Stripes in Old San Juan

Dress: Loft Bag: Kayu Shoes: Marc Fisher Earrings: BaubleBar Sunglasses: Randolph (c/o) Lips: Bite Beauty in Quince

If you follow me on Instagram (and hopefully you already do!), then you know that I recently went on a girls getaway to Puerto Rico with three of my girlfriends. Between the Boston weather and each of us having some crazy times at work recently, it was a much needed trip and the perfect way to escape a bit.

Just under a four hour flight away, Puerto Rico was an easy place to get to with guaranteed warm weather for a four day trip. While we spent most of our time laying on the beach or by the pool (with tropical drinks of course!), we did do a little exploring- mainly to find yummy food and (more) delish drinks! I absolutely loved three of the places we visited and I would highly recommend them to anyone making a trip to Puerto Rico soon:

  • La Factoria– this cocktail and wine bar is seriously amazing (actually on the list of top 50 bars in the world!) and is a must visit for anyone headed to Old San Juan. When you first walk in you’ll think it is only the front bar, but walk through the doors towards the back and you’ll find a few other bars in another speak easy style room. Their homemade ginger beer was amazing and I fell in love with the lavender mule featuring it. We had so much fun chatting with the super friendly bartender (he went to school in MA!) and getting recommendations from him too. If you visit, just know there isn’t a sign outside so just look for the bar on the corner of San Sebastian and San Jose.
  • Marmalade– this restaurant was recommended to us by several people and it did not disappoint! The restaurant only offers tasting menus- we did the four course menu- so definitely go with an appetite. Their famous white bean soup is a must order! I also had the kale pasta and snapper as two of my courses and loved both! For a tasting menu, the portions were very generous- so would stress being hungry when you go 🙂 The décor was also super modern and at the risk of sounding cliché, it had a very “city” vibe to it.
  • Lote 23– Our bartender at La Factoria recommended visiting Lote 23 and we were all SO glad he did. Lote 23 is a collection of food trucks/kiosks in the Santurce neighborhood of San Juan. We went there for a late lunch on our last day and I couldn’t resist sharing the whole thing on my insta-story. There were so many amazing choices for food, including authentic Puerto Rican food at the La Alcapurria Quema kiosk, delish frites at the Bayard and refreshing popsicles from Senor Paleta. Definitely don’t miss a visit to Lote 23 when visiting!

Besides the fantastic weather, great food and drink, I loved exploring Old San Juan. The colorful homes like the pictures here are a total dream- we all picked out our fave as we walked along. It was such a colorful, fun place to visit filled with the friendliest people. Definitely a trip to remember!

xoxo, Jenna


  1. April 17, 2017 / 10:07 am

    I have wanted to visit Puerto Rico for a long time. It’s been on our list for girls trips or a couples trip – someday!
    Sounds like you ladies had a blast and visited some really cool spots.

    • Jenna at Boston Chic Party
      April 17, 2017 / 8:45 pm

      I think you will love it Kristen! The weather is obviously amazing, but it was super pretty, colorful and the people were SO nice. Highly recommend!

  2. April 17, 2017 / 1:07 pm

    Oh how I love Puerto Rico!! I went for a girls trip two years ago and it was such a blast and I can’t believe how inexpensive it was!!
    xx Tess | Sequins are the New Black

    • Jenna at Boston Chic Party
      April 17, 2017 / 8:44 pm

      It’s such a fun spot for a girls trip! Agree- we were dying over how inexpensive the drinks were out 🙂
      Thanks Tess for stopping by!

  3. April 19, 2017 / 8:17 am

    I’ve been dying to go! Looks like it was a ball and thanks for the recs! xo

    • Jenna at Boston Chic Party
      April 22, 2017 / 9:27 am

      You definitely should! It’s so easy from Boston with the direct Jet Blue flights 🙂

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