Travel Tips for a Badass Vacation

Give ‘em Dates and Cost

When planning a trip with friends, I almost always pitch 3 things: where I’m thinking, what specific dates, and roughly how much it’ll cost. For dates, I pick 3 times that work best for me, and send either one or two of them in my initial pitch; it gives people something concrete to look at, and skips the back and forward of trying to mutually pick a date. For cost, I either look up a hotel I want to stay at and give the cost for that, or average out hotels in the general area I’m looking to visit. Just the 2 pieces alone makes it soooo much easier for folks to be able to commit.

Location: Saving Money is Expensive

Don’t get me wrong, I love a good countryside retreat, but when it comes to vacationing, location is everything. It’s easy to balk at the higher hotel and Airbnb costs downtown and look at cheaper options closer to the suburbs, and I’ve definitely made that call before, too. But think of it this way- you’re visiting DC and you decide to stay in Virginia, maybe near Tyson’s; it’s a solid area, and there are decent food options, right? While you save a couple hundred bucks over your trip, you’re paying more with your time- it’ll be an hour roundtrip to any major attraction, meaning that the impromptu, “stumbled upon this fantastic place” encounters become so much harder, since your options are limited with $50 Ubers.

Daily Highlights

There are 2 routes you can go with a trip- on one side you have ultra planned, down to the hour schedule, and the other side is going with the flow. I’m a fan of having one or two major things each day- think scheduled excursions, or even a specific area of a city to explore. It gives folks something to look forward to, and gets around the “I dunno, whaddya feel like doing today?”

It’s a Special Occasion, So Let’s Eat

I like to either start or end a trip on a high note, usually by going out to a nice-ish dinner. I’m not necessarily saying to go for a white tablecloth restaurant and have a 5-course meal, but something in the $40-60pp range sets a special tone for the trip and reminds us that we’re here to treat ourselves. I’m always a sucker for a nice modern Italian place (modern meaning they don’t have Sinatra playing)

Cash is King… And a Good Backup

This is more for international trips, but you can solve most problems for $500. Don’t have to spend it, but I’ve been in the shitty situation of having to change accommodations last minute, and the joy of finding an ATM that’ll dispense USD while in rural Jamaica.

Picnics are your Friend

Some of my favorite travel memories are doing to-go lunches at Harvard Square in Boston or Central Park in NYC. Find a nice park and a nearby sandwich pace (not a chain, of course) and take it to-go on a bench. It saves some money on dining-in, gives a break from the hustle and bustle, and gets some fresh air at the same time.

Travel is Part of the Journey

When in bigger cities, it straight up takes time to get places, so I like to make an adventure of it. Take NYC for an example- why take the subway to Dumbo when you could take a ferry? People don’t usually commute via boat, and it gives a different perspective of the city. Or if you’re driving, find stops along the way to break it up; a friend and I drove SF’s Pacific Coast Highway, and the handful or so stops we took on our way to Big Sur were easily among the highlights of the trip.