Tips for Planning The Best Multi-Destination Trip

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Into today’s modern world, we are often granted very little vacation time or we are so busy with our jobs, social lives, and families that holidays are sort of pushed to a back burner. Many of us only have the ability to travel on holiday once or twice a year and as a result, we might plan a trip that highlights multiple regions of country, multiple countries, multiple cities, or all of the above. We spend weeks thinking about where we’d like to go and then it’s time to plan our trip within an allotted time frame. This process can seem daunting and many might not know where to start. Where will you go? What will you do? What is the most affordable option? How will you get around? Where will you stay. Discovering these answers is the fun part of planning the best multi-destination trip.

All of these questions can be overwhelming and before you know it, you’re sitting at a computer desperately searching the web unsure of what you should do. A multi-stop trip is complicated, I’m not going to lie. It requires quite a bit of planning if you want to have a nearly stress free trip. You have to align everything and really keep your schedule in mind. But with a planning and and my tips, visiting multiple destinations during one trip will be all the more possible. So, let’s go and dive straight into my tips for planning the best multi-destination trip.

Is a multi-destination trip a good idea?

Tips for Planning The Best Multi-Destination Trip | My Normal Gay Life
Chambery Street Scene

You might be considering the prospects of planning normal week long trip to one destination or a multi-destination trip for your next holiday. The idea of visiting a few new destinations during one trip is very appealing but also can feel a bit overwhelming. On the positive side of things, a multi-destination trip is a great way to see and experience multiple destinations. There is absolutely nothing wrong with visiting just one destination but if you don’t get much holiday time then scheduling a few destinations lets you maximize your vacation time.

Since you will already be in a specific area, it can also be much more cost effective to go from one stop to the next verses the cost of flying between your home and your destinations. This is especially true for people living in countries in the Western Hemisphere, such as the United States, who wish to travel to say Europe or Asia. Flights start out at hundreds of dollars and have a duration of 6+ hours depending on your destination. If you’re already in France, why not go ahead and visit the UK, Belgium, Germany, or Italy. They’re so close to one another so its a much more viable situation. Most importantly, a multi-destination trip will feel like an adventure and you will definitely have some interesting experiences.

Things to consider for a multi-destination trip

Plan your multi-stop trip with these tips
TheAndrasBarta / Pixabay

When planning a multi-destination trip, many of the things you need to consider are the same as a normal trip where you visit one destination. The only difference is you will need to consider these factors for each of your destinations as well as for the trip overall. Here are some important factors you should definitely consider if you are hoping to take a multi-destination trip.


I am not a proponent of basing the time you’ll travel on seasons alone because pretty much every destination has its merits during each season. You’ll have a unique and interesting experience during spring, summer, fall, winter, dry, rainy. So do not let the season limit your travel. Bear in mind the shoulder season, or the season when fewer people visit a destination, can equal major savings. Hotels, transportation, and attractions such as monuments and museums all have lower prices. Decide what your goals are for the trip. What do you want to do and what do you want to experience? Then use this information to make a decision as to what time of the year to go.

Time Constraints

Tips for Planning The Best Multi-Destination Trip | My Normal Gay Life


When planning a multi-destination trip, you need to take your time constraints into consideration. This might be one of the most important aspects of planning your trip because you need to have a firm understanding of just how much time you have to do the things you’d like to do. The number of destinations during your trip will definitely depend on the amount of time you have to travel. The best thing to do is not be over ambitious. Feeling excitement about travel is great but planning too much in your time window can make a trip stressful and far less enjoyable. There is no pride in spending such a small amount of time in anyone destination because you hope to get that check mark for visiting lots of destinations. Travel is about the experience and maybe learning or understanding a place. You can’t do that if you pack your schedule too full.

Here is what I suggest for your multi-destination trip based on your travel time. It’s important to note I would personally lean towards fewer destinations so that you can have a better experience and not worry so much about travel time and such. Quality over quantity is a concept you should live by. Just because you can fit in 8 countries doesn’t mean you need fit them in.


  • 1 week: 2-3 destinations
  • 2 weeks: 3-4 destinations
  • 3 weeks: 4-5 destinations
  • 4 weeks: 5-6 destinations
Getting Around

Most people want to save money while traveling and I assume you are one of those people. Of so, you’ll want to make sure you determine how you will get from Point A to Point B, and C, and so on. Being aware of the costs of transportation ahead of time allows you to plan your budget more accurately. Today there are many, many ways to get around including flying, trains, buses, ride shares, and renting a car. Be sure to check all possibilities to determine what makes sense for your budget and time constraints. It’s also important to take stock of the various routes you might take and the costs associated with them.

Tips for Planning The Best Multi-Destination Trip
ManuelaJaeger / Pixabay

Determining where  you will stay and for how long is vital for a multi-destination trip. Decide what your total preferred budged for lodging is taking into consideration the number of destinations you hope to visit and the average cost of lodging in the cities and towns you plan to stop in. Then try to stay as close to that budget as possible. It’s important to know how many days you will stay in each destination and then decide what type of lodging you prefer for each. Today there are many different options for lodging including hotels, hostels, and Airbnbs. Depending on your needs, you could do one type throughout or a combination of all of them. You might even consider buying a spot on a sleeper train if you’re traveling a long distance. In this way you can save money by combining lodging and transportation.

Planning the best multi-stop trip

Make Strasbourg one of your stops!
Strabourg, France
Step 1: Choose Your Destinations

You can’t very well plan any kind of trip without first knowing where you are going. While I’m sure you have some idea of just were it is you’d like to go, I am willing to go out on a limb and say you likely have a number of destinations in mind. In fact, you probably are a bit over zealous and have far too many destination ideas and don’t know where to start. Well, first write every single one of these destinations down on a sheet of paper or put them in a spreadsheet so it is easier to keep track. At this point, don’t worry too much about distance or time. This is the dream stage of your planning. Just get these ideas in order.

However, you may want to consider general location of each of your destinations when choosing so it is easier and more viable to plan when you are booking things later. Use Google Maps to help you decide the geographic region you’d like to visit. Then eliminate any of the destinations from your list that aren’t in that region. List the remaining countries or cities in order of how strong of a desire you have to visit each. Simply rate each destination on a scale of 1-3 with 1 being the least amount of desire and 3 being the most. Now move on to the next step.

Step 2: Research
Researching Your Multi-Destination Trip
StockSnap / Pixabay

At this point you should have a much clearer idea of where you’d like to go during your multi-destination trip. It’s time to start figuring the details. Nevertheless, you should prepare yourself to change your initial plans as you research. You might discover a certain destination eats up far too much of your current budget or another potential destinations has a lot more to offer.  Whatever the case might  be, make sure you remain flexible throughout your planning process.  Here are some things you should find the answers to through your research that will help you make decisions regarding your plans.

Why Visit the Destination?

You need to have a clear idea of why you want to a visit a place. What do you hope to see and do when you arrive to the city? Are you interested in the foodie scene, history, gay culture, or something else? Are you hoping to relax, be active, or a combination of them both. Make a list of things you’d like to see and do while your in each destination. Make it as long as you’d like but remember you can’t possibly see and do everything so perhaps it is best to limit these activities to your top 10 for each place. If you have no idea then you can simply Google search what to see in your destination” for a quick look at the most popular things to do. I always search for “off-the-beaten-path attractions in [destination]” and “things to do near [destination]” as well. I like to do a few things that aren’t your typical touristic activities so the last search queries are helpful. You’ll find lots of blog posts and guides published by a variety of people and organizations to help you determine what you would like to do. My personal advice is to trust smaller bloggers more as they are not necessarily totally sponsored by every destination and brand. You can trust them.

You can also check my blog, My Normal Gay Life, for a lot of travel information and stories.

How long will you visit?
Tips for Planning The Best Multi-Destination Trip
On excursion in the Galapagos Islands

Determine how long you will stay in each of your destination taking into account the overall amount of time you have. For instance, if you have one week and you’re visiting two destinations then you need to determine how much time you would like to spend in each location. You also need to take travel time in consideration. That means if it takes half a day to travel from Point A to Point B then make sure to block off a day for travel. Trust me…you’ll be glad you didn’t plan anything for that day you’ve blocked off because things don’t always go as we plan them.

Where will you stay?

Be sure to research your lodging options for each destination. Determine what you need or want from your lodging situation and then compare the costs of your different options. There are many, many different options these days to fit any budget. You might consider a hotel, Airbnb, or a hostel, to name a few. I don’t do hostels anymore but they are very affordable way to make travel happen.

Costs at destinations
Tips for Planning The Best Multi-Destination Trip
stevepb / Pixabay

The best way to get a general idea of how much things will cost at each of your destinations is to Google search”prices in [your destination].” It’s important to take stock of prices and get a general idea of how much you’ll spend in each of your destinations so you can determine which make more sense for your budget needs. It could be that you need to adjust your travel plans to avoid money stress. Trust me, it isn’t worth going to a place if you might not have enough money to fully experience it.

For instance, a few years ago I decided to spend three months traveling around Europe. I planned everything out down to the last dollar. I knew exactly which countries I’d visit and what I’d do. Everything was planned. But during the trip I unexpectedly decided to make my way to Israel for a travel conference. That lead to me being invited to Romania for a travel and tourism campaign which was not part of my original plans. As a result, my funds were stretched pretty thin towards the end of the trip. Madrid was where I spent the last three days of trip and I didn’t really do much exploring or anything. Of course, I was definitely exhausted which played a major role in my enthusiasm but I also didn’t have much money to work with at that juncture. I’m telling you all of this because it is really important to take costs associated with your trip into account. Your trip will be so much more fulfilling if you’re prepared.


You absolutely need to research transportation options for each of your destinations. It’s easy to forget you’ll need to get around while your traveling so this is your reminder. If you’re like me then you are traveling with a specific budget so you’ll want to compare the costs of different transportation options to see which fits the best in your budget and time constraints. Considering both these factors is very important because it doesn’t matter how cheap it is if it is going to take a large chunk of your time getting from one destination to another. Sometimes its best to spring for a slightly more expensive option if it means you are saving time. Once you’ve determined potential transportation options, you can take these into consideration along with the costs of visiting your destinations and your lodging costs in order to make a decision about everything.

Step 3: Book Things
Tips for Planning The Best Multi-Destination Trip
JESHOOTS-com / Pixabay

Now that you’ve done all your research, it’s time to take those decisions and put it them into   action. This can be one of the fun parts or it can be stressful depending on your personality. For me, it’s super fun to book my flights and accommodations. I feel like a superstar when I get a great deal! Once you’ve done this then you are set for your trip. But you might want to get everything organized. Check out my tips for that bit further below.


Skyscanner Screen Grab

Book your flights well in advance of your trip for the best deal. The general rule is you should start looking for and booking your flights about 100 days out from your trip. That is approximately 3 months. If you do this any sooner then the flights will be much more expensive and if you wait to book too close to your desired departure time then flights will also be very expensive. My current favorite flight search engine is Skyscanner which searches the internet for the best flights for the destinations and dates that you enter. Once you decide on a flight, Skyscanner will transfer you to the site where you can book it.  You can also use Google Flight Matrix which allows you to see the cheapest flights in a given time period but doesn’t let you book them. Be sure to sign up for an account with the airline you are flying with. This will earn you miles which you can use on future trips.

Train and Bus Tickets

Tips for Planning The Best Multi-Destination Trip

When it comes to train and bus tickets, I find the prices remain fairly steady. Therefore,  if you’re planning to travel by bus or train, you don’t need to rush to book the tickets. This will give you a bit of flexibility. If you find that you are enjoying a specific destination and would like to extend your stay, it’s a lot easier to do so if you wait to book these tickets. The same cannot be said for airline tickets as you need to book these in advance. If you’re traveling through Europe, Flixbus is an affordable bus option for getting around and, in my experience, the service is pretty good.

Booking Lodging 

Tips for Planning The Best Multi-Destination Trip

There is a plethora of lodging choices and a huge selection of options for booking lodging these days. Your lodging might include hotels, hostels, and home stays. You might decide to Woof, pet sit, or even Couchsurf. Throughout my travels, I have experienced pretty much all of it. However, there are three methods I primarily use today.

I will admit these days I find alternative housing options seem like a lot of work. To me, the convenience of booking a hotel and having everything I need readily available is just to simple to pass up. Today there are a million different hotel choices that fit any budget. My favorite site for reserving hotel rooms is Not only can you book hotels on the website but you can also book hostels, apartments, and other rental properties if that’s something you are looking for. In addition, Booking offers a lot of discounts throughout the year so I’ve really gotten the best deals by using the service.


This service is great for booking last minute hotel deals. There are times when I decide to extend my stay or simply visit a place unexpectedly and I need to find an affordable place to stay quick. HotelTonight makes all this possible with its easy to use interface that breaks hotels down into categories based on price and amenities. I’ve scored some pretty luxurious stays with this service all while saving a pretty penny.


I don’t think there are many people today who have not heard of Airbnb. This service allows you to book stays at normal people’s homes for a short period of time or longer extended stays. You can choose from a number of different types of homes. Rent a room in someone’s homes, a studio apartment, a castle, a house shaped like a shoe, or an entire cabin…the possibilities are pretty endless. Using Airbnb means you are going to have a more local experience which is why I love the service. But that also means you may or may not have amenities that meet your average hotel criteria.

Organize Your Information

Tips for Planning The Best Multi-Destination Trip
Engin_Akyurt / Pixabay
Keep a Notebook

Personally, I have a notebook where I write everything down when planning a trip and organize it by category. This is where I keep lists of the things I’d like to see and do for each destination, how much they cost, and approximately how much time is recommended for these attractions. It’s basically my go-to source of information once I arrive at my destination. I never know what I really want to do each day so I typically don’t plan this out. I simply look at my list and decide in the moment. My notebook is also where I write down recommendations from locals I meet. As a travel blogger, its important that I keep detailed notes so I can write about the experiences later. But this can be very helpful for you too.

Google Sheets

I also use Google sheets to organize the most important information. If you have a google account then you have access to Google Drive. By using this, you can access this information anywhere in the world. Your spreadsheet should include the following categories should include information such as:

Date: Break your spreadsheet up by each day of your trip. That means the first vertical column of your spreadsheet should have each day of your trip listed out.

Location: The city and country or place you are visiting on that day.

How Long: Include how many days you plan to visit each place.

Lodging Booked: Booked or Not Booked. It’s simple. Update this when you’ve booked your lodging for this location.  This helps you keep track of whether you need to book lodging for a place.

Lodging Details: Include your hotel or Airbnb address, contact details, and any other pertinent information such as lock box code.

Flight Booked: Just like your lodging, indicate whether or not you’ve booked your flights are booked.

Flight Details: And just like with lodging, include your flight details in this field. Include information such as flight number, boarding time, flight duration, connection information, baggage allowance, etc. Anything that might be helpful later should be included here.

Transfer Information: How do you plan to get from the airport, train, or bus station to your hotel and vice versa? Do you need to go from one airport to another for your connecting flight? Make sure to plan this out ahead of time and include those details here. It’ll make your trip far less stressful if you already have this figured out.

Visa: Do you need a visa? If yes, then make sure you figure out what you need to do ahead of time. If you  have arranged your Visa then indicate that in this category. If you aren’t sure then you can check to see if the country you plan to visit requires a visa here.

My Maps

Tips for Planning The Best Multi-Destination Trip

Google offers the ability to create your own maps of any destination in the world. Once you’ve done all your research, you can pin each monument, attraction, restaurant, coffee shop, museum, etc into your own personal Google Map to help plan your itinerary for each day. You can color code and add icons for each category of place which will make it easier to organize and navigate. The best part is if you are traveling with a companion or companions, you can share the map with them. This allows for everyone’s input and better trip planning.

Other Tips for a Multi-Stop Trip

Travel Insurance
Tips for Planning The Best Multi-Destination Trip
Enjoying wine and our health in Ohio!

Purchasing a travel insurance policy can be very beneficial should the occasion arise when it is needed. It’s one of those expenses that is no fun to but offers a safeguard for your health and a number of other issues. I’ve known people who were hurt or became extremely ill and needed medical attention. A travel health insurance policy ensures you will be taken care of in these situations. If you need to leave the country you’re visiting to head to another, often travel insurance policies will help with the costs of transportation whether it be via plane or a helicopter. You definitely don’t want to be in a situation where the full costs of your emergency care rests on solely on your wallet. So get a travel insurance policy for your own peace of mind.

Think of Budget

You likely have a million ideas about places you’d like to see and experience in mind but always keep your budget in mind. Planning too much or having too many expensive dinners can lead to a lack funds during your trip which might mean you need to make up for it. The only way to make up for it is usually to take funds dedicated to something else. If you’re trip is limited due to poorly managing your budget then it’ll be a less fulfilling experience. Simply keep that budget in mind and you’ll do just fine.

Connecting Flights
Tips for Planning The Best Multi-Destination Trip
cegoh / Pixabay

When booking flights for your multi-destination trip, you will likely see some deals that seem absolutely incredible. Maybe you’re heading to Portugal and you found a flight for $300. Well, that flight actually comes at a greater cost in the form of your time. You need to really look at the length of connection times. Is the deal really worth it if you have to spend 17 hours at another stop? Also that 17 hours layover is 17 hours detracted from the time you have to explore and experience your destinations. Trust me, long layovers are only ever fun if you want to explore the place your at and you have the time to actually do it.

When it comes to connecting flights make sure you consider these things.

  • Duration of your layover
  • Number of connections
  • Do you need a transfer?
  • Fly on single ticket (this means less stress about checked bags)
  • Stick to one airline and its partner airlines (less stress about missing your connection)
Back Up Funds

I recommend having some funds set aside just in case you need them for whatever reason. It might be the case that you get sick or you might just run low on funds. It’s always nice to have a little padding for your budget…just in case.

Get Planning!

Tips for Planning The Best Multi-Destination Trip

Now that you are armed with a fairly fool-proof guide to planning your very own multi-destination trip, what are you waiting for? It’s time to start planning your dream trip out and getting all those details down on paper. Even if you can’t take the trip right this second, the steps I’ve listed above will help you start manifesting that trip. The first step to making it a reality is taking the idea and making it something more tangible. Plus having it written down will help you research things over time and maybe you can figure out how to make your dream trip work in your budget. Just remember to be flexible and have fun with it!

Are you ready to plan your dream multi-destination trip?

J Harvey

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Tips for Planning The Best Multi-Destination Trip

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J. Harvey

J Harvey is a travel writer based in North Carolina. With two masters degrees, he decided to forget working a normal 9-5 job and instead create a travel blog focusing on travel for a more inclusive community. He hopes to increase LGBT representation within the travel industry while inspiring others to travel in whatever capacity.

J. Harvey has 185 posts and counting. See all posts by J. Harvey

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