Trip Planning 101 – How I Plan My Trips

There are two types of people: people that would happily give their credit card over to a travel agent so they can sit back, and people who look forward to planning trips almost more going on the actual trip. Guess which one I am?! (I do take payment via Venmo, cash, or PayPal if you are interested in my services)

There is, however, an art to planning trips. The internet, of course, makes the process easier than ever, but it’s also an overwhelming resource to have. So where to begin? I’ll tell you my process of how I book trips, stay organized, and make itineraries that I’m (almost) always happy with. Here we go.

  1. Start with flights

    Obviously, lol. One of the most fun ways to book a trip is to give yourself a window of time that you can travel and book a destination based off that and wherever is cheap at the time (instead of just searching for flights to Rome, for example). This way, there’s still some excitement left in where you’re going and what your trip could end up looking like. Something to always keep in mind: If you want a trip in Italy, your flight doesn’t have to land in Rome. Look at surrounding airports, even outside the country/city you truly want to see.

    Google Flights is my top resource for booking, as they show convenient calendars with options to customize the length of the trip, good flight prices highlighted in green, and a new feature now stating whether a bag is included in the price or not.

    Read up on my cheap flight tools and tricks to see more on how I get the best deals.

  2. Befriend Maps

    One of the most disappointing things about planning trips is thinking you can bop over to another city/country just to realize it’s not close at all. I always look at Google Maps to see what’s a) realistic, b) possible, and c) available. For example, if you’re on a short weekend trip and a city you want to see is 6 hours away, you probably shouldn’t squeeze it in– it’s not realistic. If you don’t have a rental car and you want to visit a remote town in the countryside, it may not be even possible. And lastly, what opportunities are out there that you didn’t even think of or know of?

    My friends and I are looking at planning a trip in the spring and there was a good flight deal into Zagreb, Croatia. I initially thought we’d visit Dubrovnik and whatever else was around there, but we realized we could see Slovenia and northern Italy without spending the whole trip in the car. Our beach-hopping Croatia trip turned into a mountain trek! My point is, being familiar with maps can completely change the route and vision of a trip.

  3. Utilize Pinterest

    This is my number one resource for planning the outline of trips. SO many bloggers share their itineraries and ideas on trips, and many times there will be 5 day, 10 day, or weekend trip itineraries that do almost all the work for you. Search keywords like “One week in Portugal” or “Los Angeles weekend trip” and you’re guaranteed to find both popular spots and places worth skipping.

    On this same note, it can be easy to get swept into tourist traps or places that may be cool, but not for you. Know what you enjoy and look for that– even if you don’t think you can find it in that spot. On our next trip, my friends and I are trying to spend more time hiking and visiting cool nature spots, rather than strolling through museums and buildings. Instead of searching for European itineraries, I’m now looking at top European hikes, best nature spots in Europe, etc. Know. Yo. Style. And follow me on Pinterest where I compile MANY itineraries sorted by continent.

  4. Read Reviews

    You know how everyone says social media is a scam and nothing is ever like it is on Instagram? Same goes for websites. A hostel/hotel/Airbnb is ONLY as good as its reviews. This part of trip planning takes time and patience sometimes, but looking through accomodation and transportation reviews is what keeps things going smoothly while traveling.

  5. Find food

    Surprisingly, this is a new addition to my planning services. I was always VERY focused on the towns we would visit and how we would get there that I didn’t spend much time looking for good food. LOOK FOR GOOD FOOD– enjoying every meal made our Central America trip 20 times better.

    Most countries use TripAdvisor as their rating website over Yelp, so start there. One tip from me: sort your food by “most reviewed” instead of “highest ranked” to see the places that a ton of people have visited. Usually those ratings are worth a little more : )

  6. Good ol’ word of mouth

    Because speaking to people is helpful sometimes! In all honesty, though, trust the locals and trust the people who have done it before you. Sometimes I get ideas from people through social media, but asking people about their hometown or trip experience is an awesome way to get some insight on something that may not be public knowledge.

    And there you have it! These methods aren’t for the people who need every spot planned out (I’m not that Type A) but for people who need a rough itinerary with ideas of what to do/eat once you get there. See below for an example of what my “itineraries” look like going into a trip. This way, you don’t waste time searching for restaurants and activities, but you still have the freedom to switch things around if needed.

How do you plan your trips? What am I missing out on?

Long Weekend in the Northeast: Itinerary

Finally, I had the time to sit down and write about our Northeast Road Trip Extravaganza. I recommend visiting in the fall for obvious reasons (leaves, crispness, etc.) but I could see this being an awesome spring or summer weekend trip. Winter for sure if you’re psychotic and enjoy being outside when it’s cold.

The shortlist for our itinerary was as follows, but please note I don’t recommend it. We were pretty rushed, and with early sunsets, we didn’t get to see as much of the towns as we would’ve liked.

  • Day 1: Fly into Boston, spend day/night in Burlington, Vermont
  • Day 2: Burlington, Vermont in morning, drive to Montreal for afternoon/night
  • Day 3: Montreal, Quebec in morning, drive to Portland, ME for night
  • Day 4: Portland, ME, Portsmouth, NH, and Salem, MA on the way back to Boston

Instead, look at these options:

If you have four days: Boston → Burlington, Vermont → Portland, Maine → Boston
If you have five days: Boston → Burlington, Vermont → Montreal, Quebec → Portland, Maine → Boston

For both trips, I do recommend stopping in either Portsmouth and/or Salem on the way back to Boston. They’re such charming towns that won’t add much stopover time to your trip back. Now! Let’s get into the highlights of our weekend trip.

Burlington, Vermont

While I dedicated a whole post to this magical city here, I’ll give you the lowdown. Burlington is Vermont’s biggest city, with a mere 42,000 people. The town is centered around Lake Champlain, an area our weather didn’t allow to us enjoy, but that I heard thrives in the summer.

We drove straight from Boston, winding through New Hampshire (a SERIOUSLY underrated state) and Vermont’s rolling mountains. Renting a car this trip is a must– not only are the views gorgeous, but I’m not sure the trip is doable without it, lol.


Ben and Jerry’s Factory Tour – Our first stop was one of Vermont’s most well-known and best tasting attractions. The tour was pretty good for its low price tag, and honoring the creators in their hometown felt pretty cool. It’s hardly out of the way to stop on the way to Burlington, so if you’re coming from Boston, I’d definitely recommend.

Around Burlington – If you’re visiting in the summer, take the time to see Lake Champlain. If not, Church Street is beautiful rain or shine. This tree-lined street is quintessential Burlington and is packed with shops, restaurants, coffee shops and more. I could’ve spent hours taking photos strolling around.

Food and Drink

American Flatbread – A hippie, homey, wood-fired pizza place with great local beer offerings and veggie specials. SAY. NO. MORE.
Citizen Cider – For those who are into cider and those who are not, you will enjoy. I never thought I wanted basil-flavored cider, but boy did I ever.
Feldman’s Bagels – Because brunch is overpriced and bagels are underrated.

More recommendations on my post, here!

Montreal, Quebec

Boy, Montreal, you ended up being out of the way, but I’m sure glad I met you. Now, I have to preface, you know when you go somewhere and it feels like everything about the place is against you? The weather, the festivities that are happening, etc.? That’s kind of how Montreal was for us. We got rainy, gloomy, and cold weather (which I actually hear is pretty common- so I’m not sure I should be complaining), and one of the main walking areas that was known for its charm was under construction.

Looking past the obvious annoyances, I could see what people loved about the city. Montreal is a modern city mixed with areas that felt straight out of Europe. Think: cobblestone streets, grand churches, and detailed architecture that you just don’t get in America. The fact that most people were speaking French probably contributed to that feeling as well, haha. It was a cool feeling, though, driving less than two hours north of Burlington and practically being transported to France.


Our activities, like in many European cities, involved walking around, admiring the architecture, and of course, finding food the country was known for. In this case, poutine, a dish with french fries covered in cheese curds and gravy.

I recommend walking around Old Montreal, specifically Rue Saint Paul. On our second day, we spent time around the Mile End area of Montreal, more of a hipster neighborhood (that was home to my favorite meal of the trip, below)

Food and Drink

Olive & Gourmando – We came here for coffee and pain au chocolat, and I would like to go back every day for the rest of my life. I’ve heard great things about the paninis, but I think you’ll score regardless of what you order.
Tsukuyomi – This was the real winner of the trip. I dream about this ramen. And because ramen is inherently a meat-based dish, you’d think you’d miss out getting a vegan ramen. BUT NO! Simply phenomenal.
The Cold Room – There’s just something about speakeasies in Montreal. We had so much fun searching for the entrance, and were greeted and brought to a dim but chic basement, if that’s a thing. My server even custom-made a spicy drink for me because I’m an asshole. Five stars.
L’Orignal – Everyone was pleased with their food here, but it wasn’t mind-blowing, and that’s what I’m looking for always.

Portland, Maine

I’m all about precursors here, and for Portland, my precursor is that I could absolutely see myself living here. I am PARTIAL to Maine now, and that just means I enjoyed it, so I’m going to continue to give my recommendations.

We drove to Portland from Montreal which was not necessarily a FUN ride in the dark, but boooooy this is where New Hampshire comes back into play. We drove through the White Mountains, passed through the most quaint little towns, and I almost cried of its beauty. Don’t let people rip on New Hampshire, you guys. I’m about to plan a trip back to the MOUNTAINS where I BELONG.

Anyway, back to Portland. It’s not the capital of Maine, but it’s the SPOT, ya know? There’s lobsters, and cobblestone streets (we are in New England, of course), and poutine again, some more seafood, and great, great beer. The people were laid-back and friendly. I felt like everyone in town was a childhood friend that had that mutual feeling of knowing better than to say hello to you in public. Does that make sense? They were cool with us being there, but did their own thing, and everyone was okay with that. On to the good stuff:


Walk around Old Port – Old Port, or the downtown area, is a beautiful mix of New England coastal charm with Portland’s artsy vibes. This is a popular walking area for tourists, but didn’t feel touristy at all. Give yourself a couple hours to browse shops and stop at the Holy Donut, which I will cover below.

Allagash Brewery Tour – There’s many reasons this should be on your list, and they’re as follows: 1) it’s beer, 2) it’s free, 3) and it’s actually super interesting. They don’t skimp on time here, and you’re given a FULL tour, as this building does everything from the brewing to the bottling and shipping. Remember to book ahead as slots fill up quickly– we had an 11am tour (not complaining though, lol).

Portland Headlight/Ft. Williams Park – I’m a liiiiittle pissed I didn’t get to see a proper lighthouse while in Maine, but you can’t win them all. This is one of the closest and most popular lighthouses to visit while in the area.

Food & Drink

Eventide Oyster Co. – Home of one of the most famous lobster rolls in Portland, as well as, you guessed it, oysters. Mostly a seafood place, we all loved our dishes– and there was vegetarian specials for all you fellow veggies out there. Grab a drink at a dive bar called Tomaso’s Canteen while you’re waiting and MAKE SURE your table is ready before you leave : )
The Holy Donut – As a Chicagoan (or really any big city lover), I have an affinity toward donuts, specifically funky ones. The Holy Donut makes donuts out of fresh Maine potatoes, giving them a rich, moist (ha!!!!) texture. Combined with their fun flavors, this was one of my favorite stops of the trip. Highly recommend.
Lincoln’s – Another speakeasy because they’re way more fun than walking into REGULAR bars! This one was tough to find, but we did with the help of a local who was more than willing to watch us look like idiots walking into back doors of random establishments. The kicker: everything is $5! Again… say no more. (Bring cash) (Thanks, Zack, for this recommendation).
Bite into Maine – We stopped here on the way out for one of Portland’s acclaimed lobster rolls. People argue this is one of the best.

Others that we didn’t see that I would’ve liked to:  Duckfat, Central Provisions, Hot Suppa

Portsmouth, New Hampshire & Salem, Massachusetts

On our way back to the Boston Airport for our flight, we took two little detours in Portsmouth, NH and Salem, MA. I had coached a cheer camp in Portsmouth a few years back and remember how much I loved the town, so we did a 30 minute stop in the harbor town. I’ll let the photos speak for itself.

Salem was an obvious stop, as we were in town October 30th. If you’ve seen Hocus Pocus in the last five years (I hadn’t) you’ll absolutely love it. However, I’ll never complain about a New England town in the fall, and that’s a fact.

Have you visited any of these places? Hopefully! Did I miss some major spots? Most likely!

Thanks for listening to my rants of excitement and amateur food reviews,

How I Save Money to Travel

One of the questions I get most often is simply, “How do you afford to travel?” Since I’m not exactly subtle about the financial struggles of working an entry-level job, (see my blog’s headline lol) I figured it makes sense for me to share my pointers on how I can afford international trips and weekend galivants throughout the year.

Now, a quick disclaimer. While I think this goes without saying, everyone’s situation is different. Some of us are working around PTO and vacation days, others around class schedules and winter breaks. We all have different salaries, different student loan payments, you get the idea. None of the below ideas are GROUNDBREAKING, but I hope it inspires you to be more conscious of spending in order to get your dream trip booked. I promise it’s worth it every time.

Please enjoy photos from my trips of 2018, and without further ado, my tips to saving money for your next vacation:

1. Examine your monthly costs

I have a whole blog post dedicated to this (coming soon), but these costs are often the foundation of our spending. Are you signed up for music services? Can you join a family plan to save a few dollars? Are you really using your gym membership or can you deal with the gym at your school/office instead? What about the Birchbox free trial that you forgot to cancel? Make sure ANY monthly cost (including cable, etc.) is something you’re using daily. Cut the ones you don’t.

2. Stop eating out

I truly think this is the number one thing that sets people back when it comes to saving. I eat out maybe 1-2 times a week (1 lunch and 1 dinner), and the rest I cook at home. It’s better for your body, it’s better for your wallet, and hopefully you’ll pick up a skill or two in the kitchen. Stop buying Chick-fil-A every day and pack a lunch. 🙂

3. Be conscious of small spends

Yes, this includes coffee runs. *eye roll because this is everyone’s advice* Drink coffee at work, avoid getting overpriced candy at the movies, and finish your not-so-great can of hairspray before buying a new one. Small purchases really do add up, and often times we’re buying things we don’t need, which is a whole other topic that I’ll get to later.

4. Open up a travel account

Not accessible for everyone (including myself), but my boyfriend has a separate travel account that he puts money into monthly. This way, it’s easy to budget for trips and you know right off the bat if you can afford to book something. If you’re not great at limiting yourself on the day-to-day spend, this may be a good tactic for you.

5. Give yourself personal challenges

Cut down/take a month off of drinking (helloooo, dry January! Join me!), don’t buy clothes for a month, or limit your grocery runs to a set amount. This kind of makes saving feel like a game, but it’s definitely not always fun 😅 Sometimes I try and see how many days I can go without spending money, which is absolutely terrible but I recommend.

6. Book the flight

Once you have your flight, you’re going (unless you’re actually willing to pay the cancellation fee, which is just BONKERS if you ask me). Knowing that I have a trip coming up is usually what gives me the push to start saving and have more discipline with my spending.

The last thing to remember has less to do with saving and more to do with the actual travel aspect. In order to afford bigger or more frequent trips, paying for an average-priced ticket, staying in hotels, and having brunch daily just isn’t in the cards (not yet, at least lol). Use these hacks to find a cheap flight and stay open to the idea of hostels or small Airbnbs. My trips usually involve public (sometimes overnight) transportation and the same hostel breakfast daily. If you want to visit somewhere, this is how you make it happen. And again, I promise it’s worth it.

If you have tips to help you save for travel, let me know! Follow my Pinterest board for more travel inspiration, stay tuned for some more itinerary posts, and good luck not spending any money at all!

Thanks for reading,