The Ultimate Guide to Booking Your Dream Getaway

You’ve designed your perfect trip, so now let’s plan the details of your adventure. Read below for the ultimate tools and tips to book and prepare for your dream getaway. This article is Part 2 of the Choose Your Adventure Series.

This article will cover the following:

  • Purchasing Airfare
  • Booking Accommodations
  • Getting Your PTO Approved

Purchasing Airfare

It’s go time! Here at Wander with Wren, I’m all for getting the best flight at the best price. ICYMI: I definitely have preferences when it comes to flight fare tracking sites and budget ticket sites, and I personally veer towards budget accommodations. Use the below tools and tips to help you find the best airfare tickets possible!

white airplane over the white sky
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Scott’s Cheap Flights:

I consider myself a SCF evangelist at this point. Thanks to this company, I’ve scored discounted flights to Hong Kong, Spain and Guatemala! There are currently three subscription tiers: Free, Premium and Elite. While you can absolutely score great deals through their free subscription, I’ve recently converted to their Premium package to take advantage of more frequent and better flight options. You can try their free trial and then upgrade to a membership using this link.

Google Flights Tracker:

A free tool provided by Google Flights, this function allows you to track the prices of airfare for your intended itinerary. Enter your desired dates and destinations, and then click “Track Prices” above the listed itineraries. Give yourself a few months in advance if you can, so that you can receive email notifications. Once the flight reaches a price you’re comfortable with you can book!

SkyScanner and Kayak:

SkyScanner and Kayak are helpful because they compare flights across third-party vendor for you. Simply plug in your desired airports and dates, and the site does the rest. Both of these sites also offer the option to track the fares.


close up shot of a passport and tickets on top of a laptop
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Take Your Time (But Stay Ready)

If you use the tools above, you’ll be able to see the fluctuating ticket prices. Don’t be afraid to wait on prices to fall, especially if you’re traveling to a place during the off-season. For international destinations, give yourself enough time to budget for the airfare. Time is on your side with International travel, too. Airfare prices are typically most affordable about 8-9 months prior to your departure, so you can be assured that deals will show up with long-term planning.

Once you find affordable tickets, be ready to pounce. If you see something amazing and you don’t grab them, you may be kicking yourself later.

For example, $500 round trip tickets from Los Angeles to Sydney is a steal. Waiting to purchase and then missing the deal might keep you up at night with regrets for not buying them immediately (*totally a hypothetical for the sake of example). Besides, if you purchase tickets in the US, you always have a 24 hour period where you can cancel the trip without penalty. Better to have the tickets rather than miss out completely.

Purchase Trip Insurance

If the last few years have taught us anything, it’s that the world can change in an instant. It’s always better to be prepared, so when you’re booking airfare (anywhere) it’s wise to purchase the trip insurance.

Pro Tip: Certain travel credit cards offer trip insurance and travel protections, so consider booking with your travel card or even go through their travel rewards portal. I always check my Chase Sapphire Preferred card benefits to ensure that my trip is covered.

Get the Changeable Ticket Option

If you anticipate a change in your plans and potentially will have to reschedule your trip, I recommend purchasing the changeable ticket option. These tickets are typically a bit more expensive, but they come in handy if you need to alter your booking. Additionally, they usually allow you to choose your seat and bring an added bag for your trip.

I personally tend to forgo the changeable ticket options when I fly domestic or my trip is locked in. However, I can definitely see the added benefits of flexibility and peace of mind, especially if there are external circumstances that may cause you to reschedule or cancel.

Booking Accommodations

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One of the best parts of trip planning is always choosing accommodations. I love scrolling through lodging options and checking out reviews and pictures. I fantasize about what my stay there would be like, and which aesthetic matches the mood of the trip I hope to have. Along with safety and cleanliness at the top of the list, I also look for proximity to the city center and opportunities for socialization. A breakfast that is included with the reservation never hurts either.

Read on for the best tools and tips to score great accommodations.



Honestly – I love That’s not a sponsored plug either, I really do love their ease and their portal’s simplicity. The selection of accommodation options are great, and it’s super easy to navigate your bookings. Additionally, many of the reservations are cancellable until nearly 48 hours before your stay, and I personally enjoy that level of flexibility in case plans change.


Similar to the site above, HotelTonight is a platform that shows you and up-to-date listing of rooms in the next 72 hour, often at a discounted rate. The beauty of this platform is in its flexibility – if you’re in a pinch on a work trip or just need a night out for a staycation, this is the site for you. I keep the app on my phone just in case accommodations fall through last-minute (always good to have a backup plan).


Hostelworld is the site that you use to find accommodations. This easy-to-use tool allows you peruse the selection and then designate which type of room you want and select the number of roomies that you want to have.

Although hostels sometimes get a bad rap for being uncomfortable (because of the youths…) there are plenty of options that are clean, convivial and cheap. If you’re on the fence about staying in one, feel free to read my article here to give you the confidence to try it out.


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Choose Your Lodging

Consider how often and long you’ll actually be in your room.

I personally only ever care about the room being clean and comfortable enough, and I prefer to spend more on activities or excursions. I tend to choose middle of the road accommodations where I can get a good nights sleep but don’t necessarily offer the amenities.

If that doesn’t sound like you and you prefer to have a luxurious stay, just factor it into the trip budget. Your vacation is customizable for you, so if you want all of the views and relaxation from your hotel room, go for it!

Read the Reviews

It’s important to read through the first page of most recent reviews on any of the sites. During the pandemic, many hotels shut down or renovated and may not be the same as they were prior to 2020. Additionally, recent reviews will not only give you a good idea of what to expect for your stay, but might also give you some needed advice.

For example, if the hotel is beautiful inside but a review notes that you have to go through a sketchy part of town to get there everyday, you’ll need to consider your safety before moving forward with the booking.

Finally, if an advertisement for a specific hotel or accommodation sounds too good to be true, then it probably is. Reviews will help let you know that the promise of an infinity pool in the hotel courtyard is paused due to renovations.

Remember to Ask About Discounts

Let the accommodation know about any different affiliations or memberships you have. Military and First responders, and members of national organizations may have discounts or specials available to them. When traveling in the USA, I will mention my AAA membership and ask if there are associated perks for members. There have been a few instances when the rate was lower for card members.

Speaking of card members; make sure to let the booking agent know if you are affiliated with any of the brand’s rewards programs and/or partnerships with different credit cards. Some cards will get you access to hotel lounges, or even discounted services like the hotel restaurant or spa.

Of course, don’t forget to mention any special occasions that you may be celebrating. Birthdays, anniversaries and honeymoons are events that will almost always get you a sweet perk for the festivities!

Taking Paid Time Off (PTO)

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A public service announcement for all of you hard workers out there:


PTO policies are a substantial component of an employee’s compensation and benefits package.

Research has shown that employees need regular time off to gain perspective and relaxation to bring their best selves to work. Additionally, employees feel well-rounded and enjoy their work more. Happy employees tend to stay at their workplace without being burned out or overworked, and can contribute more to their teams. So, for you workaholics out there, taking your PTO will help you work harder and better year round! For the rest of us who just enjoy vacation, see below for helpful tools and tips to get your PTO requests approved!


Plan Ahead

Plan ahead to the extent you can anticipate your travel dates. For longer trips, consider booking your trip at least three months in advance, especially if you will be taking a longer vacation.

Planning ahead also gives you enough time to tie up projects at work and/or delegate them to someone else. Additionally, planning trips earlier make the dates solid and immovable, so there’s no way you can take on that last-minute project. Sorry, boss!

Communicate Dates Early and Often

Dear Supervisor,
I am requesting these dates XXX for vacation.
Please advise by XXX of this week.

Full disclosure, I used to get nervous sending these emails. Like I was skipping out on work or doing something wrong. But then I remembered that PTO was literally part of my compensation and by not using my vacation, I was actually letting my hard-earned money go down the drain.


Then, remind your supervisor often about your upcoming dates you’ll be out. If you’re really considerate, you can send a project status email for the work you’ll be delegating to others while you’re out.

Because you’ll be offline.

Fully logged off.

On vacation.

Get Creative

No need to take long stretches of PTO if your situation doesn’t allow for it. Get creative and make the travel itinerary work for you.

If you see a holiday weekend approaching, consider bookmarking your travel dates before and/or after that weekend. That way, you get more vacation without using your PTO time.

If you work from home, use those remote policies to your advantage! Many workplaces now include a hybrid or remote-flexible model where you can work from home. Feel free to take a trip during the weekend and extend your stay in that location to work there. If there’s solid WI-FI, working from a hotel room should be an easy sell (if you decide to tell anyone at all)!

Pro Tip: If you work at a large organization that values face-time, consider working out of a different regional office for a few days to get the perks of a vacation. For example, my company has a New York office. If I want to have a vacation in that city without taking days off, I could go and enjoy a long weekend in the city and then work normally during the week in office.

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Photo by EVG Kowalievska on


There are plenty of options when it comes to finalizing your dream getaway details. From booking airfare to accommodations, take the time to make reservations that work for your trip. Communicate and get creative at work to make sure that you can go on the vacation that you’ve earned and actually use that PTO. You’ll be glad you did when you’re on vacation, logged off and enjoying the destination!

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