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Planning a Trip

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We’re often asked if we’re taking a guided tour or have booked some kind of package. The answer — at least to date — is no! I do all the planning for our trips. Which amazes people. I like researching and planning trips almost as much as I like taking them. And I think anyone can do it.

Here’s my planning process. I know people who just show up and go day to day. I also know people who schedule every minute of every day. We’re somewhere in between. Because — Libra and Pisces here — we sometimes struggle with decision-making (we went to an all-inclusive resort on our honeymoon specifically to avoid decisions more difficult than whether to leave the resort and when, and which nights to eat at a sit-down restaurant rather than the buffet), I have essentials planned and options researched before we go. 

Oh, and a little background: We’re from the United States, land of chain hotels, chain restaurants, and no public transportation. We try to avoid the first two and use the last when we travel. We’re also not full-time travelers. (We wish!) Nope, we have day jobs and take a traditional vacation a couple of times a year. 

Decide where to go

Someone asked me once how we decide where to go. Which made me think: How do we decide? Here’s how I broke it down.

When are we going?

Lots of planning advice starts with where you want to go. I start with when.

We don’t travel during the summer. It’s the only time the weather is reliably good at home, so we tend to stay home, or visit the family cottage. Summer is also when people with kids travel, which means larger crowds and higher prices. So we generally travel during shoulder season, when the weather is still decent but crowds are smaller and prices lower. Since shoulder season varies from one destination to the next, knowing when we plan to go is an important factor in where we go. We also travel in winter to avoid winter. That can mean peak prices but at least we avoid snow!

What kind of trip do we want to do?

We enjoy the outdoors, wildlife, and other cultures. We like hiking, snorkeling, hanging out at the beach, wandering around new cities and towns, and visiting museums and botanical gardens. Some trips edge more toward the wild and natural, others more toward the urban and cultural. Lately we’re trying to do our trips with extensive hiking sooner than later, before we get too old to do it!

How much time do we have?

Our travels are constrained by available vacation time. This factors into choosing a destination, since it takes time, effort, and money to get there and back. We generally take at least two weeks because:

  • We want to get into vacation mode and stay there for a while.
  • If we’re going to spend time and money getting someplace we want time to enjoy it.
  • On a short vacation, even one day of bad weather can wreak havoc. More time means greater flexibility, and less pressure to do something right now.

Now, where do we want to go?

We have kind of a loose laundry list of places we would like to go, some more than others. Reviewing that list based on the answers to the above questions narrows down our options for our next trip. 

For example: 

  • If we’re going in winter or spring and want to spend time snorkeling and hanging out at the beach, with maybe some hiking thrown in, we might go to the Caribbean. But we wouldn’t plan that trip for the fall (AKA hurricane season). 
  • If we’re going in the fall and want to mix some beach time with historical and cultural sites, we might choose Greece or Spain. In winter or spring, it might be too chilly for swimming, but still good for sightseeing, and maybe some hiking.

Plan the trip


With some idea of where we want to go, it’s time for research. I like to start with a good guidebook for a high-level overview then gradually get more into the details. I often already have an idea of some things to see or do — or we wouldn’t be looking at that destination! — but often find more once I start researching. 

I used to buy physical books. (After all, that was once the only option!) Lately I’ve migrated to ebooks. For travel planning I prefer my iPad rather than my Kindle:

  • the maps are easier to read and to expand
  • the links will actually take you to the website
  • the photos are in color

You can highlight entries too, like you would in a book. Using a different color for each category helps me identify what each item is. (I often download them to a Google Sheet so I can sort an filter but I’m nerdy that way.) 

I’m trying to get a general feel for the destination. It’s kind of the brainstorming phase. And while I start with a guidebook, that often leads to links for different websites, which in turn leads to other sites … 

The itinerary

At this point I have a rough idea of things that we could see and do. Now I start analyzing and prioritizing, to narrow it down to what we reasonably can do. Because I have yet to plan a trip where we have time to see and do everything we want to! 

With a pretty good idea of must-dos and like-to-dos, I start building out an itinerary. I use a simple spreadsheet with numbered days where I jot down where we would be and what we might do with our time at each place. This isn’t super detailed. My goal is not to schedule every day but to group activities based on geography and time needed so we make the best use of our time. A spreadsheet keeps it compact so I can see the whole trip and move things around easily. (Now that I think about it, I may try using Trello for this phase.) I like to use Google Sheets because it’s highly portable; I can view and edit from anywhere, even my phone if necessary, and use it as a reference while we’re traveling.  

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One of the benefits of a loosely planned trip is that we can rearrange chunks of itinerary as needed due to weather or illness. On our first trip to Hawaii we dealt with both a nasty sinus infection and record rain and flooding by adapting our plans. 

Which brings up something else we’ve learned: If something is a must-do, we don’t leave it until the end. One reason we’ve been to Costa Rica twice is because we missed out on Corcovado National Park our first time because they canceled all the boats due to high seas the day we planned to go. When we went the second time we planned that for our first day in the area, not our last.

I also allow time for traveling from place to place. I used to be more optimistic but now typically allow at least a half-day to move from one location to the next. (And I’m more likely to plan day trips from a central location too.)

Book the trip

Book lodgings

I like to book lodgings before we leave. It saves time while we’re there, and saves stress about where we’re going to sleep! Sometimes I book lodgings first; sometimes I book flights first. It depends on which I think is going to be more of a constraint. I book lodgings about 6-12 months out because we end up in some remote locations and we prefer smaller B&B-type places. The best ones fill up fast.  

To get the best value on lodgings we focus on things that are important to us:

  • What are must-haves in a room? We like clean, functional, and safe. We need to have our own bathroom. We don’t care about a TV and probably won’t even turn it on. A place to sit outdoors is a definite plus as is a fridge. 
  • What about amenities? A pool? (We’re beach people.) Free parking? In many cities, there may be an extra (hefty) charge for hotel parking or no parking at all. In the Boston area we found a place in burbs with free parking and a free shuttle to the local train station so we could commute to the city. 
  • How about location? We like to walk to drinks and dinner, so we look for places that are walking distance to bars and restaurants. In larger cities I may even research restaurants before booking, to make sure we’re in a good neighborhood.
  • What’s the budget? I look for places that meet our criteria at the lowest price. I’m happy if it’s less than $100 per night, but I often have to go higher. Beware of fees not included in the nightly rate when comparing prices. Some hotels charge “resort fees” that you can’t avoid. Some vacation rentals and Airbnbs charge a cleaning fee. Then again, there may be extras included in the price, such as breakfast or transportation. Breakfast included can save time and money. (Eat a full English, American, or Costa Rican breakfast and you can skip lunch!) 
  • What’s the cancellation policy? Many of the smaller places we like charge for cancellations. I understand why they need to; if I’m not completely sure of our plans, or it doesn’t cost more, I go with free cancellation. After COVID-19 probably more so.  

As for where and how I find a place to stay:

  • I start with any guidebook recommendations that meet our criteria.
  • often includes the smaller bed and breakfast, guesthouse, or pension types of lodging we like.
  • TripAdvisor often includes places that you can book direct that aren’t listed elsewhere. If there’s no link to a website I Google search them. I’ve also turned up some surprising deals through Expedia and other third parties. 
  • I’ve found Airbnb a good source in places where more traditional lodgings are either scarce, expensive, or both, though I’ve heard about them pricing residents out of popular locations so I try and avoid anything that looks like that. 
  • Regardless of how I find a good place, booking lodging direct is often the most economical, though not necessarily the most convenient. With some smaller places it might be the only option.
  • Shop around; I’ve seen the same room listed on different sites for different rates and with different rules. 

I’m not looking for the absolute best option. Just for a great one.

Book flights

I use a comprehensive search engine to research prices and schedules but then usually book the flight directly with the airline. I like Momondo for its extensive filters and quality ratings of flights. I often book 6-9 months out to get a good flight at a good price. I know you can often get lower prices if you wait but it often seems the prices aren’t that much lower and the schedules are worse. 

Some tips for looking:

  • Do the math on extra charges like bag fees, seat selection, etc. (if you’ll want those things) when comparing prices.
  • Round-trip airfare used to be much cheaper than flying into and out of different locations (“multi-city” when searching). Lately I’ve found it cheaper (or cheap enough) to go with more convenient flights, like flying into St Croix and out of St Thomas. 
  • I’ve been on enough delayed flights that my minimum layover is now two hours to change planes if flying within the USA, longer if flying internationally and going through customs and immigration. It’s just not worth the stress of running through airports and possibly missing a connecting flight.

Book other transportation

Traveling in the US usually means having a car because we lack public transportation in all but some large metropolitan areas. But that’s not true worldwide. We try to avoid renting a car if we can.

  • Flying is often the quickest and the most expensive, though you don’t see much along the way. (Depending on security, it may not be that much quicker.) 
  • Trains are often in the middle as far as speed and cost, more comfortable than planes or buses, and often scenic. We love trains. 
  • Buses (or coaches) are usually the slowest and cheapest. 
  • Renting a car gains you maximum flexibility at a cost. We sometimes rent a car just for the few days we really need it.

Other options we’ve used:

  • In the Virgin Islands and Greek islands ferries connect the islands, usually — but not always — cheaper than flying. 
  • In Costa Rica shuttles are popular. These are like airport shuttles, but take you door-to-door from your lodging in one city to another.

Your research may turn up different ways to get around. In some cases, as with shuttles in Costa Rica, we had to book ahead of time. In others, you may be able to save money by booking ahead. We saved a few hundred dollars (over the cost of a railpass) by booking train tickets in advance for Great Britain; in some cases for only 10% of what we would have paid if we bought the tickets the same day. 

Don’t forget local transportation. Sometimes there’s a transport card or packet of some kind that you can (or must) use. Some cities offer options designed specifically for visitors. Some offer options designed for local residents that can also be used by visitors. Guidebooks often are a good starting point. 

We often combine options. When we took a road trip to the east coast, we drove our won vehicle but knew we didn’t want to deal with driving and parking in downtown Boston. So we stayed at a hotel in the suburbs that offered a free shuttle to the local train station and took the train into town. In San Francisco, we parked the rental car at the hotel and didn’t move it until it was time to leave town. In Belize, we used a combination of local flights, shuttles, and car rental. 

Pre-book attractions

Sometimes you have to. Sometimes you can save money. Sometimes you can save time standing in line. Sometimes both!

On our first trip to Britain, I booked most of our tours and attractions in advance. Except for Windsor Castle. So we spent three hours waiting to get in. 

Other preparations

Keeping in touch

Free WI-Fi is common but may not help with phoning or texting. I use email whenever possible. We’ve used apps like Facebook Messenger, WhatsApp, or GroupMe over Wi-Fi to stay in touch with people we know. For local businesses sometimes you need to phone or text. Find out what offers your mobile provider has and, if you think you will use your phone a lot, consider getting a local SIM card. 

We have Sprint, which offers international coverage that works for occasional or emergency needs and covers lots of countries. Usually, we just use that. (While I’ve found regular Sprint support hit or miss, their international support has been excellent.)

In Australia and New Zealand we purchased local SIMs and a local plan for one phone, since we were in each country for 3-4 weeks. It was easy and cost-effective. The hardest part was getting the phone unlocked in the first place! 

If you don’t speak the local language, I’ve found Duolingo a fun and free way to learn, and Google Translate has come in handy. It’s amazing how much you can communicate without language. One of our favorite examples was a grocery store in Greece. We couldn’t understand when the cashier told us how much we owed, so she typed the number into a calculator and showed us. Brilliant! 

Paying for things

We use credit cards when we can since they take care of the currency exchange. We got a credit card that doesn’t charge foreign transaction fees. If anyone offers to charge you in your own currency rather than the local currency, don’t take the deal! You won’t get the advantage of the exchange rate that the credit card gets you.

Even in the developed world we’ve found smaller businesses that accept only cash. And in less developed parts of the world cash was the only option. 

We usually wait until we arrive and use an ATM to get local currency. ATMs and foreign-exchange booths at airports typically have the worst rates and/or the highest fees, so if we need to have local currency in hand when we land, we get it before we leave. Our credit union, for example, offers any amount of foreign currency for a flat $14 fee. 

We’ve been to a couple of places that are cash only AND where ATMs were rare and sometimes not functional, and at least one place (Drake Bay in Costa Rica) where everything had to be paid for in cash AND there was NO ATM. We did some serious cash planning on that trip. Again, research helps!

In some countries we’ve been to — Costa Rica, Belize, the British Virgin Islands — you can use US dollars. Change may be in the local currency.


We have a whole section on packing. Planning can spill over into packing. 

  • Knowing what activities you’ll be doing guides what clothes to take. 
  • We carry a folder with anything printed, like pre-booked attraction tickets, so it’s easy to find.  
  • TripIt is a great app for tracking transportation and lodging. It’s super easy to use since it monitors your email and adds plans to trips automatically. (You can also add things manually.) It sometimes notifies me of flight changes before the airline does!
  • I’ve already mentioned Google Sheets, which I use primarily for planning. It then becomes a reference while we’re away. 
  • We use Google Drive for storing backup documents. 
  • I hang onto any email communications like confirmations just in case. 

We like good old-fashioned printed notes too. I make one page (or so) quick reference guides for each day or location with information about:

  • where we’re staying, how to get there, and how to contact them
  • anything scheduled, like transportation or tours
  • any “to-do” items like getting local currency, a SIM, booking tours once we’re on-site, picking up tickets, etc. 
  • a list of restaurants that sound good
  • a list of sights we’re interested in, with hours and directions as needed
  • sometimes a map of the local area, with key places (to us) marked

With printed info you’re not completely dependent on your phone battery or signal. It’s handy for both crowded urban areas as well as the wilderness or the beach. There’s a sample of one of our notes pages below.

same notes

Have fun!

We do enough planning and research that we can relax and enjoy our trip. Without being SO regimented that travel becomes yet another chore!

We like to spend our evenings talking about the day: what we enjoyed, what we didn’t, what could have gone better. I also try to keep a journal as we go so the whole thing isn’t a giant blur later. It’s fun while we’re on the trip and fun to review later.

And it helps in planning future trips!