Perhaps one of the coolest opportunities that I’ve had with this blog happened last week. I got to partner with my favorite airline, JetBlue, plus another favorite brand, J.Crew Factory, for a tropical getaway! Dying. And what’s even better is that you, too, have the chance to win a JetBlue Getaways Trip for two and a $1,000 J.Crew gift card to help pack your bags.  Pretty much the best kind of vacation set up EVER. Plus, 3 first place winners will $250 J.Crew gift cards. So fun!




While I’ve flown JetBlue plenty of times this was my first time experiencing their JetBlue Getaways program. The whole idea behind the service is to make booking your trip exceptionally fun and easy! You can book everything right on JetBlue’s site, ensuring that you’re getting the best price. I highly recommend you take some time and browse the site and learn more about their destinations. If you’ve ever flown JetBlue then you know that they know how to provide a fantastic experience with the best possible flight for you. Think easy check in process (have you tried their new JetBlue App?), in-flight entertainment options and wifi, and THE BEST airline snacks! So you know you can trust the top rated hotel partners that they’ve already discovered for you!



(Wearing J.Crew Factory Gingham Shell Top and J.Crew Factory Striped Tote)


My friend Gray and I headed to San Juan, Puerto Rico and stayed at the Condado Vanderbilt Hotel. It completely exceeded my expectations and was pretty much an instagram paradise. I can’t wait to go back some day!



Condado Vanderbilt, San Juan, PR



When we weren’t hanging by one of the pools we spent our time in Old San Juan. It dates back to the 16th and 17th centuries and is full of color and charm. And really nice people. I expected to enjoy our trip but I had no idea how much I would love old San Juan. When I travel I like to keep my schedule pretty open so that I can explore and get tips from locals. I love “restaurant hopping” so that I can try as many local vibes and dishes as possible.




(Wearing J.Crew Factory gingham top, stripe tote, jeweled sandals, and stone necklace)




And there were so many beautiful doors…


IMG_0780-2 IMG_0770 IMG_0765


This one below is to one of the thinnest buildings in the world!




(Wearing J.Crew Factory huarache flats and black seaside sandals)



(Wearing J.Crew Factory stripe dress, stripe raffia tote, and tortoise sunglasses)




(Wearing J.Crew Factory embroidered tank top and tortoise sunglasses)




Be sure to enter to win your own JetBlue Summer Getaway + a $1,000 J.Crew Gift Card to help pack your bags! And hurry because the Sweepstakes ends on June 15th! Want to browse the travel destinations (of course you do!)? Check them out right here!


PS: When going somewhere tropical I usually try to pack fairly casual and comfortable so that I can enjoy each day to it’s fullest. Here are a few of my favorite things that I packed for this trip! And PPS: The whole J.Crew Factory site is currently 50% off!


Thank you to JetBlue and J.Crew Factory for partnering on this post.


Comments: 8

8 Responses to “San Juan Trip Recap + Win A Summer Getaway”

  1. Ashley says:

    What a fun girls getaway! San Juan is such a cool place to explore. All the colors are beautiful there!

  2. Katie Fegert says:

    Looks like you had a wonderful trip! We went to San Juan a few years ago and stayed at the Marriott just down the beach from you! I was surprised how much I loved old San Juan. To this days it’s one of my favorite beach vacays we’ve ever been on!

    I love the way you captured the vibrant colors of Old San Juan!

    -Katie –

  3. I just returned from Old San Juan last week and had to most amazing time! I too was intrigued by their rich history and the local foods! Yum!! Loved your photos, too and that you could experience it all with a good friend. You really captured the energy of this charming city! Great post

  4. Kellie McLain says:

    Hey! You inspired me to go shopping at j crew and I already love JetBlue! Thanks for such a great blog that I look forward to reading for the style, class, charm and ingenuity!!

  5. Emma says:

    This trip look unbelievable! I would love to visit San Juan someday- it looks amazing.

    Emma | Seeking the South

  6. carrie says:

    How fabulous! It looks beautiful. So colorful.


  7. Love quotes says:

    This place is must visit

  8. […] Loved reading about Chassity’s trip to San Juan. […]

Join the Conversation

powered by chloédigital
Image 01 Image 02 Image 03 Image 04 Image 05 Image 06 Image 07 Image 08 Image 09 Image 10 Image 11