Anguilla has been at the top of my bucket list for years, thanks to one of my favorite singers, Monica. She often talks about Anguilla as one of her go-to and favorite vacation spots, so it’s been a dream come true for me to visit FINALLY! If you’re unfamiliar with Anguilla, British West Indies (BWI), it’s a small British Overseas Territory in the Caribbean, boasting some of the world’s most beautiful and pristine beaches, like Shoal Bay and Meads Bay. It’s just a short three-hour flight from Miami, with neighboring islands like St. Maarten, St. Martin, and St. Barth’s accessible via a short minute ferry ride—or, if you prefer, a small plane that’ll get you there in about 7 minutes.
Flight Redemption: 10,000 miles + $69 in taxes and fees
American Airlines (American Eagle) operates the only two direct flights into Anguilla Airpot (AXA). Many travelers opt to fly into St. Maarten (SMX) and then take the ferry over for day trips or longer stays. The cash price for my flight was just over $700; however, I only paid $69! Back in March, I shared American Airlines’s biggest redemption sale, offering flights for just 5,000 AA miles each way. I found availability from Chicago to AXA (with a stop in Miami) for 10K miles total, plus $69 in taxes and fees. To top off my experience, I received complimentary upgrades to business class as an Executive Platinum member, maximizing the value from my miles even further!
Zemi Beach House Resort
For accommodations, the top resorts you’ll hear about include Aurora Anguilla Resort, Four Seasons Resort & Residences, Cap Juluca (a Belmond Hotel), and Zemi Beach House Resort. After researching options for my first solo vacation, I decided on Zemi Beach House, a Hilton LXR property—and it did not disappoint (read my review here)!
The room rate averages 110,000+ points per night, which is common for a higher-category Hilton stay redemption. Thankfully, I had two Free Night Certificates from a sign-up bonus I earned in Summer 2023, redeemable for standard availability (now up to 150,000 Hilton Honors points a night).
Fifth Night Free
One of the best perks of Hilton Honors redemptions is their fifth-night-free benefit when you book five nights using points. For my 7-night stay, I used those two Free Night Certificates and 440,000 Hilton Honors points. My trip fell over Mother’s Day weekend, and the total cash price for my stay would have been around $13,782! With the resort averaging about $1,200 per night and a 13% island tax, adding another $2,200 (waived on award stays), I was pleased to have a total out-of-pocket cost for accommodations of $0! That gave me a value of just over 1.5 cents per point, well above the typical .05 Valuation for Hilton Honors redemption value.
Maximizing Your Points
It never ceases to amaze me how the power of points and miles can transform a travel experience. With Anguilla being a small island that can get quite pricey, I spent an entire week in pure paradise and luxury for less than $70!
This unforgettable experience was made possible by maximizing my everyday spending through credit card sign-up bonuses. By paying for our rent, taxes, and business expenses, as well as being strategic with our travel cards, we can travel like this multiple times a year for nearly free!
If you’re not already in the game, our website offers many free resources to help you get started. We also provide a paid Award Travel course for personalized, one-on-one guidance. Feel free to book and check out our services through the services tab!
