How to Plan a Multi Destination Trip

TMP 98 - Multi-destination trips
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Jenn: Hey everyone! Welcome back to the Travel Mug podcast. This is Jenn, joined as always by my partner in podcasting, Meggan. So this week, Meggan, we are going to walk you, the listener, through booking a multi destination trip. So, if it's your first time booking a trip like this, it can be really intimidating to know where to start, and I remember booking my first one back in 2015. It was a lot. Actually, while we were preparing for this episode, I tried to boot up my old MacBook to see if I could find my itinerary, and I couldn't find it. I was so disappointed because I really wanted to see how much I tried to jam into the trip.

Meggan: How much has Jenn changed over the years?

Jenn: There are so many moving parts to planning this type of trip and we want to make it as easy as possible For you. So Meggan, I know that you book a lot of these types of trips. You have a lot of experience. So let's start with the order That people should book things in and how far out do you think that people should typically book?

Meggan: I think this is a really good question. And, I mean, obviously I can only give advice based on what we do with our multi destination trips. They are often in June. So we do tend to get the basics in place in October, the year before, at the latest. For our upcoming Iceland trip, which isn't multiple countries, but it's definitely many stops and stays.

We actually booked it in September, but I really think I, it's only because I was getting anxious to like it and I was getting like this really big sense of FOMO. We don't normally book that early, but we did book that early, uh, for this one. Now, the reason we find, uh, this far out works for us, Although it has gotten a bit tighter in the last few years is because there's still a lot of choices available that far out. Now you might be surprised to know that even like, October to June, not everything was available.

so there's many folks out there that are planning that far out besides us. But typically you have your pick of flight times, car rental choices, and accommodations, of course with some exceptions.

There were a few places in Iceland we wanted to book and couldn't get them.

Jenn: Wow, that far out. Yeah.

Meggan: But as far as what we book first, we definitely go in this order. So, flights, transportation, so that just essentially means car rental, and then accommodations. Like, we could sleep in the car if we have to, but if we don't have a car, we can't get to the places.

So, definitely flights, car, and then, uh, accommodations after that.

Jenn: Yeah, I definitely agree. I've always booked my flights first before anything else. And then because we don't usually rent a car, I would typically book my accommodations first and then figure out transportation and if we need to book something in advance, like a train ticket. I would do that, but yeah, I think if you're renting a car, you should definitely have that up there to make sure that there is a car available for you.

Meggan: Indeed, indeed. So talk to us about how you go about or, or let's talk itinerary.

Jenn: Yes, building your itinerary. I mean, that's kind of, this is like the meat and potatoes of your trip planning, really, right? So, now that you have your big things booked, your flights, your accommodations, alright, let's build the itinerary. So, it is important to be realistic about how many places you can visit in one trip.

You don't want to switch places every night, or even every other night. It will get a little bit old. It'll make things really, really busy, and you may spend too much time in transit. and not enough time actually enjoying the place you're visiting. I've seen people post in Facebook groups where they're taking like multiple, multiple flights within like a two week vacation, and you don't want to be taking five flights in a two week vacation. you'll way too much time in the airport.

So how many places is too many or too few? It's really hard to say and it does depend on where you're going. Like for me, I can spend a whole week in a large city like London and you still won't see it all, right? But maybe in a smaller city, like when we visited Inverness, in scotland, I mean we were there like a day and a half and we were like, okay, that's that's enough

Meggan: good here. We're

Jenn: A week would be way too much Um, so for me personally during a two week trip I wouldn't stay more than like four to five places depending on how far apart They are and how much time you'd spend in transit if I was going for a week I really wouldn't visit more than two places. Maybe a third place with a day trip.

I really like to be able to dig in and go deeper rather than shallower and more places, if that makes sense. Meggan, what is your opinion on this? I think you have one.

Meggan: I think I have a lot of opinions on this and it is very, I want to preface this by saying individualized. It's whatever makes people happy, what they want to do on their trip. So whatever Jenn's opinion is, or whatever my opinion is. You're going to do what you want to do because it's your trip at the end of the day.

but I, what you've sort of just mentioned, we don't necessarily think about it the same way when we're planning travel. So what we do is we look at Google Maps, we've talked about this before, and we see what we want to do based on stuff we have found. Through research, like I know you're going to talk about usually online in the year leading up to the trip.

So whether it's following Instagram pages or Facebook pages or just other sources, and then we sort of build our quote unquote itinerary around that, because you will be aghast to know that I don't write down an itinerary.

Jenn: Shocked.

Meggan: I know. Um, but we don't really put any real limitations on stops or number of nights in one spot.

It's not really something we think about. So on Google Maps, there are different symbols that you can use, such as either a heart or a green flag or a star to, like, mark individual places. And we've started using the green flag for things that we want to do. So we know on this trip to Iceland, we want to do 25 of these flags.

And again, knowing we may not make it to all, but they're there. So we then say, okay, how many things are there to do in this one area? Does that constitute one night, two nights, or three nights? And then we plan from there. When we are usually halfway sort of through the trip planning, we talk about, okay, how many nights are left, before we need to fly home, what do we still want to do, and sort of see if we're on track of getting, you know, back around to where we actually need to fly out from.

Now, we can't see and do everything, but we do try to fit a lot of it in. So for instance, in 2022, we stayed in three countries. We visited five, we had 13 nights and we stayed in six different places. So for our upcoming trip to Iceland, we're staying in eight places in 14 nights. Again, that's not for everybody, but.

Um, we also know, and this is how we think about it, the transition, if you have a rented car, from place to place, we can see some of the attractions then too. So it doesn't just need to be in the town that we're in. We treat travel days as adventure days as well, so not just driving to get somewhere, but also to see the things along the way.

So essentially, we know how many nights we have, then we base our itinerary around what we want to do, and there are no specifics in mind around the number of stops. We just sort of plan it as we go, and we don't build in any like specific downtime, we just find it. So some days are really busy, other days we get out in the morning, we nap in the afternoon, whatever the case might be, but every day, in our minds, we plan to do stuff and then we just have some chill time whenever that stuff is over, if that makes sense. So that's sort of how we plan it. So a little bit different. Our itinerary exists. It's just more on a map than in a list. Don't get me wrong. I do have a list in my notes app just to be sure that Can I check things off?

I do like a list. Don't get wrong. But this is just sort of how we go about it. But talk to us about sort of your, um, approach to this.

Jenn: Yeah, so I start by doing research, of Do your research, , on like what I want to do in the area or the country that I'm visiting. So when we were planning our Scotland trip, I knew that we were going, well, firstly, the Scotland trip was a little bit difficult in the fact that I knew I had to be on the Isle of Skye for these specific dates for a wedding.

So that kind of throws a little bit of a monkey wrench in, but, um, I knew that I wanted two to three days in the larger cities like Edinburgh and Glasgow, uh, in order to see the things that I wanted to do. And then based on my research, I knew we didn't need as much time in Inverness or Fort William, which I actually loved Fort William, and I could have used a little bit more time, but you know, you never know until you get there, right?

Um, so I knew that that's kind of how I needed to be, and so we did kind of the, the Isle of Skye was in the middle, so we kind of broke it down on what we were going to do before we got there, and then what we were going to do after we left there, and it just kind of made a circle, which was Very convenient.

Um, it is important to note the travel distance between the places that you want to go. and, and you may have worked this out already when you were planning your transportation, but sometimes travel can take most of a day depending on where you're going and how you're getting there. Especially if flying, I guess.

Meggan: No, that is very true. And I think, you know, when we're mapping it out, we make sure. Um, generally, when we're traveling around, let's say Iceland as an example, that our, our travel per day isn't more than like two to three hours in the car. Just because we're not trying to spend our days like racing to get somewhere or spending a whole day in the car.

So that's, we do really be mindful of, we be mindful, are, we be mindful. No, we are mindful, I should say, of, of that because we don't, it is vacation and we don't want to be spending it just in a car and we've never had alternate, um, flights during a vacation. So that's not something we've ever experienced before anyway.

Jenn: Yeah, so when we planned our honeymoon, so we flew Halifax to Iceland, spent, um, two or three days in Reykjavik, and then flew, um, Iceland to London, and then spent a week in London, and then took the train to Paris. and spent five days in Paris. So those days where we were either flying or on the train, I really didn't, I did plan things because I was crazy and tried to jam in as much as possible, but now I wouldn't really plan things.

I would kind of let those be more of downtime days and just acknowledge that it will take most of a day if you are flying or you have a long Train rides that it's not just the, you know, two to three hour flight. It's the lead up of getting to the airport and then waiting at the airport and then getting on the plane and then getting off the plane and getting your luggage. If you've checked luggage, it takes way longer than you think that it's going to and we do want to highlight the importance of having downtime in your schedule. I mean, Meggan doesn't necessarily build it in. I have to build it in in order to force myself to take it. So, I it's It's good to have days where you don't have much planned or you can kind of go with the flow because travel burnout is a real thing and it will make your trip much less enjoyable if you experience it.

Meggan: I completely agree. So obviously going to places, you've got your itinerary, you've got everything booked, but something else you really want to think about, um, and we wanted to take some time to talk about, are entry requirements, and a lot of countries will have different specifics, and of course, this will depend on A, where you're going, B, where you're travelling from, and How long you'll be staying.

So certain countries do require visas to visit. This has a lot to do again with your home country and some countries will issue them to you on entry and others you actually need to apply in advance. So this is something you're gonna have to research. Uh, we don't wanna, we can't list every country. So please check on this one while you're actually planning your travel so that you aren't refused entry, especially in case you need to get it in advance.

That would suck.

Jenn: Yes,

Meggan: Now for how long you can stay in a country, this of course again varies from region to region and would be more of a concern really for longer term travelers as most countries will automatically allow you to stay for two to four weeks or even longer, but there are regions such as the Schengen area in Europe. It consists of 27 countries that you can travel between freely. Once you've been admitted entrance, however, after 90 days, you got to get out and you got to be out for another 90 days. So you are essentially allowed 90 days in 180 day period. And it is important to get your passport stamped when you first enter the area.

you may be asked to show that. And penalties for overstaying can include a fine, deportation, or entry bans. They be serious.

Jenn: They're serious.

Meggan: very serious. Um, something to also keep in mind if you are traveling between countries via car, so a car rental, is that some countries require you to have a sticker in your window paid for and purchased in advance of entry that allows you to drive on their highways or freeways without paying a toll.

So in 2022, as an example, we had to have one for Switzerland and for Austria. We rented our car in Germany, so we didn't need to worry about that country. It was already there. We did go to Italy for lunch on that trip and also into Liechtenstein. We did research for both and neither required it. so even though these countries were in the Schengen area, At the country border, we weren't actually stopped for passports, which is such a strange thing, especially being a Canadian. We're asked for passports obviously everywhere, but our vehicle instead was checked to ensure that we had the sticker on the windshield. Didn't care about your passport, but show me your sticker. Now, we only found out this information by reading blogs before we left Canada on our trip, so we knew what to expect, and you're actually able to buy the stickers at gas stations as you are getting closer to the border.

Jenn: That makes sense.

Meggan: Yeah, so you don't buy them in advance. It's something you do as you near the border. And as a side note, and no one's going to be surprised by this information, the one for Switzerland was wildly more expensive than the one for Austria. So like, Switzerland definitely keeps it consistent.

Jenn: yeah, they uh, they definitely do. I actually, I, I need to do a little bit more research into this and it probably will turn into a Travel Tip Tuesday coming up soon, but I saw someone post in a Facebook group that they An entry requirement to they were going to Spain was proof that they had enough funds for the length of their trip, so they had to show that they had at least 100 and something euros worth of money.

In order like for each day of their trip Um in order to be yeah, and I didn't know this was a rule and apparently it's not always Um checked or enforced But it it can be especially if you don't have a return flight booked if you just have a one way ticket So yeah, I read about that this week and I was like I put that little nugget aside to research more for later so more on that to come but Yeah.

Meggan: definitely. Wow. I'd never heard of that. And one thing you actually just remind me of in terms of Entry requirements as well is if you are traveling one way, there are some countries that require you to have an a ticket already booked to leave. So, some people just do it at the airport when they arrive, they're like, oh, crap, I need to have an exit ticket.

So keep that in mind too. Sometimes it can be pretty gray online from what I understand if you do or you don't, but it's something you should keep in mind, especially if you're again, long term traveling and just going from place to place.

Jenn: All right.

Meggan: Talk to us about some tools. What can people use?

Jenn: tools. So just some tools to help you plan. We've talked about some of these before, but, um, some of my favorites: when trying to figure out the best way to get from point A to point B, if you're not renting a car, I love Rome to Rio. And of course, Google Maps. So, Rome2Rio is great because it gives you all of the options, including driving, public transit, ride share, walking, flying. and it also will give you approximate costs and how long it will take. And it usually kind of gives you like, this is what we think the best option is. And it's so nice. I don't ever book anything on their website, but I do use it. I, I don't know. You know, I'd rather just book on the right websites, but it is a great, um, website to kind of plan if you're not sure how to get from point A to point B.

Google Maps is also great, but it doesn't give you the approximate cost, so, I mean, it's there. for organizing everything, I love a Google Doc. I just list everything in there. I list out the days, what we might do, uh, where we're staying, how we plan to get around, restaurant ideas, kind of all those things.

And then you can print it out or you can just access it on your phone on the Google Docs app. It's also great to be able to kind of zoom out and see the big picture and maybe notice that you're trying to do too much if you've got, you know, 10 things jammed into every day.

Meggan: Right.

Jenn: So we have talked about the benefits of booking directly with hotels before, and I, I do stand by that advice, however, in the case of a multi destination trip, it is sometimes nice to book everything through one website, like Hotels. com or Booking. com. I like it because you can have all of your confirmations in one place. So that's just something to consider, you're not like, Logging in to multiple different things to try to find confirmation numbers or addresses or dates of stay. Um, it's all in one place. And you may earn a free night after booking a certain amount of nights. And who doesn't like free stuff?

Meggan: Well, exactly. And one thing about, we use Booking. com in particular, as you're booking, it tells you your itinerary nights in a row, so that if you're trying not to incorrectly book your next stay, you know what dates you already have booked, and it's so much easier to keep, like you said, keep track of things.

But even as you're booking, it keeps you on track that way.

Jenn: Yeah, that's really nice. And so, one little hack that I like when I'm looking for activities or itinerary planning, I look at a bus tour that is going to that destination, and it kind of gives you an idea of some things to do and how many things you can do in a day and kind of the travel distance between them.

You can just steal their itineraries. I mean, they're just out there for the world

Meggan: Yeah. You're on Rome2Rio, you're on bus tours, you're taking people's ideas and you're like, thank you so much.

Jenn: so much.

Meggan: I love that for you.

Jenn: Alright Meggan, talk to us about the money.

Meggan: Let's talk about cash and currency. So we did a Travel Tip Tuesday not long ago about how we feel. and the consensus is that having some cash in the local currency, on you while you're traveling, it's smart and an important idea. We 100 percent stand by that. Now, really how much actual cash you take with you is a personal choice with what makes you feel safe and secure, but ensure that if you are going to different countries, as part of your multi destination trip that you have a bit of each.

So we mentioned that the Schengen area earlier, and you can use euros in 20 of 27 of those countries. So not all of them, of course Switzerland's one of them.

Jenn: Of

Meggan: Um, so not all, like that's the thing. You think, oh well they're in the Schengen area, they're the euro, not necessarily. So this is why it's important to do research, know the currency.

And for the love of all that's holy, order it in advance at your bank in case they don't keep it on hand and you'll feel good knowing that you have what you need. A credit card while traveling, if that's available to you, is also highly recommended, especially for renting vehicles, hotel stays, plus the security of Knowing you have it if you needed it.

When I first started traveling, I just had a visa that had a $500 limit. I was young and I was just like, in case I get into a pickle, at least I have this. Um, now debit cards and withdrawing cash in different locales is also an option, but understand you may not always be close to an ATM machine. Uh, the ATM machine, if there is one, may not be working.

And keep in mind there's most likely going to be fees. So I, we try not to take out money on location unless we really need it. We've done it, it's not a big deal. but just make sure you take it, uh, in the local exchange rate, not your banks.

Jenn: Alright, so, everything is booked. You've ordered your money from your bank, and it's time to pack, Meggan. I know it's your favorite thing.

Meggan: have no tips here. This all you.

Jenn: Like, I mean, packing is hard for almost everyone, and even those who travel often. So, one of the things consider is whether or not you'll be able to do laundry on your trip. Because then you can wash and re wear, which is amazing. So, obviously you need to consider if you need anything formal, or if you need any, like, particular items for activities like hiking boots, for example.

Meggan: try to wear those if I need them because they're usually heaviest.

Jenn: Definitely. So one of the things that can get tricky is if your multi destination trip will include different climates.

Meggan: Oh, that just makes me feel so uneasy just thinking about

Jenn: Yeah. So I, when we went to, when we went on our honeymoon, so of course we went to Iceland first, which it was, Um, early ish October at the time. So it was like 3 to 5 degrees Celsius. So we were wearing our winter coats. And then we went to London where it was like 15 degrees Celsius. So you didn't need a winter coat.

So I did have a winter coat and a spring coat. And so lots of layers. The layers are your friend. And I mean, it depends on the weather and what you have at home already. You maybe don't want to go out and buy a whole new wardrobe, but if you live somewhere very warm and you're going where it's winter, you're going to want to go buy winter clothes.

so you could do a t shirt and a sweater and like a raincoat or a lighter coat instead of a big puffy jacket if you only think you're going to wear that puffy jacket once. But then you can just take the sweater off if it's warmer and do the t shirt and the coat. So Layering is your friend, and like you said, wear the bulkiest items on the plane so that you're not taking up precious suitcase space.

I always think of that in Friends where he's wearing all the layers of clothes. I

Meggan: if I could, I would

Jenn: Also consider what type of bag you'll bring. So, of course, you can bring a roller bag suitcase, but if you're going to be lugging it in and out of hotel rooms a few different times, plus taking it, maybe you're taking it on like public transit.

That might be a pain in the butt. So we like to use hiking backpacks in this case. There's so much easier to carry around. The downside of them is finding your stuff in them and especially, you know, if you want something that's in the bottom, but that's where packing cubes really come in clutch here because you can just take out the whole packing cube.

There's all your clothes. Look for what you want and then put it back in. So those are my packing tips. We do have a whole packing episode if you want to go listen to that. It's way back there. It's one of our, it's one of our most popular episodes, but it's, it's definitely one older ones too.

So, uh, yeah, more packing tips can be found there.

Meggan: and we have a packing list on our website as well. If that interests you, um, I didn't have a hand in that because I shouldn't be involved in things that have to do with packing. I'm literally, I can't wait for June for a multiple, uh, bunch of reasons, but I will definitely be giving a packing update once that's all taken care of.

I wait to see if I succeed or fail. Well, you know what? That is it for this week's episode. We have tried to cover as much as we can to help you get started on things to think about when you're booking multi destination trips, but if we've missed anything or you have tips and tricks to share, as always, we would love to hear from you.

This podcast is based on research and our own experiences, but we all have a lot to learn. So do let us know if we've missed anything or if you have something to share as always, thank you so much for tuning in. We love having you here to help support the show.

You can buy us a coffee link is in the show notes. You can leave us a review on Apple or Spotify or share the podcast with a travel loving pal. And until next time, bye friends! Bye!