Escaping Toronto's brutal winter for a few slow, sun-soaked days on one of the Caribbean's most beautiful islands.

Running From Winter (And Not Looking Back)

Toronto in December hit different this year and not in a good way. We're talking early winter temperatures that should legally be reserved for January and February. After a month of battling a nasty cold that just wouldn't quit, I made an executive decision: I needed the sun, the sea, and the Caribbean, and I needed it immediately.

Destination: Anguilla. And not for the first time this island has a hold on me that I genuinely cannot explain. It's not the most budget-friendly Caribbean option, and it's not the most activity-packed island either. But that's exactly the point. Anguilla is where you go when you need to slow all the way down.

This was also my 13th country of the year something that had been on my vision board and bucket list, and a goal I'm still pinching myself over. Many of those trips were paid brand partnerships, which is something I never take for granted. When you grow up dreaming about seeing the world and then it actually becomes your life and your livelihood? That's everything.

Day One: Lobster, Rough Seas & Ice Cream in a Waffle Bowl

Lunch: Crayfish at the Harbour

We rolled in around noon with absolutely zero plans, which was completely intentional. The whole point of this trip was slow living. No early alarms, no packed itineraries just vibing. First order of business: food. I went straight for the Allen Harbour crayfish, because in Anguilla, you eat the seafood and you eat it without guilt.

The Beach & an Ice Cream Detour

After lunch we headed to the beach, but the sea was having a whole moment rough waves, not the calm turquoise we came for. We decided to scout a calmer spot for later and took the practical route: ice cream. I ordered a vanilla ice cream in a waffle bowl with hot fudge, found a gorgeous viewpoint, and just sat in the beauty of it. Sometimes the detours are the best part.

Dinner: Sushi, Sangria & Lychee Dessert

After a quick rest back at the house (a random headache came out of nowhere the sun is not always your friend), we got dressed and headed out for dinner. I kept it light with sushi and sangria, which hit the spot. The real showstopper was dessert: coconut ice cream topped with some kind of lychee mousse magic, fresh watermelon, and a little something extra. It was beautiful and delicious and I thought about it for the rest of the trip.

Day Two: David's Restaurant & Just Letting the Day Happen

Day two had loose plans we were going to do the colourful Moke cars and drive around the island, but the rain had other ideas. No stress. Plans shift, and in Anguilla, improvising usually leads somewhere good.

Lunch at David's

We ended up at David's for lunch, and I will always recommend this spot. The food is consistently good, the vibe is easy, and the seafood is fresh. The mussels alone are worth the visit I could eat them every single day. There's a fly situation (Caribbean dining al fresco comes with that), but don't let it put you off. The food more than makes up for it.

We also had rum punch, obviously. If you're in Anguilla and you want the most efficient, no-fuss drink that will absolutely do the job in one glass — get the rum punch. One. That's all you need.

Day Three: The Yellow Moke & Island Sightseeing

Friday. The day I had been waiting for. We rented Mokes those iconic, colourful open-air mini Jeep-style cars that people cruise around Anguilla in and I specifically requested yellow because I needed it to coordinate with my outfit. This is a lifestyle. We had them for four hours and set off with no real plan except to explore and take pictures.

The Arch: Supporting Local, Seeing History

One of our stops was The Arch a beautiful natural rock formation on the island. It costs $5 to visit and that money goes directly to supporting local businesses, which I always think is worth it. The views from there were stunning. We learned from the local guide that the arch used to be accessible from the other side, but the roads and cracks in the rock mean they've had to restrict access for safety. Still absolutely beautiful from where we stood.

Last Day: Malhana's, Final Seafood & Farewell to the Island

We were originally supposed to head to St. Martin on this day, but I made the call to stay. A half-day in St. Martin before immediately flying out just didn't make sense it felt like rushing for the sake of it. St. Martin will get its own full trip. Anguilla deserved the rest of our time.

Malhana's

A friend's recommendation took us to Malhana's a spot I'd only visited once before when scouting event venues. The energy there was incredible. Great music, great people, a proper Caribbean party vibe. It turned into one of the highlights of the whole trip, which is exactly the kind of thing that happens when you leave room for spontaneity.

One Last Plate of Seafood

Before heading to the ferry, I needed one final dose of Caribbean seafood. Fresh, good, simple the way it should be. We squeezed in a little last-minute exploring, grabbed our food, packed our bags, and made our way to the ferry port for the crossing to St. Martin to catch our flight.

Why Anguilla Deserves More Than a Day Trip

A lot of people visit Anguilla as a day trip from St. Martin and while I get it, I think it does the island a disservice. St. Martin and Anguilla are two completely different vibes. Anguilla is slower, more refined, and genuinely restorative in a way that you can't fully experience in a few hours.

Yes, it's pricier than Jamaica and some other Caribbean destinations. And yes, the summer months are when things really pop. But even in December, the island has a quiet, easy energy that I keep coming back to. If it's your first visit, aim for at least three days. If you're coming from St. Martin on a budget, do a day and a half minimum you'll thank yourself.

Quick Tips for Visiting Anguilla

🦞 Eat the Seafood: Crayfish, lobster, mussels don't come to Anguilla and skip the fresh Caribbean seafood. David's and the harbour spots are great starting points.

🚗 Rent a Moke: Renting one of the colourful open-air Moke cars is one of the most fun ways to explore the island. Book in advance and yes, coordinate your outfit.

🍹 Rum Punch First: One rum punch in Anguilla will do what three drinks elsewhere might not. Start there.

🌊 Check Sea Conditions: Some beaches get rough depending on the day. Have a backup beach in mind so a rough sea doesn't derail your plans.

📅 Best Time to Visit: Summer is when Anguilla really comes alive with events and energy. December is more relaxed but still beautiful — perfect for a low-key, restorative escape.

⏱️ Stay at Least 3 Days: Don't do Anguilla as just a day trip from St. Martin. Give it time. The whole point of the island is to slow down and that takes more than a few hours.

Anguilla, it is always bittersweet to leave you. The food, the people, the pace, the sea there is nowhere quite like it. Until next time.