In many ways Puerto Rico was our very first “big” trip as a family. We had been so tied down with work and school over the previous 10 years that we never had never left the continental U.S. together. We had kept very busy exploring our local area, but Puerto Rico was the trip that gave us our first taste of something very new. Granted, just a few months after our visit hurricane Maria arrived and complete devastated much of the island. Thankfully, now most of Puerto Rico is once again open for business! If you are nervous about international travel, Puerto Rico is a great place to test the waters without really leaving the US. It has beaches, mountains, a rainforest (the only in the national park system), and a culture very different than the rest of the United States. It really feels like you are in a different country, without having to worry about passports, currency exchange, or getting a visa.


[ D A Y • 1 ] Norfolk → Miami → San Juan, Puerto Rico

It started off as a long (albeit fun) day of travel for our crew, but helllooo Puerto Rico! This was our first time in the air as a party of four, and although traveling with an infant is never easy, overall it went really smoothly. Penny rocked both flights and our layover @The AMEX Centurion Lounge in Miami was fantastic (as in Dom offered to watch the babes and momma got both a manicure and a massage! Not a bad way to start the trip!). We arrived in San Juan at about 2300 and headed straight to our Airbnb in the heart of Old San Juan to catch some much needed rest (This was also the very first time we had used Airbnb, too! So many firsts this trip!).

[ D A Y • 2 ] Old San Juan: Castillo San Cristobol, Casa Bacardi

The first leg of our journey we spent exploring Old San Juan, a city that in many aspects reminded us of New Orleans (maybe that’s why we loved it so much). Vibrant colors, cobblestones, huge trees, and welcoming people filled the streets.


We began the day with breakfast at the Waffelera and then made our way to San Cristobal to see one of the TWO fortresses separated by less than a mile right at the edge of Old San Juan. Ponce de Leon began making settlements in Puerto Rico in 1508 and the Spanish influence is everywhere!

We then caught an Uber to the Bacardi Distillery for an excellent tour and some education on the process of making rum. For the rest of my life, the seating area by the bay outside the distillery will remind me of the moment Britt checked her email and got confirmation that she passed her board examination making her a board certified Doctor of Physical Therapy. We couldn’t think of a better reason to toast our Cuba Libres as we headed back to Old San Juan, stopping for some delicious Puerto Rican food at Raices, while taking in the Spanish Architecture and amazing sunset along the way.

Waffel Era:

  • Hours: 0800 – 1500, Closed on Tuesdays
  • Admission: Entrees ~ $5 – 12 USD


Castillo San Cristobol:

  • Hours: Daily, 0900 – 1800
  • Admission: $5/Adults (16 and older), Free for Children 15 and under, Annual Passes for San Juan National Historic Site $25

Casa Bacardi:

  • Hours: Monday – Closed; Tuesday – Friday: 0900 – 1630; Saturday to Sunday: 1200 – 1630
  • Admission: Free


  • Hours: Daily, 1100 – 2300
  • Admission: Moderately priced ($15-25/entree)

Raices Tip: Make sure to try the Mashed Green Plantains stuffed with any of the various options – delish! There is also a kid’s menu available for smaller portions for the littles.

[ D A Y • 3 ] Old San Juan: Cathedral de San Juan Bautista, Old City Gate, Paseo de La Princesa, Raíces Fountain, The Butterfly People, Castillo de San Felipe del Morro

We awoke excited for our second full day in Old San Juan, and headed to breakfast at Cafi Cultura where we got our first real introduction to a theme that would recur for the entire trip…Puerto Rican Coffee is AMAZING. We then ventured out to check out Cathedral de San Juan Bautista and to see the Old City Gate, one of the original openings in the thick, towering walls that once enclosed the entire city.


We strolled along Paseo de La Princesa, a promenade on the south side of the city (much of which is outside the old city walls) where there are lots of food vendors + café’s. You’ll pass by Raíces Fountain here, too, where Miles (had we let him) could have easily stayed all. day. long. mesmerized. We hung out in this area for a bit longer before meandering into the gallery of The Butterfly People (we couldn’t take photos inside this shop, but if you check out the link below you’ll see some of their beautiful pieces). I wished we could have afforded a piece for Penny’s room as each one incorporated the most beautiful colors and the attention to detail was perfection!!


We finished the day with our favorite part of the Old San Juan portion of our trip – flying an overpriced kite on the lawn of an 18th century fort at sunset. Sometimes it’s the simplest parts of a vacation that leave the biggest memories and impressions, and this was no exception.

The memory of Penny running around barefoot on the huge grass lawn overlooking the ocean while the soaring kite kept a smile plastered on Miles face will be one that we will never forget. This may very well have been the moment where we decided life was too short to stay in one place and travel started to whisper our names. The next morning we would head to Culebra, a small island off the northeast coast, where we planned on spending a few days relaxing with the surf and sand.


Cafi Cultura:

  • Hours: 0800 – 1800 Tuesday – Sunday, Closed Mondays
  • Admission:  $8 – $20/entree

Cathedral de San Juan Bautista:

  • Hours: 0800 – 1630
  • Admission: Free

Old City Gate:

  • Hours: 24 hours
  • Admission: Free


Raíces Fountain:

  • Hours: 24 hours
  • Admission: Free

Paseo de la Princesa:

  • Hours: 24 hours
  • Admission: Free

The Butterfly People:

  • Hours: 1100 – 1800
  • Admission: Free


Castillo de San Felipe del Morro:

  • Hours: 0900 – 1700 from June – November, 0900 – 1800 from December – May
  • Admission: $5

[ D A Y • 4 & 5 ] San Juan → Farajardo → Culebra

No hotel chains, few restaurants, one gas station. Full of diamond dust sand beaches, solitude, turquoise blue water. For the next two days, we called this beautiful piece of paradise our home away from home. Two days was certainly not long enough, but I am glad we made the effort to get here (it’s a bit of a trek with the local ferry, but so incredibly worth the hassle). On top of being on one of the most gorgeous islands I have ever seen, we somehow also landed the best Airbnb on the planet for this leg of our trip! We were the first family with small children that our host family hosted and upon arrival they made sure to pull out all the stops. Pack ‘n Play for Penelope, indoor toys, baby bathtub, sand toys, inflatables for swimming for both kids, kid’s shampoo and sunscreen, etc. – all BRAND NEW! We are so grateful for such hospitality and plan on returning for a visit in the future. We get no affiliate pay for Airbnb, but that doesn’t matter. If you someday find yourself on the island of Culebra, you NEED to stay Here.

Our first night we checked into our Airbnb quickly dropped off our bags and headed to a local beach that our hosts had told us about to play for a bit. Have you read about beautiful Flamenco Beach? Well, this one is on the other side of the horse shoe except you have to do a bit of off roading to get there. Don’t get us wrong, we saw some golf carts head down the dirt path, but a jeep was a lot more fun!


By the time we got settled in the room, got the kids changed, and found the beach we were running low on daylight. We made the most of the time had by splashing around before heading back to shower and hit up Dingy Dock for dinner, another local recommendation. Tables are literally right on the edge of a covered dock and we spent the evening watching the sunset over margaritas and fresh caught red snapper. As a bonus, there are HUGE tarpon which live near the dock. Miles had a blast feeding the bones of the snapper to the enormous fish below.

The next morning we were SO EXCITED to head out for the day as we knew what was in store. The weather was perfect and there were multiple beaches on our “must experience” list. First order of business though was to take the top and the doors off the Jeep and load all four of us up to head to Pandeli to pick up some breakfast and coffee. There aren’t a lot of places on the island that open early, so pickings are slim. We found Pandeli to be a good mix though of tourists and locals and the food to be pretty good overall. From Pandeli it was off to the beach to do some exploring. We spent the day driving from beach to beach and taking as many off road trails as possible.

By the end of day every one was pretty wiped. However, before turning in we ventured back to our favorite spot to say “goodbye” to Culebra. We were rewarded with a deserted white sand beach and one of the most breathtaking sunsets I have ever seen. I will forever be grateful to Dom for picking up the camera here and capturing me breastfeeding our daughter Penny in the calm ocean waters while we soaked up the last few minutes of light.To this day it’s one of my favorite pictures of motherhood.


Our final morning we booked it to Pandeli for some breakfast eats to-go and then it was back to our favorite beach for one last swim (we just couldn’t let it go!) before saying goodbye to our hosts and heading to the ferry. Goodness I am going to miss Culebra so darn much. For the previous 10 years, our relationship had been go-go-go (!!) and this was the first trip that we were able to just sit back and “just be.” Neither one of us brought study materials and we didn’t have any work responsibilities. Plus we had already sold our house, so we didn’t even have to worry about a mortgage or the hassle of home ownership! It was pure bliss in that enjoying each other’s company was the main goal.  Culebra helped foster this with its off-the-beaten-path feel, hospitality, and the laid back vibe – it planted a seed that has only kept growing larger since we left.



The life of a soon-to-be little globetrotter just waiting for the ferry. As a side note, check out how much we packed for this trip…holy moly! To be fair, we are toting around carseats in the big Clek bag, too (something that we don’t always do in Asia). I do think though that the past 1.5years has helped us grow and taught us a few things about traveling more efficiently. Fun to look back on our first “big” trip and see how far we come!

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  • Hours: Ferry leaves Ceiba at 0630, 1030, and 1330 daily, with an additional 1600 trip on Sunday
  • Admission: $2.25 one way, $4.50 round trip

Carlos Jeep Rental:

  • Admission: ~$70/day for 4 door Jeep


The “Secret Beach” next to Flamenco Beach:

  • Hours: Sunrise to Sunset…it’s a beach
  • Admission: Free
  • Parking: Free! Just pull over on the sand road

“Secret Beach” Tip: The Beach will be on the road on your way to Flamenco. Look for a dirt road right before a big sign about 1km before arriving at Flamenco. It’s about a 15 min drive via Jeep on the trail to get there.


Dinghy Dock:

  • Hours: Daily, 1100 – 1500 and 1800 – 2130
  • Admission: ~$12 – $20/entree
  • Parking: Free street parking

[ D A Y • 6 – 7 ] Culebra → Farajardo→ El Yunque: La Coca Falls, La Mina Falls, Big Tree Falls

After arriving back in Farajardo via ferry we picked up our rental car and drove to the El Yunque area. El Yunque, the only tropical rainforest in the national forest system, and one of the most enchanting places we have ever been was beautiful! We spent a good amount of time hiking over the next couple days in the rainforest, checking out La Coca Falls, and heading to La Mina falls where we packed a lunch and spent the late morning swimming in pools fed by waterfalls and lounging on the rocks. La Mina Tail is fairly short (0.7mi), but there are areas where you are able to add on distance if you desire. Big Tree hike is a little longer, and also ends in a nice waterfall, although its a bit harder to swim in.


La Coca Falls:

  • Hours: 0730 – 1800
  • Admission: Entrance to the park is free.
  • Parking: Free

La Mina Falls & Big Tree Trails:

  • Hours: 0730 – 1800
  • Admission: Entrance to the park is free.
  • Parking: Free

La Mina Falls Tip: La Mina Falls itself was beautiful, but fairly crowded both with locals and with tourists taking a dip. If you hike past the main falls there are a series of smaller falls, each with its own cool, clear swimming pond. We were able to hike far enough up that we had our own private swimming area, which was great for the kids.

[ D A Y • 8] El Yunque: El Yunque Trail, Seven Seas Beach


In a somewhat ambitious move, we decided to wake up early the next day to head back to the rainforest and hike the El Yunque Trail, which takes you to the highest peak on the island and affords you some incredible views of the forest, mountains, and ocean in the distance. We knew it would be a bit of a challenge to carry the kids to the top, but it was well worth it. Near the top, an older married couple stopped us and commented to Miles how lucky he was to have parents so eager to show him the view from the top of Puerto Rico. It put a big smile on his face, and was a great reminder of how putting in a little more effort can pay off exponentially when traveling.


Despite the humidity and heat, the kids did great. Miles completed about 5 kilometers through the forest on his own and we carried both of the kids for the rest (thank goodness for babywearing!). On our way back to our Airbnb, we stopped to eat at a great little restaurant on the edge of the forest. From there, our plan was to head to the Seven Seas Beach in Fajardo, but when we arrived we were out of cash and couldn’t find an ATM to get the $5 entry fee for the beach. We ended up walking farther down the road to the free beach – which wasn’t nearly as good with more trash and lots of local chickens. Next time, we will make sure to have plenty of cash on hand, and would recommend you do the same!



El Yunque Trail:

  • Hours: 0730 – 1800
  • Admission: Entrance to the park is free.
  • Parking: Free

El Yunque Treehouse:

  • Hours: 1100 – 1900 Monday – Wednesday; 1100 – 2100 Thursday; 1100 – 2300 Friday and Saturday
  • Admission: About $10 – $15 per entree.
  • Parking: Free

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Seven Seas Beach:

  • Hours: Sunrise to Sunset. Re-opened post Maria March 28, 2018
  • Admission: $5 – have this on you, as there is no ATM nearby!
  • Parking: Free

[ D A Y • 9 – 11] El Yunque → Ponce: Parque de Bombas, Museo de Arte de Ponce, Hacienda Buena Vista Coffee Plantation

We finished our Puerto Rican adventure in Ponce, the second biggest city on the island, and one farther off the normal tourist beaten path. Founded (and named for) Juan Ponce de León’s great grandson, Loiza Ponce de León, Ponce served as an important southern base for the Spanish in Puerto Rico until the U.S. took over in 1898. We found a great deal at the Hilton there, so settled in to enjoy the last few days of our trip before heading back to the continental U.S..

We started off at “Parque de Bombas,” the island’s first firehouse turned museum. It was right up Miles’ alley, with lots of historical fire fighting equipment as well as some beautifully painted Lions (not sure if he liked the firetruck or the lions more).

Next, we headed to the Ponce Art Museum to learn about and admire the vejigante masks. While they reminded us of Beetlejuice, these masks can trace their history back to medieval Spain. During the Ponce Carniva each year, characters dressed as Vejigante walk amongst the crowd singing, and playfully whacking random passersby with their vejigas (dried, inflated cow bladders).

That afternoon, we headed to Hacienda Buena Vista Coffee Plantation, founded in the 19th century and powered completely by gravity fed water. Dom and I enjoyed the coffee (you’ve got to be sensing a pattern by now), while the kids played along the waterway and chased the chickens around. They give an amazing tour, complete with delicious espresso at the end, but make sure you log onto their website and reserve your spot beforehand, as spots fill up quickly. Ponce is one of the largest coffee producing regions on the island and Hacienda Buena Vista Coffee Plantation didn’t disappoint.

On the drive from Ponce back to San Juan for our flight back to the Continental United States, we made one last authentic Puerto Rican stop to eat on “The Pork Highway.” This is a three mile portion of Route 184 which is lined with several different lechoneras (restaurants which specialize in slow-roasted pig (Lechón)). It was delicious, and the food, music, and mountain scenery made for one last great memory of Puerto Rico before heading to the airport and crossing that jetway to begin the next chapter of our lives.

Puerto Rico, we will forever be grateful in how you helped introduce us to the joy of traveling as a family.  Now, back to VA to begin our cross country drive to WA, and our flight to Japan! Adios, Puerto Rico!



Parque de los Bombas:

  • Hours: Open Wednesday – Monday, 0930 – 1800
  • Admission: Free

Museo de Arte de Ponce:

  • Hours: Wednesday to Monday: 1000 – 1700 (last admission at 4:45 p.m.), Sundays: 1200 – 1700 (last admission at 4:45 p.m.), Closed Tuesday
  • Admission: Free Entrance for Members, $3.00/Students and adults over 60 years, $6.00/General Public

Museo de Arte de Ponce Tip: Military folks, this museum has in the past (including the year we visited – 2017) been on the Blue Star Museum Program which means that during the summer months free admission is offered. Members of the nation’s active-duty military and their families, including National Guard and Reserve qualify for this program.


Hacienda Buena Vista Coffee:

  • Hours: 0800 – 1600 Wednesday – Sunday, Closed Monday and Tuesday
  • Admission: Free


The Pork Highway:

  • Hours: Not really published anywhere, think lunch and dinner hours.
  • Admission: Lechón with all the sides was about $5-7. Worth. Every. Penny

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