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The Guide to Planning an Amazing 1-2 Week Trip

Updated: Dec 8, 2019

So you've decided to take some time off of your day to day and explore a new place - wonderful! But where to start ? This step-by-step guide walks through how we approach trip planning - hope it helps!

Amalfi Coast
Chilling in the Amalfi Coast

So many places to go and so much to see - but with so little time - where do you begin? This guide assumes you already chose the location (state, country, wherever?) - but if you are still undecided, why not check out the New York Times 52 Places to Go and see if any of them tickle your fancy (adventure? cultural? foodie? beach?).

Helpful (overall) tips

  • Find as cheap of flights as possible. We usually watch for them on Scott's Cheap Flights or Dollar Flight Club, leverage Google Flights Explore, use points, or try booking on a Thursday.

  • Decide if you have any must-dos. Then build the rest of your trip around those.

  • Google sheets is your friend! We like to start by building out a super simple itinerary on a spreadsheet, calling out any things we want to make sure to include.

  • Be flexible, the most fun part of these trips is throwing away part of your itinerary based on recommendations from locals or things you hear while you are there

  • If you're planning for plane travel between destinations (like our Azores trip), try to jump around less then you think you'll want to.

  • We prefer to rent a car when doing a lot of travel. Though for more remote areas, make sure to do this somewhat early - and watch out for limited automatic cars outside of the United States

  • Download Google offline maps for the locations you'll be visiting before you go. This will be your savior for when you don't have wi-fi or service traveling

  • No need to grab cash anymore, converting at the airport is a robbery. Instead, get a card with no ATMs fees and no international fees (like this Schwab one we love)

Itinerary - This will obviously change based on the trip you are taking, but this is the general flow that we've found to maximize adventure, fun and relaxation.

  • Day 1: Travel, settle in, light exploring and planning anything you haven't done yet

  • Day 2: Good days for intense activity / adventure / hiking

  • Day 3: Good days for intense activity / adventure / hiking

  • Day 4: Good days for intense activity / adventure / hiking

  • Day 5: Travel somewhere new and take it easy

  • Day 6: Good days for intense activity / adventure / hiking

  • Day 7: Winding down with a more relaxing vibe (small town, beach, etc.)

  • Day 8: Winding down with a more relaxing vibe (small town, beach, etc.)

  • Day 9: One last (but easier) adventure!

  • Day 10: Relaxing last day and travel back

Now for the real details!


The Trip!

Ok, with some of the general tips out of the way and a loose itinerary - it's time to really dive in.

Where to stay?

  • We are pretty obsessed with staying in tiny homes and yurts (like we did in Zion & Bryce) - so would highly suggest that for anyone!

  • Other than that, we look at (they have a pretty decent rewards system) and Airbnb. While we generally prefer Airbnb, the one con is not being able to leave bags with them after check-out like you can in hotels, though always worth asking.

  • For, we look for the lowest price we can get with a 9+ rating. And will use to cross reference, since they use a different review system.

What to do?

  • This one is where the most variation will occur based on who you are and what you like. Though our main tip is plan less than you think you want to do - we love activities, but otherwise you'll leave the trip less relaxed than you entered it!

  • Read blogs and begin tracking activities and/or places you see mentioned a lot. We normally search for blogs that lay out an itinerary the same length we're planning for to get started (like our 10-day Alaska trip) and like to look for more off-the beaten path recommendations

  • If you like hikes like we do, use Alltrails to find which ones fit you best. If you want to avoid crowds, it's always good to get an early start for hikes, plus then you'll get your exercise out of the way in the morning!

  • Some popular activities may have limited space, so plan to book them early and then plan the rest of your trip around that

  • Think about how much sunlight you'll get during the day based on time of year you are going (i.e., I had really long days in Scotland, which enabled me to fit much more in)

Where to eat / drink?

  • For foodies, this might be the most important part of the trip!

  • While in the states we Yelp everything, though that doesn't seem to work as well for other countries. For these trips, I tend to lean more heavily on blogs and TripAdvisor

  • We are huge fans of local beer/pubs and coffee shops to get more of ambiance of the place we are visiting. Also they are great relaxation points between activities

  • Try to immerse yourself in the food your destination is known for - maybe a cooking class? A hole in the wall? Or whatever your heart desires!

  • For day-time activities, make sure to have snack, snacks and more snacks - don't want anyone being hangry

Patagonia, Argentina, El Chalten, Mt. Fitz Roy
Trekking in Patagonia (El Chalten)

Final Thoughts

(less relevant for this post, but sticking to our normal blog format)

Would you recommend to your friend / family? We would highly suggest taking 1-2 week vacations regularly! We all need it to re-set, gain some perspective and generally chill out :)

Would you return? We tend to not return to the same place for a while, unless there was a lot we missed - but hey, if you really love somewhere, why not!

Favorites to speak of:

  • Lodging: Oof, this one is too hard - there are so many good spots. Basically anywhere that has a bunch of character

  • Activity: Canyoneering! We could go canyoneering for days. I've now gone in Interlaaken, the Azores, Zion & Bryce and Slovenia and would suggest all of them

  • Eating: This may just be nostalgia, but out of everywhere I've visited - this Sabich (pita stuffed with fried eggplant, hard boiled eggs, Israeli salad, parsley and tahini sauce) in Israel.

  • Drinking: Also too hard to say - but really any cool pubs, speakeasies and/or coffee shops that we can lounge at

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