Our Approach to Planning. Ten steps to the perfect trip: travel itinerary, flights, accommodations

Steve shares the 10-step framework for planning trips, from choosing destinations that truly fit to pacing days so the fun lasts. Anchors, alternation, and a single shared Google Doc turn daunting into ease without losing the spark.

• choosing a destination by connection, food, climate, culture, relaxation
• using guidebooks and searches to find anchor experiences
• building a shared Google Doc with confirmations and backups
• alternating city and country to manage energy
• one main activity per day and making options optional
• booking must-see sites and stays ahead to protect spontaneity
• why group travel thrives in a home over hotel
• flights with price alerts and regional comparisons
• visas and entry rules done on official sites
• revisiting and revising plans while asking locals for food

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See pictures of the fam on their adventures on Instagram @wwggwithstevewebb

If you like the theme music check our Steve's album with the links below

https://open.spotify.com/album/0boqNyhBk1U1sww21uEWaD?si=RRG2ZItGSImrpIN14t_c2g

https://themostfamousstevewebb.bandcamp.com/album/national-treasure

Some of the drumtracks on the interstitial music were originally derived from the Pocket Queen’s New Breaks Vol 1

https://www.thepocketqueen.com/

Contact Steve:

stevewebb0201@gmail.com

Sample Itinerary:

https://docs.google.com/document/d/1UtzpCxd0WuKVkOZGtyIZG94nsf-KLO8yFMWMyXsbfGs/edit

Transcript

Season One Finale And Setup

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We've made it to the final episode of season one. If you haven't checked out episodes one through six about our adventures through Thailand, it's all there waiting for ya. And if you haven't followed the podcast yet, do that too by hitting the little plus sign and the show's homepage. That way you'll know when season two, our experience in London, Greece, and Switzerland arrives. I'm working on it as fast as I can do it well. So it'll be done when it's done.

Why And How We Plan Trips

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Every time we come home from a trip, friends and family inevitably ask me, How'd you plan all that? So this episode is dedicated to that question. My name is Steve Webb, and this is where we're gonna go.

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We wonder where we're gonna go. We wonder where we're gonna go. We wondered where we're gonna go.

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This episode will provide a play-by-play of how we pull a trip together. My goal is to make it easier for you and your crew to get out of town and see something new. Most often, we're traveling with six people. Besides Christy and I, it's three teenagers and a man in his 70s. It's a big responsibility to lead a crew that size. And the pressure compounds when you're tired and it's hot and you're hungry. Having a plan laid out relieves a lot of that pressure and actually allows us to live more fully in the moment. We found that it's best to cover as many bases as we can ahead of time. Plus, the kids like a good answer when they ask, what are we doing today? I'm gonna do my best to offer as much detail as possible. Take from it whatever you need. This is just a framework or a set of tools to help with the job. Also, I have to acknowledge that if you ask AI for a plan, for example, what's a good itinerary for three days in London? It will give you a pretty good answer. So if that's your speed, you can quit this episode right now. However, we really enjoy knowing why something is worth seeing and doing. Understanding context provides the story of what makes something relatable or horrifically unrelatable but fascinating to you or someone in your crew. You'd have to prompt AI like five times to get that far. By then, that's just research and we're back to where we started, so you better not quit this episode just yet. The list I'm about to share is not something to try to accomplish in one day. You will not pull it off and you won't have any fun trying. It's a process we start about six months ahead of time and work our way through step by step in short bursts, set on keeping the vibes high along the way. And before I get into it, I must give credit where credit is due. Christy is a PhD planner. She's the master craftsman of this process. I could get us there, but without her foresight and focus, there'd be a lot more bumps along the way. We are a great team, but I have a tendency to start daydreaming about pork buns and paella somewhere in the third quarter, and she's got a gift for keeping her head in the game so we can get the job done.

Starting Early And Roles At Home

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For us, planning starts in bed with coffee on Saturday or Sunday mornings. Side by side, propped on pillows, we figure out where we're gonna go.

Step 1: Choose The Destination

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Step one, pick a country or region of the world. A good way to start is with time and distance. If you have a week-long spring break, you're not gonna want to fly to the other side of the planet. But if you have a whole month to work with, you might want to do just that. We also take into account what might resonate with the kids, especially on our first trips. Iconic structures like Big Ben and the Eiffel Tower have woven their way into our culture through movies and books. Seeing these sites in real life had an effect on the kids and myself far greater than I would have anticipated. We introduced travel to our children with these familiar yet far-off places and it set a tone. Now they're more open to go anywhere for the sake of the adventure, and it doesn't have to be familiar. But starting that way was really fun for us. Food has a huge influence on our choices. We get excited about cultures that take pride in the food they prepare. And it's great for the kids too. Full immersion into a food culture can transform a picky eater. Now climate might be a factor for you. It certainly is for us. We live in upstate New York where it's cloudy for much of the year. So sunny places are important. Especially when we're trying to escape the harsh winter. I suppose that if I was from Tucson, Arizona, the misty green hills of Ireland might be calling me. We also look for a nice mix of culture and relaxation. We like chilling on the beach as much as anyone, but we like some action too. So we choose places that we can easily stagger chill days with culture and activities. So if you boil it down, we tend to pick a destination based on what might connect with the kids, then food, climate, culture, and relaxation. You might be childless and into architecture, bullfighting, and ping pong. That's cool too. What I'm saying is that you need to decide what's important to you and your tastes when choosing your destination.

Step 2–3: Guidebooks And Google Doc

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Step two. Order the guidebooks and get the coffee going. It's a weekend morning and we're back at it from the comfort of our bed. The guidebooks tend to be the beginning. Rick Steves and Lonely Planet are great time-tested choices. We'll read sections of the books and get a feel for the area, and then do some searches based on that reading and see what else is around. I might type in fun things to do in Thailand, or most unusual things to do in Thailand, or best thing to do with teens in Thailand. Be careful with that one. But you get the idea. Before long, you'll see that certain things appear no matter what keywords you search. Step three, we start a shared Google Doc, make a list of the things we'd like to check out, and begin to form the itinerary.

Thailand Example And Anchor Points

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I'll stick with Thailand for this example because it's fresh on my mind. We were going to take a month to see as much of Thailand as we could. We also knew that we'd probably fly in and out of Bangkok because it's the biggest city with the best deals on international flights. The top of the list we've been working on read Bangkok, one of the islands, the city of Chiang Mai, and we threw in Cambodia because Anchor Wat kept coming up in our searches and it looked really impressive. Plus, it's fun to check another country off the list since it's right there next door. Often there's one thing that sparks the most excitement between us. For this trip, it was an elephant sanctuary just outside Chiang Mai. Hanging with the elephants sounded so cool. Whatever excites us the most, we tend to book first and build out from there. There are several elephant sanctuaries, so we did our best to read lots of reviews, testimonies, and the general mission statements. We definitely wanted to visit Happy Elephants. We landed on the Elephant Nature Park, checked the availability, and made a reservation, which ended up being about two-thirds of the way through our month-long window. Making those initial choices is a big step in sketching the actual itinerary.

Step 4: Order And Pacing

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Step four. Lay out a general schedule and assign a number of days per place. This might be the hardest part for us. Based on the availability of the elephants, knowing that we'd start in Bangkok, and staggering the city with the country, the order of the trip began to fill in and our document started to take shape. Four or five days in Bangkok, we picked that number based on feeling and our things to do in Bangkok list. It seemed about the right amount of time to see some great sights and get out of there before the intensity of such a big city wore anyone out. A week at the beach on the island of Kosamui was to follow that big city stint. Then to Chiang Mai, which is a city but a less intense one. Plus, some of the activities we were looking into had us getting outside of the city anyway. So the Chiang Mai stop was an alternation of city and country within a bigger alternation of city and country. Then we were off to Cambodia for a few days and back to Bangkok to close out the trip. Based on firsthand experience, we know that staggering city sightseeing with country or beach relaxation is imperative. Too many consecutive museums or historic marvels will breed contempt in the youth. I'll dig deeper into that when I get to step six, but first step five.

Step 5: Why We Prefer Airbnb

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The truth is we love Airbnb for so many reasons. As you can imagine, on a month-long trip, we spend a lot of time together. Having a home where everyone can have their own room with some privacy and a little downtime is a lifesaver. A big part of such a long trip is managing morale. So staying someplace where we can spread out rather than a cramped hotel room is a big help. Airbnb saves money and trouble. For our group, we'd have to rent at least three hotel rooms, so the house is often less expensive. We also hesitate to leave our teens in their own hotel rooms because of the potential for mischief and sneaking out. With an actual house, they all have their own space, but we're all under one roof. A small caveat, we later learn that two of the three teens snuck out anyway. So no matter where you stay, keep an eye on those rascals. Between you and me though, there's a little comfort in knowing that some things never change. Have you ever gone to a hotel pool and there's nowhere to sit and there's strange children running and screaming everywhere? Well that won't happen with an Airbnb. With your own private home, we often get our own private pool. Or how about when you go out to a delicious dinner on vacation and you want to take the leftovers but there's nowhere to store or reheat them? Or maybe you'd like to stretch your dollars on vacay by not eating out for every meal. Well guess what? Homes have kitchens, and I bet by now you can guess where the best place to rent a home is. In addition to a kitchen, there's often a laundry room and a dining room and other amenities that you'd find in a home. We've had so much fun simply playing cards at a kitchen table after a long day of exploring. You might miss those opportunities in a regular hotel. Okay, just a couple more and I'm done. When you rent someone's home, it's typically in a neighborhood. I love this because it's such a great way to get closer to the local culture. And when you're renting someone's home, a lot more of the money goes back to the local family that owns the home rather than a big hotel chain. Airbnb execs, if you're listening, my email is in the show notes. Feel free to reach out and I will provide the address of where to send the check.

Step 6: Daily Activities And Pace

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Step six. Start to fill in your daily activities. Bullet point each day with an activity next to the date. Before our first trip as a blended family, Christy told me about a trip she took to Rome with her kids. There was a heat wave in the city that summer, but the itinerary was so full she worked those kids hard. The Panthenon, the Roman Forum, the Trevi Fountain. By the time they got to the Coliseum, everything was falling apart. Can we just relax? They cried. And she, not immune to the heat, snapped. This is one of the coolest cities in the world, damn it, and we're gonna see it. And with that, she dragged them to the Sistine Chapel. As you might imagine, the cultural gravity of the structure and its contents was left unabsorbed. It wasn't until later that evening, when the sun relaxed its relentless assault, that she was able to reflect. Perhaps seeing one or two sites in good spirits is a lot better than seeing four or five while melting down into a puddle. In other words, pace yourself. Stick to one main activity per day and stagger your busy days with slower, easier days. You might not be able to see everything in every place, but the general mood of the group will be a lot better. Another thing we do if we feel like we've pushed them to the limit is to make an activity optional. Sometimes the kids and her father will hang back at the house while Christy and I go out on a little side adventure. They get to relax and we get some time alone together. And with that, everybody wins. Step 7. Book

Step 7: Book Ahead And Organize

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as many things ahead of time as you can. When I was younger, I had some hippie aversion to planning. I thought it somehow ruined the go with the flow experience. Well, it doesn't. It reduces your thinking about logistics and eliminates the worry that places will already be booked by the time your hippie ass decides something might be fun. Some nice planning ahead will translate to a flow experience. With the work done ahead of time, you can keep your head up and soak it all in on the way to seeing something great. It's especially important for the most famous sites. The Sargata Familia in Barcelona is literally the most unreal, amazing building I've ever seen. The word touristy can't even keep up with it. Everyone's there, but they should be. So if you think you can just show up on the day of, you're crazy. And you'll miss something truly beyond comprehension. This is where our friend, the Google Doc, really starts to mature. On the dock, enter your reservation codes, Airbnb addresses, websites, and confirmation numbers. Having all this information in one place makes everything easier. Plus, you can share your itinerary with friends and family. Below the itinerary, for each city and town, we keep a running list of other ideas and activities that didn't make the first cut, just in case one of our favorite picks doesn't pan out. Christy works in her office during the week, so she takes care of a lot of the bookings since she's right there at the computer and some things are easier to book during business hours. I work by myself outside most of the week, so I'll listen to audiobooks or anything I can find relating to our destination and try to learn more about the culture and enhance the ideas list.

Step 8–9: Flights And Visas

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Step 8. Book the flights. For our shorter or regional flights, we use kayak to help us get the best deals. For the big flights, we use a feature through Capital One called Hopper. Hopper offers low price alerts and will notify you when it's time to buy. It's the best way we found to get great rates on international flights. Any Capital One execs out there? You know where to find me. Step 9. What do you need to enter a country? Places like Cambodia and the Dominican Republic require special visas with a fee attached. It is so much easier to fill these things out and pay the fee ahead of time on the government website than it is to arrive at the airport and have to wait in another long, sad line. And finally, step 10.

Step 10: Revise And Eat Local

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Revisit and revise. We're always checking in on the Google document and making adjustments. Even throughout the trip, we may get to a place and learn about something new that we have to try, or we may decide to cancel our tour because our schedule feels too packed. It's best to be flexible and open to the world as it changes around you. And as far as food is concerned, we're usually just looking while we're there. We'll often ask our host or an Uber driver for recommendations. And we'll keep our eyes open for places that seem to be filled with the locals. Sniffing out the best restaurants is a skill you can develop the more you travel. Of course, there's Google and Google reviews, and we use that all the time, especially if we're really hungry and a little desperate. Often, though, the most authentic places aren't even on Google, so it's better and more fun just to ask the people you encounter along the way. Overall, your best bet might be to look around while you're wandering and sightseeing and make a note or drop a pin on your phone for places that catch your eye. Then you can easily return before extreme hunger and desperation kicks in.

Final Advice And Motivation

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You gotta get going. So there it is, our approach to planning and 10 steps. I'll include a link to one of our itineraries in the show notes. Just remember to start early, break it down into little pieces, and have fun. If you follow these steps and give yourself enough time, the bulk of the trip will come together in a relatively low stress way. No matter what you do though, you're going to feel some stress. For every single trip, the day or two before we're scheduled to leave, we will undoubtedly spiral into a minor psychosis as we take turns saying, What the hell are we even doing? Or let's just not go, this is stupid. The only cure for this is to plow through it and get in the car or on the plane. The feeling won't be able to keep up. Another time we might feel stressed is before we start planning. The project seems too daunting, and we're wondering how the hell are we gonna do this? My favorite cure to this is to type six simple words into a search bar and watch the world open up. So before you talk yourself out of an adventure because the planning seems too hard, just sit down in a happy place and try it out. Type fun things to do in, then enter a place you've always wanted to go.

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Boom boom, you gotta get go. Boom boom, you gotta get go.

Season Wrap And Calls To Action

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We made it to the end of season one. Remember, follow the podcast so you know when season two arrives. You're gonna wanna hear about our trip to Greece and London and Switzerland. Also, share the podcast with your friends that love to travel, even if they're just the vicarious type of traveler.

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We wonder where we're gonna go.

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If you want to see some pictures of the fam and I on our adventures, follow me on Instagram at wwgg with Steve Webb. This show is written, recorded, and produced by me, Steve Webb. With music by me, Steve Webb. If you like the theme song, check out my album National Treasure by the most famous Steve Webb anywhere you stream music. If where we're gonna go has been fun and informative for you, please leave a review on your favorite podcast platform. Thank you so much for listening. I hope you've enjoyed the trip.