We just got back from an amazing yet short vacation to San Juan, Puerto Rico. It was my second time there and the boyfriend's first visit. I didn't get to see much of the island on my first visit because I was there for my friend's wedding so this time, I vowed to see and eat as much as I could. Since the point of the trip was to unplug and unwind, we didn't have an extensive to-do list. With that said, that meant I was only taking a carry-on bag and filling it with low key items perfect for lounging on an island. Here are my essentials for a five day trip to Puerto Rico. Check out my sun essentials here.  

THE TRAVEL OUTFIT

An easy shirt dress is the perfect no-fuss piece to wear for the four hour flight to San Juan, Puerto Rico. Add a scarf just in case it gets cold on the plane. I prefer flats over boots because unless you have global entry, you'll have to take off your shoes during the security check in. The Louis Vuitton Neverfull MM is the perfect bag to fit all the essentials you might need on the flight. Dorothy Perkins Shirt Dress, $28, DorothyPerkins.com; MARC JACOBS 'Pop Bouquet' Scarf, $195, Nordstrom.com; Rag & Bone Wool Fedora, $195, NeimanMarcus.com; Le Specs Sunglasses, $60, Net-a-Porter.com; Zara Lace-up Ballet Flats, $39.99, Zara.com; Louis Vuitton Neverfull MM, $1260, LouisVuitton.com  

THE CARRY-ON

Away 'The Carry-on' Luggage, $225, AwayTravel.com; Steamline 'The Editor' CarryOn Luggage, $485, SteamlineLuggage.com; Louis Vuitton Keepall Bandoulière 55, $1760, Louis Vuitton.com; LeSportsac Classic Extra Large Weekender, $200, Bloomingdale's

THE EVENING ESSENTIALS

Puerto Rico is still an island with the locals enjoying sun year round. Their style is non-fussy and infused with Latin flavor. If you plan on venturing into Old San Juan, Fajardo, Rio Grande or other parts of the island, make sure you pack practical pieces. First of and foremost there are a lot of cobblestones so you're sure to ruin your vertiginous stilettos walking through La Placita. Opt for chunky heels, wedges, flats or a block heel, which is what most of the locals wear on Friday and Saturday nights.

 L'Agence The Chantal Skinny Jeans, $225, ShopBop.com; Intermix Terrence Striped Top, $119, Intermix.com; J.Crew Chambray Shirt, $80, Net-a-Porter.com; H&M - A-line Denim Skirt, $29.99, HM.com; J.Brand 811 Mid-Rise Skinny Jeans, $160, Net-a-Porter.com; Equipment 'Layla' Washed-silk Camisole, $100, Net-a-Porter.com; TWO by Vince Camuto Embroidered Dress, $80, Macys.com; Stuart Weitzman NearlyNude Sandals, $395, LaneCrawford.com; Sam Edelman GiGi Sandals, $75, Lord & Taylor; Aquazzura Tulum Fringed Suede Sandal, $325, NeimanMarcus.com  

THE POOL & BEACH ESSENTIALS

Joe Fresh Bikini Bottom, $8, JoeFresh.com; Joe Fresh Stripe Halter Bikini Top, $8, JoeFresh.com; Patagonia Kupala Top, $55, ShoeBuy; Gigi Burris Breakaway Straw Floppy Hat, $169, Neiman Marcus; Topshop Sequin Pineapple One-Piece Swimsuit, $52, Nordstrom; Solid and Striped - The Ballerina Color-block Swimsuit, $160, Net-a-Porter; Tommy Bahama Lace-Up Chiffon Caftan, $118, Nordstrom.com  

DAY TIME ESSENTIALS

Finally grab three day time looks that can go from poolside to lunch for the five day vacay. I love a long maxi that can double as a beach coverup, a romper that can go from poolside to site seeing and a caftan versatile enough to double as a dress. Rachel Pally Long Cutout Dress, $238, Shopbop; Yumi Kim Liz Romper, $239, Shopbop; Yumi Kim St Tropez Caftan, $124, Shopbop