How to plan your next trip like a pro

how to plan a trip

DIY travel planning made easy

Welcome to Travel Planning 101, your crash course in planning your ideal trip. You can create the best vacation you’ve ever been on with a little preparation and some tips from the pros. Start with this guide the next time you’re ready for a new adventure.

Start with your destination

This is the fun part! Where do you want to go? Is there somewhere on your bucket list you’re excited to check off? What’s on sale on your flight tracker app?

Start gathering ideas from online trip planning resources, guidebooks, and personal recommendations. Pick a few cities that look interesting, then narrow down where you really want to go and what you think you can fit in.

Is your destination known for castles or hot springs? Craft beer or Italian food? What’s nearby within a short drive or train ride? Can you do anything unique here you wouldn’t be able to do anywhere else?

Pick your dates

The easiest way to decide when to travel is to think about your ideal travel weather and local events.

For example, visiting Japan in the spring is lovely if you’re lucky enough to hit prime cherry blossom season, but the views and temples are equally beautiful in the fall, when flights are also cheaper. If you don’t mind a little heat, visit in July to enjoy the summer festivals.

  • Pro tip: Watch out for peak travel times, when tourist sites will be packed and prices will be higher.

Local events, holidays, and festivals can also help you narrow down your dates. As you get closer to your travel dates, check for new events or changes to your plan.

  • Farmers market
  • Craft or art market
  • Rotating art display
  • Concert or play
  • Holiday-related event

Book your transportation and accommodation

Time to book the only two things that matter.

  1. How to get there
  2. Where to stay

First, what’s your budget? Do you have a set spending limit or do you just want to get a good deal?

Get your flight, train, or rental car in order depending on where you’re going. Use a travel tool like Skyscanner, Google Flights tracker, or Scott’s Cheap Flights to get alerts for flight deals.

Browse hotels, vacation rentals, and sites like Airbnb to find the best deals for where to stay. In beach towns, a week long vacation rental might have the best value, while Airbnb or a hotel might be your best choice in a city.

Think about your travel style

Once you have your flight and accommodations nailed down, you have your travel guardrails. You can decide how much you want to fit in to your schedule.

  • What do you like to do? Are you into hiking, shopping, museums, food, or all of the above?
  • What’s your speed? Would you rather hit as many sites as possible or have a little downtime?
  • What’s your daily budget? Do you like to save on everything or spend a little extra for nicer experiences?
  • Who are you traveling with? Do you need to accommodate someone else’s schedule or style?

Match your plan with your personality

Once you’ve thought through how you like to travel, make sure your plan is designed for you. Don’t plan to hit up a bunch of museums if you hate art just because you feel like you have to go to the Guggenheim or Musée d’Orsay. If you know you’ll be ready for lunch by 11 am, don’t plan to get to a big museum at 10:30.

The more you travel, the more you’ll get a sense for your ideal way to travel. You can even create a list of travel rules for yourself, like this one.

  • Travel 5-7 days for the US or Europe or 10 days for Asia.
  • Pick 2-3 main cities with a few day trips.
  • Plan 2-3 big activities a day.
  • Don’t walk more than 5-10 miles a day.
  • Only fill half your suitcase.
  • Bring 1 less shirt and buy a souvenir shirt.

Make your plan easy to use

Your trip plan can be anything you want. Make a list or spreadsheet, or use a calendar or app like OneNote. Pick a format you’ll be able to use and edit easily.

For traveling with a group, Google Calendar is ideal for sharing schedules. It’s free, and it works on any smartphone. You can set up your plan as basic as Monday – Bronx or get detailed by event like Dinner Reservations at The Plaza – 7:30 pm. Share events with your group so you can pick what you want to join up for and when you want to fly solo.

Finalize your travel itinerary

You’ve done your research. You’ve booked your dates. You’ve picked your format.

Now it’s time to craft your plan. Take your list of activities and match them up to your dates. Think of it like a puzzle. Your goal is to group activities together based on location and variety.

  • Which events are close to each other? What can you walk to?
  • When do you need to take public transit? Can you make an efficient route?
  • Is there too much walking on one day? Where can you take breaks?
  • What if the weather’s bad? Are there indoor activities nearby?
  • Did you plan for too many of the same thing on one day?
  • Can you avoid crowds or entrance fees on a certain day?
  • Will this activity be closed on a certain day?

Make a start on your plan and tweak it in the time leading up to your trip.

Pack for your plan

Now that you have a basic plan, you’ll know what to pack and what to leave at home. Start by checking the average weather and temperatures when you’ll be going to give you a sense of your wardrobe.

Then go through your list of days and activities to decide whether you need fancy clothes for a nice dinner or a rain jacket for a mountain hike.

Prepare for things to go wrong

Consider what happens if something doesn’t go according to plan and how much of a damper it would put on your trip. If the restaurant you picked is full, you probably still have options for dinner. But if you miss your train because you forgot your passport, you might not be able to get your trip back on track.

Sort out the most important parts of your plan that could go wrong, do what you can to prevent an issue now, and prepare a backup plan.

  • Look up the bus schedule before you arrive so you know when the last bus is.
  • Print or save a copy of your tickets and travel documents in case your phone battery dies.
  • Set a backup alarm on your phone in case you sleep in before your flight or train.
  • Scout local stores open late if you need late night supplies.

The ultimate backup plan? Travel insurance. You can get a cheap policy that covers you for emergencies and unexpected costs during your vacation. You might even have some trip coverage already, maybe with your credit card or car insurance.

Stay flexible

Not everything will go according to plan. And that’s okay.

The point of making your plan is so you know your options. You know the best way to go from point A to point B. You can optimize your route so you don’t spend all day walking in circles around the city. You have picked out places you’d like to go near where you’ll be.

When things don’t go according to plan, you’ll be prepared with alternatives to make the most of your trip. You can find a solution that will make the best of a bad or terrible situation.

And don’t be afraid to deviate from your plan. Set aside some time for planned wandering. Pick a neighborhood and spend an hour or two exploring side roads, taking in the view, or taking a break. Activities might take more or less time than you’d planned or the weather might change your plans, so have backup ideas and activities in mind.

Final thoughts on your trip

Armed with the complete guide to travel planning, you’re ready to craft your ideal trip itinerary. You’ll enjoy your travels that much more by being prepared and knowing your options. You can leave with the confidence that you’ve done everything you can to start your trip off on the right foot.

Have a trip planning tip we missed? Let us know in the comments.

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