Creating Your Best Travel Itinerary – Tips & Strategies

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Traveling is one of life’s great joys, offering opportunities to explore new places, experience new cultures, and connect with family and friends. With so much to consider when planning a trip, it can seem overwhelming. Creating an effective travel itinerary is an essential part of any successful trip, as it allows you to make the most of your time, budget, and experiences. It can be difficult to know where to start, but with the right tips and strategies, you can plan the perfect itinerary. In this blog post, our Strideley Travel Agents discuss some tips and strategies for creating your best travel itinerary. We’ll cover preparing for your trip, researching and budgeting, and developing an itinerary that fits your travel style. We’ll also provide some tips on how to make the most of your itinerary while you’re on the road. Ready to hit the road or take to the skies? Read on fellow traveler!

Table of Contents

1. Research Your Destination

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Before you book a trip, it is important to research your destination. Doing some research before booking anything for your trip – think plane ticket, restaurants, hotels, activities –  can save you a lot of time, money, and not to mention the added stress of planning your trip. Doing some research can help you become  informed about the local culture and traditions, climate, and laws where having more knowledge of your destination can help you avoid any potential issues you may encounter while at your destination – whether that is a domestic destination or abroad. Knowing the local language can also be beneficial, as it can make it easier to communicate with the locals and get around without any confusion – of course, figuratively speaking.

Researching the local cuisines, restaurants, and the local suggestions can help you get the most out of your trip by experiencing some of the region’s best dishes at popular restaurants and locally recommended dishes as well.

2. Make a Rough Outline of Your Itinerary

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When planning a trip it’s near impossible to follow the entire itineary to the T. This is especially true when you’re traveling with family, friends, and coworkers. Everyone seems to have an opinion on what to do, what to see, how much to spend, and how long to stay. But have considered planning a trip using a spreadsheet?

Yes, yes, we know. We look at spreadsheets all day long at work and another spreadsheet is the last thing we’d want to look at when planning a vacation. Planning using a spreadsheet allows you and your party to input ideas, activities, weather forecasts, and other essential planning ideas for your trip.

Don’t know where to start and need help planning? Consider planning your trip using these core spreadsheet pillars (best organized via tabs). What to include in a travel itineary:

  • Master Schedule
  • What-to-do Ideas
  • Potential Food & Restaurants
  • Budget & Costs
  • Important Reservations


Master Schedule:

Yes, it’s exactly what it sounds like. The Master Schedule. When planning your trip it’s important to make a rough outline of your itinerary – things you want to do, where to eat, and what to do and when. How to organize your travel schedule?

Consider organizing your trip  based on day (your X-axis) and hour (your Y-axis) and populate your spreadsheet in a matrix format. By organizing your trip in a matrix format you’ll have a high-level overview of what to do, eat, or see on any particular day. This is especially helpful when planning lunch or dinner reservations. Doing this allows you to plan your activities accordingly with ample time to make it to your restaurant reservation.

What-to-Do Ideas:

Organizing your spreadsheet based on tabs is a clear, easy, and effective way to jot down your ideas and collect the ideas of your family and friends on what the party wants to do during the trip. While there’s no guarantee the party will be able to do everything that the group suggests, having a repository of what-to-do ideas helps to add transparency to the group planning . Of course, you can also make it a habit to use a spreadsheet for personal and solo travel as we. At Strideley Travel we love organizing schedules for our valuable clients and we organize our client schedules using spreadsheets along with a slew of other professional travel tools. Need help figuring out what to do during your trip? Check out our destinations page for ideas, attractions, and our recommended places to eat. 

Of course, you’re more than welcome to message us on Socials (Facebook, Instagram) or contact us right here on (Contact) for recommendations on how to plan your travel.

Potential Food & Restaurants

We love food and we think you love food too. Strideley even has an article detailing our foodie adventure and experience! (See “A Foodie’s Cruise Come True”). With your spreadsheet open, take recommendations from your group, consult Yelp!, Google, and other review food review websites to discover your next favorite meal. On this tab, consider adding:

  • Name of Restaurant
  • Address of Restaurant
  • Checkbox if Reservation is Required
  • Average cost (denoted in dollar signs) ex. $ for inexpensive, $$$ for very expensive
  • Area within the city

Organizing your food and restaurant recommendations allow for easier planning on where to eat based on which part of town you’ll be in.

Budget and Costs

Travel can be expensive and organizing your schedule and itinerary based on spend tolerance can help you and your group plan what to do, where to eat, and what to see. With money not being anyone’s favorite topic to discuss amongst friends, having a chat based on the average dollar amount you and your party are willing to spend helps plan activities.

On the spreadsheet budget and costs can be estimated or actual to your spending. Having an estimated cost can help plan the budget with the group and limit spending according to the budget. If you’re anything like us, you enjoy having more money in your pocket at the end of the day. Throughout your trip and at the end of the trip the budget tab can act as the source of truth when it comes to splitting costs. Add in receipts and costs on the spreadsheet and divide by either item or collective party. Doing so will ensure everyone is accounted for and there would be no hard feelings regarding payments back to the originating purchaser.

Important Reservations:

Planning a trip is tough and with activities and attractions of what to do or see at your destination, it’s easy to forget about important lunch or dinner reservations. Sometimes we get too caught up in the moment to realize that the non-refundable reservation deposit might be forfeited just because we lost track of time. While planning your trip add in any important dates and details to your reservation tab so that you and your party won’t miss the nice lunch or dinner reservation at the restaurant. Or if you need help, Strideley Travel agents are here to help you make those reservations for you and keep your party, and itinerary, on track so you can continue to enjoy your destination without the added stress of planning. 

3. Strive for Flexibility & Set a Realistic Budget

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Be Flexible with your Planning

Raise your hand if you’ve ever traveled with a family member, a group of friends, or with coworkers? Ever had a disagreement on what to do with your fellow travelers? Rest assured, you’re not alone. At Strideley we’ve had a few mix up’s and disagreements but in the end we’ve compromised and have learned to be flexible.

Being flexible helps the group and helps everyone enjoy everything the destination has to offer. From deciding on where to eat to which attractions to see, it’s always better to be flexible to accommodate everyone’s wants and needs as well as to keep the dynamic of the group. Trust us, there’s nothing worse than traveling with an angry and mad family member or friend.

Budget, Budget, Budget

Unless there’s a unanimous decision on budget prior to the trip, every person has a specific spending tolerance. Without discussing budget prior to the trip it is easy to overspend since there’s so much to see and do – most of which requires spending money for dining, entertainment, transportation, and lodging. Being aware with how your money is spent allows you and your party to see more of what everyone wants to see, enjoy more of what the destination has to offer, and participate in activities that will create experiences and memories for you and your party to take home.

Plan early with your group of friends, family, and other travelers and strive to assess everyone’s spending tolerance prior to the trip. A few hours of planning might just save you hours of frustration when you’re on your trip.

4. Balance Relaxation & Adventure

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Relaxation and Adventure. Peanut butter and Nutella. Yin and Yang. What do all of these have in common? They all represent a balance of flavors, energy, and feng shui. When planning a trip with your family and friends, it’s important to find a balance between relaxation and adventure. It’s very possible to do everything you want to do during your multiple trips to New York but trying to cram your entire New York City trip in one weekend, is – dare we say it, impossible. Our time is limited when we’re traveling as we’re juggling seeing the many attractions and sights your destination has to offer.

Yes, it’s admirable to try to visit and see every attraction and sight but would  actually enjoy your time at your destination if you felt rushed? It’s important to balance time with relaxation and resting before your next adventure. Doing so will help you enjoy your trip and you’ll feel compelled to return once the trip is over to explore and learn more of your destination.

5. Plan Time for Reflection & Contemplation

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Being busy all the time used to define who we are. However, times have changed and it’s acceptable to take moments to reflect and contemplate your experiences. Reflection and contemplation are powerful tools for personal growth and increased self awareness and confidence. As you return home from your trip with your friends, family, and acquiantances, it’s important to reflect and express gratitude for the experience you’ve just had or shared with the people most important to you. When talking with others about your travel experiences, you’ll feel good talking about the amazing things you’ve seen and done. All your stories wouldn’t be great without reflection and contemplation of the time spent at your destination.

As you plan your next vacation, remember to keep these five tips in mind. Research your destination, make a rough outline of your itinerary, strive for flexibility, balance relaxation and adventure, and plan time for reflection and contemplation. In doing so, you ensure and solidify a travel experience and a life much richer.

We at Strideley Travel Agents take our own advice seriously and we, too, instill these strategies and tips to help us travel better and travel stress free. Message us on Facebook, Instagram, or right here on (Contact Strideley) for ideas and travel suggestions for your next adventure.


At Strideley, we are dedicated to creating unforgettable travel experiences that reflect the true culture of a destination. Strideley’s Travel Agents help busy professionals plan custom travel experiences. Strideley’s Travel Consultants advise on things to do, what to see, and provides exclusive access to member-only experiences.
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