If you read my travel itinerary, you know that we spent two weeks in the Caribbean this summer. During our travels, I shared several pics and stories along the way via IG and FB. The questions and comments rolled in, which motivated me to blog about our trip. Traveling always inspire me both personally and professionally. In this post, I want to share the beaches we relaxed on, the food we devoured, and the cities we toured while visiting Puerto Rico, Anguilla, & St. Martin. Find out where we stayed, how we got there, things I learned, and what I would (or wouldn’t) do again. This Caribbean vacation didn’t disappoint

First Things First: Transportation

Puerto Rico

Our first stop was PR, which we had a direct flight (4 hours) from IAH to SJU. We pre-booked a rental SUV using Hot Wire spending only $45 USD a day. We were able to drive the streets of San Juan, Carolina, Dorado, and many more areas, but I must warn you, the locals are a bit aggressive when it comes to driving. After a little time spent on the road, you will quickly adjust and have no issues getting around. I worked while on the plane…and drank wine! My mom and Aunt even made this part of the trip with us!!

Anguilla

Next stop on the map was Anguilla. Anguilla is not an easily accessible island from Houston, which is why I decided to visit this luxurious island during this trip. The flight from PR to Anguilla is rather quick. After boarding a teeny tiny plane (Seaborne Airlines), you will fly over the most beautiful waters so try to grab a window seat if you can. An hour later you will arrive at an exceptionally small airport where island time officially begins.

We arranged a rental car through our villa which was at the airport ready to hand over the keys, okay we had to wait on them a little while but get used to this, remember it’s island time. Traveling the streets of Anguilla is quite different than the roads in Houston. For example, plan to drive on the left side of the street instead of the right. It is painless and straightforward to get a driver’s license here. So don’t let this stop you. Getting around on the left side of the road is very easy to adjust; try it out! When you get the keys to your rental car, you will pay a small fee (maybe $15) and given a temporary license. It is more affordable to rent a car and drive yourself around than taking a taxi or hiring a drive bot are quite expensive on the island.

St. Martin

Being as we only had a week in the Anguilla/ St. Martin area, we didn’t have enough time to stay on both islands overnight. We decided to stay overnight in Anguilla but planned a day trip to St. Martin. Getting to St. Martin is painlessly easy, and there are a few different ways to do so. You can hop on the public ferry for a few dollars or take a boat over instead.

We opted for a private boat to customize our adventures. Captain Jo Charters is who we chose; they had great prices and packages, but the service was even better.!! We enjoyed fresh Pina Coladas, rum punch, and more! More about this later. Going between the two islands is a quick 20-minute boat ride.

Puerto Rico – Round 2

Before heading back to Houston, we planned for two additional nights in Puerto Rico. Remember me mentioning the difficult and expensive costs to travel to and from Anguilla from Houston? It was easier and cheaper for us to do this rather than flying directly to IAH. We also had another island we wanted to visit while in PR, so this allowed us to do so…so we thought. Our flight on the 24th from Anguilla to PR was canceled and rescheduled for the 25th, which meant we had to cancel our excursions to Vieques and other surrounding beaches. We didn’t let this unforeseen event ruin our day. Seaborne airlines accommodated us for food and housing and put us on one of the best beaches in Anguilla, Mead’s Bay. When life gives you lemons, you know what to do! Finally, we hopped back on the tiny plane, took the hour flight, and landed in San Juan for the final leg of our journey.

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Where to Stay

Embassy Suites, Dorado PR

Affordable (approx. $175 a night) and family-friendly beachfront resort. This part of the trip was a group effort, so we didn’t choose where we stayed. Not a resort I would typically pick, but it is in a great location, and the price can’t be beaten.

Songbird Villa booked via Airbnb, Rendezvous Bay

Great location, large size that can accommodate up to 10 people, affordable ($600 per night total), infinity pool, full-size kitchen, beautiful views. While I do recommend this villa, I will mention I felt like the floors were dirty and there was a bit of an ant problem. A little TLC, and these issues could quickly be resolved. If you see the listing and noticed it says elevator and fireplace, please note that these items cannot be found on the property. A BIG bonus is that a 6-person golf cart is included with your stay!

Turtles Nest Resort, Mead’s Bay

As I mentioned, Seaborne Airlines accommodated our stay here, so I am not sure of the exact price, but I believe it was around $400 a night for the 2-bedroom suite. Gorgeous views, quiet resort, clean, AC (that worked WELL!), water activities, THE WORKS.

Marriott Stellaris Casino and Hotel, San Juan

We spent one final night in Puerto Rico, just 4.5 miles from the airport. Let me tell you, this resort is very nice, clean, and family-friendly. I highly recommend this resort! You can walk to shops, restaurants, cafes, and more in the heart of San Juan just miles from El Morro and Old San Juan.

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Where to Eat & Drink

When we are on vacation, we eat and drink…a lot. Best places to eat and drink are listed below by location.

Puerto Rico

La Terraza: great atmosphere, food, wine, and dessert!

La Taberna: has the BEST coconut mojitos. I really loved their tacos too!

Di Zucchero: Italian food and beer garden and let me tell you; it is incredible. The best food, cutest vibes, great drinks! I loved their frozen strawberry mojito.

Anguilla

Sunshine Shack!! On Rendezvous bay. The best mojitos and fresh grilled seafood.

Elvis’s Beach Bar at Sandy Ground is such an eclectic bar with great drinks, excellent food, and even better service! Local chickens will be happy to greet you.

MUST EAT CRAYFISH! We enjoyed the fresh-caught crayfish while on Sandy Island. There is only one place to eat and drink and it will NOT disappoint.

Straw Hat at Mead’s Bay: get their frozen mojitos…be prepared for an unexpected punch! We ate there twice!

St Martin: at Pineal island we dined on the water with the freshest seafood. Karibuni is such a delicious eatery! You can choose your lobster from their trap waiting for you at the boat dock. The service was so excellent; Maddox even got served a virgin drink alongside a massage!

Must-See Places

Puerto Rico

Vega Baja Beach

Vega Alta Cerro Gordo: Fun beach with locals all around! I loved being with the locals and getting to experience their culture truly! Make sure to get the ice cream when you see the man pushing a cart on the beach. He works hard, and the ice cream is delicious!

Culebra-Flamenco Beach: We chartered a boat with 46 of our friends. While here, be sure to see the war tank that has been painted. We missed this photo op.

El Morro and Old San Juan

Get a local Piragua (snow cone). SO good!

El Yunque Forest

Casinos: La Concha & Marriot Stellaris

Market Place: is such a unique place. During the day it serves as a gas station/deli/convenience store. By dark, this place transforms into a fun bar with a great dance floor.

Anguilla

Mead’s Bay: one of the prettiest beaches on the island.

Rendezvous Bay: a beautiful quiet beach

Pinel Island: feed iguanas and enjoy the shallow calm water! You can even grab a few chairs and let the staff serve you. You can also do a little shopping with handmade goods from the locals.

Snorkel at Creole Rock: I may have just enjoyed the pina colada’s while everyone else partook in this adventure.