Planning a domestic or international trip? It can be so exciting (always is for me!), and diligent planning will help make it everything you imagined. With decades of trip planning behind me, I’m sharing some tried-and-true travel planning ideas and tips in this article. And as a retired educator, I like to use a technique I used with my students: considering the 5 Ws (Who, What, When, Where, Why) plus H (How) – factors students use to gather information and in writing, making sure they address all relevant bits of data. It sure works for trip planning, too!
Trip Planning Considerations
1. WHO – Solo, Couples, or Larger Group
How many people are traveling with you? Are you traveling solo or with a partner, friends, or family? Will this be an intergenerational trip or a group of friends with all their wants and interests to consider?
If the trip will include others, have a brainstorming session where everyone comes with their wish lists of activities and attractions they want to experience, along with the number of days and budget they’re comfortable with. You could start a shared document (in Google Docs, perhaps) or a trip planning app, so everyone has a voice and can share ideas easily.
2. WHAT – Road Trip, Cruise, Land Tour, DIY?
I have traveled all those ways and liked each for different reasons. Even when we cruise or take an escorted land tour, we dig into their itineraries and decide what to do in each area during downtime. We learned on our first cruise and escorted land tour that it behooved us to research before leaving home to make the most of our limited time in a place. It’s paid off well.
3. WHEN – Time of Year is Important
How much time have you allotted for the trip? What season are you planning to travel? Will you be traveling in peak or shoulder season? Popular spots can get very crowded during peak travel season, often in the summer. Opting to travel in a shoulder season – in this case, spring or fall – can mean fewer crowds and still pleasant weather.
4. WHERE – Discover All Your Options
This is probably pretty obvious. I’m guessing you know where you want to go. Perhaps you may not have thought of interesting spots or activities (like food, bike, walking, historical, cultural, brewery/winery/distillery, or photography tours), hikes with beautiful vistas, and lesser-known places in the area you’ve targeted. It might be worth checking out all your options in the early planning stages. Perusing online travel review sites (like TripAdvisor and Yelp) may help discover opportunities you may not have thought of.
5. WHY – What You Want to See
Are you most interested in historical spots, beaches, or specific events – maybe Oktoberfest in Germany, European Christmas markets, the Calgary Stampede, festivals, concerts, and sporting events (FIFA, the Olympics, or a baseball/basketball/football/hockey game)?
6. HOW – Wish List, Transportation, Lodging, Tours
This is probably the one part of trip planning that requires the most thought and time. This includes specifics on what you most want to see, how long that will take, where you’ll stay, and how you’ll get from place to place (e.g., plane, train, ferry, car).
Key Trip Planning Considerations & Resources
1. Decide on a time and financial budget.
These may be the deciding factors for other trip planning considerations below. It will help frame your trip – how much time you are allotting for the trip and how much you are comfortable spending on it.
2. Get a Guidebook
Check out our several guidebooks. Each has its own perspective, ideas, and tips on places. I usually get 2-3 books from the public library to learn about specific places, like the cities in the state/province/country I plan to visit. Guidebooks can provide rich information about a place’s history, culture, and food.
Guidebooks are helpful for all of our trips – even the cruises or group escorted land tours (because there’s almost always downtime to consider and plan for).
3. Develop a List of “Must-Sees”
This includes cities, villages, historic sites, natural wonders, museums, amusement parks, and sporting events and music festivals. Distances play a major role, but sometimes so do dates and times of festivals, market days, walking tour schedules, museum schedules, sporting events, and so on.
Here’s where you need to consider your traveling buddies’ interests. Although your travel group may decide on a destination, what experiences does everyone value? Add them to the list!
“Must-Sees” on Cruises and Land Tours
On cruises and escorted land tours, you often have a choice of excursions, so realizing what you want to do and see, not included in the cruise or tour, and planning for it can make your trip much more meaningful and satisfying.
4. Create a Detailed Itinerary
Begin developing a daily itinerary with the dates, destinations, and what you plan to do and see. Then, add specifics as you progress with deciding on transportation and accommodations. Sometimes you must juggle the number of days in a place if you have too many “must-sees” and need another day to make everything work out comfortably. Beginning an itinerary early on will help you decide on the next several items: transportation and accommodations.
Map it Out!
Maps can help fine-tune plans. Figuring out travel times (e.g., walking, driving, flying) between destinations is important so you know if your itinerary is reasonable. Pad the daily schedule with some downtime to have a break and enjoy your time away. You can do this by marking up a paper or online map or even a dedicated trip planning app.
Key Itinerary Headings
My itineraries have varied over the years, and most have key columns:
- Date (day of week and date),
- Day (1, 2, 3, etc),
- Location/Destination (includes links to accommodations), and
- Activity (things we want to see and do – with links for each stop along the way).
Note that having the day of the week in the itinerary is sometimes critical as many museums and some restaurants and attractions are closed on certain days of the week. For instance, if I had planned to visit a museum on Day 4 but then realized it was a Monday when the museum I planned to visit is closed, I’d need to adjust days and activities.
Escorted Land Tours Extra Headings
If taking a cruise or escorted land tour, fill in the itinerary with the dates and activities/excursions provided by the cruise or tour company. For escorted land tours when some daily meals are not included, add a column for “Meal” and place a B, L, and/or D for each day, signifying the included meals.
Adding the extra information helps determine where the “holes” are – the times or meals where nothing is planned – and a place to focus on researching options. It could be a museum, a scenic walk, or a relaxing meal..
5. Decide on and Book Required Transportation
Will you transport yourself by car, plane, train, ferry, and/or rental car? Make reservations for planes and rental cars as soon as your itinerary is set. This can be 6+ months in advance of your trip. You can often schedule your train and ferry rides closer to departure, usually up to 2-4 months ahead. The key is to book what you can far before your trip to ensure you get what you want when you want!
If planning to fly to your destination, remember that you can book round-trip, one-way, and multi-city flights. Multi-city reservations allow you to have one reservation for airfare to/from multiple cities and can often result in cost savings.
If planning a domestic road trip, here’s a helpful article: Best Tips for Planning the Perfect Road Trip.
Add transportation details to your itinerary.
6. Book your Accommodations
There are so many options, and each has its allure. Choose what appeals to you best, and consider proximity to your “must-see” sites.
B&Bs and Inns
These are usually smaller places with fewer rooms than hotels, but can come with charm and personal attention.
Hotels
Hotel chains offer consistent quality and amenities and are often situated in city centers. Often, frequent travelers choose this option because their loyalty programs award points for future stays.
Short-term rentals
Staying in a condo, apartment, cabin, or house short-term rental usually offers more space than a guest room at a B&B, inn, or hotel. In condos and apartments, there are often relaxing sitting/group gathering spaces, a kitchen, and often a washer and dryer – a huge plus when traveling. In larger properties, there are usually a variety of attractive indoor and outdoor amenities like game rooms, firepits, outdoor kitchens, and other recreational attractions. Please read my article How to Find the Perfect Vacation Home Rentals for more suggestions regarding finding the ideal short-term rental.
TIP: Look at your intended itinerary and a map to figure out what you can see and do from your accommodation. Maybe instead of packing and moving to another city on a multi-city trip, you could take a day trip there and then return to your accommodation. Some tour companies have day trips to popular destinations and can pick you up at your B&B, inn, hotel or short-term rental.
Add accommodation details and links to your itinerary.
7. Take Care of Trip Details
Once the itinerary, transportation, and lodging reservations are made, it’s time to dig into the details. For more specifics on what to do when planning a trip, please read my article, Travel Planning Timeline: the Ultimate Countdown Checklist, which has a step-by-step guide on travel planning essentials.
Related Articles: Trip Planning
- Driving in Europe: What You Need to Know
- Expert Tips for Traveling to Europe for More Fun, Less Stress
- How to Find the Perfect Vacation Rental
- Renting a Car in Europe
- Stay Powered Up: A Traveler’s Guide to Power Banks
- Travel Lightly: Top Ten Tips to Pack for Your Next Trip
- Trip Planning Timeline: the Ultimate Travel Countdown Checklist
Final Thoughts
Planning a trip is work – sometimes a lot of work. Granted, DIY trips you plan yourself are the most demanding regarding research and planning. But, there’s still some work to do when planning a cruise or an escorted land tour.
No matter the type of trip, the rewards are great with a detailed itinerary because you have some control over what you see, where you stay, where to eat, and so on. Dedicating time to the effort will undoubtedly pay off, as you can customize it to your interests.
Happy travels!
Comments?
Please share your suggestions for planning trips. What planning system works best for you? Your thoughts can help other travelers. Thanks! 🙂
