcastle built on one of the most beautiful beaches in the region. Step it up and stay at the Towers at Pacifica, where adults are spoiled with 24-hour butler service—the only drawback is the constant noise of other couples celebrating the fact that they’re in paradise with no kids.
That’s not to say this isn’t a place for children. Quite the opposite, as families will love the space and amenities offered at Pueblo Bonito Sunset Beach. And if you’re in that villa mindset, Pueblo Bonito Montecristo Estates offers three-bedroom units with private infinity pools. There’s not a bad choice to be made here.
As far as drafting, I have two ideas: head to The After at Quivira, a truly fulfilling sports bar setting, or stay outside and enjoy the Cabo evening while grabbing snacks and treats at La Choya Wandering Kitchen. Then celebrate a decent draft with a round at the epic Quivira Golf Club, for which Jack Nicklaus truly outdid himself.
Reynolds Lake Oconee
All this talk about golf makes me think of only one U.S. resort community: Reynolds Lake Oconee. With five courses that guests can play (the sixth is private), it’s already one of the best getaway choices for families and small groups, but there’s an entirely different amenity here that would make for the best fantasy draft setting imaginable. Of course, I mean the Sandy Creek Sporting Grounds, which offers a variety of exciting outdoor activities, including archery, fishing, and an off-road course with awesome Land Rovers.
But the reason I’ve included everyone’s favorite southern vacation destination is the sporting clays—aka “Golf with a Shotgun”—which could make for the best draft pick lottery your league has ever considered. Each team manager could meet at the five-stand, which is a compact clay course, and the best scores dictate the draft order. An especially clever league member might even slip resident shooting champion Jasper Copelan a few bucks to make it a little easier.
As for accommodations, the Ritz-Carlton Reynolds Lake Oconee exists as one of the most luxurious lodges in the country, but families will definitely enjoy the various cottages in the National Club and The Landing, if they’re available.