This amazing trip would have cost $20,413 if we had paid cash. But by using points and miles, our travel and lodging expenses were only $1,756.

Two of the main driving factors for this trip were two Hilton free night certificates that would be expiring. I did a search for best places to use Hilton free night certificates and one of the hotels that came up was the Hilton Cancun Mar Caribe All-Inclusive Resort.

The other factor was wanting to visit the Caribbean and Costa Rica. For this I did another search: best use of Hilton hotel points. One of the results was the Zemi Beach House Hotel & Resort in Anguilla. Rooms here are $1,200/night. Points costs start at 90,000 points/night and go up from there. We were able to book some time in April for 110,000 points/night and by booking four nights we were able to take advantage of the Hilton’s book four nights and get the fifth night free program.

In researching hotels for Costa Rica, we found that Hilton’s Botanika Osa Peninsula Curio was highly rated as a great value for points so we booked three nights there.

In April, Kate and I flew to St Maarten. We had a quick tour there and then took the ferry to the island of Anguilla. We stayed at the amazing Zemi Beach House Hotel & Resort. The $1,200/night rooms were free with points. Plus, Hilton has a program to stay for four nights and get the fifth night free. On top of that the upgraded our room. So we grabbed five nights on the beach. Kate picked up her SCUBA certification while we were on Anguilla. Night kayaking was another highlight.

From Anguilla, we went on to Costa Rica for four nights. We had one positioning night in San Jose, then we flew a turboprop to Puerto Jimenez. We stayed in the beautiful Botanika Osa Peninsula Curio for three nights. We received an upgrade to a large suite. This resort had monkeys, crocodiles, sloths and more right on the property. But the main attraction in the area is the Corcovado National Park. Here we saw three kinds of monkeys, tapers, anteaters, coatis, sloths, wild pigs, etc.

From Anguilla, it was on to Cancun. After one positioning night, we spent two nights at the fabulous Hilton Cancun Mar Caribe All-Inclusive Resort. We again received a room upgrade. We had planned to dive at the MUSA (Museum of Underwater Art) while here. But unfortunately, high winds closed the harbor and all dive trips were cancelled. We took a Chichen Itza & Ekbalam Tour with Cenote tour. I thought that we had the guide from hell but Kate liked him.

We managed free business class seats for the entire trip except for the dang turboprop flights which didn’t have any point options so we had to pay cash.

THAT SOUNDS GREAT, BUT HOW DID YOU DO IT?
For the flights from San Francisco to St Maarten; We flew business class on American Airlines. The cash price for these flights would have been $6,089 (for non-refundable flights. Refundable flights like you get when using miles would have been even more). We used 190,000 miles and paid $11 in taxes. To get these miles, we used the bonus miles from opening our CitiBusiness AAdvantage Platinum Select World Elite Mastercard and from using shopping portal bonuses and subscription bonuses.

In Anguilla, at the Zemi Beach House Hotel & Resort, the cash price would have been $6,816. Instead, we used 440,000 Hilton points. To get these points, we used the bonus points from opening my American Express Hilton Honors business credit cards and by transferring some points from my Amex account to Hilton (Amex had a 1:2.6 transfer bonus at the time). We got the Amex points through Welcome bonuses from opening the Amex Business Platinum cards

After Anguilla, we flew from St Maarten to San Jose, Costa Rica in business class on Avianca. The cash cost would have been $1,723). But instead we used 40,000 Avianca LifeMiles and paid $221 in taxes. We got the LifeMiles by transferring points from my Amex account (there was a transfer bonus of 1:1.15). We got the Amex points through Welcome bonuses from opening an Amex Business Gold card.

We arrived late into San Jose so we spent the first night in at the Country Inn & Suites by Radisson (found out that it wasn’t really a Radisson anymore when we got there, but they still gave us a room upgrade). I had some Hotels.com OneKey cash ($75) and we paid the remaining $16 out of pocket.

From San Jose we flew on Sansa Airlines to Puerto Jimenez. This airline didn’t have any point options so we paid the $660 round trip fare out of pocket (ouch!)

In Puerto Jimenez, we stayed at Hilton’s Botanika Osa Peninsula Curio. The cash cost would have been $670. But I used my $300 annual Capital One travel credit to bring down the price to $370 and paid that in cash (We could have just used points, but this was a better value to use the credit and pay the remainder in cash).

After flying back to San Jose on Sansa, we flew business class on Avianca to Cancun. The cash cost would have been $1,097. But we used 44,800 LifeMiles miles and paid $215 in taxes. We earned the LifeMiles through an Amex transfer and we earned the Amex points through the Welcome bonus from opening Kate’s Amex Business Gold card.

We arrived late into Cancun, so we spent the first night at the Hampton Inn by Hilton Cancun Cumbres. The cash cost would have been $138, but we used $138 of my annual Chase Reserve travel credit. The Chase Sapphire Reserve card has a $300 annual travel credit. 

We then went to the Hilton Cancun Mar Caribe All-Inclusive Resort. Cash cost would have been $1,227 but instead we used two Hilton free night certificates. We got these certificates by meeting the Amex Hilton Honors business card bonus of spend $15,000 or more in a calendar year and receive a free night certificate. But, you say that $15,000 sounds like a lot! Well, we had already spent $5,000 on each card in order to meet the initial welcome bonus of 150,000 and 165,000 points. So, since we only had $10,000 to go on each card, this was the best time to shoot for a free night certificate. But, you say, $10,000 is still a lot! True. For the $20,000 ($10,000 on each card), we spent about $5,000 on everyday spend (utilities, restaurants, Amazon, etc.) and we put the other $15,000 on property taxes. Locally, we are charged 2.3% to pay property taxes with a credit card. So paying our property taxes with these credit cards cost us $345. So for a cost of $345, we received two Hilton free night certificates plus the points on the spend to get those certificates (100,000 points). And the 100,000 points alone was worth way more than $345.

For our flights home, we flew American Airline business class from Cancun to Austin. Unfortunately, after that there weren’t any business class seats available and we flew economy the rest of the way to San Francisco. The cash cost would have been $1,901. But we used 55,000 American Airlines miles and paid $140 in taxes. We obtained these American Airlines miles by earning them through Basq Bank. Basq bank has a 20,000 American Airlines miles bonus for opening an account. Then you earn additional miles for maintaining a savings account with them.