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Back in March, my friends and I went to San Juan, Puerto Rico for my bachelorette trip. As much as I absolutely love traveling with Thomas, it was fun to switch things up and take a trip without him for once. We went Thursday-Sunday and my company ended up giving us all that Friday off, so I got lucky and ended up only having to take 1 vacation day.

I am definitely not the type of person to enjoy typical bachelorette party activities like drinking, strippers, or a lingerie party. Instead, I opted for what a trip that felt true to me and how I like to travel. Puerto Rico was chosen because we wanted to go somewhere where the drinking age is 18 (my sister isn’t 21 yet) and you don’t need a passport to get to – those 2 criteria narrow your options down pretty fast. We largely planned this trip as a group (unusual for me as I typically do all the work planning/booking trips) and it turned out to be an extremely well-rounded trip. This entire itinerary is applicable to anyone planning a trip to San Juan, not just a bachelorette trip.

Day 1

All 5 of us were flying in from different cities, so we landed sporadically throughout the day. Though we hadn’t planned it this way, the girl who landed first was the one who had rented the car, which was perfect because she was able to pick the rest of us up from the airport.

Airbnb

Bachelorette party decorated bedroom for the bride

Since there were 5 of us, we chose to stay in an Airbnb instead of a hotel. I booked this incredible house that had 4 bedrooms (5 beds) and 3 bathrooms, so everyone had plenty of space. There was a pool and a great common area/kitchen/dining room where we were able to cook breakfasts, play games, and hang out. Every room had an AC unit and there was Wi-Fi throughout. The house also had a gate and room for 1 car to be parked, which worked great for our group.

The house is in a gated neighborhood near the beach, but it’s a bit far from Old San Juan, so we were happy to have a car to get where we needed to go. The effects of Hurricane Maria in 2017 were still visible 5 years later, as there were several houses that still had severe damage both in the neighborhood and around the city.

We spent the afternoon at the Airbnb decorating and putting together gift bags (it was a bach trip after all) as we waited for everyone to arrive.

Kumo Rooftop Bar

On our first night, we went to Kumo, a rooftop bar/restaurant at the top of the Waterbeach Hotel with stunning views. The restaurant is Japanese and all the food was perfect for sharing. I was surprised when all the meats/fish came in chunks on skewers, but we loved everything we ordered.

As we were starting to wrap up our dinner, a storm rolled in unexpectedly and we had to grab our plates and dash for shelter to avoid getting drenched. The staff was so nice and accommodating and moved us to a dry, covered table where we were able to finish our food and order dessert.

Day 2

Horseback Riding

Our first activity of the day was a 2-hour horseback ride through the foothills of the El Yunque National Forest. We were a little early, but there were turtles on the property that we enjoyed while waiting. When it was time for our tour, they had to weigh us to ensure our horse was the right size, and this definitely was everyone’s least favorite part but at least it was in kilograms instead of pounds (they use the metric system in Puerto Rico).

The guides were really friendly and the horses were calm and easy to control. They knew I was the bachelorette (our t-shirts gave that away), so they put me on a white horse which was really cute. One of my friends has competitively ridden horses, so she definitely knew what she was doing more than the rest of us, but no one had a hard time.

Lunch at Stuffed Avocado Shop

We tried to eat lunch at Chocobar Cortes, but the wait was too long for how hungry we were, so we ate at Stuffed Avocado Shop directly across the street. This turned out to be a huge win, as the food was incredible. The restaurant is somewhat similar to Chipotle, but every bowl includes an entire avocado and I was in heaven.

After lunch we decided to satisfy our sweet tooth and headed directly next door to Chocolato for some gelato.

Cabana Rental

We rented a cabana for the day at Condado Ocean Club and spent the afternoon relaxing by the infinity pool, enjoying the included bottle of prosecco, and walking on the beach. Condado Ocean Club is a hotel, but you can get access to the pool by renting a cabana. In the afternoon, the pool was in the shade of the hotel, so it was a bit on the chilly side (in March) but not so much that it ruined the fun.

Dinner at Santaella

This is an upscale Puerto Rican restaurant that is really rooted in the island’s culture. It’s located in the “party district” and there were lots of people and music playing in the streets around Santaella, especially later at night, but the restaurant has a much calmer vibe inside. The best dish was definitely the Lacón Asado (caramelized braised pork shank), which was the size of my head and perfectly tender.

As with many of the places we went in San Juan, we saw many other bachelorette groups at this restaurant. Puerto Rico is a great destination for these trips, but it would be a good place for a couple or family to visit as well.

Day 3

Food Tour

You may be thinking “she went on another food tour?” and the answer is a resounding YES. Food tours are my favorite way to experience a new culture, and this ended up being everyone’s favorite activity of the trip.

We got to try many local foods including coffee, pastries, popsicles, piña coladas (which are originally from PR!), sandwiches, and mofongo (mashed plantains), and more. I don’t even like plantains most of the time but I loved the mofongo we had and it was fun to get to mash it ourselves.

In addition to taking us to several local restaurants, our guide showed us all around Old San Juan and provided a great history of the island and shed light on the current political divisions with different groups supporting Puerto Rican statehood and independence. I didn’t realize how hilly Old San Juan is, so be prepared to walk up/down a lot of inclines.

There were ~10-12 total people on this tour, but that number was small enough to keep it intimate and we all chatted and got to know each other throughout the morning.

Mini Boats

Our next stop was a mini boat tour of the bay. Only 4 of us went on this tour, and the mini boats each fit 3 people max, so we split up into pairs. The most fun part about these boats is that you get to drive them yourself, rather than just being a passenger. I absolutely loved controlling the boat and getting to go fast.

While you’re driving you can’t hear much over the sound of the boat and the water, but the guide in the lead boat made a handful of stops at significant places like the Governor’s Mansion and Fort San Felipe Del Morro to explain the history and answer questions. Staying within earshot proved a little tricky as the boats had a tendency to drift apart, but I felt like I got all information.

I will note that this was not the best activity to do right after a food tour because we were all very full. If you get seasick easily, this is also probably not a good tour for you as the wakes of the boats can make for a bumpy ride.

Dinner at Sofia’s Old San Juan

On our last night, we ate at an Italian steakhouse. I don’t drink much and one of my friends doesn’t drink at all, but our waiter was able to whip up some delicious virgin strawberry mojitos. Unfortunately, the entrée I ordered came full of bell peppers that hadn’t been listed on the menu. I really hate bell peppers and there were so many that this dish was inedible for me. Thankfully, our server was happy to get me another dish and my replacement pasta was much better. For me, the best part was the chocolate cake – everyone else was really full by dessert which just meant more for me!

Day 4

Our Airbnb was nice enough to let us leave our bags in the corner while we went into town. Our rental car had been returned earlier than morning since one of my friends had an early flight, so the rest of us used Uber to get around the rest of the day.

Calle de la Fortaleza

When we got to Old San Juan, we put our name in at Chocobar Cortes and walked around while we waited for our table to be ready. The buildings in this part of the city are colorful and storied. We’d gotten to see a lot of this area on our food tour, but on this morning, we specifically sought out Calle de la Fortaleza, which is covered in umbrellas, kites, or other colorful pieces, making for the perfect photo op.

Based on my prior research, it seems that they regularly change out the umbrellas, which is why you may see several versions of the street in photos online. I definitely recommend getting there early. When we arrived, there was no one there and we were able to take as many photos as we wanted. Even after a few short minutes several groups had arrived and were vying for a photo.

Brunch at Chocobar Cortes

Chocobar breakfast in San Juan, Puerto Rico

As the name implies, this restaurant is all about chocolate and they really do put it into just about everything, even the avocado toast. Our waiter even gave us cheese to dip into our hot chocolate – I was nervous about this combo but it was surprisingly decent.

On our food tour, we’d tried a Mallorca Iberica, which is essentially a croissant-like pastry with ham, cheese, and guava butter. Another unexpected food combination, but this one was amazing, so I ordered another here and we all split some marbled waffles.

Castillo San Felipe del Morro

This is definitely one of the most iconic places in San Juan, and for good reason. Construction of the fort began almost 500 years ago and it has been the site of many battles over the centuries. Now it is open to tourists to explore and learn from. Entry tickets were $10/person and we were able to walk up and buy tickets onsite. Even if you don’t want to pay to go inside, you can sit on the large grassy area around the fort and enjoy the view (when we were there lots of people were flying kites on the lawn).

Popsicles

One of the places we’d stopped on the food tour was the popsicle shop Señor Paleta, where we had parcha (passionfruit) popsicles. On our last day, the temperature was the hottest of our stay and we were sweating, even in March. I insisted on grabbing another popsicle to help us cool down before we grabbed our bags and went to the airport.

In addition to fruity flavors, Señor Paleta serves popsicles in dairy-based gelato flavors like chocolate or birthday cake. You can also have them drizzle sauces and toppings on top to almost make it like a popsicle sundae.

Other Activities

We couldn’t fit everything into our 4-day trip, so if I come back to San Juan, here’s what I’d do:

Bacardi Factory Tour

Located on the other side of the bay from Old San Juan is Casa Bacardi, which is the world’s largest premium rum distillery. They offer three different tours, all of which include a history of the famous rum. Beyond that, you can add to your experience with a rum tasting or mixology class.

Bioluminescent Kayak Tour

We all really wanted to do this tour but couldn’t make it fit into our schedule. You can take a glass-bottom kayak into Laguna Grande and see the water lit up by millions of glowing plankton. The full length of this tour with transport from San Juan is fairly long and there’s no guarantee you’ll see the bioluminescence, as many factors impact its occurrence/visibility, including the phase of the moon. However, if you have time, I think this could be very worthwhile.

Natural Waterslides in El Yunque

There are so many activities you can do in El Yunque National Forest, from ATVing to hiking, but I would really like to explore the natural waterslides that you can go down and swim in the water below.

Exploring More of the Island

There’s a lot more to Puerto Rico than just San Juan. If I come back, I may take time to visit other areas such as nearby Dorodo or Ponce on the other side of the island. It would also be really fun and relaxing to spend a day on a catamaran, which you can do from many places around Puerto Rico.

Tips/Tricks

I definitely recommend renting a car. I had originally been opposed because I thought parking would be such a hassle, but we would have spent so much time and money on Ubers.
- Uber is an option and we did take a couple Ubers on the last day after our rental car was returned. We had to wait a while for them to arrive and had one cancel on us. There is no Lyft in San Juan.
- As helpful as it is to have a car, know that the roads are not very well maintained & there were a lot of reckless drivers on the road, so be extra careful.
- Parking was easier than we expected. We valeted the car at hotels and Old San Juan has parking lots/small garages.
Puerto Rico is US territory, which means:
- There’s no need to exchange currency because they use USD.
- You don’t need a passport to travel if coming from the United States.
- The drinking water is just as safe as in the US.
Not every phone plan has good service in San Juan. Those of us with AT&T and Verizon didn’t have any issues but people on smaller networks did.
Remember to bring cash to tip your guides. Just like in the US, tipping is expected on tours and at restaurants.
We went in late March and while it was warm every day, the last day was in the upper 80s and we were sweating, so be prepared and dress accordingly.
Think about hurricane season when picking a time to visit. Atlantic hurricane season runs June 1-November 30. I’d personally hate to have to cancel a trip due to a hurricane, so I’d avoid these months.
Book your reservations for tours and restaurants in advance to guarantee you can do what you want. Puerto Rico is popular and tours will book up!
None of us knew any Spanish, but everyone we ran into spoke English and menus were printed in both languages.
When you arrive at the airport to return home, you have to scan your bags through an aphid detector and declare that you aren’t bringing pork products back to the US. They do this to prevent the spread of unwanted insects and other substances. We didn’t know we had to do this, so we had to retrace our steps before could check our bags.