A Trip to the Caribbean with Two Kids Under 3

A couple of weeks ago we set out for our first trip with two young kids (our infant daughter and our 2 year old son). Our son has been on several trips, including a vacation in Ireland at 15 months, so we weren’t really worried about travelling with him, but our daughter has been a challenge in the sleeping department so we didn’t know what to expect. The logistics of the trip were less than ideal so that was just another factor that we’d have to deal with and we expected the stress to be exacerbated by the young ones in tow.

We must say, for the most part, we were very pleasantly surprised! Both our son and daughter were awesome, better than we could have ever hoped for. The only problem we encountered was that our daughter slept terribly in St. John. She slept worse there than she has slept almost anywhere, but we managed. She did great on the trip down and back, despite getting her up at 2:45am on our day of departure, and needing to spend the night in an airport hotel on the return. In fact, at the airport hotel, she slept the best she had in a really long time. We braced her car seat against the wall, strapped her in, and she slept for 7 straight hours!

Unfortunately, our travel companions (my sister and her family) were hit with several more significant obstacles, including a vomiting 7 year old and a sister with pneumonia. They recovered and made the most of their visit, but it wasn’t an ideal vacation for them.

We learned several lessons from this vacation in preparation for our trip over the pond to Scotland in May. One is that we need a second stroller. I used the chest baby carrier to carry our daughter through the airport, etc, but she really needs her own seat. We also were lucky enough to learn ahead of time to make two car rental reservations for our St. Thomas airport pick up. We had read that Budget was notorious for accepting reservations for many more cars for a given period than what they had in their fleet. And, lo and behold, we arrived to learn that there were no cars, despite having made a reservation nearly a year in advance. So, given this information, we had made a second reservation at Avis. Thank goodness we did. I can’t imagine trying to schlep all of our stuff and our kids to the ferry via an open air taxi. Avis came through and gave us the car we had reserved. I will be writing a letter to Budget explaining my disappointment. If we had not had a car at Avis, it would have put a huge damper on our vacation given that it was high season in St. Thomas and St. John and finding an available rental would have been difficult at best.

I’ve attached several photos below documenting our trip. It truly was a fun time had by all and although I can’t speak for the others, I can say that our family would return in a heartbeat. We, without a doubt, will be back to St. John as soon as we’re able. It’s the perfect family spot in the Caribbean.

In order to make this trip possible, we used a combination of airline miles and hotel points. This vacation would not have been attainable for us without them. We stayed at the Westin in St. John whose going rate for a standard room during the week we visited was $650 per night. That far exceeds our budget but we were able to use Starwood Preferred Guest points (the Sheraton, Westin, etc. loyalty program) at 16,000 per night. Last time we went to St. John, it was only 12,000 points per night so we did have to use more points than I had planned for. But it all worked out. I must note, we received these SPG points over the course of several years by signing up for 3 separate credit cards when bonuses were particularly fruitful. Please let me know if you’re interested in this credit card and I can provide the best offer currently available.

We used United Airlines miles to fly from Boston to Washington, DC, and then onto St. Thomas. We needed three seats (our daughter was eligible to fly in our lap) which cost 17,500 per seat for a total of 52,500 miles and $5 per ticket. For the return, we used 20,000 American Airlines miles plus $12.50 per seat (80,000 total for a family of four) to fly from St. Thomas to Miami to Dallas to Boston to London. Clearly this, was not the quickest way for us to return and although we did try to route directly from Miami to Boston, it worked out fine as we stayed the night in Miami at the Sheraton Airport Hotel. This hotel cost us 4,000 SPG points which was perfect for a decent night’s sleep before making the trek via Dallas the next day.  You’ll see that we used 20,000 miles per seat as opposed to the going rate of 17,500 from the Caribbean to Boston. This is due to the fact that we are continuing our trip to London in a few months (I wrote the details of taking advantage of this American Airlines rule in this post). So, in essence, we’re getting one way tickets from Boston to London for 2,500 miles each. Not bad if you ask me!

The main items that we weren’t able to pay for using miles/points were our food/misc items, the resort fee of $40 per night (plus tax) at the Westin, and our rental car. Please note, if our food/misc bill seems a little low, we packed a lot of food with us and ate in our room 2 out of 3 meals a day. I’ve broken down our expenses below and what we used for miles and hotel points. All our miles and hotel points were acquired by signing up for credit cards…


Out of Pocket Expenses







Resort Fee + Tax

 $                          390




 $                            60



Car Rental

 $                          309




 $                          300




 $                            50




 $                            65








 $                      1,174







Miles/Points Required











BOS-STT 3 Seats 52,500 United Miles $15 Taxes
STT-BOS-LHR 4 Seats 80,000 AA Miles $50 Taxes









Westin St. John 5 Free Nights 16,000 per night, 64000 total, 5th night free


1 Cash&Points 4800 points, $90 cash


Sheraton Miami Airport 1 Free Night 4000 Points


So, there you have it. Our 6 night vacation (7 including our night in Miami) for four to St. John only cost us $1,174 out of pocket. Hopefully we’ll be able to replicate this trip in the near future! Please let me know if you have any questions. I would love to help you take a similar trip with your family!


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