Anguilla Trip Roundup
our first time to anguilla!
One of our close friends invited us on a long weekend getaway to one of their favorite places, Anguilla, for her birthday! We’ve never been to the island before, but after falling in love with the BVI on our cruise in 2019, we have been welcoming any opportunity to go back. Eight of us left on a Thursday and went home on a Tuesday, so we had four full days there. Excited to dig into our trip and answer some of your most frequently asked questions.
You may remember Karina Lopez of @KCYouThere and KCYouThere.com, as she was my wedding planner turned friend. We’ve collaborated on a few posts over the years, in case you missed them, you can check them out here. Some of my favorites include 7 Reasons Why You Need A Wedding Planner, Navigating Your Engagement Post-Pandemic and my personal favorite, Breaking Boundaries with Martha Stewart Weddings.
Outfit details can be found underneath each photo, click on the link to shop the looks.
WHAT I PACKED
I wasn’t entirely sure what to pack/bring, but I decided to focus on lots of swimsuits, cover-ups, sandals, and easy dresses. If you can’t already tell, BK and I thoroughly enjoy a beach vacation, so I’ve got tons of outfit inspiration on the blog from all of the previous trips that we’ve done. If you’re planning a trip soon, I have a post on some of my favorite travel outfit formulas on this post. If you’re not already using packing cubes, I can’t recommend them enough. I recently shared a tutorial on how I like to use them here and have more efficient packing tips on this post! We love our Away luggage; check out my previous review here. But for more luggage picks, check out my curated list here. BK and I brought one medium-sized checked bag and one rolling carry-on for the trip, and it was perfect.
We intended to be gone for an extended weekend of Thursday-Tuesday, so we planned for five nights/four full days. I brought lots of swimsuits, cover-ups, dresses, pajamas/loungewear, sandals, jewelry, sunglasses, and undergarments. I like to create a list on my phone and think through the different events and things I’ll need before packing, that helps me feel organized and prepared!
OUTFIT DETAILS (WEARING 16 IN SUIT/XL IN COVER UP USE CARALYN10)
MY + BK’S SWIMSUIT DETAILS (WEARING 16)
WHERE WE STAYED
Welcome to
Anguilla
We flew from Buffalo into St. Maarten (connected in Atlanta) and then took a ferry to Anguilla. It is definitely not the easiest/quickest trip but thankfully everything went smoothly on our way there. Our friends have been coming to the island for over a decade, and they’ve always stayed at the Four Seasons Resort. The property was beautiful, with sleek, modern design and breathtaking views.
WELCOME TO ANGUILLA
WELCOME TO ANGUILLA
OUTFIT DETAILS (WEARING XXL IN COVER-UP + 16 IN SUIT)
I ALSO REMOVED THE PADDING AND WORE THESE NIPPLE COVERS INSTEAD, THEY’RE AMAZING. USE “CARALYN”
WHAT WE DID
As soon as we arrived,
we grabbed lunch at the hotel’s Sunset Lounge! To be honest, we spent the majority of our time in our swimsuits at the resort. This was one of the first trips in that we didn’t have a full itinerary and truly went with the flow, especially since we were traveling in such a large group.
The only major day we had planned was the day after we arrived, we chartered a boat with Good Living Charters to St. Barths for the day. We took a cab to the port and met captain Jel, who took great care of us. The ride to St. Barths was quite bumpy but arguably worth it because we quickly fell in love with the island. As soon as we arrived, there was a row of shopping (all tax-free), and we found ourselves at Eden’s Rock for lunch. It was fantastic! Luckily, the sunset ride back to Anguilla was smooth.
what we ate and Drank
For the rest of the trip, we stayed on the Four Seasons property and ate most of our meals throughout their different restaurants and at the pool. They have a fantastic breakfast buffet I enjoyed made-to-order omelets each morning. We ventured out to Picante for dinner one night, within walking distance of the resort. It was fantastic and we had great service, highly recommend their spicy margarita. On the last day of our trip, we took a water taxi to Sandy Island, where we enjoyed a fantastic seafood lunch and lots of rum punch. We also planned on going to Straw Hat for dinner (many of you recommended it), but we didn’t end up making it there, maybe next time!
OUTFIT DETAILS, WEARING 16
OUTFIT DETAILS - WEARING XL, USE CARALYN15
OUTFIT DETAILS - WEARING SIZE XL
other things worth mentioning,
I always like to prepare for beach/pool trips with a spray tan. If interested, I have a recent post of my sunless tanning and bronzer favorites here! That way, I arrive tan (which helps me feel more confident in a swimsuit), and as it fades, my natural tan appears, so I maintain color throughout. If you’re looking to keep a sunless tan throughout your trip, I would highly recommend Luna Bronze or St. Tropez products.
I kept my makeup pretty simple throughout the trip because it was really hot! I used my top five summer beauty favorites and also packed a bunch of my vacation beauty must-haves.
OUTFIT DETAILS // @KCYOUTHERE
OUTFIT DETAILS - WEARING SIZE XL IN BOTH
OUTFIT DETAILS - WEARING XL
OUTFIT DETAILS - WEARING SIZE XL IN BOTH
As I mentioned, we spent most of our days and evenings poolside. I was glad I brought a few extra swimsuits because I often wore two daily. I saw a bunch of swimsuit-related questions, I strongly encourage you to check out the swim tab of my blog and my swim ‘22 highlight for more in-depth reviews and sizing feedback. Summersalt is currently having an end-of-summer sale, they’re one of my favorites! I typically wear XL in all cover-ups and 14/16 in swimsuits, depending on the style and how I’m feeling. Feel free to leave any specific questions below!
If you’re looking for more outfit inspiration, check out the shop tab of my blog, which I update daily with my outfits. I also have many options saved to my Amazon Storefront, including many under $50 finds.
ON OUR WAY TO SANDY ISLAND
OUTFIT DETAILS - WEARING XL
OUTFIT DETAILS - WEARING XXL
Thank you so much for taking the time to read through our latest adventure!
It was a short but fun-filled trip filled with indulgence and no regrets. Grateful to our friends who showed us the island for the first time. Be sure to leave any questions below and check out the travel tab of my blog for more trip roundups and travel inspiration.
xx CMK