Looking to Brighter, Better Days

July 1, 2020

AKA: A refreshing post that looks to the future and doesn’t contain the phrases “in these uncertain times,” “webinar,” or “Zoom meeting.”

We’re still in mourning over the loss of 2020. Like many, we went through the stages of grief. For us, it was a little more extended and went something like this:

Shock, denial, drinking (the good stuff), anger, eating ridiculous (takeout) food, drinking, bargaining, cooking (seriously?), drinking, depression, testing, testing, testing, drinking (the… less-than-good stuff, because it didn’t much matter any more)…

The stages were going by at a normal pace, but after more than a month of our beloved bars, restaurants and airlines closed or shutting down, we lingered way too long in a few of them.

We were finally on the road to acceptance when the year turned even uglier and more tragic. And just when it looked like 2020 really was going to continue its not-so-slow spiral forever, we realized something critical:

This is the perfect time to plan 2021 travel because, contrary to the media’s popular belief, the show will go on. And we desperately need a getaway car lined up.

And the truth of travel is that the farther in advance you book airline tickets, the better the prices. The whole last-minute-deal thing is very 2010, alongside the phrase (but not the sentiment) “YOLO.”

So let’s start planning some *bleeping* warm weather vacations for next year, getting some housekeeping out of the way first.

Disclaimer: This post assumes that 2020 will indeed end, people will be safe, borders will open, airplanes will no longer be strange sights to see, and toilet paper and disinfecting wipes will flow like Evian water.

With that aside, let the planning begin.

Ground Rules: If you’re a beach flipper (c’mon, you know who you are), you may want to just take your fashionable resort wear (you can even default to the 2020 collection, since no one saw it) and head to Turks & Caicos. If your resortwear is more on the utilitarian side, head to Playa del Carmen or Tulum. And you can stop reading this post.

But if you’re instead looking for a little variety and activity with a side of much-needed humidity, we can help.

Normal people book vacations for five to seven days. Normal people also arrive at their hotels and take in the sweeping panoramic views of crystalline blue water, feeling happy, relaxed, and a little awestruck. Normal people don’t feel trapped in this new paradise and start wondering how they’re going to fill three, four, or even five days.

Clearly, we’re… Less than normal. So during our most recent five-day warm-weather getaway (in Costa Rica in March, on the cusp of the rest of the world hunting down TP), we were triggered to compare every destination: the pros and cons, which ones we would return to and why. We had nothing else to do. We hiked for hours each day, drank wine at lunch, walked the entire town, read several books, and were now incredibly busy watching a shirt dry.

Creating a list of destinations seemed more productive than starting the chalk countdown of days we’d been in captivity, or betting how long it would take for the shirt to be fully dry.


Why do people pick the locations they pick? What is it that really gets you excited about a place or a hotel? Since I’m talking about “normal” people, so we can only speculate. For us, there are criteria:

  • Doesn’t have to have a beach, but water is preferable.
  • Needs to have a better than 75% chance of sun and light. For me, my skin and I crave humidity in the winter—it’s a restorative necessity when the Minnesota wind has sucked all the moisture out.
  • Cannot, under any circumstances, involve a cruise ship in any capacity (we’re thrilled that more of the population will be on board with this opinion now).
  • Cannot be an all-inclusive resort (we like options and an exit strategy).
  • Needs to have something to do. We’re all for relaxation (well, not really), but give us a hill, a bike, some fishing, some culture, history, architecture, a great small town. Something. Anything.
  • Direct flights are best, but some of our favorites do require a Chick-Fil-A stop through Atlanta (when you frame a layover this way, the connotation improves dramatically). Although we should note that getting to one of our favorite spots (Belize) employed an unprecedented three airplanes, with four stops and one particularly adventurous leg in the co-pilot’s chair.

We like interesting, unique hotel experiences and great local restaurants, but sometimes you’re just asking for the impossible. Getting this, with all the above, is what we in the biz (the wine-drinking, travel-loving biz) refer to as a “unicorn.”


Mexico is usually an easy go-to, with short, direct flights and plenty of cool culture, but there are only a few places we’ve found that are both safe and not crawling with beach-flippers.


For hotels that are higher up and give those stunning vistas that you’re probably on the lookout for, La Casa Que Canta or Tentaciones will do the trick. Both are within walking distance to an actual town, with that elusive actual-town charm and decent restaurants, and it’s good exercise.  La Casa is on a hillside with incredible views. Tentaciones is even higher with better views, and boasts two great restaurants. It also may be the smallest (four – five rooms), most personal, and most cost-effective hotel you may find… Possibly anywhere.

If you must be right on the beach, Thompson Hotel isn’t a bad choice, but defect at dinnertime to eat at the restaurants of the above.

San Miquel de Allende:

Another actual town with plenty of color and charm, with the negative being that there’s no water except the hotel pool. But the weather is ideal: warm during the day a little cooler at night. For flights that have to go through Mexico City, it’s worth staying there for a few days to eat your way through what’s a burgeoning food destination. The Rosewood is the move for hotels; it’s in a great location and has amazing details in the new property with a rooftop view for days.

San Jose del Cabo:

Let us be clear: This is not Cabo San Lucas. This is the legitimate town, with small shops and a town square. If you stay at the Viceroy, which is on the beach, it’s an easy walk into town. There are a of other pricey hotels on “the corridor,” (Esperanza, Montage, Las Ventanas) but the beaches are a bit rockier and you have to drive to get into town.

Central America:


The further south you go, the more you really get away—but you also add more puddle-jumper flights (sometimes sitting in that aforementioned co-pilot seat—FYI, we are not actually qualified for that). Our favorite spots in Belize are in the forest reserve, jungle, or beach side further south, away from Ambergris Caye and into Placencia or Punta Gorda. Staying at the Gaia Riverlodge, Copal Tree Lodge (spring for one of the signature canopy suites to make this one worth it), or one of Francis Ford Coppola’s getaways makes this kind of trip magical.

Costa Rica:

Most people head to Peninsula Papagayo, the Four Seasons, or the Andaz—and there is absolutely nothing wrong with these spots if your idea of a good time includes golf and monkeys.

We prefer Las Catalinas and Casa Chameleon, where you can peel yourself out of bed to spend the mornings hiking off last night’s tequila and you can combine views with beach options.

South America:

Do not discount South America. Even though the flights are longer, it’s still the same time zone (handy, and means no time wasted on adjusting), and longer flights (like to Argentina) are often overnight. And our new favorite (Colombia) is only four hours from Atlanta and that handy Chick-Fil-A. Cartagena gives those tropical vibes while still bringing in South American culture, and Tayrona National Park should definitely be considered.

Puerto Rico:

And last but not least, let’s not forget Puerto Rico, in a class of its own.  San Juan is an incredible city (especially when the cruise ships aren’t around) and it’s always a great time to support this incredible place. Our favorite spot to stay is in Condado, where it’s an easy walk into old town San Juan, and there’s great access to all the incredible restaurants (thanks to Chef Jose Enrique, Jose Santaella, and others).

To stay, the Condado Vanderbilt is the big, old dog, but we prefer O: LV Boutique Hotel, or the more reasonable and brand-new Serafina.

Stay safe—but go forth and wanderlust.  The show will go on.

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