Hello First name / friend!

 

I'm always thinking of destinations through the lens of my clients and the people I love (sometimes they're one and the same). Whenever Anguilla comes up, I think of my brother. His travel brief is beautifully simple: beach, fresh fish, a soccer ball, and a backgammon board. That's it. So this Travel Tuesday, in honor of Hoog number one, let's head to Anguilla for easygoing Caribbean luxury at its finest 🇦🇮 Just one plane and a quick boat from many major airports.

 

This 16-mile sliver of paradise is all about slowing down and soaking it up. With intimate boutique resorts, beach bars that double as local institutions, and some stunning stretches of Caribbean sand, you'll wonder why it took you so long to get here.

 

Here's what awaits on Anguilla's shores:

 

📍 33 beaches that are somehow all postcard-perfect
📍 Open-air beach bars serving world-class fresh catches
📍 Sunset sails, steel drum sessions, and golden hour magic that makes you lose track of time

 

If you're craving sun-soaked simplicity with serious style, this quick guide covers what you need to know: where to stay, how long to go, and how to make it all effortlessly unforgettable.

 

 

Anguilla runs on island time…in the best way. But its tropical weather and quiet luxury rhythm still follow a seasonal flow. Here’s how to time your trip just right:

 

🌤️ Winter (December to April): Peak season, and for good reason. Think warm, dry days, calm seas, and ideal beach weather. It’s also when the island’s energy is at its best—vibrant, but never crowded. Book early if you're aiming for the holidays or spring break.

 

🌺 Spring (May to June): A sweet spot for fewer crowds and better rates. The weather stays warm and breezy, and you’ll still find plenty of life at beach bars and local restaurants—just with more room to stretch out.

 

🌧️ Summer & Early Fall (July to October): This is hurricane season in the Caribbean, and while Anguilla sees fewer storms than some islands, many properties close for maintenance. You might score a deal, but it’s a more unpredictable time to visit.

 

🌞 Late Fall (November): A quiet reawakening before high season hits. Great for relaxed travel, early winter sun, and securing the best resort spots before rates rise in December.

 

As long as you need to unwind, which is exactly the point. Long weekend? Full week? Two weeks? We're not here to check boxes or race through attractions, so honestly, it doesn't matter.

 

That said, five to seven nights hits the sweet spot for most travelers. It's enough time to properly decompress, sample a handful of those legendary beaches, dive into the local food scene, and maybe, just maybe, muster the energy for a snorkeling trip or sunset sail.

 

 

Anguilla's top resorts are small, boutique, and beloved—which means they fill up fast, especially during peak season (December through April). If you're eyeing winter or spring travel, book at least 4–6 months out to lock in the best rooms, ocean views, and restaurant reservations.

 

Feeling spontaneous? Shoulder season (May through November) gives us more flexibility for those last-minute "I need to disappear" moments. Just know that summer brings heat, humidity, and the occasional tropical shower.

 

If you're craving that quintessential laid-back, delish food, gorgeous-beach-and-not-much-else vibe, this is your island. If you need museums, nightlife, shopping, or a packed itinerary to feel fulfilled, skip Anguilla and head to St. Martin or St. Barths instead.

 

Anguilla is the epitome of fly-and-flop—the art of doing absolutely nothing while eating incredible bites with postcard views. It's about reducing overwhelm, reconnecting with yourself (or your travel companion), and remembering what it feels like to slow down.

 

 

Most travelers fly into St. Martin first. Direct flights from major cities including NYC, Atlanta, Chicago, Miami, D.C., and Paris make it easy. From there, you're just a 20-minute ferry ride, quick puddle jumper, or private boat transfer away from Anguilla's shores.

 

The St. Martin connection isn't a hassle, it's an opportunity. Want to split time between islands? The proximity makes it seamless to design a two or three-island Caribbean experience. 

 

Think dramatic archways, neutral palettes, and simplicity that feels fresh and young, not stuffy resort vibes. Set on a long stretch of pristine beach, it's gloriously secluded yet buzzing with a hip energy that works equally well for romantic getaways or stylish friend groups who want sophistication without the stuffiness. 

 

The Family choice - Malliouhana 

 

The island's legendary clifftop icon, where bold pops of coral, turquoise, and sunshine yellow create that quintessential Caribbean joy against dramatic bluff views. It's got serious design credentials and enough activities to keep everyone happy, from snorkeling adventures to poolside lounging with those unforgettable Meads Bay panoramas. 

 

The Group stay - Ani 

 

Private all-inclusive villa estates where your entire crew takes over sprawling clifftop compounds with infinity pools that literally disappear into the horizon. The villa comes with a dedicated team including your own chef, so you won't have to worry about a thing. Complete privacy, five-star service, and many pinch-me moments incoming.

Anguilla makes relaxation look effortless, but getting the details right, from ferry connections to restaurant reservations to the right room, takes local intel and timing.

 

Small island, smart logistics. Those St. Martin connections and inter-island transfers can feel overwhelming when you're trying to coordinate flights, ferries, and ground transport. I handle the puzzle pieces so your journey flows smoothly from departure to that first beach bev.

 

The good stuff isn't always obvious. Sure, you can find the good beaches online, but knowing which local fisherman serves the island's best catch, or which sunset spot the crowds haven't discovered yet? That's where meaningful travel happens—and where having someone with local connections makes all the difference.

 

Intimate means limited. Anguilla's boutique resorts and best restaurants don't have endless availability, especially during peak season. GT clients secure access to the experiences that matter to you before they're fully booked, so you can focus on what you came here for: doing nothing, beautifully.

 

If you’re craving a destination where time slows down, the sand feels like powder, and the ocean is always the right shade of blue—Anguilla delivers.

 

⛱ P.S. It's worth repeating! Anguilla’s top properties book up quickly, especially in winter. If this island is singing to you, let’s start planning now so you can secure the best rooms, views, and travel dates.