How to properly execute a long, fun weekend

Your IV host on the top-floor patio of New York City’s Whitney Museum

A long weekend is one of life’s true pleasures – and it most certainly has tremendous potential for getting you to the point where you’re having more fun than anyone else you know. The thoughts herein are therefore all about improving your “long weekend skills.”

Why are long weekends so great!?

Quite simply, long weekends provide for a break in the routine. They’re different, and different is good for the soul. They also have a “Before, During and After” effect. We get to anticipate the fun we’re going to have; we get to have the fun; and then we get to re-live and re-tell the stories about how fun is was.

How awesome is that?

Frankly, awesome enough that thinking through, writing down and sharing an official Intentionally Vicarious Amazingly Fun Long Weekend Process is something I must do. (After all, as the official IV guy, I’m already having more fun than anyone else I know!)

But before I get carried away… Let me acknowledge that we’re all unique individuals, and will therefore put a bit of a different spin on the details of the process, its proper execution and the overall definition of great long weekend skills. Cool! I love that. That’s how we all get better and better at having more and more truly great long weekends.

For the record, I just completed one of the best long weekends ever in New York City.

And yes, I’m claiming my bragging rights for it! I’ll share the itinerary and some detail at the end of this post, so you can replicate bits and pieces of what we did.

So here’s the outline of the IV Amazingly Fun Long Weekend Process:

  1. Develop a great plan
  2. Get out of town
  3. Be with people you care about
  4. Think hard about exactly what you want to do
  5. Food – Think Food – Eat Great Food
  6. Plan the next amazingly fun long weekend

1) Plan Your Amazing Long Weekend

I already mentioned anticipation. Working on a plan to have fun is fun in and of itself. AND it pretty much forces you to anticipate the fun you’re about to have. The steps:

  • Think hard about what you’d like to do and see.
    • Ask other people for suggestions. (friends, family, business contacts, etc.)
    • Search the web for ideas; Google “Things to do in XXXX; Use Trip Advisor.
  • Book a very, very full schedule (…with some built-in dead time – for new opportunities and activities that present themselves, to take a nap, whatever…)
  • Specifically plan things you will not do. (e.g., read e-mail, call the office, etc. On my recent Amazingly Fun Long Weekend in NYC, I watched exactly ZERO football. It’s been decades since I did that, and I did-not-miss-it!)
  • Do 4 days and 3 nights (If you have more time and money, do a real vacation. Otherwise make sure you have to leave before you want to leave.)
  • Write it all down! (Personally, I use my normal calendar to note what, when, where, addresses, phone numbers… Everything I need so I don’t have to hunt stuff down later.)

2) Get out of town

This is a break in the routine. Stay home or even in your hometown and you will get sucked into some aspects of your routine. You’ll end up having just a long weekend instead of an awesomely fun long weekend.

Pick a destination that intrigues you, even if you can’t explain why it’s intriguing. Break the damned routine!!!

Remember that airline travel sucks. It does. There’s no way to get around it, so plan for it. Me? I’ve got two foolproof methods that work for me. One – I bring my iPad with at least 5 books I haven’t started yet. Two – Airports and airplanes sell booze. (Sometimes I combine the two methods.)

Do NOT stay in a 1 or 2-star hotel. You’ll notice the crappy room every time you walk into it and worse yet – first thing every morning. 3-star hotels are fine for business travel, but if you have the $, opt for the 4-star room. In my opinion, 5-star hotels are a rip-off providing nothing more than phony accoutrements you think you’re supposed to like.

If humanly possible, pick a hotel that’s close enough to some of the stuff you want to do that you can walk to them. There’s nothing better than a walk through an unfamiliar city to make it more familiar and to suck in the local color and character.

3) Be with people you care about

This is hugely important! It’s no fun to be with someone when you’re thinking, “I hate his/her guts” half the time. Visit family and friends that live in the destination city. SHORT visits! (Check the photo below to see the awesome lady who saw fit to be with yours truly!)

BONUS TIP: Look up and old college friend. I’ve done this quite a lot and am always amazed at how I can pick up the friendship right where it left off – even if that was 40+ years ago!

4) Think hard about exactly what you want to do:

  • Do some things you traditionally like. (For me, that’s Museums, Symphonies, Theater and Sporting Events. For you it’s whatever it is.)
  • Walk around!!!
  • Do some things you don’t do very often. (Like go to a museum, a classical music concert, a Broadway play or a bull fight.)
  • Do some totally new/different things. At least one anyway…
  • Don’t do a few things – BREAK the routine!
  • Walk around – a lot!

The last thought regarding activities is to think in terms of creating new traditions. I’ve gone to a New York Philharmonic concert five years in a row now. I intend to go again every year for the rest of my life. It’s a tradition, and it’s awesome!

Food – Think Food – Eat Great Food

For me, eating at a great restaurant, or an unusual restaurant, or an iconic one or a whatever one is a blast. Treat yourself! For me, an Amazingly Fun Long Weekend includes at least one high-end great meal and at least one meal in some hole in the wall joint. (Check out the restaurants we hit this past weekend in the itinerary below.)

Plan the next amazingly fun long weekend

Re-read what I said about planning up above. Planning is fun. Planning an Amazingly Fun Long Weekend while you’re on an Amazingly Fun Long Weekend is even more fun.

BONUS TIP: Write down the places to go again and things to do again. Write down the places NOT to go again and things NOT to do again.

S0 that’s the IV Amazingly Fun Long Weekend Process. To review:

  • Develop a great plan
  • Get out of town
  • Be with people you care about
  • Think hard about exactly what you want to do
  • Food – Think Food – Eat Great Food
  • Plan the next amazingly fun long weekend

Central Park in the snow – Why this awesome lady hangs out with me remains a mystery…

My last great itinerary from 12/7/17 thru 12/10/17 follows. When’s the last time you did a trip this cool? Am I still having more fun the you? 🙂

  • Fly Atlanta to New York LaGuardia (About 90 minutes in the air to go about 900 miles)
  • Uber from LGA to the 4-Star Ameritania hotel (About 2 hours to go about 8 miles – recall the tip about books and booze…)
  • Meet my brother-in-law and sister-in-law (who live in Brooklyn) for dinner at Guantanamera
  • Share a drink in the hotel lobby bar and say goodbye
  • Crash
  • Breakfast at the decidedly hole in the wall Cosmic Diner (Try the 52nd Street Omelette!)
  • Soak in the Whitney Museum of American Art
  • Uber from the Whitney toward Lincoln Center and text with daughter number 1 who knows NYC to get a tip on where to have lunch
  • Lunch at the Landmarc in Time Warner Center on Columbus Circle
  • Hear the New York Philharmonic perform Mozart’s Sinfonia concertante in E-Flat major and Beethoven’s 5th, YEOW!!!!!
  • Dinner at Balthazar
  • Crash
  • Breakfast at Sarabeth’s (Bloody Marys so good you’ll wish you had a hangover!)
  • Walk to the New York Metropolitan Museum of Art (It was Christmas season, snowing and Central Park was simply spectacular!)
  • Soak in a few hours of The Metropolitan Museum of Art (The David Hockney exhibit was over-the-top cool!)
  • Lunch at Azalea (Gotta’ love the intensely over-qualified bartenders looking for that big break on Broadway)
  • See Wicked at the Gershwin Theater (The very first Broadway theater I’ve ever been in that had comfortable seats!)
  • Go back to the hotel and take a nap!
  • Dinner at Butter (Yes, you need to order the cauliflower entree. It was amazing!)
  • Crash
  • Back to the Cosmic Diner for breakfast (Lox & veggie omelette this time, Yum!)
  • Walk to the Museum Of Modern Art
  • Soak in MOMA
  • Uber back to LGA, and fly home to Atlanta
  • Defrost the chili in the freezer, pop a bottle of wine and relive this particular Amazingly Fun Long Weekend for the first time

Now get out there and implement your own vicarious.
Do it now and post that IV Score!