Victora Station trains London

The Perfect Trip is Possible: Here’s my Planning Process

A couple days ago, I set up some basics about how you can make travel a rich part of your life, even if you aren’t rich! (I sure ain’t.)

I’ve planned trips for groups large and small for 20+ years, and (IMO) we take great trips! And we make them affordable.

Today I want to talk about my process of planning a trip — what I do and when, how I organize it, and the kinds of decisions I make.

If you haven’t yet read the initial post, please take a minute to check it out.


Step 1: Do your research & get buy-in

In my first post, I shared my perspective on selecting good travel companions and planning ahead for your budget.

You’re going to need some buy-in from your travel group before you can plan the trip, so research is key. Your goal is to make people a reasonably accurate offer, like “Hey! We could spend 10 days in Italy in May for about $1500 per person, plus food. Want to come?”

TIP: Keep a spreadsheet of costs, make it public to the group of potential travelers, and ask people to pony up money early on if they intend to travel.
If you don’t have the money to float a loan to your fellow travelers, then you need clear payment deadlines, with the final money due at least 30 days before travel.
You can also ask people to purchase a plane ticket themselves on a particular flight, since that’s usually the greatest expense. 

For right now, I just want to emphasize that you need to do some research before your excitement gets the best of you. No one wants to accidentally spend 50% more than they initially planned because hidden costs beat you up along the way.  That’ll ruin a good travel friendship for sure.

You’re looking for trends (for things like airfare and lodging costs); ideas for food, events, or attractions; and pitfalls to avoid (bad times to be in that place because it’s crowded or the weather is bad or things are closed).

You’re also looking for gems of advice from travelers who’ve been there recently — what’s closed recently? What’s the unexpected hassle? What museums are a waste of time and money? What are the hidden gems?

Google these:

  • Best times to travel to your intended destination, including “best” = cheapest or = least crowded or = events to see. There’s a lot of great wisdom on the forums at TripAdvisor, even if the data is sometimes a few years old. People there will talk about all kinds of details you won’t find elsewhere.
  • Most crowded vs the benefits of off-season — if you have flexible travel dates, take some time to weigh the pros & cons (and costs) of going off-season when things are cheaper, but many restaurants and attractions may be closed or operate on reduced hours.
  • Basic patterns of prices for flights — Google “when to buy tickets to [designation]” and read the advice. Use Google Flights to track best times to buy. I also like to check Kayak and set up an airfare alert so I’m ready to buy.  I find the best deals 6+ months out OR about 3 months ahead of the trip. 
  • Basic travel distances from place to place (like train routes in Europe) –Google Maps and Apple Maps both provide train distances and times in their apps / online. Are your travel timelines reasonable?
  • Open/closed times for any “must-see” attractions.  Many museums are closed one or two days of the week.
    For example: If you’re going to be in Florence, Italy, from Sunday through Tuesday, your only actual day for visiting museums really is Monday because you will find it hard to fit in a museum on a travel day. The Accademia gallery which houses The David is closed on Mondays, and you’ll miss it entirely with these travel dates. 
  • Hidden gems — literally Google this phrase for your intended location and see what comes up.

TIP: Most of Europe is on vacation from late July through August and almost every city is 1) hot as hell and 2) closed.  Don’t go during this time. Also beware of traveling around Easter (especially to Italy) or Christmas / New Years unless you know what you’re doing.  

With your research in hand, you should be able to ballpark an estimate for the trip’s costs, using mid-range airfare and a typical lodging estimate, plus $50 a day (at least) for food & transportation.

If you’re traveling as a group, take into account the savings of splitting things (like an AirBnB among several people, but don’t assume you’re going to pay a lot less than you would traveling alone.

Once you’ve got buy-in for the trip dates (loose or fixed) and rough number of travelers, it’s time to start putting up money.


Step 2: Buy airfare when you see a good deal (doesn’t have to be the “best” deal)

I’ve done trips where people paid me for their tickets and I set them all up, and I’ve also had people get their own airfare.

My suggestion is this: Unless you know these people really well and want to lend them hundreds of dollars in an unsecured loan (basically) by buying their tickets for them, ask people to buy their own ticket on a particular flight once you’ve located a good deal.

That said, if you want to make sure everyone is seated together on the flight or your travelers would prefer you take care of this hassle on their behalf, here’s how to buy tickets for a group:

What you’ll need:

  • a credit card with a high enough limit for all the tickets you need to purchase,
  • legal name information from everyone’s passport*, including first / middle / last name exactly as printed on their legal ID
  • legal date of birth for all travelers,
  • Global Entry Number or TSA Pre-Check (if applicable)

*Passport required for all travel outside of US borders. People who live in states using the new federal-style drivers-licenses can fly domestic without a passport.  Obtaining a passport takes at least 6-8 weeks, so anyone in your group without a passport for international passport (or minors without a drivers’ license if you’re flying domestic) will need to get started on this well before departure date. 

Warning: Do not mess up the date of birth or name information on the ticket!  Double- and triple-check when entering info, and ask the travelers to double-check the reservation. You can often call an airline and fix a mistake within 24 hours of purchase.  You should not expect a person can travel if the name or date of birth does not match their legal ID.

About good deals on airfare – it’s a gamble

There’s nothing more frustrating than buying tickets for $550 and then seeing the price drop to $490 the next week, but that’s how this game goes.   You’re unlikely to guarantee you’re buying the absolute cheapest ticket, so get an agreed amount from your group (top amount) they’re willing to pay, and drop it down $50 for luggage fees and wiggle room.

TIP: Search for flights with enough tickets in the lower fare class for your group, and let folks know that you’ll provide the flight number and a purchase window – 24 hours – during which they need to grab their tickets. If they miss the window, their price may rise considerably. 

This is a good test for your group – are they willing to buy in when it comes to it?

If you’re purchasing for the group as a whole, watch out for limitations of the number of seats available in the cheapest fare classes. Airlines often limit these. If you’re traveling in a group of 12, all 12 of you may not be able to buy the Super Saver ticket.

Know the general airfare for the route so you can recognize a good deal when you see it.  I know tickets to Europe run $800+ from my regional airports (2 hours away, two major cities), so anything $600 or less is truly a good deal for me.  

About those cheap airfares

Should you fly Super-Save or Ultra-Economy or other “bare-bones” classes?  Ehhhhh…. I personally don’t think they’re worth it.  Let’s break it down:

PROS of the Cheap Airfares
  • You really can get a ticket for much less than standard fare, sometimes hopping to Europe for $300-400 roundtrip.
  • If you have short legs and don’t mind having zero legroom and sitting in a middle seat in the back of the airport on top of the bathroom, it’s a way to get somewhere when you don’t have actual money.
  • If you can pack everything in a backpack, you can avoid the bag fees.
CONS of the Cheap Airfares
  • Have you ever ridden for 8 hours in a plane without stretching your legs? It’s hell.
  • Do you plan to pack your own snacks, enough to keep from starving for 15-24 hours?
  • The back of the plane can be rough, so bring earplugs, and grit your teeth if they park you in front of the lavatories.
  • You probably can’t pick your seat before you arrive at the ticket counter, so you’re going to be in a middle seat and you probably won’t be seated near your travel companions.
  • Your checked luggage fee WILL be an extra expense. On international flights, a standard ticket will often cover the first bag for free, saving you $50 which you’ll have to pay yourself on a super-saver ticket. (Ditto in-flight extras like pillow & earbuds for the in-air movie screens, or food on the flight.) Do the math before you buy a cheaper seat – are you saving any money?

If I sound biased, I am. I’m too old to fly 8 hours smashed into a middle seat between two strangers.  Back-of-plane seats make me a little airsick.

I hate everything about flying in the 21st century (customer service is dead, tbh), so it’s worth it to me to pay $75-100 more so I don’t hate my life on the travel days.

You do you.

TIP:  Watch out for weight limits on luggage. The budget airlines in Europe often limit your carryon to ~10 kg (22 lb) and your checked bag to maybe 15-20 kg (35-45 lb). Many domestic American airlines still allow 50lb bags. I’ve been on trips where people had to pay $50-$100 extra on the spot to fly on their budget Europe flight because their luggage was overweight on the Continent when it was fine in the US.

Park Guell, Barcelona
Park Guell, in Barcelona, from our trip there in June 2018

Step 3: Set up lodging

I’m going to do a separate post on choosing a great AirBnB as my next post, so find that here in a few days.

You’ve got a window of time to sort out lodging, though generally “earlier” is going to be better than later.

The available stock of housing and hotel rooms dwindles as you approach any given date, and if you’re traveling to attend a major event (like the Super Bowl or Mardis Gras or a big concert), you may even need to book a year or more in advance.  The bigger and more popular the event, the further out you need to plan. 

Personally, I think it’s wise to set up your lodging arrangements as soon as you possibly can after buying plane tickets.

Hostels are great for the young (and young at heart)

If you don’t mind sleeping in a  room with 10 other people, it’s hard to beat a hostel. These low-cost places have protected travelers for decades, and we used them plenty for school trips and for ourselves “back in the day” to keep costs down.

Since the rise of AirBnB, we’ve personally shifted to renting a house and splitting the cost rather than staying in a big dorm room. But some of our favorite travel memories in New York and Chicago and Boston came from the hostels where we stayed.

If you’re relatively young, don’t mind strangers, traveling in a small group or alone, and need to save money, you should look into a hostel if you’re headed to a large American city or any cities in Europe.  Hostels International have been running facilities for decades, and you can read extensive reviews online. They really are safe, and you can meet a lot of great folks from around the world.

Why I use AirBnB

This is my pitch:  Even though AirBnB brings a host of other problems with it, such as contributing to gentrification in older neighborhoods and gobbling up the stock of available housing, it provides two things that a hotel doesn’t: 1) my money is going directly to an individual or small business usually rather than a national chain, and 2) as a traveler, I have a much better experience than I do with a hotel room.

If you’re in a group, then AirBnB (or HomeAway or VRBO) are no-brainers because you can stay in an entire house – kitchen, TV, and sound-system included – for less than what you’ll pay for equivalent hotel rooms (or at least you’ve got more room to spread out).  You can find properties that fit 12-20 people, enabling you to enjoy your trip amidst friends.  I don’t really understand why anyone stays in hotels, honestly.

I do advocate for cities to impose taxes, fees, and regulations on AirBnB renters to offset the negative consequences on local housing prices. Don’t complain if you have to pay an additional fee for your AirBnB.  Think of it as a quality of life upgrade – because that’s what you get when you stay in someone’s home instead of on a big commercial property.

Lodging logistics

Be mindful of these elements, plan for them, and add them to your spreadsheet: 

  1. How long will it take you to get from the airport to your lodging? Is there public transportation or will you need a taxi/Uber?
  2. Allow at least 30-45 min extra at the airport to get bags, plus 30-60 min if you have to go through customs as well, before you’re ready to head out.
  3. How close is the hotel/AirBnB to points of transportation like taxi stops, metro stations, or the train station?  Read the fine print and look at Google Maps before you settle. I’ve rattled a suitcase across a mile of cobblestone streets before, and it sucks and it’s long and after a while your arms hurt.  Don’t do that.
  4. Does everybody have their own bed?  Are the beds for couples large enough to suit them?  (A “double” bed in America is quite small. A “double” or “queen” bed in Europe is probably two twin beds pushed together with the gap between mattresses probably in the middle.) Also, sleeper couches suck for anyone over 10 years old. You’re going to be exhausted sometimes. Make sure you’ll get a good night’s sleep.

Like I said, I’ll cover more of this in my AirBnB post. For now, aim to have your lodging settled no later than 3-5 months before you go.


The Japanese garden & display in the center lobby of the Bellagio in Vegas

Step 4: Do the math on museum entrance fees, train / public transportation costs, etc and communicate to your group

This is the last category of planning and expenses and it tends to catch people off-guard.

You can easily drop $20-50 per person daily touring a city as you pay fees at museums (which are pricier than you’d expect), splurge on the guided tour or audio companion, and pay for transportation from  point A to B.

There’s no substitute for a spreadsheet and good old-fashioned research. It takes time, but this is how you finalize the trip costs so your fellow travelers aren’t surprised by the real cost of the trip once the dust settles. 

Track these elements and give your group a cost estimate for one or two major activities each day

  • Museums:  Cost of admission (adults, kids, veterans or teachers, etc); Is there a “city card” or “tourist card” that gives discounts?; days open / closed; hours of operation during the season you’re there (expect different hours in summer vs less-popular seasons; are advance reservations required?  What’s the minimum number of people to get the group discount?
    — You might also do some legwork to find the best 2-3 museums in a city, then poll your group for their top picks. Will you split into two groups and visit separate places?
  • Events: Extra ticket required? Multiple stages or areas? Security requirements (clear bag? no bag? no camera? etc); cash only concessions?
  • Special Excursions: AirBnB Excursions, tour companies, and other travel guides can give you a once-in-a-lifetime chance to explore the city or take a helicopter ride or drive a Ferrari.  You might assist your group with making these arrangements, but they should foot the bill. We generally poll our group before traveling and try to give everybody at least one thing off their list. 
  • Free Things: Sometimes the best experiences are free, like walking Central Park in New York City or going to the Navy Pier in Chicago at night to enjoy the lights over the water. The view from a rooftop balcony or stopping off in Pisa to see the leaning tower from its square – these cost nothing but they will be beautiful.   Even better – buy a sandwich from a street vendor or pop into a nearby grocery store for some cheap eats, and picnic on the grass! 
  • Public Transportation: Nearly every system offers pay-per-ride (do you need a travel card? Can you pay in cash? is it bills or coins? do you need exact change?) as well as touring cards where you can hop on/off certain routes throughout the day for a flat fee.   Track the per diem cost of public transit and let people know what to expect. 
    Every transport system has a home page with visitor info for tourists.  You can also hit up the travel section in a bookstore and do some reading in a guidebook for the latest advice.   **Learn to use the bus system! 
  • Trains and Inter-city Travel, or Car Rentals: If you’re hitting multiple cities in Europe (etc), you’ve got to travel between them. Check the prices (and baggage fees) associated with the short-hop intercontinental budget airlines.  We tend to travel by train instead because we like looking out the window.
    You may find that a single rail pass is cost effective, but point-to-point tickets in Europe are also very affordable if you can stand taking the risk not having reserved seats. (Only the busiest international routes are a concern, most of the time.)
    For car rentals, we use Europcar.
    Track everything in your spreadsheet. I like to insert lines to show travel days, list to/from cities, and calculate which mode of transport will be the right blend of cost and speed. 
  • Uber or Taxis or Ride-Share: Depends on the city. Uber and Lyft are about as problematic as AirBnB (as is everything in the “sharing economy,” really, but boy they are great when you’re in a strange city. I’ve happily Uber’ed everywhere in Vegas, DC, Chicago, New York, Savannah, Atlanta….  Sometimes the public transportation is closed or you’re headed out beyond the lines. Check the Internet before you go to find out if Uber/Lyft are available, and use the app for a quick price check. If not, figure out what taxi services are available and typical fares. It’s usually 2-4x more expensive to ride-share than to take the bus or metro, but when it’s midnight and you’re dead tired, there’s something nice about just going straight home.
  • Phone service: Everyone needs to decide whether they’re going to buy international service for their phones before traveling. If not, how will they stay in contact with the group?  You can buy mobile hotspots and WiFi options too, but often you can find internet cafes (in Europe) and hotel/AirBnB lodgings with decent-enough wifi to check in while you travel.  Really, it’s valuable to have texting (at least) so you can find your group if you get separated.
  • Travel insurance: Read this

TIP: We are firm believers in “one big thing per day” or “two smaller things.”  This isn’t a death march, it’s a vacation. You can’t see it all. Down-time is good. 

Once you’ve added up flights, lodging, museums (etc), and transportation day-to-day, the only expenses left for folks to worry about are food and souvenirs.  If you’re staying in a home or hostel, you have access to a kitchen where you can buy groceries to take care of breakfast and either lunch or dinner.  Or snack on street food and save restaurants for certain days on the trip.


Final thoughts

It might look like a lot, but really trip planning is pretty simple – it’s just a lot of details that someone needs to take responsibility to set up. You need tickets to get there (usually), a place to sleep (cheaper if you can stay with friends), and stuff to do.

You also want to make sure everyone is fully aware of the hidden costs which tend to slip people’s mind: museums, events, and transportation around the city.  Plan ahead and plan wisely, and then people only have to pay for food and souvenirs!

Finally, understand that as the trip planner, you are signing up for the stress and anxiety of making sure the plan works. If something falls apart once you’re on the road, be ready to step in and solve the problem. Unexpected failures can happen, and even the best plans can go wrong.  

You’ll get better with experience, but you can mitigate the risk by 1) doing extra research before you go, 2) everyone traveling with a back-up credit card with a high enough limit to get themselves home if needed, and  3) having a plan B in place for the most typical problems (missed flights, a horrible experience the first night at your lodging, losing your wallet, etc).

Next up, I want to talk about finding a great AirBnB and about planning adventures people will love. I’ll also round up my favorite travel helper products, because we’ve picked up some favorites over the years. 

One of our favorite AirBnB “Excursions” while in Barcelona took us out on a sailboat on the Mediterranean Sea so we could watch the sun set. Best $90 I ever spent, honestly.

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