Are you interested in hearing more about how I plan my trips? If so, read on, and I’ll describe the next major trip I am taking with Dearest Husband. I’ll let you know when and how I initially researched each trip, what and when has been booked, and what my next steps will be to complete my trip planning process. By the end, you will be certain that my blog name should be CrazyBankerChickTravels.net. If not, cheers and Happy New Year, you just got 30 minutes back! I’ll be back to writing about actual travel experiences shortly.
The seeds of my 2019 travel plans were planted well before 2018. For several years, I have maintained a list of most-wanted destinations, on a spreadsheet that also includes whether I see the destination as best with a group, with kids, with husband, and what months/seasons would be best to visit (generally: I prefer the “shoulder seasons” unless a destination is really weather dependent). However, I also need to factor in our kids’ schedules; for example, this summer we will be sending one off to college, but we won’t know the dates for several months when she decides which school to attend. Hence, the entire month of August is off the list for major trip planning in 2019. Other key dates such as graduations, weddings, Husband’s trade shows, etc., can also be a factor in choosing travel dates.
Since I’m still tied to an office, I also need to plan out my time away from work – unfortunately, I haven’t figured out how to travel as much as I want and still have my banking career. Generally, I allocate between 13-17 annual vacation days to up to two major trips. There are typically a few long-weekend, 1-2 day trips as well, but these are handled a lot more spontaneously.
When I Book Flights and Lodging
Since I’m a confessed “obsessive travel planner”, my significant trips are generally booked, at least on a skeletal basis (required flights, maybe a hotel or two), 9-12 months in advance. I then utilize the intervening time to plan an actual itinerary.
So right about now you are probably saying “OMG Banker Chick you must be kidding me! I don’t know what I want to do or if I’ll be available that far in advance! So many things can happen!” While this is true, I’ll attempt to make my case in a Q&A format:
Q: Why should I start booking so early?
A: Three reasons:
- In my experience, the best opportunities to book a long-haul flight, hopefully using points, is just after a flight becomes available. On most airlines, seats are released 11-12 months before travel. I only pay actual $ for an overseas flight if it’s an exceptional bargain (which is tough to do at the last minute, for a popular destination, in a nice weather season).
- While it’s unusual for hotels to fill up that far in advance, for certain destinations and timeframes, choices become limited as the date approaches. I like choices, so knowing my dates early means I can research and choose from literally any lodging.
- I’ve found that committing to the dates early makes it more likely that I’ll actually travel. It is far too easy to talk about a trip, discover that the price is prohibitive or the best hotels booked, and say “eh, maybe next year”.
Q: But what if something changes and I can’t make the trip?
A: Yep, this is a risk. There are two ways to manage this risk:
- Carefully read the terms & conditions of all travel bookings. In most cases, points-based flights can be changed or cancelled with very minimal change fees. The airlines don’t mind getting that free seat back to sell. Similarly, most hotels do not require upfront payment, or if they do, may offer free cancellation up until a certain date closer to travel.
- Buy trip insurance. While certain travel uncertainties, such as trip delays and lost luggage, are covered by a good travel credit card, full trip insurance packages such as those offered by Insure My Trip also cover cancellation of a trip due to illness of the traveler or a primary family member, and medical costs while traveling. Many policies also offer a “cancel for any reason” or “cancel for work reasons” rider, for an extra cost. Per the bullet point above, carefully read the terms & conditions.
Costa Rica, March 2019
Costa Rica has been on my “most wanted” list for years. It’s billed as safe, friendly, and most of all, beautiful with a diverse landscape that is dramatically different to my own. So, why now?
This one came down to timing. Husband and I will celebrate our 10th Anniversary in March, 2019, and want to spend this special day in a special destination. March can be chilly in most of the Northern hemisphere, and anticipating time spent in a sunny climate is the best antidote to a chilly East Coast winter. We also considered Aruba (where we own a timeshare), but decided we would rather explore a new locale; Hawaii, where we spent our honeymoon in 2009; and Australia, but decided that this year, we didn’t want to dedicate the full 2 -3 weeks really needed to justify the long flight and expense.
Step 1: Initial planning and Research for Costa Rica
Once I’ve identified a likely destination candidate, it’s on to my bookmarks menu. As I research trips or come across interesting travel sites pertaining to my “most wanted” list, I make sure to bookmark interesting sites under a detailed “Travel” menu, by country. Once I decide to book a trip, the destination gets its own top billing on the bookmark menu until the trip has taken place (then, the bookmarks return to the general “travel” category).
Step 2: Determining what we want to see, possible overnight destinations, and booking flights
Utilizing these sites and others, the next step was to determine exactly where in Costa Rica we might want to go. Quickly recognizing that the country’s climate and topography is extremely diverse, and that we would be comfortable driving our own rental car, I realized that we would want to stay in more than one overnight destination. Whenever this is the case, and when there is more than one major international airport, I look into the possibility of an “open-jaw” flight:
Open jaw means flying into one airport, and out of another. Although there is a cost of transportation between the two airports (in this case, a one way car rental fee), I like the possibilities and time savings of not having to backtrack.
At this point, I spend a lot of time with my favorite mapping tools. I look at the various destinations mentioned in the travel sites I’ve previously saved, as well as Tripadvisor, Fodor’s, and other general travel sites. I Google images of various towns and cities to see if they look like they match what I’m looking for. I print a map and mark potential destinations, to get a sense of their proximity to the various airports.
Since booking the flights usually comes first, I determined that an open-jaw itinerary utilizing two Costa Rica’s major airports, Liberia, and San Jose, which are about 3 – 4 hours apart by drive time, could work. Then, I research the best flight options. Into A, and out of B? Into B, and out of A? on what dates? Can I cover a weekend? Two weekends? In this case, we wanted to enjoy Costa Rica on the actual date of our anniversary, so I worked around that. I was able to secure First Class seats from our local airport, Newark, to Liberia, returning form San Jose to Newark. We are paying for the flight down, with a very reasonable mid-3 figure fare, and utilizing points for the return. Happy with the overall travel cost and getting some First Class pampering for our big anniversary, I booked these flights in early June 2018.
Step 2 1/2: Buy Trip Insurance. If I’ve paid for flights, presumably utilizing a nonrefundable fare, now is the time to buy the trip insurance. If all flights are booked using points, this can wait until I’ve made a significant cash payment for some element of the trip, for example, an AirBnB stay.
Step 3: Finalizing overnight destinations and # of nights in each place
OK, phew. Flights are booked. Now, I take another look at my potential destinations. What is there to do in each place? How far is it from each airport, and how far are the destinations from one another?
My definite preference is a minimum of 3 nights in a given location, with the small exception of an airport hotel sleepover prior to an early flight. 3 nights give you two full days where no travel is required, to fully explore a destination. Of course, more can be better, but I start with 3. I also prefer to keep travel time between overnight destinations to about 1/2 day. This gives time for a leisurely pace.
In Costa Rica, I realized that while we will never be able to enjoy the whole country in the 10 days we have allotted to the trip, we should be able to spend time in two of Costa Rica’s most reknowned climates: the Pacific coastal beaches, and the Arenal Volcano/ rainforest region in the northern central part of the country. My goal on a first trip is to sample some of the more popular locales first. Who knows when we will return? Highlights and generally highlights for a reason. Maybe that’s not too adventurous of me, but I also want to make sure that I’m spending my hard earned money, and 10 precious travel days, in a worthwhile manner.
Once I’ve centered on my overnight destination(s), I begin researching hotels or other lodging options. To choose a hotel, my primary sources of information are direct hotel websites and TripAdvisor.
A note on TripAdvisor:
While I utilize its “Traveler Rankings” as a general guide, I do not believe that a hotel rated #2 of 20 is infinitely better than one rated, say, #9 of 20. It’s probably a better choice than the ones rated 19 and 20, so to save time I generally only dig deeply into the top 40-50% of ranked hotels for my desired destination, and within that group, the ones that fit my budget. I look at price, overall star rating, and then I do the real dirty work: I read traveler reviews. The most important thing here is not to let any single review make your decision. Here are the types of reviews I make sure to read:
- Most recent – here I quickly look at the most recent 15-20 reviews. If more than a couple are less than 3 star, that may be a bad sign. But not necessarily.
- Worst reviews – those with 1 and 2 stars. How recent are they? What are the actual complaints?
- are they extremely subjective? (i.e. the food stinks, the beds are too hard)
- is it clear that the traveler had reasonable expectations ? In this category are those complaining that their Costa Rica resort was “too hilly” and it was hard to walk around. Um, did you look at a map/ photos?
- typically at least 30% of these are related to booking issues: “they didn’t have my reservation”. Unless this is a frequent complaint, I tend to believe that in the age of computers, resorts that are otherwise well-reviewed do not just “lose” a reservation.
- Another 30% or so are typically dedicated to a service rant regarding a particular individual. I usually disregard these, unless it’s a frequent or recently repetitive complaint. But if it was that frequent, the hotel wouldn’t have an overall 4 star rating.
- Reviews from the season I intend to travel – for obvious reasons
- “Average” reviews: those with 3 stars. I find that these reviews usually include a lot of good information and “pros and cons”, and are generally not written by someone with an axe to grind. Your con, might be my pro (ie, “it was too quiet, and there was nothing happenning at night” or “too many children”).
I will comment here that I’m less of a TripAdvisor fan now that it seems to be more focused on being a travel booking engine than a traveler review site. So, I also read reviews on Booking.com and Hotels.com for good measure. Hey, it’s still better than relying on the hotel website’s own reviews.
Step 4: Exploring destination options and booking activities that require booking.
Now: I know where I’m staying and for how many nights. By this point, I’ve also created a running, stream-of-consciousness set of notes on the overnight locations, including activities specific to the hotel. These might look something like this:
Guanacaste – Papagayo
beaches, small towns dry & dusty in March
river or national park, wildlife
waterfall or white wtaer rafting a possibility
one small casino in Tamarindo 1 hr drive from Papagayo
shuttle to Four Seasons or sunset catamaran
Arenal – La Fortuna –
Mud baths, volcano hike, hanging bridges, hot springs **bring bug spray**
spa, cooking class on site?
zip lining available but bumpy car ride
coffee and chocolate plantations
There’s a lot more – my notes pages for a 10 day trip are typicallly 4- 5 full Word Doc pages of this rambling, and at the end I include general tips and a packing list.
Again, for this I utilize TripAdvisor, focusing primarily on the now VERY HARD TO FIND (are you listening, TA)? destination forums. Again, comments on the forums are taken with a grain of salt, but it becomes clear pretty quickly who the real destination experts are.
A key at this point: do any of the activities we really want to do, require prebooking?
You may not believe me, but although I’m an obsessive planner, I would rather NOT prebook every activity down to the last minute. Instead, I prefer to prebook only activities that meet one or more of the following criteria:
- can’t miss,
- unavailable without a reservation, or
- will have to wait in a 3 hour line
For example, the Sistine Chapel during Easter week. Otherwise, I create a set of options that we can review each day and decide what to do based on the weather, our energy level, or what someone at the bar told us about the previous evening.
Step 5: (optional) Create itinerary balance view calendar
For long trips, I think it’s important to ensure that the itinerary includes a balance of busy days, travel days, and rest / optional days. As I already noted, I like to spend several days in a location, rather than traveling day after day after day, with a trip that ends up being no more than the view of a car or train window. I have found the best way to visualize the “busyness balance” of a trip.
A snapshot of an early itinerary balance view calendar from my recent Scotland-Ireland trip (I ended up changing this a bit, but you get the idea):
As you might imagine, the color codes have a meaning: Green = unplanned free time or very minimal time requirements, explore options; Red = booked; Blue = travel.
I did not feel the need to create a balance view calendar for Costa Rica, as there will be a plenty of downtime on this trip, on purpose. It’s more important for a sightseeing-heavy itinerary.
Step 6: Create Detailed Itinerary
This is my piece-de-resistance, and the result of all this effort. For each trip, I create a word document (actually, I’ve been using Pages lately), day by day, including every booking: flights, hotels, reservation #s, contact info, website links, and pictures.
I’m currently finalizing this for my March trip, and my goal is to have it completed 1 month before travel.
The average document is about 10 pages long, and can be longer depending on the trip length and number of destinations. I use large font and lots of photos, so this isn’t as much as it seems. But it allows us to take a quick look, and visually see our days and options. I also include a list of restaurants in each location, from reviews on TripAdvisor, Yelp, and TA forum mentions. I don’t always stick to these restaurants, as I love to stumble upon a place, but sometimes it’s nice to just say “I’m feeling like pizza” and not have to go to far to find a decent one.
These itineraries function as my own personal guidebook for my trip. They are uploaded to icloud and downloaded to my iPad so they can be visible even if I’m offline.
Since this detailed personal itinerary document maybe be hard to picture, I’ve added a link here to the first 5 pages of my Scotland & Ireland 2018 itinerary – I hope you’ll get the idea! Scotland Ireland 2018 itinerary
Step 7: Upload Itinerary and reservation confirmations / emails to icloud.
We’re almost there!!! This is where the excitement starts to really build, and the trip is close. During the last few weeks prior to the trip, I will create .pdf documents of all confirmation emails, and related documents. These go in specific folders in my icloud drive labeled Flights, Lodging, Car Rentals, Trip Insurance, etc. If possible, I carry no paper – occasionally, though, a reservation will specify that I need a printed copy.
Step 8, which may overlap with steps above: start planning the next trip.
This is arguably the most important step of all. Step 8 should be started preferably before the prior trip, so there is ALWAYS something to look forward to, even on the last day of an amazing trip. In this case: Prost! to Oktoberfest in Munich, September 2019!
I hope you’ve enjoyed reading about my process, and maybe picked up a tip or two. Maybe you completely disagree with my process, and prefer to just wing it: if so, more power to you! There’s room for every travel style – I just like mine best 🙂 .