sample itinerary

Planning a Trip

Table of Contents

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. Which surprises me. I like researching and planning trips almost as much as I like taking them. And I think anyone can do it. Here’s how I do it.

I know people who just show up someplace and wing it. (I’ve done that) I also know people who schedule every minute of every day. (not me.) 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.) I’d also rather not spend travel time finding a place to sleep, figuring out if there’s public transportation and how to use it, and waiting in line to buy tickets, if I can avoid it. I want to be enjoying where I’m at.

A little background on us:

  • We’re from the USA, land of chain hotels, chain restaurants, and limited to no public transportation. We try to avoid the first two and use the last when we travel.
  • We’re not full-time travelers. (We wish!) We take distinct trips, which are the focus of this blog.
  • We don’t have children so you won’t see any tips for traveling with them. That also means we’re not limited to traveling when school is out. In fact, we do the opposite.

Decide where to go

Someone asked me once how we decide where to go. Which made me think: How do we decide? It kind of goes like this.

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:

  • Summer is when people with kids travel, which means larger crowds and higher prices.
  • It’s the only time the weather is reliably good at the family cottage, so we go there.
  • We like gardening (I blog about that here), and there’s lots to do in the garden then.

We try to 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. Sometimes you can’t avoid high season. That can mean peak prices but at least we avoid snow!)

What kind of trip do we want this time?

We enjoy outdoorsy things like hiking, snorkeling, wildlife, and hanging out at the beach. We also like more urban activities like wandering around cities and towns, visiting museums, other cultural sites, and botanical gardens. We try to balance the two though some trips lean more toward the wild and natural, others more toward the urban and cultural.

How much time do we have?

Now that we’re retired our travels are no longer constrained by work schedules or available vacation time (yay!). We try to go for at least four 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 somewhere 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 even if it’s raining or we want to relax.

Even when we were still working we went for fewer two week trips rather than more frequent shorter jaunts.

Now, where do we want to go?

We have a list of places we might want to visit, or revisit, organized by which season is best for that location. As we run across travel inspiration, we edit that list. 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 (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.
  • At the end of this phase I have a location (for example, France, the trip I’m currently planning) and a time of year (late spring).

Plan the trip

Research things to see and do

With some idea of where, when, and for how long we want to go, it’s time for research. I start with a guidebook if I can find one. We often already have an idea of some things to see or do — or we wouldn’t be looking at that destination! — but I find more once I start researching. I know there’s a lot of information for free online and I’ll end up there; I find it handy to have a comprehensive guide to start with.


Lonely Planet and Rough Guides are the ones I turn to first. I find them comprehensive and well-organized and they cover price ranges that match with ours. I’ve used Rick Steves for Europe recently but supplement them because he doesn’t cover everywhere we want to go. The areas he does cover he covers in great depth, and I like the introductory walks he includes for most destinations. But he says nothing at all about places he doesn’t cover; like they don’t even exist.

I mention the guidebook(s) I used in the Resources for each trip, along with any significant online sources I can remember.

I used to buy physical books. (After all, that was once the only option! Maybe that’s one reason I like guidebooks: When I started planning trips there was no online.) 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
  • ebooks are more portable (I can bring them up on my phone)

You can highlight entries too, like you would in a physical book. I use a different color for each category: Sights/Activities, Lodging, Food & Beverage, Notes. I usually export the highlighted items to a spreadsheet so I can sort and filter but I'm nerdy that way.

* I replaced the iPad with a cheaper 8” Kindle Fire. It works well for reading guidebooks but for web browsing I like a bigger screen.

This is kind of the brainstorming phase. While I start with a guidebook, that usually leads to links for different websites, which in turn leads to other sites …

At the end of this phase I have a collection of possible destinations (for example, Normandy, the Loire, the Dordogne, Provence, the French Riviera, Paris, maybe Strasbourg? the Atlantic Coast?) with things to see and do at each stop. I usually do this about a year ahead of time but it can really be done any time.

Outline the itinerary

At this point I have an 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 in the time available. 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. My goal is to figure out:

  • Which places to visit
  • How much time to spend in each place
  • In which order to visit them

I use a simple spreadsheet with numbered days where I jot down what we might do on a given day. This isn’t super detailed. My goal is not to schedule every day but to group sites and activities based on proximity and time needed. 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.

sample itinerary
A sample of part of an itinerary.

One of the benefits of this is that we can rearrange chunks of itinerary as needed:

On our first trip to Hawaii we dealt with both a nasty sinus infection and record rain and flooding, which led to leaving out and/or rearranging some of the things we’d planned.

  • In Japan we rearranged days to account for a museum closure that
  • I hadn’t noted and an activity we didn’t find out about until we got there.

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 multiple times 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.

Don’t forget to allow time for getting 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, by the time you pack up, switch places, check in, and resettle.

I now know:

  • about how many nights we’ll spend at each destination
  • what we’ll likely do at each destination
  • which order to visit them, and how we’ll get from point to point
  • how long the whole trip will be

This phase is the longest and also one of the most entertaining. I’m plotting the storyline of the trip but I haven’t committed to any costs or timelines. I like to be finished with this phase about 6-8 months out so that I can take advantage of any deals on flights and book key lodging before they’re sold out. This is the level of detail you see for planned trips on the blog.

Book the trip

Book lodging

I book lodgings before we leave. It saves time while we’re there, and saves stress about where we’re going to sleep! I typically book 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 we focus on what’s important to us:

  • Our must-haves in a room: We like clean, functional, and safe. (Duh.) 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, and A/C if it’s going to be hot.
  • Amenities: The older we get the more we appreciate an elevator. Laundry can be a plus. A pool is nice if it will be hot but we’re more beach people. We don’t care about a gym.
  • 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 first, to make sure we’re in a good neighborhood. We try to use public transportation when we can’t walk so I make sure that’s nearby if we need it. I’ll pay more for lodging in a central area to save on transport time, cost, and hassle.
  • Cost: I don’t really budget. I look for places that meet our needs 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. Many vacation rentals and Airbnbs charge a cleaning fee and/or a service fee. Sometimes there’s an extra (hefty) charge for hotel parking or no parking at all. Then again, some places may include extras such as breakfast or a free lift to the local train station or port. A free breakfast can save time and money. (Eat enough and you can skip lunch!)
  • 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 probably more so.

The key thing is to know what’s important to you and not be distracted by shiny things that don’t matter to you. I’m not looking for the absolute best option. Just a great one for us. You might only sleep and bathe there, but it’s your home away from home and can really set the tone for your stay.

Here’s how I find a place to stay:

  1. I start with any guidebook recommendations that meet our criteria. I don’t think I’ve ever been disappointed with one. They’re often full because lots of people use that guidebook.
  2. My next stop is usually because they list the smaller bed and breakfast, guesthouse, or pension types of lodging we like. For our recent trip to Asia I used Agoda, which is related to I’ve also turned up some surprising deals through Expedia and other third parties, though I rarely use those.
  3. TripAdvisor often includes places that aren’t listed on the booking sites. If it doesn’t have a link to the property’s website I Google search them.
  4. I’ve found Airbnb a good source in places where more traditional lodgings are either scarce, expensive, or both, like remote locations near national parks. We’ve had good luck with Airbnb, though I know it has its issues. I try to find hosts that are renting their vacation home while they’re not using it or are renting space on their property, though it can be hard to tell.
  5. If I strike out with all of those I’ll dig into Google maps or websites of local tourist organizations or sites for key tourist draws, which sometimes list lodging options. The Blue Ridge Parkway, for example, is tricky because it weaves through out-of-the-way towns and villages.


Don’t rule out hostels because you don’t want to sleep in a dorm. Many have private or family rooms with baths that are just as comfortable as a more traditional hotel room, though less expensive and with more spartan decor. They also tend to have shared kitchens.

Regardless of how I find a place, booking direct is often the most economical, though not necessarily the most convenient. With some smaller places it might be the only option. Shop around, because I’ve seen the same room listed on different sites for different rates and with different rules.

I book lodgings as soon as I can. Many US national parks open reservations a year in advance and may sell out in hours (or even minutes). In places with repeat visitors, people may book the following year when they leave. I include information about where we stay on this blog.

Book flights

I use a comprehensive search engine to research prices and schedules but then book the flight directly with the airline. I like Momondo or Skyscanner for their extensive filters and quality ratings of flights.

Some things that I’ve learned, sometimes the hard way:

  • 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 Venice and out of Rome, than to book roundtrip and circle back to your starting point.. 
  • If using miles or points they’re often priced each way anyway, so I just get one-way flights. For example, I was able to get both of us flights to St. Lucia using my points, and flights back from Barbados using my husband’s points
  • Check the amount of layover between flights. 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. It’s just not worth the stress of running through airports and possibly missing a connecting flight. I’ve also become more willing to pay more for a direct flight.

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 a bit longer but it often seems the prices aren’t that much lower and the schedules are worse.

We don’t include information about flights on this blog because it’s so dependent on your starting point.

Book other transportation

Traveling in the US usually means driving because we lack public transportation in all but some large metropolitan areas. But that’s not true worldwide. Guidebooks can provide general information on getting around – including available passes and discounts – and more specific information on getting from one place to another. Rome2Rio and Google maps can be good free sources for discovering options for getting from one place to another.

  • We like traveling by train when we can. Trains are often (but not always) in between planes and buses for speed and cost, are more comfortable than planes or buses, and often scenic. It’s also often easier to get to the station. We love trains. And I love The Man in Seat 61 for information specific to train travel.
  • Flying is often the quickest and the most expensive way to get around, though you don’t see much along the way. Depending on security, it may not be much quicker. Airports are usually outside of cities or towns, requiring extra time and cost to get there and back.
  • Buses (or coaches) are usually the slowest and cheapest. If we take a bus it’s usually because it’s the only option. One challenge with buses can be finding the bus stop. It took us about an hour to find our bus stop in Matera on our Italy trip.
  • Renting a car gains you maximum flexibility at a cost. We try to avoid renting a car if we can. We sometimes rent a car for just the few days we really need it. In the past finding a car to rent was almost guaranteed. Recently there’s been a worldwide shortage of rental cars. Don’t assume one will be available last minute.

Beyond the standard options above, here are some other, more specialized options we’ve used:

  • In the Virgin Islands and Greek islands ferries connect the islands, usually — but not always — cheaper than flying. Ferries aren’t always an option between islands, though. Sometimes flying is the only option.
  • 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. We use those a lot there.

The need to book transportation in advance can vary and can change the cost. Do the math on passes and discounts to see if they help with costs.

  • Sometimes booking ahead may not be necessary but may save money. On our first trip to the UK we saved a few hundred dollars (over the cost of a rail pass) by booking train tickets in advance; sometimes for only 10% of what we would have paid if we bought the tickets the same day. On our second trip we got senior rail passes that saved us ⅓ the ticket price. (You don’t have to be a UK citizen to get one.)
  • In Australia we got a discount on our USA – Australia flight by booking all of our flights within Australia on Qantas also.
  • In Thailand booking an ongoing ferry or speedboat could be done with the hotel desk a day or two ahead of time.
  • Costa Rican shuttles must be booked ahead of time.

Don’t forget local transportation. Sometimes there’s a transport card, discount card, or package of some kind that you can (or must) use. Some places 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, with the local transport organization’s online presence offering details. You may want to figure out how much you will use public transport to see if a given pass or card is worth it.

We often combine options on a given trip:

  • When we took a road trip to the east coast, we drove our own vehicle but 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, ferries, and car rental.

Discount train tickets often open up 120-90 days before departure. Other options can be available sooner. I’ll book transportation as soon as I can. We post information about transportation we used on this blog for each destination.

Book attractions

Sometimes you have to. Sometimes it can save money. Sometimes you can save time standing in line. Sometimes all of the above! 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.

  • Many places offer one or more combo tickets or passes designed for visitors. Like cable TV packages, they seem to always include things you’re not interested in. Check to see if a given pass is good value for you given what you will visit. (Sometimes they may include hidden gems. In Florence one of our combo tickets included entry to the Palazzo Davanzati, which ended up being one of our favorite spots.)
  • Scheduled visits are becoming more common. For very popular sights – such as the Roman colosseum, the the Nazrid Palaces at the Alhambra, or the Grand Palace in Bangkok – you may need to choose an entry time in addition to booking in advance, with limited spaces available.
  • There may be a short advance booking window. If you’re not seeing tickets available it could be because of that, not because they’re sold out.
  • Getting tickets through a third-party can be convenient or it may require you to pick up the tickets from someplace far from the site. It can also be a scam. Also beware of websites that look official but are not. Official sites are generally the cheapest but may be less easy to use. It can be difficult to tell the difference.
  • I try to avoid booking outdoor (weather dependent) sights and activities in advance. Snorkeling, for example, is highly dependent on local conditions.

I generally book attractions 1-3 months out unless I need to do it sooner because of limited access. I’ll buy tickets for anything that I’m sure we’ll visit because it saves valuable time queueing and I find it easier to purchase online.

We post information about passes and tickets we use here on the blog.

Other preparations


Know the entry requirements for your destination(s), which will vary depending on what passport you carry and possibly by how and from where you’re arriving. With a US passport you can often just show up, but not always. Sometimes you need to apply for and receive a visa ahead of time. Sometimes your passport must be valid for at least six months. Sometimes you need an outbound ticket and/or evidence of sufficient funds. There may be a tourist tax or other entry fee. Guidebooks are a good starting point, supplemented by official government sources.

Beyond the official documentation required for the places you’re visiting, there’s also the results of all that planning you did. Here’s what we do:

  • We carry a folder with anything that must be printed, like visas or tickets, so they’re easy to find.
  • We carry a printed list of the hotels we’re staying in, just in case we get separated or need to get a taxi. (This was handy in Thailand and Japan, where we had the names in Thai and Japanese too.)
  • We use Google Drive for storing documents. We download key pieces, like digital tickets, to our phones so we can get to them even without a network connection.
  • TripIt is a useful app for tracking transportation and lodging. It monitors your email and adds plans it recognizes to trips automatically. (You can also add things manually, though that’s sometimes more trouble than it’s worth.) It sometimes notifies me of flight changes before the airline does!
  • I use Google Sheets for planning. It then becomes a reference while we’re away.
  • 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 location with information about:

  • where we’re staying, how to get there, and how to contact them, for when we arrive
  • anything scheduled, like transportation or tours
  • any “to-do” items like getting local currency, booking tours once we’re on-site, picking up tickets, etc.
  • a list of sights we’re interested in, with hours and directions as needed
  • a list of restaurants that sound good
  • 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 (or your own memory). It’s handy for both crowded urban areas as well as the wilderness or the beach. 

Keeping in touch

Free WI-Fi is common in lodgings and many restaurants and cafes but may not help with phoning or texting. We use email and apps like Facebook Messenger or GroupMe to stay in touch over Wi-Fi with friends and family. Many local businesses use WhatsApp so we do too. The deadzone is typically when you’re walking around. Find out what international offers your mobile provider has and, if you think you will need data beyond that, consider getting a local SIM card (or an eSIM if you can).

We usually purchase a local SIM — or more recently an eSIM — for one phone. It’s easy and cost-effective. Many plans are data only. Some offer a local phone number for calls and text, though those usually cost more. Our sweet spot seems to be a data only plan. We aren’t heavy data users and prepaid plans abroad invariably cost less than we pay at home.

If you don’t speak the local language, I’ve found Duolingo a fun and free way to learn, and Google Translate also comes in handy. (We had a lot of fun with the photo option while in Thailand and Japan.) 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. Make sure the credit card 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. If you have a US credit card like we do, it’s probably not chip-and-pin, which is common outside the US. Be prepared for it not to work at some unattended card machines. One reason I purchase tickets and things ahead of time is to avoid this potential problem.

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

We usually wait until we arrive and use an ATM to get local currency. ATMs and foreign-exchange booths at airports can have worse rates and/or higher fees, so if we must 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. On our most recent trips to Europe and the UK we deliberately held out about $20 worth of pounds and euros for our next trip so we’ll have some local money when we land.

In some countries we’ve been to — Aruba, Bonaire, Curaçao, 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, since knowing what activities you’ll be doing guides what clothes to take. 

Have fun!

My goal is to do enough planning and research that we can relax and enjoy our trip once we get there. Without being SO regimented that travel becomes yet another chore and source of stress!

We like to spend our evenings talking about the day: what we enjoyed, what we didn’t, what could have gone better. I also 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, fun to review later, and handy when I post about the trip on this blog.

And it helps in planning future trips!