Enjoying Vacations & Trips


Vacations are breaks from life’s major routines.

Plan everything you can before you go on vacation.

A day trip doesn’t require much planning at all.

Learn a few tricks and plan a little before going into nature.

Multi-day trips require a bit more planning, often weeks in advance.

Your vacation starts when you leave your house.

Keep yourself safe in an unfamiliar culture.

Unless you want a boring experience, don’t stop at the guided tour.

Always end the vacation on a good note.

Why have vacations?

The broad purpose of a vacation is to remove yourself from the routines of life, though the destination will determine if it’s a relaxing, thrilling or enlightening experience.

The most rewarding vacations always come after you’ve succeeded at something huge.

You can have fun anywhere, but planning ahead can make your vacations and trips much more rewarding.

Before you start

Ask why you’re going:
  • Vacation planning is extra stress, so it’s only worth going to if you want to.
  • If you’re worried about losing something free you’d otherwise lose (e.g., an expiring timeshare), really reconsider your vacation.

Set a budget:
  • By setting a limit, you can recklessly spend up to that amount.
  • If your priority is to save money, don’t go on the trip.

Plan for the worst and hope for the best:
  • False idealism ruins your happiness as soon as you encounter any issue.
  • Before traveling, get a health checkup and immunization for anything from your destination country.
  • Even in the tropics it can get very cold at night, so pack appropriately.

Plan ahead as much as possible:
  • Start as early as possible to ensure you can schedule the time off and have everything you’ll need.
  • If your vacation will be around a major holiday, start planning a year ahead.

Keep everything trip-related in one place:
  • Destination, departing airport and airline, departure date and time
  • Any transfers or trips to a second destination
  • Returning airport and airline, returning date
  • Tickets and confirmation numbers for all travel arrangements and events
  • Contact information for everything

If you’re going with others, everyone should enjoy themselves:
  • Everyone has their own unique preferences, so only choose activities everyone will like.
  • If you need, schedule days where people split up to do what they prefer.

If you have children, keep them engaged:
  • Mind the extra costs and time associated with children.
  • Hold each child personally responsible to carry their own luggage, and have a plan if they lose it.
  • Surprise them during the trip with new toys or books.

Do as much work beforehand to offset the inevitable pileup of activities when you get home.

Day trips

Generally, a day trip that isn’t overnight won’t require much planning.

Get your local area’s most recent guidebook or tourist guide to find new things to do.

Always research beforehand (and make phone calls) to make sure the event or location will be open.

Consider what to take and consider the items the venue won’t allow.

Routinely open venues like museums, parks, zoos, and movies require practically no planning:
  • Go to the event, bring what you want, enjoy your time there.
  • Get a map of the location before you go to know what you’d like to try.
  • If you go to the zoo, wear the same colors as the zookeepers for the animals to come up to you instead of backing away.

Get a ticket for festivals, concerts, exhibitions and cultural events as early as possible, but make sure everyone has time off for it.

If you’re leaving your personal effects, store them out of sight:
  • Put your valuables underneath your car seat or in the trunk.
  • Hide money and smaller items inside an old lip balm canister.
  • Put larger objects inside a cleaned-out lotion or shampoo bottle.

Outdoor trips

Budget for gas money, parking, food, and entrance fees.

Research where you can dine out, or bring food and drinks for the whole trip.

Freeze gallon jugs of water for your cooler, then drink them as they thaw.

Keep matches and cell phones dry with condoms or rubber gloves.

Bring everything for a fire:
  • Bring lighter fluid (or WD-40) and matches or a lighter.
  • “Joke candles” (candles that you can’t blow out) work well to light a fire.
  • Use scrap paper or old rags as kindling.
  • Unless collecting firewood is illegal, don’t bring firewood.
  • Add sage to a fire to keep bugs away.
  • Make a Sterno container:
    1. Cut cardboard strips to the width of an Altoids tin’s height
    2. Densely wind into an Altoids container
    3. Fill the tin with wax

Bring everything you need to cook:
  • Learn how to cook before you must depend on it, or at least have a backup plan.
  • Propane or charcoal stove and a grill or griddle
  • Skewers, tongs, spatula, ladle, and knife
  • Dish set and silverware
  • Scissors and can opener
  • Tablecloth, if you want
  • Coffee/tea
  • Cooking spray, salt, and pepper

If you can, brush up on basic first aid skills before you go and bring a simple kit:
  • Rubbing alcohol and triple antibiotic ointment
  • Bandages
  • Eye drops
  • Pain reliever
  • Skin lotion

Make a portable hand-washing station with an empty laundry detergent container.

Bring multi-use supplies:
  • Duct tape is reliable for securing nearly anything.
  • Tin foil serves as a reliable moisture barrier, a wrapper for cooking food directly in the fire, folding as dishes to eat, a marker for navigation, and as a reflecting signal or firestarter.
  • You can also put tin foil on a pizza box to create a s’mores oven without a fire.
  • Paper and plastic bags, toothpicks
  • Dish towels, dish rags, and towels
  • Tissue paper
  • Extra batteries for everything
  • Twine, newspapers, and clothespins

Plan for a hike:
  • Wear good-quality hiking boots.
  • Bring enough water and snacks for everyone.
  • Closely observe the least physically active members’ needs.

If it’s nearby, visit a beach:
  • Always pack umbrellas or sunscreen.
  • Keep sand from getting on your electronics by using them inside sandwich bags.
  • Either bring a shovel to dig out a seat or bring beach towels, blankets, and beach chairs.
  • Jam a clean plunger in the sand to use as a can holder.
  • Bring kites, beach balls, footballs, frisbees or a volleyball and net.
  • Use a fitted sheet to keep sand out.
  • To keep your sandals from overheating, set them face down.
  • When you leave, sprinkle baby powder on things to remove sand when you leave.

If you want a more unconventional outdoor adventure, go beyond camping, beach trips or hiking:
  • Sailing, kayaking or canoeing
  • Surfing, paddleboarding or cycling
  • Fishing
  • Swimming
  • Target shooting with a bow or gun

An overnight camping trip takes much more planning than visiting for part of a day:
  • Honor the Leave No Trace guidelines and leave everything the way you found it.
  • Unless you’re experienced, bring your own shelter:
    • An RV is convenient, but it’s barely “camping”.
    • Bring a tent with stakes, sleeping bags, and pillows.
    • Use an air mattress with a pump or get foam tiles.
    • To minimize bugs, lay out a ground cloth (like a tarp) below you.
    • Find your shelter at night with glow-in-the-dark paint.
    • Pack the right clothes:
      • Wear synthetic materials like polyester or nylon (cotton absorbs moisture and wicks heat when wet), and bring an extra outfit just in case.
      • Keep multiple layers for nighttime.
      • If you plan on swimming, bring a swimsuit
    • While it may feel counter-intuitive, bring sunglasses and sunscreen.
  • Pack toiletries:
    • Toothbrush and toothpaste (dab toothpaste on a paper plate and let dry to make travel toothpaste)
    • Disintegrating toilet paper (or sandwich fresh leaves in between dead leaves)
    • Uunscented deodorant (to avoid attracting mosquitoes)
    • Prescription medication
    • Glasses or contact lenses case, saline, and lip balm
    • Camp soap (to avoid polluting the water)
  • Bring survival gear:
    • insect repellant and bite remedy (alternately, rub vodka into your skin)
    • Flashlight, headlamp, lantern, and fuel
    • Improvise a light by facing a light source on a jub of water (like strapping a headlamp inward or placing a mobile device under it)
    • Bucket, water jug, broom, and work gloves
    • Hammer, nails, saw, rope, shovel, ax, screwdrivers, and camp knife

Planning multi-day trips

Schedule time off work for the trip, and give 1-2 days if possible before and afterward to recover from jet lag and travel stress.

Arrange for everything in your absence:
  • Have someone watch your house and if you have a pet arrange for a sitter
  • Arrange for childcare if your child isn’t going
  • Ask the post office to hold your mail
  • Empty your fridge

Get the required paperwork done as soon as you can:
  • Verify your passport is current with the correct visas.
  • Get traveler’s checks or small denominations of foreign currency.
  • Most countries need cash, especially poor ones, but you can get by with bank cards in wealthier ones.

Learn the local laws and customs of the region you’re visiting.

Traveler’s insurance is always worth the expense if you’re visiting an unfamiliar culture, though a standard renter’s or homeowner’s insurance can cover at least part of the risk.

Reserve your transportation:
  • Fly if your trip is more than 1,000 miles away.
    • If you have two people, pick a window seat and aisle seat for the chance to have an empty seat in between (you can ask to swap seats with the middle person otherwise).
    • To keep your sleep cycle, schedule a night flight.
  • For shorter distances, avoid flying and consider alternate transport like trains or long-distance bus.
  • Arrange for transportation to and from the airport or depot.
  • Have a backup plan if you miss any flight or transfer.

Reserve your lodging:
  • Try to find places close enough to the events you want, but far enough away that you can afford it.
  • You can negotiate many things like hot breakfast in bed for free (if they offer a hot breakfast buffet) or a room upgrade.
  • For a unique lodging experience, try Unusual Hotels Of The World.
  • If you request it, the hotel can’t guarantee a king-size bed, so call to confirm and call the day before you leave.

Buy tickets for every event you can before leaving, and have a backup plan for the ones you can’t.

Plan a general itinerary:
  • While it feels like work, it lets you have the most fun.
  • Unless you rush it, you can usually only attend 3-4 attractions each day.
  • If you prefer, create a few lists instead of a day-by-day plan:
    • Must Go To, that you feel are critical for your vacation
    • Want To Try, which fill in gaps
    • Wish To Try, which will probably not happen

The week leading up to the trip

If you’re going to a different time zone, adapt your sleep schedule a few days beforehand, since even 1-2 time zones can disrupt your circadian rhythm.

When packing, only consider legitimate needs:
  • Most people over-pack because they don’t realize they can buy what they need when they’re there (e.g., toothpaste) or want to maintain their entire lifestyle while on vacation.
  • Only bring what you can’t live without or can’t buy at your destination.
  • If you can go minimal enough, bringing a carry-on will make life dramatically easier.
  • If you can’t carry-on a suitcase, avoid checking it at an airport and mail it to your destination after informing your lodging.

Make two near-identical lists when packing: everything you need to pack, and everything to verify when you’re ready to come home.

Pack everything into as few bags as possible.

If you’re traveling with others, mix each person’s possessions across checked bags to ensure a missing bag won’t ruin the vacation.

Make your bags distinctive to find them more easily in a pile:
  • Paint or print something on your bag
  • Tie a brightly colored cloth to the bag
  • Use a visually unique tag
  • Take a photo of the bag tag and store it on your phone

Plan for basic toiletries:
  • Soap, shampoo, and conditioner (though hotels often give them free)
  • Sunscreen, sunglasses, umbrella
  • Vitamins, prescription medications, decongestant, allergy medications
  • Toothbrush and toothpaste
  • Razor and shaving cream or electric shaver
  • Makeup, skin care products, nail trimmer
  • Hairspray, hair gel, hair dryer
  • Deodorant, cologne or perfume, body powder
  • Tissue packets, basic first aid kit, lip balm

Pack clothing:
  • Remember shirts, pants, shorts, jackets, sweaters, shoes, swimsuit, and hat.
  • Since tourists are prime targets for scams, wear clothing that makes you appear poor or middle-class for the region.
  • Fold your clothes in the same shape to make them stackable.
  • If you need more space, use packing cubes with vacuum sealing or roll into military-style cylinders:
    1. Fold in sleeves or flared ends to make a rectangle.
    2. Fold the left and right sides inwards towards the center, overlapping each time.
    3. Roll it up, then tuck it in to make it stay.
  • With longer trips, only pack 2-3 days with laundry soap and wash your clothes at your destination.
  • Pack extra underwear and socks.
  • To save space, roll socks and underwear into shoes.
  • Cover the bottoms of the shoes with old shower caps.

Bring fun distractions for the trip:
  • Deck of cards and pocket board games
  • Pens/pencils, notebook, puzzle books
  • Reading books, clip-on reading light, pocket flashlight
  • Laptop, mobile devices, music player
  • Extra batteries for everything
  • Power converter if you’re traveling internationally
  • Camera and charger
  • Snacks while in transit

Bring reference items:
  • Frommer’s Travel Guide, guidebooks from travel agencies, and paper maps for your destination
  • Pre-downloaded mobile device maps for the region
  • GPS unit or GPS-enabled mobile device and charger
  • Any necessary paperwork or documents like driver’s license or confirmation printouts

Bring any other conveniences or needs you want:
  • Battery alarm clock
  • Snacks
  • Luggage locks
  • Bags to hold dirty laundry
  • Pocket sewing kit

Before you leave, double-check everything:
  • Clean out all wallets and purses of anything hard-to-replace that you don’t need to bring.
  • Turn off the thermostat and set the sprinklers.
  • Lock all doors and windows.
  • Unplug all appliances and computers.
  • Set the radio, TV, and lights on plug-in timers
  • If you’re leaving your car at the airport, remove all valuables from it
  • If you’re not using it for at least a week, unplug your car battery and top off the gas tank:
    • Unplugging the battery ensures it won’t drain.
    • Filling up the tank both prevents moisture from building up in the tank and the seals from drying out.

A vacation starts when you leave your house

However, it isn’t stress-free until you get there:
  • Traveling to and from the destination can be stressful.
  • Keep enough paper literature to read.
  • Add a half hour to each deadline to permit room for error and time to relax.
  • Expose yourself to natural light at your destination to quickly realign your body clock.
  • If you must take a nap in a public place, prevent theft by strapping your bag to your body.

Make traveling comfortable:
  • To keep your blood flowing, stand up about once an hour.
  • To cut down on jet lag, stay hydrated and avoid alcohol.
  • Many hotels allow takkyu-bin, where they’ll send your luggage to its next destination for a small fee (i.e., another hotel or an airport).

Since the locals understand the area more than maps, don’t be afraid to ask people for directions.

Use the Las Vegas twenty dollar bill trick to ask for an upgrade to your room when you arrive:
  1. Increase your chances by arriving earlier in the day while they’re preparing rooms.
  2. Slip the desk clerk a $20 bill with your credit card when checking in and ask if they have any complimentary upgrades available.
    • Make sure other guests don’t see you do it.
  3. Generally, if they can’t find anything they’ll return the $20 tip.
  4. Even if they’re unscrupulous and keep the tip, it’s a $20 risk for a much nicer room.

While amenities like water bottles and wireless Internet often come with a fee, you might get them free by asking in advance.

If you’re not sure if your bed is damp, set a small mirror between the sheets for a few minutes to see if it fogs up.

Stay up until bedtime to realign your sleep cycle.

Don’t let your guard entirely down

Make your stay safe and fun:
  • Distrust anything peculiar or kind from other people.
  • Secure your wallet to your pants with a chain.
  • If you want a stranger to take your picture, give it to someone you know you can outrun.
  • If you ever happen to lose your phone charger:
    • Most hotels have a huge bin full of phone chargers other people have left.
    • If you still have a USB cord, many hotel TVs have a plug on the back.
  • The front desk clerk at the hotel often charges a reasonable rate to run errands, plunge toilets, tie bow-ties, deliver towels, and make breakfast.
  • Many “eco-friendly” options like opting out of cleaning your room are tricks to give the housekeeper less work, so ignore them if you want a clean room.
  • Housekeepers may steal from you, so keep all valuables with you when you leave each day.

Poor countries are notorious for crimes against tourists:
  • The people there can easily take advantage of tourists who don’t know the local customs or social standards.
  • You may think you’re fine because they’re doing something immoral, but they know how the law works more than you.

Watch service workers carefully:
  • Service workers like drivers, waiters, and shopkeepers might drop your change and pick up similar-looking but less valuable coins.
  • A cashier can appear to talk to you while also on the phone while trying to take a photo of your credit card with their phone to reproduce later.
  • A cashier might count painfully slowly for you to impatiently take significantly less change than you’re due.
  • A man claiming to be a doctor might offer papers for sale that he’ll claim will give a fraudulent insurance payout, but insurance companies are aware of this and won’t pay a claim.

Unsolicited kindness could be a scam:
  • Some people will give you something, and may even try cramming it into your hand, but do not take it unless you know the price.
  • Rented and for-hire cars are often conspicuous in undeveloped countries, and some people will puncture a tire, flag you down to help you out, then steal from you while you’re distracted.
  • Taxi drivers might offer free drugs to you, then later fake policemen will threaten to throw you in prison unless you pay a “fine”.
  • A taxi driver might offer to help you with your bags but will look like he’s in a rush and will drive off with one of your inconspicuous smaller bags before you can notice.
  • Generally, your safest bet is to have someone trustworthy as a paid guide.

Unsolicited kindness could also be theft:
  • If you seem confused at a cash machine, a man will help you out but will memorize your PIN for when he picks your pocket later.
  • Someone will drop a ring in front of you and ask if it’s yours, then will inspect it when you say no and say it’s real gold, then will charge more than it’s worth to sell it.
  • A pickpocket will warn you about people stealing cell phones and wallets, then watch where you instinctively grab for an accomplice to pick your pockets later.

Pay attention to how much you’re paying:
  • Often, many vendors in poorer countries will place the price at about 75 times a legitimate market price for the item.
    • They know they can exploit your feelings of guilt, but even while they look poor they’re still doing very well for themselves.
    • If you still feel guilt, direct your money to a legitimate charity or church in the area.
  • Some people offer cheap overnight bus trips, but will rummage through your bags and anything valuable while you sleep.
  • Some taxi drivers take intentionally longer routes or go the wrong way to exploit a tourist’s ignorance of the area to increase the fare, so get out if you see it.
  • Taxi drivers sometimes use altered meters that run a higher rate than normal.

Your driver might convince you that your hotel is closed down:
  • He might redirect you to another highly overpriced hotel in an awful location.
  • He might guide you somewhere else where a jeweler will offer you very cheap gems, but the gems will be worthless.

Watch for pickpockets in extremely crowded areas like trains, concerts, and train stations.

Mind what people do at your lodging:
  • Two men dressed as hotel staff will knock on your door for a routine room inspection, then one will distract you with conversation while the other will steal your valuables.
  • Someone will slide a delivery food service menu underneath a hotel door with no intention to serve food, then will collect your credit card information from the order you’ve placed.

Watch for “free” things:
  • Someone will forcefully start to make a bracelet on your wrist and then demand payment for it.
  • Someone charming will offer a rose to your girlfriend at an unreasonable price and make you feel guilty for not buying it.
  • Someone will drop their shoe brush for you to pick up for them, then thank you and shine your shoes in appreciation, then demand payment for it.
  • An old woman will offer a sprig of rosemary and say it symbolizes friendship and will try to read your palm, then demand payment and curse you if you don’t pay.
  • A friendly musician will offer you a free CD, then will demand payment and intimidate you with his friends.
  • If you’re lying on the beach, someone might offer a free massage and give a free sample even if you decline, then demand payment.
  • An attractive woman will approach a single man and ask if he wants to go to a bar or nightclub, then he’ll get the bill at the end of the night.
  • When you’re at a table, a man might offer free peanuts and dump a pile of them on the table, then will demand payment as soon as you touch one.
  • Attractive girls will want to practice their English with you and will return the favor by taking you to their favorite restaurants, then leave before the bill for an extortionate amount.
  • If you’re taking photos, someone may offer to take a picture of you and your companions, then either demand money for the service or run off with your camera.

Many beggars are con artists:
  • Attractive girls will want to practice their English with someone, then their story will turn into a guilt-ridden sob story and they’ll ask for help.
  • A small child will ask for a tourist to help write a postcard to family back home and make them feel sorry for him.
  • A large group of Gypsy children may surround and harass tourists until they give money.

If something is out of place, it’s usually for a reason:
  • An identity thief might call your hotel phone (usually in the middle of the night) claiming to be the front desk, then say there’s an issue with your payment and ask to verify your credit card information.
  • When someone sees a wallet on the ground, their instinct is to reach for their wallet to see if it’s safe, and someone will be watching to pick their pocket later.
  • While waiting in a ticket line, someone dressed in official-looking clothes may offer a higher-priced ticket to bypass the line, but the tickets won’t work.
  • Some beggars ask for change to learn where you keep your money, then will pickpocket you later.
  • Someone will hand you a broken camera and ask you to take a picture of them, then drop it as you hand it back when it doesn’t work, and will then demand payment or pick your pocket in the confusion.

Someone distracting you could be stealing your things:
  • Some street performers using a side-street cup game or magic trick to draw your attention, with audience members often accomplices to the theft.
  • Someone might subtly spill ketchup or bird poop on you, bring it to your attention, then offer to clean it off.
  • Someone might throw a baby or a doll wrapped like a baby at you for an accomplice to rifle through your bag.
  • Official-looking fake policemen will approach you and tell you about counterfeit money circulating and ask for your wallet, then look through it and steal some of your money.
  • Someone will try to sell you a map and unfold it in front of you to block your view while someone else picks your pocket.
  • Children pretending to be deaf will ask you to sign a charity petition and will pick your pockets under the clipboard while you’re writing.
  • Gypsy children will try to sell you newspapers and open them up to distract you while they pick your pockets.

Don’t stop at the guided tour

Tourist traps are expensive and unfulfilling:
  • Companies tailor everything as safe, predictable, reproducible experiences.
  • Some concierges are paid to recommend tourist traps, so ask the hotel clerk about local events.

Try new, unconventional experiences:
  • Wander around the local city center.
  • Meet people and talk with them.
  • Watch and observe how people behave.
  • Try the local food in off-the-path restaurants.
  • Drink in out-of-the-way bars.
  • Try a new food to create a permanent connection in your memory to the place.
  • Go to your most remote desired location first, so that the civilized place you return to is a comparative relief.
  • Even a vacation disaster can become an adventure if you change your attitude about it.

Turn off mobile devices:
  • Unplugging from others is liberating and fulfilling.
  • Escaping from life is the entire reason you had a vacation in the first place!

End the vacation on a good note

It’s always nice to grab a unique souvenir you’d never be able to get back home, but you can often have it mailed to you later by searching online.

Always clean your suitcases after staying in a hotel since bed bugs often travel in them.

Remember that you’re going on vacation to have fun, and you’re doing it right when you want to go back to your lifestyle afterward.