2016 Travel Goals and Hacks Recap!

For the first time last year I listed out travel destinations and goals I wanted to accomplish in 2016.

Read My 2016 Travel Goals

Fast forward to now:

I was able to visit 30% of the list but added a few more destinations to the list that I had not planned. Looking back those goals may have been a bit ambitious with regards to money and time.

The Travel Goals list included:

1) London/Copenhagen/Oslo/Amsterdam

2)Italy (Rome, Milan and Florence)√

3)Taste of Chicago√

4) Grand Canyon/Antelope Canyon√

 5)Brazil (Sao Paulo, Rio)

 6)Australia (Sydney, Melbourne)

 7)Auckland, New Zealand

 8) Toronto, ON

What wasn’t on the list that I added?

NYC, Phoenix, Las Vegas, Chattanooga and Havana, Cuba

Let’s recap each destination and what I learned and any key savings that you can use.

New York 

I had a chance to spend the a day here before catching an evening flight to Milan. I’ve only visited NYC once before and the weather was terrible and it was cold. This time it was rare but it was warm and sunny. My uncle was our tour guide and I got to see the bridge, taste great Chinese food, argue with NYer 😀 and hang out. It was fun. I loved the mini tour. Thanks again Uncle!

Brooklyn Bridge



Key Savings for this trip included:

20% off a Hilton Hotel


Italy (Milan, Venice, Florence, Pisa, San Gimignano, Sienna, Rome, Naples, Capri, Sorrento)

This was my first big trip of 2016. It is one I am MOST proud of. We had a short window of vacation time and neither one of us had been to Italy beforue. I became intrigued with Italy after meeting LivItaly Tours in 2015 at the TBEX Conference. The team was so inviting and I corresponded with them while planning the trip. There was a lot of doubt as to if we could see so much in 8 days but we did it and made 95% of our trains, boats and flights on time. We made it back in one piece, no pick-pocketers and our luggage was not overweight LOL. I REALLY LOVED ITALY and can not wait to return! I learned a lot more about European travel and felt really immersed in the culture.


Brunelleschi's Dome


Key Savings for this trip included:

-Emirates 2 for $897 deal from JFK to Milan. This runs often at the beginning of the year.

-Saved $200 off 2 tickets from ATL to JFK by redeeming points due Southwest credit card and 50K points offer.

-$35 off my first Airbnb in Rome using a referral code for first time Airbnb users.

-Booked some train tickets in advance for deeper discounts, some were booked while in Italy but as flexible in case something happened and it did. We missed our train in Rome and was able to get on the next one at no charge!

-Since we ended in Naples, we used easyJet to get back to Milan as opposed to over 8 hours on the train. The flight was $76 with bags and around 1 hr. Book in local currency to avoid conversion fees.

-Booked a lot of tours in advance and used Viator for some.

Related Articles

See Tuscany in Two Days!

10 Tips for Rome!

A First Timer’s Guide to Airbnb

Las Vegas

I chose this city to fly into to get to the Grand Canyon and other attractions. I literally booked the flight with points on the morning of the flight. I found the hotel while on the airplane. This was my 5th trip to Vegas after I vowed not to return after the 3rd. 😀 It was cheaper to fly into Vegas than Phoenix or any other Arizona regional airport.

Arizona (South and West Rim of the Grand Canyon, Antelope Canyon, Horseshoe Bend and Phoenix)

After picking up the car in Vegas we headed under 2 hours to the west Rim. It was nice but a huge tourist trap as you can’t take your own camera so you have to pay for the pics if you go out onto the Skywalk. It was here that I learned of my fear of heights. As SOON as I stepped on the glass my heart dropped, it took me a while but I walked across and even had a photo shoot :). Afterwards we pondered staying at the resort where we had no cell phone or internet service or to keep going. We got in the car and hi-tailed it out of there to beat the dark. There are no street lights on this route, no cell service, not many gas stations. We headed to flagstaff and once again made reservations last minute. This drive was an additional 2 hours. We made it to a Hilton property that was interesting to say the least. There weren’t many nice properties in Flagstaff as you can imagine these hotels have seen there fair share of Route 66’ers. The next morning we woke up and headed to Antelope Canyon on a whim. It was memorial weekend and no one picked up their phone or had openings for a tour. When we got there one opened up! This was about 1-1.5 hours away. After Antelope we headed across the way to Horseshoe Bend. I had a lot of fun here with photos. Following we headed to the South rim for amazing views at Matheson. This park is massive and really deserves more than a few hours. I wished we stayed the night but we headed to Phoenix once again a race to beat the sun set. We drove through fire smoke, elevations so high and late at night and made it to Phoenix in 3 hours. We stayed the night in Phoenix and visited  the ritzy area of Scottsdale. After Phoenix we returned to Vegas where I kicked my feet up and enjoyed the Venetian. We were so tired we changed our flight to leave a day later to enjoy relaxation. I am glad Southwest allows for free changes. WHEW I’m exhausted just thinking about that trip. However, it was an amazing trip. Next time I want to visit Sedona. I really enjoyed the beauty the U.S. has to offer. It was a frightening road trip, sometimes very boring but we made it.

Horseshoe Bend

Grand Canyon

Key Savings for both Las Vegas and Arizona trip included:

30% off with Dollar Rent-A-Car

-Saved $600 off 2 Roundtrip tickets from ATL to LAS by redeeming points due Southwest credit card and 50K points offer.

-Orbitz “Orbucks” Redemption of $50 off Vegas room to get the room down to 13.00

Hilton Gold MVP for 20% off room

-Marriott discount due to calling while in route to hotel at 12 am and asking for the best price 😀

Related Articles

How to Score a 4 Star Vegas Hotel for $50 or Less!

Top Vegas Hotels and Activities

How To Earn 50K Southwest Points!

Fast Track to Hilton Honors Gold Status in a Week!


Chicago/Taste of Chicago

This was a trip I’ve been adamant about since 2014. I tried in 2015 and everyone flaked. I even purchased tickets the to Erykah Badu concert that was apart of Taste of Chicago. 2016 I was determined to go no matter what. I booked the hotel in January and my flight in April (with points of course). It was my first trip to Chicago and won’t be my last. The food itself is a little overrated at Taste but the city comes alive during the summer. That weekend was filled with music, dance and culture. I had a chance to experience music and food at Taste, attended Chicago Dance and a festival at the DuSable Museum of African American History!

Sydeck Chicago


Taste of Chicago

Key Savings for this trip included:

-Half off Uber using Uber Pool, claim $20 off your first Uber ride.

-Saved $320 off 2 Roundtrip tickets from ATL to MDW by redeeming points due Southwest credit card and 50K points offer.

Hilton Gold MVP for 20% off room

Related Articles

Skydeck Chicago: Experience Chicago In One Stop!


This was a very much needed break. As a creative it’s important to use self-care. Click the photo to read about the amazing suites at Loews!

Loews Atlanta

Chattanooga, Tennessee

I made it up to Chattanooga for the first time in probably 10 years. It was well overdue. I went to visit my good friend who I’ve travel with often. It was fun to explore Chattanooga

Savings here included a lot as this was a short drive to Chattanooga and all I paid for was food and entertainment. I loved Ruby Falls and the FOOD!!!

Ruby Falls

Lookout Mountain


Havana, Cuba

 I’ve just completed this trip less than a week ago so I am still compiling lots of great content. I enjoyed this trip more than I thought I would. One thing for sure, I want to learn more Spanish. The culture and music were my favorite. It also doesn’t hurt that its a quick plane ride from Atlanta. This is a trip I am most proud of as I was able to get the cost down to $281!

 Havana, Cuba Car

Key Savings for this trip included

-Over $100 off FLL to Cuba using 4,500 SW points plus Southwest Companion pass

 due Southwest credit card and 50K points offer.

-$35 off Airbnb using a referral code for first time Airbnb users.

Related Articles

Ready To Jet Set to Cuba? Read This First!

Jose Marti (HAV) Airport Review

A First Timer’s Guide to Airbnb

no one deals like we do!

What did I learn or improve on this year?

  • I learned how to pack better. I’m the person that packs for the what ifs and has rarely paid for a checked bag due to who I fly with, this year I did better due to having to hop travel on every form of transportation in Italy.
  • I improved on using more loyalty program hacks and status matches. I surpassed this 2016 goal by obtaining 110,000+ points with Southwest, earned a Companion pass and earned bonus points with Hilton. I’ve also started making progress on SPG/Marriott. In 2017 I want a free 3 nights or more hotel stay solely from points.

  • I’ve learned to enjoy the moment. Being in Cuba without internet allowed me to snap less and live in the moment!
  • I improved a lot in blogging and advanced in my own career path in Marketing as opposed to my traditional B2B/technical sales experience.

To sum it up! This year’s travels were filled with points, spontaneity and creativity!

In 2017 I want to visit:

Cabo San Lucas, Mexico

Denver, Colorado


Return to CUBA!

That’s it for now. I could put more on the list but we see what happened this year.Travel is the goal, wherever it may lead me! Click To Tweet

WHAT’S ON YOUR 2017 LIST and What did you learn this year!?

If you love it please share! Thanks!


If you love this article check this out!



Like this post? Join our email list so that you don’t miss anymore travel tips, hacks and deals!

* indicates required

This page contains affiliate link(s), which means we receive compensation for items purchased through the link (s). The compensation helps us keep this website free. Please view our Disclosure Policy for more information.


Like this post? Join our email list so that you don’t miss anymore travel tips, hacks and deals!

* indicates required

Kim H.

Kim H. is the creator and chief editor for Work Hard Travel Well. Born and raised in College Park, Ga. She is a true "FILA" :) and UGA Alumna. Go Dawgs!