A refresher on what we covered in How to Plan Your Trip 101:

• You have thought about where to go and either have a particular destination in mind, a few options, or are completely open to any location

• You have considered the pace of travel - whether you want to visit a specific destination or take a road trip - and how often you want to be on the move

• You have determined your traveling companions (of lack thereof)

• And, you have a sense of your budget

Now is the time for the rubber to meet the road and to actually book your trip!

There is no one right order in which to book the elements of your trip and particular factors may make certain ones higher priority for you than others. In each section below, we will cover what factors you may want to consider to prioritize or de-prioritize these elements, and tips and resources that we use in making these decisions ourselves.

Flight

Reasons to prioritize:

• We typically book our flight first since the exact arrival time at the destination will influence the rest of our trip. For example, if we want to spend a day in the city where the airport is, a red eye that arrives at 6am local time will give us ample time to explore and perhaps we don’t even need to spend the night there. Likewise for the return flight, it is important to ensure you are able to get to the airport in plenty of time. If your departure is at 10am, you likely don’t want to spend the prior night hours away.

• Flight prices can vary significantly depending on when you book and the particular flight. Your best bet is to book your flight when the price is good instead of booking it out of necessity based on other factors of your trip.

Sites we use for research and to book:

• Historically, we have relied upon Kayak to be able to easily search multiple options. Some of our favorite features: (1) the site shows data on whether they recommend you ‘book now’ or expect the price to drop so that you have a gauge of the airfare; and (2) ease of trying different variations to see if alternative airports have better options compared to our home airport.

• Our new favorite site is Scott’s Cheap Flights. While we originally started off with the free version, after booking a flight to Paris at less than half the normal price, we upgraded to the premium option, a good deal at $39/year.

Accommodations

Reasons to prioritize:

• Popular spots can book up quickly during peak seasons. Making sure you have several options that meet your requirements is smart before booking a flight.

• If you or any traveling companions have limited mobility, make sure you find options that will meet those needs. This can be harder than it sounds. When traveling with an older relative who needed to mostly avoid stairs, it was quite difficult finding a rental house that had a first floor bedroom.

Sites we use for research and to book:

We find that the accommodations we stay in can be broken down into three categories. Here are descriptions of each, tips and tricks for successful stays, pros and cons of each, and how we decide where to stay.

Rental homes

Where to look: We have used HomeAway, VRBO, and AirBNB. Their sites allow you to easily filter to identify features that are important to you.

Tips & tricks for successful stays: read the fine print - not all places include sheets and towels or basics you would expect at a hotel (like soap). This is not a big deal if you plan for it. AirBNB allows proprietors to rent out rooms or parts of their home. If you do not want roommates, make sure you select the “entire house” filter. Make sure you have a general sense of where the home is located compared to where you want to be. If you imagine staying in a city center, you do not want a rental on the outskirts of the city.

Pros and cons:

Pros: typically you have an equipped kitchen and can opt to cook, which can be a cost saver and a nice break from restaurant dining; you can live like more of a local, often in a residential area; you have more options for space to accommodate your interests and traveling companions - the right number of bedrooms, perhaps a private garden or rooftop terrace. These can be more cost effective than other accommodation options but are not always.

Cons: you never fully know what to expect - some stays may be better than others - and there is a little more uncertainty. For example, when we went to Iceland and stayed in AirBNBs, about a week before our trip, I realized we had not received any final confirmation check-in details from one place. I contacted the proprietor through the website and as a day or two passed, I started to panic that we wouldn’t have a place to stay. I finally called the phone line, realized I didn’t even know how to pronounce the owner’s name. Luckily, everything was fine, but I would never have a similar worry with a major hotel chain. Another con is that since many places allow you to check yourself in, you can ‘live’ as a local without necessarily coming into contact with anyone. You are on your own to locate a local grocery store and the like.

How we decide when to use a rental option: If we are going to a particular destination, we find this often suits our needs better than other types of accommodations. It provides us with extra space, access to a kitchen, and more flexibility. In most cases, it is also more affordable than staying in more traditional places.

Traditional Inns and B&Bs

Where to look: My favorite site to check to figure out what options exist in a location and to get a sense of which are highest rated is TripAdvisor. I have a soft spot for multi-course, elegant breakfasts so when we are staying at B&Bs, I check out the caliber of their breakfasts. Some only offer continental breakfast fare, so if there are other options, I move along.

Tips & tricks for successful stays: Make use of the inn or B&B’s proprietor and interactions with other guests. In most cases, the proprietors are well-versed in their local area, can offer history, recommend restaurants and even help make reservations at hard-to-book spots, and suggest off-the-beaten-path options. Some places have built-in intermingling options for the guests - either a happy hour or group seating at breakfast. This can be a great way to meet interesting people and hear their stories. When we were in Vancouver in 2014, we met a couple from Australia that were on a multi-month trip. They had recently come through somewhere we were going later on our trip and made some recommendations.

Pros and cons:

Pros: accommodations are usually unique and interesting, not cookie-cutter; you can often find inns and B&Bs in great, central locations (cities) or beautiful, natural areas (rural); and you have the advantage of someone at your fingertips who knows the area

Cons: it is often difficult to be completely anonymous, especially at smaller places (which most are), the buildings are often older and can have all the “quaint charms” that come with that - inconsistent water pressure, creaky floors, and the like.

How we decide when to use an inn or B&B option: We are most likely to use these when we travel as a couple and so only need one room but want it to be more interesting than a generic hotel or when we are traveling with another couple but on a road trip where we will have a number of stops.

Hotels

Where to look: We would recommend finding a specific hotel brand where you can take advantage of their point system. We use Marriott, as Lindsey often stays at those for work travel. Building up points can lead to free stays, room upgrades, other benefits like late check-in or check-out, and, in the case of Marriott at certain hotels, free breakfast. Beyond a specific brand’s website, we also use TripAdvisor to locate a highly rated option in our destination. This is also helpful to narrow down where to stay if, for example, Marriott has several hotels in a city.

Other details

While we consider the activities, flight, and accommodations to be the main events, there are other details that you may need to book, depending on your trip. In short, here is an overview of each as well as a few tips.

Rental Car

Overview: Book after your flight so that you can include your flight details in your booking. This is particularly helpful so the rental company is aware if you are delayed and does not assume you are a no show.

Tips:

• Pay attention to whether the cars are manual or automatic. We have found in some countries, certain rental companies only carry manual transmissions so make sure you know what you are booking.

• We would recommend going with a major, known rental brand. Travel books typically have recommendations, or you can do a Google search for major rental companies in a certain country. These are also the ones most likely to have easy access at airports.

• Make sure the pick-up and drop-off location IS actually at the airport, not several miles away.

• Review your car insurance policy to understand what it covers for rental cars. Many insurance policies insure you as the driver, regardless of where you go, making any additive rental insurance that the companies try to sell duplicative and an unnecessary expense.

• Know how you will navigate. Will your phone GPS work and be reliable? Do you want to add-on a GPS in the rental car? Sometimes you can add those once you arrive, but that is subject to availability.

• Be flexible with car size and type. Sometimes going up or down a class can cause a significant cost differential. But make sure you have enough room for all passengers and luggage, as well as a vehicle that will be successful on the roads. Do you need a 4x4 for steep mountain passes?

• Check out pre-pay options. We have found that many rental companies offer a discount if you pay the entirety upon booking based on the estimated payment (which they will later adjust if you keep the car for a longer or shorter period of time).

Ferries

Certain destinations or visits on your trip may require the use of a ferry. If so, make sure it will be available when you need it to be. If routes book in advance, consider pre-purchase of your ticket.

Other Activities

While we personally avoid locking in too much of our trip in advance to provide more spontaneity once traveling, if there are certain activities that are high on your list - tours, certain museums, etc. - consider purchasing tickets in advance. This can ensure you have an entry time for popular attractions and can provide online discounts for certain spots.