Spring Break in Anguilla (What I Packed, Wore & Loved Most)

Hello hello!! Last month we took advantage of aligned Spring Breaks, and went in search of sunshine and warm water in Anguilla! Mr. Sugarplum and I spent a few nights there last Summer for our anniversary, and knew right away we wanted to experience more…and bring the kids!

And full disclosure, I may or may not have chosen it to ensure Sloan spent her Spring Break with us, ha! Turns out, free vacations are great incentives for adult kids!

We rented the most incredible house, spent our days hopping between postcard-perfect beaches, and and our nights stretched out over long dinners and lots of laughter. It was simple, but also kind of magical…you know the kind of trip that just works without trying too hard!

I shared a fun recap of the trip HERE, and our full highlight HERE, with videos of where we stayed and ate, along with all our fave spots, beaches and activities, but I know y’all love to have it on Hi Sugarplum for easy reference, as well!

What I Packed & Wore //

Anguilla is laidback and tropical, with a touch of boujee for dinner…so I packed lightweight fabrics, breezy silhouettes, and pieces that could go from beach to dinner without much effort. I leaned into color, relaxed fits, and anything that worked with salty hair and sun-kissed skin.

Everything is linked below each look to make it easy to shop or recreate, plus a try-on video if you want to see more of the look.

Dress (Small) | Sunglasses
Video Try On HERE

Swim (6-size up) | Pants (XS) | Hat | Sunglasses
Video Try On HERE

Swim (6-size up) | Dress (XS) | Hat | Sunglasses
Video Try On HERE

Dress (Small-size up) | Purse
Video Try On HERE

Matching Set (Small) | Necklace | Purse | Earrings
Video Try On HERE

Swim (Small) | Bag | Sarong | Sunglasses
Video Try On HERE

Swim (Small) | Bag | Sarong | Sunglasses
Video Try On HERE

Coverup (Small) | Bag | Sunglasses
Video Try On HERE

Tank (Small) | Shorts (Small) | Sunglasses
Video Try On HERE

Top (Small-size up) | Shorts (Small-size up) | Bag | Sunglasses
Video Try On HERE

Dress (XS) | Purse | Earrings
Video Try On HERE

Swim (Small) | Coverup (Small) | Sunglasses
Video Try On HERE

Matching Set (Small) | Necklace | Bag | Sunglasses
Video Try On HERE

Swim (XS) | Sarong | Bag | Sunglasses | Hat
Video Try On HERE

Top (Small) | Shorts (Small) | Bag | Hat | Sunglasses
Video Try On HERE

Swim (Small) | Pants (XS) | Sunglasses | Hat
Video Try On HERE

Swim (Small) | Top (Small-size up) | Pants (XS) | Bag | Sunglasses
Video Try On HERE

What I Packed //

There was definitely a lot of mixing-and-matching going on, I loved how versatile these styles are…makes for easy packing and endless outfits!

Shop everything I packed HERE and watch how I packed my carry on HERE!

Where We Stayed //

We got beyond lucky renting Three Dolphins Anguilla! It’s one of those gems that’s actually even better in person! With a bigger group, having space to spread out (and a kitchen, pool, and multiple hang spots) made everything feel easy and relaxed.

Morning coffee overlooking the water, afternoons by the pool, and evenings all together before heading out to dinner…it truly felt like our own little slice of paradise. Truly a spectacular property, I’d highly recommend.

Travel Tip: We saved by booking direct and reserving just 3 of the 5 bedrooms.

Three Dolphins Anguilla

Three Dolphins Anguilla

Where We Ate //

The food in Anguilla is so good—like, so so god! Truly the best of any island I’ve been, so you really can’t go wrong. We kept it a mix of casual beach spots and a few nicer dinners, and every place had its own vibe.

A few favorites from the week:

Veya Restaurant – such a special setting tucked up in the trees…definitely our standout dinner
Tasty’s Restaurant – local, flavorful, and one of those meals you keep thinking about after
Village BakeHouse – perfect for a casual breakfast or coffee stop
Blanchards Beach Shack – easy, toes-in-the-sand lunch and so good
Straw Hat Restaurant – one of our favorite spots for a long, relaxed lunch
Scilly Cay – such a fun little outing…feels like an experience, not just a meal

Beach Days //

Every beach in Anguilla feels like the beach…you know? But these were the ones we went back to (or wished we had more time at):

Meads Bay – easy, beautiful, and great when you want food and beach in one spot
Rendezvous Bay – wide open and perfect for long walks
Crocus Bay – a little quieter and tucked away
Shoal Bay East – that water color…it almost doesn’t look real

We’d usually pick one for the day and settle in…most Anguilla beaches have multiple beach shacks and clubs with chairs and umbrellas available.

Anguilla Don’t Misses //

A few of our favorite experiences, and are 100% worth working into your trip:

Sunset drinks at the Four Seasons Resort and Residences Anguilla Sunset Bar – the views are unreal
A beach day at Sunshine Shack – laid-back, colorful, and just fun
Dinner at Veya Restaurant – worth repeating because it was that good
Day passes at Belmond Cap Juluca – such a beautiful property and a really easy way to enjoy it for the day

Getting There & Getting Around //

A quick little logistics rundown, because Anguilla is one of those destinations that feels remote—but is actually pretty easy once you know the plan.

We flew into Sint Maarten (more flight options and usually better rates), then took a 30-minute water shuttle over to Anguilla with Calypso Charters. The transfer was smooth, easy, and honestly a fun way to arrive—it sets the tone right away.

Once we got to Anguilla, we had a rental car arranged through our rental house, which I definitely recommend if you’re staying a few days and want to explore different beaches and restaurants. They met us right at the dock, got us set up, and we were on our way.

Only thing to note—Anguilla follows British driving, so you’ll be on the left side of the road.

For the way home, we flew directly out of Anguilla’s airport, which was definitely the easier option!

I’ve found myself thinking about this trip more than most—not just because Anguilla is so beautiful (it really is), but because of how it felt. Easy days, great meals, everyone together…and the kindest, most welcoming people everywhere we went.

If Anguilla has been on your list, consider this your nudge—it’s just as special as it looks, and even better once you’re there. And if you want to see even more of our trip, check out this video highlight on my Instagram HERE.