Our 3+ Week Honeymoon on Airline Miles & Hotel Points!

3 week honeymoon started at the Westin Punta Cana

Our Honeymoon

Beth and I just finished up celebrating our wedding day with our loving family and friends just a couple days ago and we have now embarked on our 24 day honeymoon visiting the Dominican Republic, Italy, and Croatia! Before we get to our honeymoon a special thanks to all of our friends and family who support us and made our wedding day a truly amazing day.

As for our honeymoon many of our friends did not really understand how we can an afford such a long honeymoon across the world, let alone why we chose those three locations, Dominican Republic, Italy, and Croatia. Haha. A combination of relaxation, exploration, and culturalization! Well thanks to my airline miles and points hobby we are able to stay at places we could not afford and fly nearly anywhere in the world for free. For this trip nearly all the flights are free minus some taxes and fees and we are flying business class to Europe! On the accommodation side of things, all hotels are free thanks to points minus some Airbnbs that we are staying at in Italy. We still got a great deal on those thanks to the Airbnb Amex offer a couple months ago.

Here is the basic outline of our trip along with how many points we redeemed for each hotel and flight.


  • From Home to Punta Cana, Dominican Republic – ~14,000 Southwest points for two. Thanks to the companion pass that let’s Beth fly for free when I fly! It is good for two calendar years!

  • From Punta Cana to Rome, Italy – 100,000 American Airlines points for two in business class! Booked before American Airlines increased the redemption price, which is still reasonable for business.

  • From Venice, Italy to Dubrovnik, Croatia – $200 for two on a nonstop on Volotea with checked bags. A lowcost airline that conveniently provides a great nonstop option for us and it is cheap!

  • From Dubrovnik, Croatia to Home – 60,0000 American Airlines points for two in economy back home with a one night stop in Madrid, Spain, just enough time to explore.


  • Westin Punta Cana – 40,000 Starwood points for 5 nights. Located only 10 minutes away from the airport in a very private area of Punta Cana and relatively new hotel.

  • Radisson Blu Es Rome – 200,000 Club Carlson points for 4 nights. Near the Termini train stop and within easy walking distance to most of Rome’s attractions.

  • Airbnb Cinque Terre – 28% discount thanks to Amex offer for 4 nights. Staying in a full apartment in Monterosso, excited to do some cooking and get a little more local feeling.

  • Airbnb Venice – 28% discount thanks to Amex offer for 3 nights. Near the Jewish Ghetto that is easy to walk to both the train station and St. Marks.

  • Sheraton Dubrovnik – 18,000 Starwood points for 5 nights. Brand new Starwood hotel just 15 minute drive outside of Dubrovnik along the beautiful Adriatic Sea.

  • Holiday Inn Madrid Bernabeu – 15,000 IHG points for 1 night. Near the Real Madrid stadium and has great access to the subway system.

Total Value of Miles & Points:

  • 28% discount on Airbnb

  • 447,000 points redeemed

  • Between $7,000 – $9,200 estimated value of all hotel and flights for both of us on points. We spent $0 on this!

  • Value per point $0.0157 to $.0205

The majority of the big expenses like hotels and flights are covered for our honeymoon thanks to miles and points. As for the estimated value above I tried to peg the low-end of the range ($7,000) at the maximum prices I would never pay the hotel rates and economy flights. As for the high-end range ($9,200) I used the approximate going rate for business class tickets and actual hotel rates. To level set I still would not ever spend that much money on just accommodations and flights for any vacation. The real value with the miles and points game is that it allows us to stay at places we would have not been able to afford anyway. No way am I forking over cash for a full fare business class ticket! But I will gladly use my points for the luxury!

Now our honeymoon trip is not entirely free, we do have to pay for food on a long 24 day trip which is expensive in itself. Tack on attractions, ground transportation, gifts, and random expenses, it is far from free. Granted we are generally frugal people so we trying to do our best not to spend too much, but it is our honeymoon! Our estimated expenses are still below what a typical honeymoon costs and we are tripling the typical length, visiting at least five countries, flying business class, and staying at some of the nicest hotels.

Hope everyone enjoyed our post on the setup of our honeymoon. We just finished up the first leg in Punta Cana! It was a perfect way to start the trip with plenty of relaxing time on the beach. Be on the lookout for more in depth trip reports later! A little teaser, the Westin Punta Cana was amazing! Nice and secluded from all the mega resorts in Punta Cana. It was maybe 30% capacity and we literally had the whole beach to ourselves on more than one occasion!

Off to explore Italy some more! First stop is Rome!

3 week long honeymoon with a stop at the Colosseum in Rome