Travel Planning

Tips for Planning your Next Trip

Don’t stress out. Vacations are supposed to be fun. You know it’s that thing you do when you aren’t working. But I get that trip planning isn’t for everyone. Maybe your ideal vacation is drinking on the beach or sailing the Greek islands. Use these tips and tricks to get you to that perfect place.

Do your homework and know your budget

Yup, you still get homework as an adult. The key is starting early and knowing your budget. By setting up travel alerts for destinations with some of the following companies, you can follow the prices. So when it’s finally a good deal you’ll know it. For example, Jon and I booked tickets to Dublin for $400 round trip which might sound like a lot. These tickets are usually $800 round trip.  Here’s a list of places I use when planning trips:

For finding deals:

For checking flight prices:

Note: Southwest Airlines doesn’t feed into a lot of these aggregators, so be sure to check their site before you book.

For hotels:

  • Google hotels – Literally Google destination hotels and it will show you all the hotels in the area. Be sure to set a date to get a good cost estimate.
  • Priceline – I’ve only used this for hotels when I know what area of town I want to stay in. Their express deals can often get you a good discount, but you have to be willing to take a chance on location/hotel brand.  Compare the deals to other hotel prices in the area. It might be a good deal for that hotel, but not for the overall area.
  • Airbnb – Not really a deal site, but often cheaper than normal hotels. If you select dates, it will give you a good idea of costs. Costs for the same house can vary because owners have dynamic pricing options.

Be flexible with your dates and destination

I know this isn’t always realistic, but it will save you a ton of money.  I look for deals then decide location and timing. You can only really tell if you are getting a good deal if you research and know your budget. It’s also good to book in advance, but not too far. This is where knowing the typical price for the tickets comes in handy. If tickets are normally $1500 but are now $700, you might want to book it now.

Research your destination

Awesome, you’ve booked tickets and know the destination. Now what? I like to look at a few of these sites to prioritize activities.

  • Rick Steve’s – For European vacation. I love Rick Steve and follow a lot of his recommendations. He has travel books, a PBS series and audio guides you can download and listen to while you walk the cities. His stuff is especially great to plan a multi-city itinerary.
  • Nomadic Matt – a budget travel blogger who has been almost everywhere. Budget travel isn’t quite my style, but his tips are great. His destinations guides often show typical prices points for lodging and meals.
  • TripAdvisor – Shows top things to do in the destinations, especially good for small towns.
  • Follow the destination’s tourism site on social media
  • Google Destination + Travel Blog – You probably already knew that one since you somehow landed here.
  • Me – Shameless plug.
  • Ask your Airbnb host or check out – Ask your AirBnb host when you get there. They often have great recommendations and some even have travel guides.

Get “free” stuff

Make sure you are signed up for the all the rewards programs. Those points really do add up. Jon and I are staying in Dublin for 3 nights for FREE. It’s my favorite when that happens. It’s primarily because I’m loyal to a hotel brand for business travel and make sure to give them my membership number. You can also sign up for credit cards which offer travel benefits. Be careful with these cards. They have high interests rates, but if used properly you can book two tickets to Europe for almost free.