How To Plan for a Month Long Trip: Complete Guide

You’ve been working tirelessly for months now, and with COVID still looming on our heads, you’re also mentally exhausted. Do you wish to plan a trip soon to rejuvenate but need it to be at least a month long to regain all that spent energy back? You’ve been waiting and saving money for too long, and now you want to plan that perfect vacation.

Here’s how you can plan a month-long trip:

  1. Plan your trip in advance.
  2. Envision that ideal getaway.
  3. Match your budget to your vision.
  4. Find experiences for your trip.
  5. Plan around COVID.
  6. Work out logistics for the trip.
  7. Book and print everything.
  8. Ask for help from a travel guide or make use of organizing tools.

When planning for a trip as long as a month, your main focus should be to stay within budget and to return home completely refreshed. Read on as we discuss each step and mention resources that can help make your trip even better.

1. Plan Your Trip in Advance

A month-long trip may require planning a few months ahead, considering your work flexibility and house life. It’s not impossible to take a month off from work or your daily routine, but it does require more exhaustive planning when compared to a mini vacation.

Consider the following before you finalize that month-long getaway:

  • Make sure your supervisor gets a request for your trip in advance to avoid any trouble at your workplace.
  • Make sure you begin wrapping up any duties you have well in advance.
  • Make sure you decide on a caretaker for any pets or plants you have.

Planning for a trip longer than a week requires months in advance as you don’t want to come back to a crisis after spending a month relaxing. Ensure you take care of everything that needs to be taken care of before you leave for your trip, or ask someone you trust to handle things for you in your absence.

2. Envision That Ideal Getaway

You’ve been waiting for quite a while for this month-long getaway, especially after those difficult or particularly stressful days when you’d wished to be somewhere else instead.

What image usually pops up in your mind when you’ve been wishing you were doing something else?

To help you visualize your trip better, answer the following questions and decide if the vision you create gives you the kind of feel you want from this trip.

  • Do you visualize relaxing the entire trip?
  • Do you see yourself being adventurous?
  • Are you alone or surrounded by friends or family?
  • Are you near a mountainous range, beach, or in a new city?
  • Do you see yourself doing some activities?

A clear vision helps avoid any regret you may have, especially after coming home from a trip as long as a month.

3. Match Your Budget to Your Vision

The one thing that makes a month-long trip the least fun is staying within a budget. With every week added to your itinerary, there are more details to be planned.

Create a detailed budget and keep the following essential costs in mind:

  • Food costs
  • Hotel costs
  • Travel costs
  • Insurance cost

There are also some ways you can save and increase your budget for other activities and amenities while spending less on the essentials.

Book Cheap Flights

Saving money by booking cheap flights is a good way of increasing your budget for other activities.

You can use Hopper to compare flights within your travel dates. Watch this video as I explain its easy to use interface in detail, so you can use it on your upcoming trip:

I also recommend using Google Flights when looking up possible flight options and airport locations for your chosen destination.

If you don’t know how to use Google Flights, watch this video tutorial:

If you want to save on flight costs, check out this video. I made sure to include very useful secrets to cheap airfares to help you out:

Book Cheap Lodging

Whether a hotel or Airbnb, a few things can help you minimize what you spend on your lodging.

  1. Book in advance. This is something we all know; a room booked in advance has cheaper rates than one that’s booked last minute.
  2. Book in discount or special offers. For Airbnb, you can use the ‘Special Offer’ feature by contacting the host directly and requesting a special discount. For other lodging options at the best rates, I recommend Hopper or TripAdvisor.
  3. Book a longer stay at the same lodge. Many Airbnb and hotels offer weekly or monthly packages. Don’t miss the discount by booking a place for twenty-eight days when you could have availed the discount on thirty.
  4. Consider cheaper lodging options. Camping or staying in shared rooms are cheaper than a private room for one.

Save Money on Food

You can plan on cooking most of your meals yourself if you have access to grocery stores. However, there are ways you can eat cheaply even while staying at a hotel.

Once you’ve decided on a budget, be sure to plan the rest of your trip with it strictly in mind. Long trips have more probability of expending more than you intended to, so sticking to a budget in the planning stages can lower these chances.

4. Find Experiences for Your Trip

Longer trips have the added benefit of gaining more experience. Your vision for this trip can drive you to choose the kind of activities you want to find in your chosen destination.

To find experiences that a destination can offer, use the following resources and enhance your trip with events worth remembering.

YouTube or Travel Blog Posts

You can search Youtube for the most visited places in a specific area. While most will review the most common tourist sites, you’ll also stumble upon videos sharing unique experiences.

I’ve shared some unique things to do in Maui, Oahu, Hawaii, and Catalina Island on my YouTube channel, Crafted Travel Company. I also have a new video about how to find those unique things in any destination.

Airbnb Experiences

This is a hidden gem that I want to share with you to help you discover things to do whenever you plan a trip anywhere.

After choosing your destination, you can scroll down to find a special section called ‘Discover things to do’ and click Experiences. It offers an insight into unique, local experiences. The best bit of this that I love is that these are written or recommended by locals. You can check out and experience the tours and events in small groups, and they’re relatively inexpensive.

When booking these Airbnb Experiences, make sure you time them at the very start of your vacation. This is because you meet locals here who can recommend tips and tricks about what else you should do for the rest of the trip.

Eatwith Website and App

Eatwith offers an innovative, unique experience that revolves around food. They’re still growing and aren’t available everywhere, but if you can find them in your destination, do try them out! You could learn to cook, eat with strangers, or experience a completely new gourmet.

If you want to keep it simple, you can also google a specific activity you wish to do in a location and plan an itinerary based on Google suggestions and reviews.

5. Plan Around COVID

Short or long, planning any trip requires you to be up to date with the travel restrictions for COVID in your country and the destination you plan to visit. Keep monitoring any updates on restrictions until the day of travel to avoid any trouble in a foreign place.

Make sure you’re comfortable fulfilling the travel restrictions imposed by your destination country. This could include quarantine for a certain number of days in a hotel at your own expense, which you need to factor into your budget and itinerary.

You may also be required to provide proof of a COVID negative test before and after traveling, and planning and making appointments is always a wise move. Some countries need proof of vaccination on arrival, and some hotels and restaurants won’t let you enter if you’re not vaccinated either.

In my video below, I talk about some countries’ rules for future travel, like travel fees and vaccination requirements:

For your specific destination, research any COVID update you should plan for.

6. Work Out Logistics for the Trip

Figuring out the little details for a trip as long as a month may not be an easy task, but you cannot skip this important step. You may not be able to visualize and predict the day-to-day for an entire month, but work out the logistics of some important events.

  • Travel to and from the airport. Make sure you have transport to and from the airport, and calculate the distance from your first and last lodge. This will help you plan the first day of activity after traveling from the airport or decide when to leave for the airport to catch your return flight.
  • Mode of transport. A month-long stay means you need to give special attention to how you’ll be traveling from where you’re staying to other places you want to go to. You may need to rent a car if your vacation requires a lot of traveling or become familiar with public transport.
  • Mode of currency. You need to research if your credit card will work as you don’t want to run out of money in an unfamiliar place. If that isn’t an option and you have to carry cash, work on an amount that’ll suffice for the entirety of the trip.

These details may seem minor to worry about, but they can be the difference between a trip running seamlessly or time wasted worrying.

7. Book and Print Everything

Once you’ve finalized an itinerary and worked on logistics, begin booking your trip. Book tickets make reservations for your lodging or even some exclusive restaurant on your list, make transport arrangements, and anything you feel needs to be booked in advance when finalizing your itinerary.

For a more than a 7-day trip, an additional step for your security is to print everything out and make copies. Leave these important document copies with a trusted person back home. In case of theft, or misplacement, you can always ask this person to send you exactly what you need to carry on the trip as planned.

Keep a printed, hard copy of your bookings and reservations with you as proof in case of unwarranted cancellations.

8. Ask Help From a Travel Guide or Make Use of Organizing Tools

Planning a trip for as long as a month may be too much if you don’t have adequate time to plan due to difficult work schedules, busy home routines, you don’t feel like getting into the nitty-gritty, or simply because you don’t know where to begin.

Being in the industry for more than fifteen years, you can always message me with any questions or if you need help planning your trip.

You can also download The Ultimate Travel Planner + Organizer from my website to help you plan everything for your trip in an organized manner.

I also have a list of books available that can be helpful to your planning, including ultimate travel planned journals for specific countries that you can check out here!

Final Thoughts

Whether you plan a trip for a day or a month, always start by visualizing what you want. Once you have your vision locked, plan around it (and COVID), and use our tips and resources to develop a fool-proof trip.

To recap, here’s how to plan a month-long trip:

  • Begin planning ahead.
  • Visualize your ideal trip.
  • Stick to a budget that fits your vision.
  • Explore your destination and find experiences.
  • Always plan with COVID in mind.
  • Don’t forget to work out logistics.
  • Book your trip and keep hard copies.
  • Use our travel guide and planner to make your life easier.


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