Let’s be real here - planning a bachelorette weekend is easily one of the best and least stressful parts of wedding planning. It’s all about you, your girls, no stress, no guys (except my one Bridesman), fun, hopefully sun, and, if I’m honest, a healthy dose of Instagrammability.

We went over a few options before settling on our final destination. Given that my wedding would be in Florida in May (Update: It’s being rescheduled thanks to Coronavirus) we opened up the options to include colder destinations, knowing we’d get our fix of sun a few weeks later at the wedding. We looked at Montreal, Colorado, and Aspen (that was before we knew exactly how much Aspen would cost. I think they should rename it “A-spend-your-savings.” That’s it for the dad jokes, I’ll see myself out now.) We also considered New Orleans and LA; New Orleans was by far the lowest price, both for flights and for Airbnbs, and LA wasn’t bad but the six hour flights from our various East Coast homes didn’t seem appealing.

We ultimately picked San Juan because it would offer us the best of all worlds - culture, food, sun, beaches, not too expensive, not too far, and no passports needed. It was the best decision ever, and I am so glad we went. Even though it was a relatively short trip - three-nights/four days; I fell completely in love with the island, the super-nice and welcoming people, and the general vibes and would absolutely make it a regular holiday destination. I am also so thankful to this great group of girls + guy that shared this with me! We weren’t overly bachelorette-y, but they made me feel special in a way that wasn’t awkward and cheesy, and we just generally had a great vacation together, the bachelorette part was just the icing on the cake for me.

Ready for some travel tips?

You can pack a whole lot into a long weekend trip to San Juan, Puerto Rico. Here’s what you should see, do, eat and drink in San Juan, or a short uber ride away.

BUT FIRST, GET INTO GEAR…

It wouldn’t be a bachelorette without some gear, right? I absolutely hate things like sashes, veils, and anything penis-themed, but I am not above a couple little situational items. I ordered an “Esposa” sunhat from Etsy before the trip, as well as some custom name straws for all the guests from Krazy Straws.

GO OUT TO EAT

We randomly stumbled upon this awesome, industrial ocean-front food court, La Marqueta, where you can get Poke Bowls, Sushi, Vegan food, classic Puerto Rican eats, Indian food, plus beer, wine and cocktails. It was definitely a standout lunch trip, and a great people-watching spot, too.

For some reason, we ended up eating a lot of pizza on this trip…I’m talking good, wood-fired pizza, but pizza nonetheless. Pirilo’s Pizza Rustica was the best, and not just for the food - it was packed with well-heeled young local folks plus a long wait to get in (they take your name and phone number at the door so you can grab a drink next door while you wait for a table.) If that’s not a great endorsement, I don’t know what is.

GO TO THE BEACH

We went to two beaches while we were here, La Playita Condado, a public beach that was okay but it was right off of the main “highway.” Isla Verde Beach in nearby Carolina was my favorite. I kid you not when I say that we had the worlds best Chicken-on-a-stick (Pichos de pollo) from a little stand run by this absolute Boss Lady at Isla Verde beach. Beach chairs were around $4 to rent, and there was no shortage of coconuts (rum optional) to purchase for $5. There was a CVS nearby to grab sunscreen and hats in case anyone forgot the necessities (some of us did), plus they also sell alcohol, which we snagged to spike our coconuts. Everyone had music blasting, the water was warm and clear, and it just felt like a great neighborhood beach day - it was not touristy at all.

GO DANCING

We hit up Club Fifty Eight at the La Concha resort for dancing on our second night in town. (We planned it specifically so that the big dancing/drinking night wouldn’t fall on the night before check-out, since there is literally nothing worse than trying to tidy up, pack, strip the beds and get the hell out of your Airbnb while hungover and struggling to live. Just trust me on this.) The club is semi-underground, literally - it’s down some bouncer-guarded stairs in the hotel’s main lobby, but has giant picture windows that look out onto the ocean, so when the lights of the DJ’s lightshow go dark every so often you get to see waves lapping on the shore a few dozen feet away. The music was Latin Top Forty and the crowd was mostly locals plus a few hotel guests.

Vivo Beach Club also has a nice open air venue; we didn’t actually come here for dancing, we only walked by on our way out of Ocean Lab Brewery and saw an event going on, but it looked like a great time. (Fun Fact - the event was hosted by a “bitcoin entrepreneur”/former child actor that John Oliver made fun of on his Bitcoin episode)

CHECK OUT A BREWERY

Ocean Lab Brewery in Carolina is worth an entire afternoon, if not the whole day - paying for a day pass to the pool at the on-site Vivo Beach Club wouldn’t be a bad idea as a great place to post up and enjoy full-service food and beer while you lounge poolside right next to a beautiful private beach. We just stopped by for beer and snacks between our day at the beach (Isla Verde is a short Uber ride away) and heading home to shower before dinner. Most folks here were pretty well dressed, and there is a nightclub on the same compound that was hosting a pretty swanky affair, so again, although we kind of “stumbled” upon this thanks to some brilliant beachside googling by Gwen, it could definitely be a destination of its own. The beer is delicious and ubiquitous - we saw it all over the island, at restaurants and in grocery stores - and the food is great too. The views of the ocean and the pool from the brewpub are stunning. One little quirk is that the brewery is located right next to the airport, so planes would pass by every couple minutes as they landed. It wasn’t too annoying, it somehow just kind of fit with the scene.

EXPLORE OLD SAN JUAN ON FOOT

 Our Airbnb was absolutely perfectly located within easy walking distance of pretty much everything.

Museo de Las Americas in San Juan - At the very least, come for the adorable coffee shop inside the Museo de la Americas, Don Ruiz. Make sure to grab a pair of mini cinnamon buns and some rose-flavored coffee while you’re here, too. Everyone knows the “Umbrella Street” from Instagram; the umbrellas have been replaced with a giant Puerto Rican flag, and it is definitely a quintessential “I came to San Juan” photo-op. Swallow your pride and just take the cheesy photo. Wander down side streets, spot cats everywhere, and just enjoy.

SHOP IN OLD SAN JUAN

Muns - Founded, owned and operated by two sisters, this shop feels very Brooklyn-by-way-of-Old-San-Juan. They have their own line of contemporary jewelry, plus a newly-added collection of cute breezy clothes that are produced locally, with organic textiles. They also had a few vintage pieces on hand, including some awesome Calvin Klein jeans that I regret not trying on (I was hot and hungover…).

DO A PHOTOSHOOT WITH YOUR BRIDESQUAD!

A couple weeks before the trip I booked local San Juan-based photographer Nina Martin for a photo session with the San Juan Bachelorette squad. I wanted photos with all of us in them, and I just wanted to capture the fun and beauty of the trip with these awesome travel buddies in a way that only a professional can. She worked with our budget, and gave us tons of beautiful shots within a few days that I will treasure forever! I wore a Lilly Pulitzer Shelli dress and a plain white cotton dress (from Target…) for the shoot.

WHERE TO STAY

I cannot speak highly enough of our Airbnb. It was huge - six bedrooms, perfect for the seven of us (two troopers shared a room) and it was located in Old San Juan, within walking distance of museums, shops, landmarks, cafes, restaurants - anything we could ask for. All that, and it was on a quiet, scenic little street that never got loud or rowdy, even at night. (Excluding us, that is.) We spent most of our time on the rooftop, which had amazing views and was great for tanning during the day and pregaming in the evening or night-capping late night. You can check out Casa Colonial in Old San Juan on Airbnb here.