Ryan and I got our honeymoon in the Dominican Republic for (basically) free, and it was actually really easy and required no crazy sweepstakes giveaways to enter. I knew that I wanted to have a really luxurious trip for our honeymoon, but I had just graduated law school and we weren't exactly in a financial spot to contribute towards both a wedding and a honeymoon, so credit card points and miles was our best option. We knew we wanted to take advantage of credit card points for a free trip, so as soon as we got engaged, we became hyper-focused on credit card points and miles.
A few years before we were engaged, I had signed up for the Capital One Venture card, and was getting miles with every purchase because it was the only credit card I'd use. What I liked about the Venture card is that you get 2x points on every purchase, and you don't have to keep track of certain categories to get the most of your points. I also added Ryan as an authorized user to my Venture card so he could put a lot of his purchases onto the card to help us build up points faster. We were able to use my Venture points to book a week-long stay at an all-inclusive 5-star resort in a swim-up suite.
Related: All about Luxury Ambar at Bahia Principe in Punta Cana, Dominican Republic
Once we got engaged, I signed up for the Chase United Explorer card to get miles to cover our flights. Although the Chase United card doesn't give you as much miles per purchase, the miles were a good value for us. I referred Ryan for his own Chase United card and got each of us a 10,000-mile referral bonus, on top of the sign-up bonuses that we hit by putting all of our wedding purchases onto our Chase United cards. We flew business class on a direct flight from Houston to Punta Cana, using my miles for the flight there and his miles for the flight back. We also got a free checked back each for our trip and two United Club passes to use on our flight.
Both cards also give you a statement credit to get Global Entry or TSA PreCheck! I already had TSA PreCheck through my job, but we got Ryan signed up through my Venture card statement credit. What's nice is that TSA PreCheck lasts for 5 years, so we're still using it now!
Traveling for free using credit card points and miles is now something that Ryan and I love to do! We're actually going on our anniversary trip for free by using the Chase Sapphire card points to book our hotel and our Southwest card miles to book our flights.