Booking Your Vacation

Rainbow over the water with a dog

So you’ve done your pre-planning and you’ve got your deal-breakers and nice-to-have’s all figured out. You should have a good idea of your budget, timeframe, and the style of vacation you’re seeking, as well as how much of the planning you’d like to do yourself. Of course, some of this may change as you move along in your research so keep a somewhat open mind within the boundaries you’ve set for yourself, and keep some ideas for your next vacation.

Depending on your pre-planning, you may want to research the following options in this order or you may want to start with airports. Any way you go, these are the things to keep in mind as you book your vacation.


You’ve narrowed down your desired destinations to under a few places around the globe, maybe even just one. At the very least, you know if you’re going by plane, train or automobile, and you’ve thought about the schedules and flexibility of each option.


You may have several airports close to you to chose from or none at all. I have a few within a couple of hours of me, but my favorite is definitely TF Green for a few reasons. It’s small, which means parking is usually easier and cheaper, the lines are not nearly as long, and there is no need for shuttles (or marathon legs) to get between terminals. The drawback is that it’s usually cheaper to fly out of Boston or Hartford — and  those bigger airports offer a lot more non-stop destinations and flight choices.

Be creative when you’re thinking about how to get to the airport. You may be able to park at a train station and take the train to the airport to save on parking, or even take an Uber or taxi to save on parking altogether. If you’re leaving extremely early, you may want to stay at the airport hotel the night before, especially if your airport is a couple hours away. The hotel may have options to leave your car as well, so it can be a win-win situation.

Most times, you can use the same site, such as, to book hotel, air, and/or car packages. These sites are great ways to bundle your information together and save some money.


There are so many choices! Do you want to trek across Nepal and stay in tea houses for a couple weeks? Is a cruise more your style? Would you like to rent a house in the mountains or on a beach? Stay in a high-rise in a city that never sleeps? Are you booking it all in advance or winging it as you go?

You have several options when it comes to seeking out your accommodations for your vacation. If I’m staying close to home, I look at AirBnB or VBSO for places to go camping or hiking, or to explore a new area of my state. There are many great sites that give you search options for hotels and hostels, such as

There are many things to think about if you’ve decided on a cruise, too. The size of the ship will determine not only how many fellow passengers you’re exploring with, but also how well it will handle rough seas and the destinations available.  The size and location of your cabin relative to the bow and stern (or anchor or engine) and the deck level will all impact your stay, and possibly your sleep, so you’ll want to book with a company that can give you all this information upfront.

Another thing to think about when booking your accommodations is the availability to cook or store food, if necessary. If you’re staying in an AirBnB in Barcelona for a week, you’ll probably have access to a market and the ability to cook what you buy, but you may not have a cooking facility available at a hostel. Hotels may provide breakfast for free or have room service available. It’s definitely worth some consideration as you book your home away from home for this vacation.


If there are excursions or experiences that you definitely don’t want to miss out on, it’s best to schedule these as you’re booking the rest of your trip. Many countries and some cities have local tourist information on their websites, or the hotel you’re staying in may have some local unique experiences to suggest. There are many guidebooks out there, but I suggest always staying open to meeting the local people and following their lead.

When you’re looking for things to do, check out sites like City Pass for local activities at a discounted price. You may even find fun things to do around your hometown that you never knew existed!

Excursion Packages

Some of us want to plan out every detail of where we’re going and staying. Some of us, like myself, prefer to set my deal-breakers and nice-to-have’s and then find a package that fits our plan. I love these and highly recommend them for several reasons if you’re open to having the itinerary set for you.

I typically travel solo, but I do enjoy sharing experiences with other travelers. These types of packages allow me to have the best of both worlds. The excursions I’ve been on have had people from all over the world sharing the experience with local guides. They’ve allowed me to get to know people and become involved in some traveling customs, like passing on the travel rock. But by booking as a solo traveler, I’ve had access to my own room, tent or cabin, which is great for introverts like me.

The best part of these excursion packages is that everything (or most things) is taken care of for you, so once you get there, you never have to wonder where you’re eating dinner or what the next excursion will be. My favorite excursion package trips so far have been to the Galapagos, New Zealand, and Peru. You’ll find these types of adventure vacations on sites such as Intrepid Travel.

No matter where you go or how you get there, there are always some things that you want to keep in mind while booking your vacation.


There are so many ways to get points now that it’s imperative that you’re getting money back on everything you spend on this vacation. Travel credit cards offer points back that you can use towards your next vacation, but there are also many hotel chains, airlines, and booking agencies that offer loyalty points. My suggestion is to determine your favorites and to look into how to optimize your cash back. You may find that by booking all your flights through Expedia on your Capitol One credit card you earn a free flight quicker than you thought possible!


Important point here- when searching to book your vacation, always use an incognito tab. This prevents the companies from increasing the prices on tickets or itineraries for which you’ve previously searched. I’m not an expert in this sort of thing, so I’m going off of recommendations I’ve heard, but it is a trick I use and it does seem to work in keeping the prices down.


One of the most important things you can have that you hope to never need is travel insurance. It’s a great idea to know what your health insurance offers, but most don’t offer support if you’re going overseas. The travel credit card that you use to book the trip may offer some trip cancellation insurance, but it may not offer evacuation insurance. Some countries have some specific requirements about health insurance coverage that they require for you to enter the country, and you’ll definitely want to have some protection if your trip gets cancelled or you can’t go because you fall ill.


Always, always, always learn enough about the culture and the language of the place that you’re visiting so that you are a good tourist. Learn a few phrases such as hello, good-bye, please and thank you, even if your guides or hosts speak your language. My biggest regret throughout my vacations has been not being able to communicate with the locals as much as I’d like. And make sure to start as soon as you book your tickets! Learning about the culture and the language is a great way to look forward to your vacation.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.