Travel Planning Guide | How To Plan A Trip With Multiple Destinations

After getting back from our trip to Italy and the Amalfi Coast, so many of you requested I put together a guide on how to plan a trip with multiple destinations. I couldn’t believe I even had people asking if I use a travel agent! I wont lie… I felt pretty cool replying it was all “me, myself & I”  to those messages 🙂

I used to find planning longer trips incredibly intimidating. Just thinking about having to book multiple flights and even deciding where to go would get me so flustered that for years we only did smaller getaways to resorts or single cities. 2017 was the year my travel confidence finally began to grow. I had the opportunity to attend two international group press trips, one to Finland and another to Serbia, where I was able to experience an extended itinerary with multiple stops. Then last December Nick and I finally pulled the trigger and planned our 10-day holiday trip to Paris, Bruges and Amsterdam.

OMG. We came back from that adventure with so many questions for ourselves. Why did we late so long? What were we so afraid of? Is getting from place to place abroad really that simple? I know it sounds cheesy, but for the longest time I had let my fear of what could go wrong hold me back from really getting out and exploring the world.

Now I’m by no means claiming to be a seasoned travel expert, but with a few multi-city trips under my belt (that were all pretty stinking awesome!) and another one coming up soon I feel confident in my planning process. It’s a team effort between Nick and I. We split responsibilities and try and plan as far in advance as possible. It’s not always easy and the need for getting blog content can make things a bit more complicated, but once you’re there and experiencing everything falling into place the stress and time spent planning feels totally worth it. Here’s how we do it!

How To Plan A Trip With Multiple Destinations

How To Plan A Trip With Multiple Destinations


figure out the length of your trip

How long you can be away from home and what can feasibly be done in that timeframe are probably the first things you’ll have to ask yourself when planning a big trip. While I’m self-employed, Nick has a traditional day job (luckily with generous vacation time!) so we normally aim for a 10 day getaway, ideally when there’s a 3-day holiday weekend. We’ll take an overnight flight on Thursday or Friday after Nick gets out of work and then come back the following Sunday or Monday. This way he doesn’t have to take more than 5-6 days of vacation and gives us enough to hop to multiple destinations abroad.

choose a priority destination

We like to choose one place that we absolutely have to go (i.e. Paris or Positano) and then plan additional stops around it. Once you make up your mind about what destination is your top priority everything else will start coming together. I usually will just Google keywords looking for example itineraries and travel guides to give me ideas of what other stops would make sense. I’ll look into the time required to get to another destination, the transportation options, how much hotels cost in that area, what activities or attractions a spot can offer and then just start narrowing down from there.

research prices & adjust stops + trip length accordingly

Going along with my point above, usually our top priority destination is also the one where we know we’ll be spending the most money. For example I’d originally thought we’d go to Capri after Positano, but after discovering how insanely expensive the hotels are and knowing we’d have already spent the bulk of our budget in Positano, we decided to end our trip in affordable Ischia instead. Flight prices can be a deciding factor too. We chose to go to Amsterdam on our final stop in December because the flights coming back to the U.S. were so much cheaper than many other European cities at the time.

get a credit card that rewards you

Signing up for a credit card with a generous rewards program was a total game changer. I have the Chase Sapphire Reserve card and I’m absolutely obsessed with it. In less than six months I’ve been able to pay for multiple flights with just points thanks to this credit card and no, I didn’t need to spend a small fortune to do so. With this card you can earn 3x points on any travel or dining purchase worldwide. Even if you don’t travel extensively internationally it’s a great card because things like Uber and food delivery services like Seamless are eligible for earning 3x points.

Other benefits that come with the Chase Sapphire Reserve include a Priority Pass Lounge membership giving you access to 1000+ exclusive airport lounges. This means no longer having to wait at the gate for your flight. As a Priority Pass member you’ll find there’s an accessible lounge at pretty much every major airport which usually include free food, alcohol and wifi, comfortable seating and sometimes even showers and sleep pods. The lounge we waited in before our flight back from Rome was INSANE. Nick took a shower in the most amazing bathroom and we gorged ourselves on made-to-order pasta without paying a dime!

The $450 annual fee is a little scary, but trust me the money you’ll end up saving via the perks will completely outweigh the fee. Right off the bat Chase will give you a $300 travel rebate– basically $300 for free credited right to your statement when they see you’d made an eligible purchase like a flight, hotel booking, car rental, etc.. The $300 rebate is  something you’ll get every year at the time of when you signed up for the card. Chase will also reimburse you the $100 application fee required for TSA Precheck or Global Entry. When I applied for Global Entry I saw the $100 fee credited back to my statement a few days later.

When I add up the $300 travel rebate, the $100 global entry reimbursement and the $2000+ worth of flights I’ve booked using points– it’s obvious to me that this card is more than worth the $450 annual fee. FYI this is NOT sponsored nor am I working with/in touch with Chase. I would never recommend a credit card to you guys that I didn’t actually use 🙂

How To Plan A Trip With Multiple Destinations


create a detailed itinerary

Once we’ve booked the big things like flights and hotels, I’ll create a massive word document breaking down each day of the trip in a clear, organized outline. I love a good detailed itinerary (blame it on my PR days) so in this document I’ll include everything. I’m talking flight arrivals/departures, confirmation numbers, check out/check in times, hotel addresses/phone numbers, any planned excursions, dinner reservations, etc.

The last thing you want to do when you’re traveling is have to search through your email for a confirmation or look up museum hours so taking the time to put all that info in one place can be a lifesaver. I usually will make the itinerary in Google Docs and add Nick as a collaborator so he can access it and make changes. I’d also recommend bringing both a print copy and saving your itinerary as a PDF to the Books or Pages app on your phone so you can access it without wifi.

make a custom Google Map for every stop

I always get asked how we’re able to see and do so much in one day when we travel so here’s the secret. Before our trip to Europe in December, Nick came up with the idea of creating a custom digital map for each city we were visiting pinpointing our hotel, public transpo, attractions, restaurants, bars, bakeries, photo opps, etc. You can do that?

How To Plan A Trip With Multiple Destinations

^ Here’s a peek at the map we created for when we went to Paris!

Yep using Google Maps you can specify a location and drop “pins” on any point of interest. It’s awesome because you can categorize your pins by color– GREEN for restaurants, PURPLE for museums, YELLOW for monuments, RED for cool spots we know we want to get a good photo, etc. We’ll not only include everything we know for sure we’re going to, but a bunch of backup activities and dining options. If something ends up being closed or we get somewhere and realize it’s not what we thought, we can just pull up the map and have multiple plan B ideas ready to go. Similar to Google Docs, you can share your map with other collaborators so Nick and I will work on these together in the weeks leading up to a trip 🙂

PRO TIP: Before your trip make sure you download your maps to the Google Maps app so you can access them on your phone without wifi. No internet = no problem.

how to find cool things to do + photo opps

Gathering content and taking photography is always a top priority when we travel. Even if you’re not a blogger, who doesn’t want to flex for the ‘gram when you’re on awesome trip?? Beyond just searching Google for travel guides and example itineraries, I’ll also go into detective mode on Instagram and Pinterest when planning a trip. I’ll search travel hashtags and see what people are posting in every location for ideas of what to do and interesting places to see. The spots that catch my eye I’ll screenshot so I can look up reviews and if I think it’s worth visiting I’ll add it to our map. If there’s an attraction or monument we are considering visiting, I’ll go to Instagram and see what photos have been posted from the exact location to get an idea of the best angles for photography.

How To Plan A Trip With Multiple Destinations
How To Plan A Trip With Multiple Destinations

^ Before any trip I’ll browse hashtags and specific locations on Instagram and Pinterest to get inspiration and see the best angles for photography

Before we went to Paris, Nick found an awesome list of the best non-touristy spots for photographing the eiffel tower on a forum for professional photographers. If I come across a photo of a really cool-looking street or somewhere that doesn’t have an exact address, usually I’m able to figure out where it is by doing a reverse Google Image search. If it’s a popular or often-photographed destination, the search will be able to tell you what is is or show you similar photos which likely will lead you to info on the exact location.

Doing all this takes some effort and requires getting a little scrappy, but putting in the work ahead of time will make getting good photos on your trip so much easier. I’ll even search “best time of day to visit EXAMPLE ATTRACTION” to plan out when we should to go to a museum or monument. If I hadn’t done research prior to visiting Rome, we never would’ve found this ivy-covered ice cream shop (that I originally discovered on Pinterest) or shot these amazing photos where it looks like we had the Trevi Fountain to ourselves.

book accomodations

My favorite website for finding and booking hotels is It’s incredibly easy to use and you can filter accommodations by really detailed parameters like budget range, location score, star rating, distance to popular attractions, property type aka hotel or bed&breakfast, amenities (wifi! parking!)– the list goes on. Once you put in your date, will show every hotel with availability and the prices of every room option. You can also see all the reviews left by previous guests. I also really like how clearly calls out if a room is non-refundable or if there’s a certain date by which you need to cancel– I can’t stand when sites try to hide cancellation policies or extra fees. Everything is just very user-friendly and no-fuss!

View of Paris From the Arc de Triomphe


print & save screenshots of all important documents

Save yourself the headache and avoid the desperate search for a coffeeshop with wifi by printing and saving all your important documents ahead of time. I like to take screenshots of my hotel confirmations and boarding passes so I have everything saved as a photo. For larger digital documents I’d suggest saving as PDFs and downloading to an offline app like PAGES of iBOOKS. This way you can access them without a wifi connection.

leave your itinerary with friends & family

I always send our finished itinerary with all the details on our hotels, flights, etc. to our family before any trip. It’s better to be safe than sorry and this way your loved ones know where you are every step of your trip.

call your credit card company & bank

If you don’t travel often, make sure you alert credit card and bank that you’re going to be out of the country. A lot of credit cards will automatically deny charges that seem out of the ordinary from your normal activity, so by letting them know ahead of time you can ensure that doesn’t happen.

pack appropriately & check for baggage limits

Before any trip make sure you look up the weather conditions and pack accordingly. To avoid overpacking, I like to bring items I can layer and mix and match. Going to be doing a lot of walking? Better bring a pair of comfortable shoes. Trust me, those cute boots that you thought were comfy won’t feel so great after 8 hours traipsing around a cobblestone-covered European city. For my favorite travel shoes make sure you check out my guide to the best comfortable footwear. Sidenote: these are THE BEST sneakers ever. I no joke wear these 75% of the time on every trip!

Also make sure you look up baggage limits for your airline! We made the mistake of not doing this before our trip to Italy and arrived at the airport only to find out our carry-on bags couldn’t be more than 25 pounds. If possible, I’d wear your clunkiest shoes and heaviest coat on the plane so these don’t take up weight in either of your bags! If you want to see how I pack my carry-on bag I explain in this post here. head on over to this handy how-to post.

Casa Angelina Amalfi Coast Hotel Review


allow for the unexpected + manage expectations

As much as I wish I could map out every minute of a trip and have it all go according to plan, it’s just not realistic. When you’re in a new place for a very limited time sometimes you just gotta be accepting of the things that are out of your control and roll with any itinerary changes. Seeing rain in the forecast the day of your boat tour or arriving at an attraction only to find it’s closed for a private event totally sucks, but that’s why it’s important to have a backup ideas so you don’t have to scramble to figure out alternate plans.

On every trip we’ve taken I would say we’ve only stuck to the originally planned itinerary for 40% off the time. Once you’re somewhere new I can guarantee you’ll decide there are things you want to do differently. The weather could change, you’ll get suggestions from other travelers, you might decide you’re not in the mood for the cuisine of the restaurant where you have a reservation– so many factors could impact your plans.

If you hate the unexpected or are prone to anxiety like me, I would suggest keeping your itinerary open-ended with blocks of free time where you can decide what you want to do on the spot. Of course plan for the things that require reservations or can only be done at certain times, but if you try to map out every minute of a trip you’re going to end up incredibly disappointed. Trust me, I know from experience. I find that I always have a better experience on a trip when I allow myself to be impulsive, versus trying to hold myself accountable to an unrealistic schedule.

Looking for more travel inspo? Then check out these posts!












- Katie


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