The Perfect Trip is Possible: Here’s How (A Series)

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Do you fancy traveling in 2020? I’m in the middle of planning the logistics for a trip to Italy in late spring, and I’d love to share my top planning tips with you! 

These are tried-and-tested ways of making a trip worth taking, but one that won’t stress you out so much you can’t enjoy it once you’re there. And no vacation should be more stressful than your daily life. 

Today’s is the first post in a short series about how I plan amazing trips for my family and friends that are affordable and fun! 

Plan your Dream Trip Now

First we need to start with the absolute basics – where are you headed, who’s going with you, and what’s your budget? From these three questions, you’ll learn how to set up the basics of your best trip ever.

Where are you going?

This is important! Are you a beach person? Mountains? Adventurer? Shopper?  Do you like cities or the country? Are you comfortable driving in urban areas, or will you be limited to what you can access via public transportation and ride share?

Look, I’ve been doing this travel planning thing for a couple decades now, and I’ve learned that people really don’t stray that far from their “type.”  If your best friend hates crowds, she isn’t going to enjoy being crushed trying to see the Mona Lisa in the Louvre.  If your husband hates hiking, he doesn’t want to climb 350 stairs to the top of a bell tower.

Further, when are you likely to go? For years, my husband and I have been relatively attached to the school year schedule due to our jobs. We have a bit more flexibility now, but for the most part we had to avoid any trips which would have taken us away from the classroom for more than a week, and anything in May or August was definitely out.

The seasons matter too. You can get much cheaper tickets to Europe on the “shoulder” seasons (spring / fall) and in winter (if it’s not the holidays), but do you want to tromp around London in the cold rain in February?  Consider what you’re “saving” with a $300 plane ticket in the off-season if none of the museums you want to see will be open.

Tip: Do your research about a city before setting your travel dates. Remember that holidays bring crowds. Off-season dates mean many local shops and attractions will be closed. 

Part of the fun here is figuring out where you want to go, and that calculation includes

    • the preferences of the people traveling
    • your likely season for travel
    • airfare costs and trends for the region you’ll visit
    • how long you’ll be gone
The Catalan flag flies over the beach in Sitges, Spain during our trip in June of 2018.

Who are you going with?

We’ve found that traveling as a couple is delightful, and traveling with friends is even better.  Whoever you love spending time with, do some thinking before deciding they will be a good fit for an extended trip.

Before inviting your friends and family to join you, ask yourself (and them) some basic questions about your travel compatibility.  You want to travel with people who share enough similarities and preferences that you can all have a good time together.

This isn’t an exhaustive list, but it’ll get you started:


    • Type-A Control Freak: Plan it down to the tiniest details, see everything, fight over lots of small stuff. One Type-A can be a great logistics person; two Type-As need to divide responsibilities and agree not to complain about the other’s plans the whole time.
    • Whatever, Man!: Just tell me where to put my stuff. I’m down for whatever, really. ( I’m also not interested in planning or details, so please don’t ask me to make decisions for the group or decide where we go next. )  Too much passivity can make for a boring trip, but the Whatever! travelers can be a buffer between the Type A’s.
    • Deceptively Invested: Acts like they’re a “whatever, man!” traveler but really they’re more of a Type-A Control Freak. Unpleasant discovery if you’re already traveling together. Your pre-trip discussions need to uncover this tendency before you hit the road.  Lay some boundaries about who’s setting up travel arrangements and how the group will handle disappointments and delays.
    • Social Butterfly: Loves people-watching, interpersonal interactions, and just spending time together.  People > Place as long as the place is interesting and not too isolated.  If this person is an extrovert,
    • Topic Geek: Whatever the niche (Museums! Food! Cars! photography! Art! History!), the geeks will dig in and salivate over the opportunities to indulge their passions. Great!  But you’ll need to negotiate among the geeks unless you’re all into the same exact thing. Everybody gets a chance to geek out — or split into subgroups and hit different areas.  Also, we have a standing rule to see no more than one museum per day – you can’t take in much more than that and survive. IMHO.
    • I’m just here for the culture: These folks are fun! They like to experience new places, foods, people.  They probably push your group to delve into some of the crannies you wouldn’t otherwise fine.
    • Anxious About Everything: Know before you go. I’ve had great travels with some folks who tend to worry, and I’ve had some less fun experiences. You’re signing up for some emotional labor to get everyone home safely, but you can also open the world to someone who might not otherwise have traveled.  You’ll need to lay out Plan A, and B, and C, and maybe D before you’re both happy.
    • I literally do not care: Unless you’re a teacher and this is a field trip, do not travel with this person.  Apathetic people bring nothing of value to the party, but they suck energy from the group.  0/10.  Not worth it.
    • Party Hard, Dude!:  You do you?  I don’t usually travel with the party-hard types, but in limited doses (or when the experiences aren’t deafening, after 3am, or involve people getting plastered) they can be a lot of fun.  Make sure everyone in the group is ok with adults being adults — meaning, adults have the right to do what they choose as long as they don’t harm the group.  (*Being too hungover to travel harms the group.)
    • I lose everything:  ohmygod. Unless you’re a teacher and this is a field trip, do not travel with this person.

The mix of personalities can  make or break a trip.  You may have to travel with different folks until you learn your own travel profile, and then it’s like dating – after a while, you just know what you like and what isn’t going to work.

TIP: Pay attention to the balance of introverts & extroverts in the group.  Two extroverts can keep each other happy. Two introverts can enjoy the silence together. But an untethered extrovert will talk the introverts to death and then wonder why everyone is mad at them. 

Brooklyn street art.  I always take photos of street art – it’s one of my favorite things.

What’s your Budget?

Here’s where it all breaks down, yeah?  How do you embark on trips of a lifetime if you can’t afford them?

I have thoughts.

First, I think it’s wise to keep everything in balance. If you’re struggling to pay your bills, you should keep your excursions close to home – day trips, in other words.  But not traveling anywhere, ever, is going to suck your soul dry. And then what’s it matter if you paid off your bills?

A case for travel as a necessity rather than a luxury

Travel is one of the best educational experiences we humans can undertake. We learn about other people and points of view. We stretch our boundaries, maybe try new things.

If you want to make travel a bigger part of your life, start saving now. $5 a week. By the end of the year, you’ve got $250. That’s enough for a nice day trip (or one every 6 months).  The habit is the key.

I’ve never valued any object or paycheck or “thing” as much as I’ve valued time spent with people I enjoy, seeing and experiencing new parts of the world.   An investment in travel is an investment in yourself, and it’s worth it.

Ways to pinch pennies and go further for less

Many many folks write about traveling on a tight budget. You can read travel books for free at Books-A-Million or Barnes & Noble or the library, and there are billions of blogs online. You have literally no excuse not to try some of their tips for yourself.

Everybody’s got their own budget hacks. Here are some of mine:

  1. Airfare and lodging are the most expensive parts of every trip, especially airfare because you can’t reduce the cost by adding more people to the group (unless you get a group discount through a travel agent).   If you can beg, borrow, or steal (just kidding) lodging somewhere, you’re already ahead.
  2. Personal connections open doors for travel. Ask politely and make it easy for the person to say no — but if you get an invitation, take it!  My earliest trips as a young adult were visiting people in Europe I knew only tangentially. They let us stay with them for free, meaning we could travel for much less than we would have paid otherwise.  Got friends? Go visit them.
  3. Know when to buy airfare. Use Google Flight or Kayak or other flight tools to research airfare trends.  Put up a fare alert for a dream trip (Hawaii? Chicago? Paris?) and watch the prices fluctuate. Get a sense for how early you need to buy tickets.  The current wisdom is that you’ll find the best prices either several months out (timing varies by location) or 4 weeks out.
  4. Any plane ticket you buy less than 3 weeks from your travel date will be hella expensive, unless you catch a last-minute deal and have the flexibility to travel.   You’re either in this for the long game, or you have travel at the drop of a hat.  Anything in between gets too expensive.
  5. We personally prefer AirBnB lodging to hotels everywhere in the world.  I understand the ways in which AirBnB is a problematic fave and how it can drive up housing prices and lead to gentrification.  But when I’m looking to travel, almost nothing beats AirBnB for a couple, a family, or a group.  In addition to beds, you get a kitchen, a living room, and a location with a personal touch.  I’ve never stayed in a hotel (at a similar price point) that can hold a candle to what I can get for $30-50 a night per person via AirBnB.
  6. Group trips can maximize savings by careful selection of AirBnB locations and keeping overall trip costs in bounds. I’ll do posts later about how I pick AirBnB lodgings, and how we keep other costs down. 
  7. Get a per diem (day) estimate from your fellow travelers of what they’re willing to pay for this trip, and agree to stick to it.  If that means taking a shorter trip but making it more awesome, people will understand!  Remember to set aside money for food and public transportation in addition to lodging & travel.
  8. Know when to go home.  You can always go back. Have an accountability partner (my husband is mine) who can “reality check” your plans. You can’t do everything in one trip.

I’ve planned trips to Italy, France & England, Central Europe, the West, Chicago, NYC, Savannah, and many other US cities that have kept below $50-100 per person per day (depending on location).

I can take you to Europe for 10 days for under $2,000, including airfare and lodging and food and public transit.  If we’re lucky, under $1500!

You know how long it takes to save $1500?
Just one year, if you put aside $28 dollars each week, or about $120 a month. Cut down on Starbucks, cancel that streaming service you only use a couple times a month, eat out less, buy chicken instead of steak (better for you anyway), cook a big batch of chili, sell some crap on eBay, buy your spring outfits at Goodwill. 

In other words – go see the world instead of sitting on your couch.

NEXT UP: The Planning Process



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