Plan a trip

The Ultimate Guide to Stress-Free Travel

Plan a Trip: The Ultimate Guide to Stress-Free Travel

Is there anything more exciting than planning a trip? Adventure! New places! Stress…

Well, here’s a guide to help you plan a trip so that you can enjoy a stress-free vacation!

This guide walks you through each stage of planning, from choosing a destination to getting ready to leave for your trip. Start at the beginning or skip to wherever you are in the trip planning process. Keep all the information you need in one place by downloading the free Travel Better Guide Planner.

Be sure to check back for updates to this guide and new trip planning resources!

FREE Trip Planner

Download your FREE Travel Better Guide Planner for Microsoft OneNote. No registration required.

Discovering your trip destination

Discover my trip destination

This step is arguably the most fun when you plan a trip! Where do you want to go? You may already have a destination in mind, but if not, read this section to narrow your options.

What type of experience do you want?

There is a destination, experience, and travel style for everyone!

Are you looking to explore historical landmarks and taste exotic foods? Do you want to see stunning natural beauty? Or maybe you’d like to relax on a tropical beach.

TripTuner is a fun way to get inspired. In addition to the trip style sliders, you can filter selections by region, view similar destinations, or view curated destination ideas. The tool lets you get a rough idea of a destination without falling down a research rabbit hole just yet.

How much time do you have for your trip?

Determine how long it will take to reach your destination. If you are visiting multiple cities, also account for travel time between cities. Time spent traveling between cities, changing hotels, and repacking adds up. That’s more time you could spend exploring! Plan to lose half a day for a hotel change plus travel time to the next city.

Once you account for all travel time, consider whether you have enough time to do everything you want to do in your potential destination.

When are you traveling?

A snowboarding trip to Colorado during summer is clearly a non-starter. But for non-seasonal activities, is there a best time to visit?

Consider the following:

Average rainfall and temperature

Those beautiful Thai temples won’t look quite as beautiful during monsoon season. Check the average rainfall and temperature of your destination by month.

You can search for cities on World Weather and Climate Information to view historical weather information in easy to read text and graphs.

Special events and festivals

Check out what’s happening in your destination around the time you’d like to visit. Maybe there’s a cool event you’d love to catch, or perhaps you want to avoid the crowds.

Here are some great resources:

Off-peak vs. peak seasons

Is there a more budget-friendly time to travel? Off-peak seasons can coincide with unfavorable weather, so it may not be worth saving a bit of money to be stuck in a constant downpour. However, peak seasons often coincide with school vacations and public holidays, so you can save some money and avoid the crowds by traveling when schools are back in session.

Travel advisories

Check if there are any major safety concerns for your possible destination. For U.S. citizens, you can locate this information on the Department of State website. Also, check any travel advisories before departure, just to be aware of any changes.

If you are traveling internationally, check your passport validity (6 months validity beyond your return flight departure is a good rule of thumb), any visa requirements, and any vaccination requirements early to allow plenty of time for processing.

For U.S. citizens, you can locate this information on the Department of State website.

What is your trip budget?

If only budget weren’t a factor! When deciding where to go, some travelers primarily look at flight cost and may jump at a deal. But keep in mind that airfare only accounts for a portion of your budget. Paying for lodging, food, and entertainment in an expensive city could erase any airfare savings, making that cheap flight considerably less appealing.

For flight estimates, use Google Flights Explore Map to estimate airfare by month of travel and trip length. Road trippers can use AAA Gas Cost Calculator to estimate their fuel costs. Additionally, take a look at tools like the Numbeo Cost of Living Index and Budget Your Trip to compare destination costs once you arrive.

Determining how to get to your destination

Travel to my trip destination

Plane, train, or automobile? If you’re traveling to an overseas destination, your options narrow considerably. If traveling by land, decide if you want to make a road trip out of it, see the countryside by train, hop on a bus, or get there faster by air. Price, duration, and personal preference are all considerations.

This section will focus on air travel to your destination.

Choosing a flight

Price isn’t the only consideration when choosing your flight. If you want to get there quickly, avoid the hassle, and don’t mind paying a premium, non-stop is the way to go.

If you choose connecting flights, consider the following:

Flight duration and layover

Pay attention to the total travel time. That cheaper flight looks a lot less attractive when you have a 13-hour layover for a total travel time of 20 hours. That’s more time you could be vacationing!

Additionally, allow plenty of time between flights, including extra time for large airports or additional security screenings. You may be tempted to attempt a tight connection, but you don’t want to start your vacation with the stress of missing connections or bags!

Hacker fares

“Hacker fares” are when you book a flight leg with one airline and the connecting or return flight with a different airline. You can find great deals with hacker fares, but they do come with some risk.

For example, if your first flight is delayed and you miss your connection, will the second airline put you on the next flight? Check if the airlines are in the same alliance and verify their missed connections or delayed luggage policies.

Tracking flight prices

There are countless articles about the best day, time, and cycle of the moon to buy airline tickets. Let a flight tracker do the work for you!

Google Flights is highly customizable, offers money-saving insights, and allows tracking prices by specific flights or for all flights scheduled for your selected dates. Check out How to Save Time and Money Using Google Flights to get the most out of this tool.

Identifying your must-see stops and eats

Find my must-see sights

You probably have an idea of things you want to see after reading about your destination. But, before you can find a place to stay and plan an itinerary, you need to know the things you absolutely must see, do, and eat when you plan a trip. After that, you should determine roughly where your points of interest (POIs) are located.

Generating ideas for trip activities

First, start with websites like TripAdvisor, TripExpert, Google Maps, or Wikitravel to see popular attractions for your destination.

Travelers sometimes feel pressure to “get off the beaten path” and discover things on their own. However, popular attractions are often popular for a reason! Or maybe the “must-see thing” isn’t your cup of tea. That’s okay too!

It’s your trip, and you can see and do whatever you like!

Next, read what other travelers and reviewers are saying to find points of interest (POIs) aligning with your preferences. You may want to browse destination-specific online forums or blog posts to add to your possible POIs.

Last, list all of the POIs and note those that are your top priority. You may not have time to do everything on your list, so you want to make sure to do your priorities.

Mapping your points of interest

You may not need to map your points of interest (POIs) for geographically smaller destinations, but mapping POIs is immensely helpful for places where POIs are spread out.

Search for each POI in Google Maps and save each to a list for your trip. Also, saving your POIs to the map will help you quickly navigate during your trip. Refer to Google Maps Help for help saving places.

Are your POIs clustered in a particular area? If so, this is likely the area you should choose for accommodations. Are your POIs spread out? Note the most centrally located area for your POIs. If any POIs are too far away for this trip, remove those POIs from your map.

Finding the perfect place to stay

Find a hotel

Finding accommodations with the price, location, and amenities that you want can be time-consuming! Kayak Hotels lets you set up price alerts, similar to those offered for flights, by city and travel date.

If you are unsure about the type of accommodations you want, use AllTheRooms to compare hotels, vacation rentals, hostels, and more from one website. On AllTheRooms, you can find the lowest prices available for any given date from websites like, Airbnb, and 400+ other websites. From the results page, you can:

  • Filter results by property types, ratings, amenities, and price.
  • Copy and share links to accommodations.
  • See your results on an interactive map and adjust your search based on local landmarks or addresses.

Like flights, you should consider factors in addition to the hotel’s price when you plan a trip. Consider the following when choosing accommodations:

Hotel location and safety

Where is the hotel located in relation to the points of interest (POIs) you identified in your map? You may find an amazing deal on accommodations outside the city but end up spending more overall on daily transportation. If you plan to use public transportation, is there a metro stop within walking distance?

Most importantly, determine if the hotel is reasonably safe and secure. Use Google Street View to view the surrounding area, and read user reviews to spot any safety concerns.

Hotel amenities

Decide which amenities you require for your stay. For example, if you are visiting France in the summertime and want air conditioning, include the option for air conditioning in your search results.

On the other hand, make sure you aren’t paying a premium for amenities you won’t use. Ask yourself if you’ll actually use that luxury spa and pool at that pricey hotel.

Hotel booking and cancellation policy

Check the hotel booking and cancellation policy. Some hotels offer deep discounts for booking a non-refundable room. For non-refundable rooms, weigh the pros and cons of the amount saved vs. the loss of flexibility to determine your best option.

Also, if your credit card provides trip interruption insurance, review the policy.

Planning your trip itinerary

Plan a trip - create my itinerary

Some travelers hate the idea of an itinerary, preferring to go with the flow or see where the road takes them. Skipping the itinerary could be perfect for a relaxing beach vacation or for an extended trip.

But what if you’re only in a city for a day, and you discover that the amazing restaurant you wanted to try is closed? Or perhaps you made a list of points of interest (POIs), but there’s no way you’ll be able to do them all.

An itinerary helps you avoid disappointment, make the most of your time, and save money!

A good itinerary should also be flexible enough to adapt to trip hiccups or exciting opportunities. Use any spreadsheet or word processing program to create your itinerary, or download the free Travel Better Guide Planner for Microsoft OneNote for the best way to plan a trip.

Use the following high-level steps to create an itinerary:

1. Fill in details for the POIs you identified earlier. You don’t need every detail at this stage. Suggested details include:

  • Priority (for example, 1 for “must do” and 2 for “like to do”).
  • Link to the POI website containing the details.
  • Hours of operation.
  • Rough estimate of the base cost in the local currency (you can convert to your currency at the end).
  • Rough estimate of how long the activity will take.
  • Additional, helpful details (for example, the frequency of tours or if reservations are required).
Planning a trip

2. Eliminate any unrealistic POIs (for example, conflicting activity times or budget constraints).

3. Compare the POI list with the map you created, removing any eliminated POIs.

4. Decide which POIs you will do on which days, focusing on POI clusters in the same area.

Real Life Example

You are visiting Paris and staying in the Latin Quarter. Both the Palace of Versailles and the Eiffel Tower light show are on your points of interest (POI) list. Your POI list shows the palace is closed on Monday, and the Louvre is closed on Tuesday. Since you expect the Louvre’s closure could make Tuesday a busy day for the palace, you decide Wednesday is the best day to visit the palace.

Looking at your POIs on your map, you also notice the Eiffel Tower train stop is on the way back to your hotel. You add the Eiffel Tower light show to your itinerary for Wednesday night. Combining these POIs means you don’t waste time doubling back another night, and you save transportation costs.

5. Add activity start times where applicable (for example, a tour).

Note: Estimate the travel time using Google Maps and note the time you must depart to make the activity! Add your departure time to “Details” or as a separate line item as shown above.

Tip: Leave a generous buffer for all of your activities, timed and untimed. You don’t want to feel rushed, and you never know when delays will happen.

Make your itinerary as detailed or as open as you would like. If navigating an unfamiliar city makes you nervous, include details like POI metro station information or map screenshots in your Planner.

If you want to stay flexible, feel free to add entries like “Lunch in Old Town TBD”—you know the area where you want to eat, but you want to see what catches your eye. Do what makes sense for your trip.

Booking your tickets and reservations

Booking a trip

It’s time to book! Remember the searches you did in tracking flight prices and finding the perfect place to stay? When the price is right, grab it!

Keep the following in mind when booking:

Select the best credit card for the purchase

If you have more than one credit card, use the card that will get you the most bang for your buck. Common travel benefits include:

  • Trip interruption insurance
  • Travel-related cash back, points, or miles
  • Additional, quarterly bonus offers for travel
  • Bonus cash back when purchasing through a bonus shopping portal

For international bookings, use a credit card with no foreign transaction fees and pay in the local currency for the best exchange rate.

Apply loyalty and promo information

Before booking, provide any airline, hotel, or travel site loyalty account information. Also, apply any promo codes received via email or from coupon sites. If this is your first time booking through a website, you can often subscribe to emails to receive a first-time promo code.

Confirm booking information

Go ahead and make any free reservations. For ticketed events like concerts and plays, decide whether you want to buy the tickets in advance or wait. Buying in advance ensures a spot but limits flexibility. Waiting to buy tickets keeps your plans flexible but risks tickets selling out.

Most importantly, confirm the dates, locations, and prices before clicking Book.

Preparing your trip documents, smartphone, and money

Planning trip documents and finances

Preparing your documents in advance will keep your trip running smoothly. Many smartphone apps can assist the modern traveler during a trip, but you need printed backups.

To clarify, smartphones may die or lose service, so don’t let your device be your only access to critical documents.

Gathering trip documents

Use the following steps to prepare your documentation. Skip any steps that are not applicable.

1. Renew or get your passport.

2. Get a visa. For U.S. travelers, check the Department of State website or the consulate. Travel Visa Pro is an easy option for getting a visa.

3. Register your trip with your embassy.

4. Print copies of the following:

  • Passport*
  • Visa*
  • Credit and debit cards (front and back)*
  • Immunizations
  • Travel health insurance card**
  • Flight information
  • Hotel information
  • Car rental information
  • Tickets and reservation confirmations
  • Itinerary

5. Backup the documents listed above to a secure cloud (for example, Google Drive, Dropbox, or Microsoft OneDrive), and give a family member access to the shared folder in case of an emergency.

*Make two copies of each document. Store a copy in your luggage and a copy in your wallet, money belt, or purse. If you lose your passport, a copy shows proof of citizenship and expedites getting a new passport while abroad.

**You are likely not covered by your health insurance while abroad. The cost of travel health insurance can be as low as $10 depending on factors like coverage, age, and trip length. You can compare plans from multiple providers at InsureMyTrip.

Setting up your smartphone for your trip

Use the following steps to prepare your smartphone. Skip any steps that are not applicable.

1. Download your travel apps before you leave for your trip.

2. Save offline copies of your Maps for navigation.

3. If you use your phone to take pictures, confirm that your photos are set to back up to the cloud.

4. Decide if you need international data access. Many carriers offer day passes, or you can buy a local SIM card in your destination. If you are traveling internationally and do not have international data, turn Wi-Fi and Airplane mode on before arriving in your destination.

5. Buy outlet adapters. Most smartphones do not require converters, only outlet adapters. Check the voltage on your electronics or appliances to determine if you need a converter.

6. Buy a smartphone power bank.

Arranging your trip finances

How much money should I bring? Will I be charged fees? Should I get local currency before I leave? Questions about money are common when you plan a trip.

Setting up access to your money

Do the following to set up access to your money while traveling:

1. Check ATM availability. Visit the Visa and Mastercard worldwide ATM locators.

2. Get an ATM card with fee rebates. Schwab offers a checking account with ATM fee rebates, no foreign transaction fees, and no annual fees. Note that opening a checking account also opens a Schwab brokerage account, but the brokerage account also has no annual fees or minimums.

3. If traveling internationally, confirm that you have a no foreign transaction fee credit card. The Savor One card is a no annual fees, no foreign transaction fees card that earns cash back on dining and entertainment.

4. Contact your card company to set a travel alert. Many chip-enabled cards do not require you set an alert, but if you have the option, set the alert.

5. Bring enough cash for on-arrival expenses like transportation to your hotel and on-arrival visas.

6. Pack a separate backup card and a small amount of emergency cash in case your wallet is lost.

Paying for trip expenses

Do the following to minimize fees and maximize rewards on your trip, particularly when traveling internationally:

1. Use your no-fee credit card where accepted. Credit cards provide fraud protection, earn rewards, and get the best currency conversion rates.

2. Always pay in the local currency for the best rate.

3. Use your ATM card with fee rebates to withdraw cash as needed. Your card provides a much better exchange rate than currency exchanges. Furthermore, withdrawing cash as needed limits the amount of cash on your person.

Packing for your trip

Pack light! As light as possible! You certainly don’t need every electronic or pair of shoes! If you forget something, you can buy it wherever you’re going. Your back and sanity will thank you.

If you are traveling by air, check the restricted items list for any checked bag or carry-on restrictions. If you are traveling abroad, note that some prescription medications may be restricted or may require a letter from your doctor. Check with the consulate for more information.

As your trip gets closer, check the weather for your destination and make any adjustments to what you’ve packed.

You can download a simple, printable packing list or use the checklist in the Travel Better Guide Planner.

Getting ready to leave for your trip!

Getting ready to leave for my trip

It’s almost time! You’ve researched, planned, and gotten excited. Now, it’s time for those last minute things.

Skip any items that are not applicable:

  • Bags fully packed
  • Pet sitter confirmed
  • Childcare confirmed
  • Departure details confirmed
  • Trash emptied
  • Dishwasher emptied
  • Thermostat adjusted
  • Ice maker off
  • Electronics unplugged
  • Work away message on
  • Smartphone charged
  • Travel apps downloaded
  • Documents, cash, and cards in hand

A printable departure checklist is available to download, or you can use the checklist in the Travel Better Guide Planner.

Questions about the guide? Any favorite travel tools that you love? Leave a comment below! I’d love to hear from you.