Booking a Trip with Fingers Crossed

Majestic Mirage - Punta Cana, Dominican Republic

I finally let Adam twist my arm a bit and agreed to book a fly away vacation for the end of 2021.  Vaccines are rolling out, hotels are offering generous cancellation terms, airlines are still waiving "redeposit fees" if you book with miles - essentially creating refundable tickets.  Time to roll the dice. 

I'm not entirely sure how it happened, but somehow in the last last week a spreadsheet was born comparing the cost of flights in points vs. miles, booking hotel separately or as a package, resorts, room categories, pictures of rooms and grounds, cancellation policies, Dominican Republic vs. Barbados and a few other islands...  Since this process seemed like just an exercise in daydreaming and a fun thing to do we even used a 10 night stay window for our reference dates. 

Turns out that with consumer friendly cancellation policies booking directly with the hotel and using JetBlue points for flights, we could book 10 nights for less than we usually budget for a 7 night stay at an all-inclusive and cancel without penalties up to 24 hours before arrival.  Decision time.  

There were plenty of pros in our favor, but still a question of how long to go for.  Do we really need to stay 10 nights?  That would mean the 19 and 21 year old holding down the fort at home for almost 2 weeks! I've got some anxiety around that. 

The only thing resembling a con was that we would have to have a layover on the way down in either New York or San Juan.  We've been spoiled by direct flights in recent years.  Since I had a bad experience once transiting through San Juan, so we opted to spend a few more points and change planes in New York.  

One day later, vacation time was approved and it was time to commit.  I was still leery about the longer trips length, but Adam raised a good point: "By the time we go it will have been 1 year and 10 months since we've left the state. It's a longer trip for less money, let's take advantage and make our return to traveling really worth it!"  I may have created a vacation monster over the years, but it was hard to argue with that logic.  

Vacation booked.