I love taking trips with B to new places we’ve never been! We always try to get a couple trips in throughout the year, some bigger and grander than the ones, and some are just longer weekends away that are more affordable and sprinkled into the mix. If you’re a working couple like B and I, not only are we juggling busy family/friend commitments and house project bucket lists, but have this thing called PTO that makes traveling as much as we want too somewhat limited… especially when you throw other life items into that PTO mix. So I’ve got a few travel trips to not only help plan out more trips, but also how to save some pennies while still exploring and eating your way through new places.
Ok! Here is how to plan an affordable and fun weekend getaway!

1. Scheduling A “Long” Weekend. We always like to try and plan trips around holiday weekends, that we already get a day off from work for, or a timeframe when we’re already going to be taking some PTO off.  For me, I like to take my birthday off, and the next day (because it’s St. Patrick’s Day, and why not) — so I already had two days that budded up to a weekend! Leaving on a late night flight, on a Thursday night can also help eliminate the need of taking multiple days, giving you a full three day weekend!  If you’re looking to take advantage of those summer long weekends (Memorial Day, Labor Day or 4th of July) — you’ll want to plan a bit more in advance to avoid higher fees or not being able to secure a place to stay!

2. Picking Your Destination – Part 1. If you have a destination in mind, then head down to tip #2. If you’re not quite sure on how to figure out where to go, there are a few ways! First determine how you want to get there, flying or driving?

• • Driving: Then if you’re driving determine what your maximum drive time will be. From there, I’m pretty old school and will pop over to Google Maps and do some ‘Destination’ plugging into of some near-ish cities or destinations that sound adventurous. Last March we headed to Chicago because it was a cool 6-hour drive and within our time limit, plus we’d never been there together – and previously we drove to Washington D.C. for a surprise trip that B planned for our anniversary.
  • Flying: Since we are planning for a longer weekend (3-4 days) we went to our local airports website and searched their nonstop flight destinations.  Our airport flies to a lot of Florida destinations, and a few in between so I started my search there — now head to Part 2. Looking for early flight times and ensuring you’re on the nonstop are also clutch to making sure you’re getting the most time and bang for buck!

3. Picking Your Destination – Part 2. Affordable is the next piece of the puzzle, we wanted to keep our long weekend trip under $1,000 and even more so if possible ($500 – $600 was our sweet spot).  So I popped onto Expedia and did a combo Flight and Hotel search for a few destinations based on the nonstop flights from our airport. We checked Miami, Sarasota, West Palm Beach, and even Charleston but they were just a tad pricey for what we wanted, and where we would want to stay in those spots.  Then I pivoted to a few East Coast cities: New York City and Philly. Since we’ve been to NYC before, we passed — and Philly was hitting our sweet spot, and the Expedia search helped me narrowed down the airlines and accommodations.

Pro-tip: When you have your accommodations and airline determined, check the native websites for those vs. booking directly through Expedia — you just might find it cheaper directly through the airline and hotel (we did!)

4. Finding Your Accommodations.  In Chicago we opted for a smaller boutique hotel, because we were able to find it more affordable than mainstream hotels (it was also in the perfect location).  Again, I looked for smaller, boutiquey spots and found Sonder — they lease out rooms in buildings in the area, all with a fun style and unique name. It’s also close to the airport, so that will make it easy to grab an Uber to and from!

• • When you’re considering where to stay, again I like to pull up a map and look at key landmarks/destinations that we want to visit and look for some that are generally walkable!
  • Reading reviews is also a great way to gain insight into smaller boutiques or spots that aren’t as mainstream like a Hyatt or Marriott.

Pro-tip: If you can pick a spot that friends or family live to save on accommodations, do it!  Even asking where family or friends might have a house or time share can be another affordable way to cover the cost of your stay!

5. Figuring Out Where to Eat. This is going to sound SOOO millennial, but it’s how I’ve found some great gems on all of our trips: Instagram. I start following traveling accounts for our destination and find all the foodie accounts to start creeping and finding all of the spots.  From donuts, to bakeries, brunches and the best dining spots — you can literally find it all and then pop over to their websites to make reservations or see full menu offerings.

I also like to find places to eat by browsing through OpenTable — this makes it easy to book a reservation for the night your looking for, and there are often user generated and restaurant provided photos, ratings and reviews and easy to flip through menus for all their offerings. Another great way is asking for recommendations from friends or family if you know they’ve been!

Pro-tip: Make a Reservation! If you can, make reservations to ensure you’re getting into the hottest spots, when you want to eat, especially in bigger cities like Chicago, Washington D.C. and NYC the lay of the land is through reservations.

6. Planning Activities. Heading to a cities travelers bureau via social media or online is another great resource to find key locations to visit or a little less mainstream spots.  Strategically planning activities around your hotel or farther away on certain days can help you optimize your travel days. Also purchasing any tickets ahead of time to visit popular landmarks is crucial, especially if you want to check those off on the early visit times!

Planning and taking that weekend getaway, and checking off more cities on your bucket list doesn’t have to eat up all your PTO or drain you bank account! We will be heading to Philly next month and I’ll be sure to share in my recaps a round up of our travel expenses along with all our yummy eats and traveled spots. Have questions? Leave a comment, below!