Hello First name / friend!

 

Have you ever visited a place that you loved, and vowed to return.  And then, since it probably took you a decade, everything you loved about it was totally different?  

 

 I HATE when that happens.   

 

I am thrilled to report that Anguilla is still the low density charming island that it was 20 years ago.  ( yeah, it took me a minute to get back there). 

 

I was a little nervous since neighboring St Maarten was NOT what I remembered, (or maybe I have just aged out of the their beach scene).  

 

I forgot to pack my thong anyway.    

 

On happy Anguilla we ran into many people that visit year after year, who book the same week at the same resort, and have made life long friends in the process.  

 

This under-the-radar island is all about slowing down. With boutique resorts, uncrowded beach bars, and some of the most beautiful stretches of white sand in the Caribbean, why didn’t I come back sooner?  

 

Here’s what you can expect to find:

 

📍 33 beaches that are all somehow all postcard-perfect
📍 Open-air beach bars with world-class grilled seafood
📍 Sunset sails, great local restaurants and live music 

 

 

 

Anguilla with its tropical weather still follows a seasonal flow. 

 

🌤️ 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 too crowded. Book way early if you're aiming for the holidays or spring break.

 

🌺 Spring (May to June): 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, many properties close. You might score a deal, but it’s a more unpredictable time to visit.  I don't recommend it… the island is pretty sleepy anyway, why go when everything is closed?  

 

🌞 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 go sky high in December.

 

 

Five to seven nights is ideal for this tiny island.  It gives you time to unwind, explore a few beaches, and check out the local food scene.

 

 

Anguilla’s top resorts are boutique and book up fast—especially in peak season. I recommend planning 4-6 months in advance for winter and spring travel to secure the dates you want, great rooms, views, and experiences. Thinking of a last-minute getaway? Shoulder season gives us a little more wiggle room.

From beach bars to boutique resorts, Anguilla is all about effortless luxury—but that doesn’t mean planning it should be left to chance. 

 

✅ Small island, big logistics. Getting to Anguilla includes a ferry or short flight via St. Maarten, and many resorts are boutique with limited availability. I’ll take care of the connections, transfers, and timing so your travel feels smooth from start to finish.

 

✅ The best moments aren’t always on Google. Whether it’s a private  sail, a beachfront dinner under the stars (and a SpaceX launch) or knowing which cocktail bar has the best sunset and is actually worth the hype.

 

✅ Laid-back doesn’t mean last-minute. Anguilla’s charm lies in its exclusivity, but that also means things book quickly. I’ll help you access the best resorts, beach clubs, and experiences before they fill up—so all you have to do is show up and enjoy.