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Over the last few years, I’ve learned how to plan the ultimate trip – whether it’s fully adventure based or sprinkled with relaxation and cultural events! From trips to Iceland, Ireland, St. John and domestic locations – it’s honestly not that hard, even when you just randomly pick a spot with literally NO idea what you can do there. Here are my top tips & ways I plan a trip!!

Budir black church in Iceland

First! Figure out WHERE you want to go. I’m always perusing flights and have a pretty good idea of what cheaper flights from Boston are (mostly Europe). Google Flights is a great tool to use because you can put in flexible dates (literally just whatever month you want!) and it will find flights all over the world for you. I’ve got a running list of places that I’d love to visit so I always check prices to get there.

LODGING: Once you’ve decided where to go, you need to find a place to stay – but first you need to figure out if you want to bounce around to a bunch of other places. Do you want to use one spot as a home base or do you want to have multiple bases? This is a good option to do if you are ok with packing up every few days, especially if you’re by yourself! It’s also doable with a larger group, it just takes a little more time.

If you’re going somewhere that’s a smaller area (ie: St. John), you are fine with one home base – in fact, I’d recommend it. If you’re going somewhere that’s a lot more spread out, it’s worth having more than one base since you can venture out farther without having to drive significant distances. Both times that I’ve traveled to Iceland I’ve used multiple bases and it’s fantastic – you also get to experience so many more areas & towns. I search multiple places when it comes to finding lodging, from Airbnb & VRBO to to general Google searches. Are you comfortable with staying with families via Airbnb? Do you want to stay at a hostel? Remember, you don’t need to stay anywhere super fancy because you’ll be out exploring most of the time anyways!

Catalina Island harbor full of boats

TRANSPORTATION: How are you going to get around? Are you going somewhere that requires a car or can you use public transportation? I’ve done both – in places like Europe, the public transportation situation is AMAZING and you can get pretty much anywhere via bus or train. If you’re going somewhere you want to explore more, it’s worth renting a car (even if it’s just for a few days) – you’ll be able to make your own schedule and stops. I’ve also done bus tours in Ireland and they were great – they had planned stops and certain routes and it was nice to not have to worry about driving/fuel/stopping/maps/etc.

Cliffs of Moher on a cloudy day

FOOD: What are you going to eat? Are you going somewhere that’s costly to eat out or can you get by eating one meal out per day? It’s always worth the research to find out what the grocery store/restaurant scene looks like. Are you going somewhere that has a specialty meal that you want to try? Do you want to budget a little more money for a special meal?

When we went to St. John we knew that it was going to cost a LOT of money if we ate out all the time (plus honestly who wants to eat out multiple times a day?). We decided to make our breakfast every day (why buy it when you can make it at home for like $5?) and we packed PB&J sandwiches for lunches. We made one dinner at home and managed to stretch leftovers from a few dinners out – when it was all said and done we didn’t spend much money on food out – we also brought my GF bread and snacks since we knew they were pricier on the island. We did the same thing in Iceland – PB&J is literally universal ????.

Anytime I travel anywhere I bring my own snacks because it’s cheaper to buy them in bulk and pack them and KNOW that I won’t get sick from eating something that’s not gluten free. If you have the ability to make breakfast wherever you stay, do it (even if that means that you’re eating microwaved oatmeal out of a mug #beenthere ????). Unless there’s a specific place you plan on eating lunch, I always recommend trying to pack that too, even if it’s just a sandwich. Whenever I go to a new place, I always research their local restaurants and see what the reviews are and then plan a few dinners out. Most restaurants publish their prices on the menu so you can budget your money that way too.

Haystack Rock at sunrise in Cannon Beach, Oregon

SIGHTS/ACTIVITIES: Is there a specific reason that you’re traveling to this place? Is there a national park you want to visit or a beach, or a museum? Figuring out what your top “wants” to see on your trip is the easiest way to start planning your route. How far apart is everything? What is your travel time going to be? If you don’t happen to make it there due to weather/transportation/time issues, are you ok with that? Is there a cost to go there? If you’re going to a national park are you better suited to plan a few days around it? Sometimes if I’m going to a place with no real plan I look on Pinterest for activities to do in that area (it sounds like that would be the last place to look but you’ll find TONS of blog posts about traveling to those places!). Prioritize what you want to do the MOST because chances are that you’ll run out of time before you run out of things to do.

Brown Icelandic horse in a field

YOUR ROUTE: Like I mentioned above, once you figure out your “wants” you can build your route around it. Are you going around a country or city? Are you visiting multiple cities? Map out where you want to visit and then sit down and think long and hard about what is the most logical route. Once you have an idea of how your days will be, start figuring out travel time and where you’ll spend each night. This is where you decide if you want to bounce around or stay in one spot. Will you need a car for any amount of time OR the whole time? Will you plan parts of your days around certain meals?

Vatnajökull glacier in Iceland

BUDGETING: This is the number one most IMPORTANT thing when it comes to planning a trip. HOW much money are you willing to spend? Do you want to spend more on activities than you do on food or lodging? Are you willing to eat microwaved oatmeal for dinner a few nights if it means that you get to do a specific activity you’re dying to do? The answer to that question is always yes ????. I try to use credit card points whenever I can while planning and tend to do a lot of my lodging booking via because over the years I’ve earned rewards from them that I can apply to future travel. I’m always willing to budge on food to push money towards activities and try to do as many free things as possible. Some countries are more expensive to stay in and that’s just a fact of life (HI ICELAND I’M LOOKING AT YOU) so you’ll have to have a bit more money to put towards lodging. Shopping around for flights, lodging and car rentals is always the time because you’re almost always guaranteed to find a deal. And honestly, no matter what your dietary needs are, packing your own snacks will save you a TON of money – as will bringing a reusable water bottle.

Planning a trip can add up realllllly quickly, so I always recommend having a spreadsheet with all your expenses (especially as you’re booking it) – plus it makes it easier to plan out your days that way. One little thing that will eat into your budget quickly and without much warning is random little snacks and coffee stops (trust me on this one). Having cash to carry for those specific needs can help keep down that cost if you’re worried about it, but if not, spend away. Not everyone has to budget to travel either – this is just how I’ve always done it. You can EASILY do long trips on the cheap if you’re willing to sacrifice a few things. OH! Another thing I forgot to mention that will help with budgeting – pack LIGHT. I mean carry-on light. Avoiding baggage fees is SO easy if you can easily fit everything into a carry-on, then you don’t have to worry about losing your bag or waiting at baggage claim for it!

There are TONS of other travel tips out there (seriously, Pinterest will help you!), but these are the best that I’ve encountered over the last few years!! I clearly really enjoy traveling and LOVE to do it on a budget, even when I think I can’t pull it off!! I can’t wait to plan my next trip!!

For more travel inspiration, here are a few posts from the past about traveling!

Iceland in the Winter // How to Plan a Trip to Iceland for 10 Days // How to Plan a Trip to St. John for 10 days

Seaside houses in Galway Ireland

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HI, I'M caitlin

New England based wedding and lifestyle photographer