A 9-to-5er’s guide on making the most of short/weekend trips

1 - ca_state_capitol
California State Capitol Building, Sacramento, CA. Got to pay it a visit on a recent three-day weekend trip.

If you work full time in America but love to travel (like me at the moment), it’s important to be selective and strategic about satisfying wanderlust. For the most part, aside from the two weeks employees are allotted every year, travel time is severely limited: there are the holidays, weekends, and maybe three- to four-day weekends.

But if executed properly, a short trip every now and then can help quench a thirst for the desire to venture off into more distant territory.

Here are a couple of actions I find useful in maximizing short travel time.

Be selective about the dates of travel

Is there an airline sale where tickets are lower for departures on specific dates? For salaried employees, this can work out well, as most of these low-cost fares tend to fall on weekdays. Is a Friday or Monday holiday coming up? For hourly employees, it’s a good idea to take off on weekends like this and maybe even request for a day off the day prior to the weekday holiday. (Keep in mind, however, if you’re planning on flying, tickets tend to be more expensive around holidays.)

Carefully decide where to go

The distance of the destination is a key decision because it dictates the time it takes to get there. (Obvious example: two to three days in New York may not be the best place to go if you live on the west coast. Unless that’s absolutely the only time you have, it would probably be better to spend more time in the Big Apple.) I prefer destinations that are not immediately close by (like Northern California, San Diego, Las Vegas, and other places about that same distance away), but ones that are not ridiculously far. (Like New York.)

2 - lands_end_san_francisco
Paid a quick visit to Lands End in San Francisco that same weekend.

Weigh out transportation options

When it comes to picking a method of transport, there needs to be a compromise between time and money. With limited time, it’s probably a better idea to fly to San Francisco from Los Angeles (1 hour) instead of drive (6 hours) even if it costs a little more. Going to San Diego is about a 2+ hour drive, and that’s relatively inexpensive if you already own a car and if gas prices hover around $3.30/gallon (like they are currently in California). There’s also bus and train, but it’s a personal decision on what means to use, depending on preference and how much time/money you’re willing to give up.

Pack light

Waiting at baggage claim for a check-in bag for a quick trip is a waste of time, so stuff all your necessities into a carry-on. Since the bulk of what is packed are clothes, plan on what will be needed. Where will you be going and what will you be doing on the trip? Some essentials I make a point to bring are:

  • Leggings. I’m a big fan because they’re so light and versatile, so I typically bring two with me on weekend getaways
  • One pair of jeans. Don’t need more than that.
  • Blouses/T-shirts/Dresses. The quantity of these depends on what activities are planned. Going clubbing? One dress/blouse to pair with leggings or jeans. Going hiking? Two shirts for getting sweaty and a pair of appropriate bottoms. (Or, I’ll use one of the leggings.)
  • Shoes. One pair for outdoor activities (walking, hiking, etc.), one formal pair.
  • Pajamas. One set suffices.
  • Water bottle. This way, I don’t always need to buy water.
  • Small first aid kit. Doesn’t hurt to be prepared.
  • Plastic bags. These are so useful for dirty clothes, shoes, and other purposes that haven’t been discovered yet. (I think I have five in my backpack.)

Roll everything up so it fits nicely 🙂

Plan a budget

Write out how much you expect to spend on: transportation, accommodations, food, transportation, activities, and miscellaneous items. Overestimate everything so you have wiggle room. Here’s an example for a three-day/two-night weekend:

Transportation: $300 airfare/$200 train/$100 bus
Accommodations: $50 for a hostel (but you can probably find one for $30/$40) x 2 nights = $100 OR
Accommodations: $150-$200 for a hotel x 2 nights = $300-$400
Food: $20 per meal x 9 meals = $180
Activities: $150
Misc (groceries, booze, admission to museums/theme parks, tours, etc.): $100

TOTAL: $630-$1,130

This might all sound too expensive for three days, but remember these are all overestimated and there is a lot of flexibility in all of these costs. Transportation can go down drastically depending on where you’re going. Additionally, there are more affordable accommodation alternatives (ex: if you stay in a hostel, it is highly unlikely you’ll spend $20 per meal because you can cook food there), like if you have a friend living in the area, Air BnB, CouchSurfing, etc.

So far, I haven’t spent more than several hundred dollars on short trips like these.

3 - golden_gate_bridge_san_francisco
Also got to drive along the Golden Gate Bridge in San Francisco that weekend.

Create a rough and realistic itinerary

Life teaches us that things don’t always go as planned. When traveling, this is especially true. A flight might get delayed and you don’t get to see that show scheduled an hour after landing. Or a Greyhound bus stopped at the Canadian border for three hours, causing you to miss a connecting bus, leaving you stuck at the station.

One mistake I’ve made is disregarding the fact I’m not an infinitely-energized machine and that it’s nearly impossible to see 50 things a day each day. So pick the most desired sights/activities and set out to do those. It also helps in making the trip feel less rushed.

Quality over quantity 🙂

Don’t take work with you

This speaks for itself, but it’s something I’ve done and seen other people do. Unless absolutely necessary, leave work behind. It’s impossible to maximize a short vacation if the mind is elsewhere, worrying about matters that can wait when you return from a trip.

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