Anguilla
April 2025
4 Days
I haven't spent a ton of time in the Caribbean, so when we started planning our babymoon a friend suggested Anguilla as a good location for just relaxing on the beach. I also had a free Hilton night to use and Zemi Beach House is a hotel I had heard good things about. Being such a small island with limited flight options, we also spent a couple days on nearby Sint Maarten which gave us more flight options to get home. Anguilla had some of the most beautiful beaches I've ever seen and the whole island was very relaxed and not crowded at all - a perfect getaway for a few days to eat, drink, and sit on the beach.
Daily Itinerary
Check-in and afternoon on the beach
Sunset and dinner at Madeariman
Morning at the spa
Dinner at Blanchard's
Lunch at Ken's BBQ
Sunset at Mead's Bay
Dinner at Blanchard's Beach Shack
Day 4
Sunday funday at Gwen's Reggae Bar
Flights
American Airlines Economy ORD-MIA-AXA: cash one-way
Hotels
Zemi Beach House: 330,000 Hilton points for 3 nights + 1 Free Night Certificate
▸ Luxury boutique resort with only 76 rooms on the white sand Shoal Bay Beach
Food (With Beli Ranking)
Blanchard's Restaurant and Beach Shack (8.1) - A sit-down restaurant and walk-up beach shack next to each other and both are worth a visit.
Gwen's Reggae Bar and Grill (7.1) - Beach shack on Shoal Bay Beach with strong rum punch, decent food, and live music.
Madeariman (7.1) - Another restaurant/bar on Shoal Bay Beach with beach seating, drinks, and food.
Ken's BBQ - Roadside stand in The Valley serving good BBQ. It doesn't look like much, but the food was good.
Full Itinerary
Day 1
Zemi Beach House
Anguilla is a small island with a population less than 15,000 so the only direct flight option from the US mainland is on American Airlines from Miami. Otherwise, flying to Sint Maarten and taking a 10 minute flight or 25 minute ferry to Anguilla is probably easiest.
We ended up renting a car from Island Car Rental and it was parked at the airport for us when we landed. Given the few times we left the resort, having a car for the full 4 days probably wasn't necessary as there's not a ton to explore on the island. But, it was nice to have the freedom to leave the resort without having to organize taxis.
Zemi Beach House is located on Shoal Bay Beach about a 10 minute drive from the airport. Someone from the hotel was waiting for us at the airport and called the hotel ahead to let them know we were on the way. On arriving, they already had a rum punch for me and a non-alcoholic drink for Gwen waiting.
I really enjoyed this hotel because it was more intimate and didn't feel like a resort factory - the staff remembered us each day and had our beach chairs already set up in the morning when we arrived.
Zemi Beach House - Anguilla 2025
Madeariman is one of several bar/restaurants right on Shoal Bay Beach with plenty of beach seating. We came here for dinner, although these definitely seemed more like daytime spots as there was only one other table eating when we arrived.
However, the rum punch and my fish were good and the views were great.
Rum Punch at Madeariman - Anguilla 2025
Day 2
Zemi Thai House
The spa at Zemi Beach House features a 300-year old Thai house which was disassembled in Thailand and re-assembled in Anguilla. The large facility has 5 total massage rooms, a vitality pool, juice bar, and outdoor garden. The spa menu is expansive and the bamboo massage I got was a great way to start a relaxing vacation.
I was debating between going to the spa here or at the JW Marriott Sint Maarten later in the trip and I'm glad I chose the Zemi Thai House Spa as the facility was more unique than your typical resort spas.
Zemi Thai House Spa - Anguilla 2025
Blanchard's Restaurant is often noted as one of the must visit restaurants on the island. Opened in 1994, the restaurant overlooks Meads Bay and serves globally inspired dishes. The atmosphere is casual, but still is perfect for a couples date or group dinner out.
Blanchard's Restaurant - Anguilla 2025
Day 3
If a friend hadn't told me to go to Ken's BBQ, I definitely would never had ended up there. Located in the Valley, there's a shelter structure over a bunch of grills and some picnic tables. It doesn't look like much, but the price is cheap and the BBQ is pretty good although I'd say it's not a place that's worth going out of your way.
Ribs at Ken's BBQ - Anguilla 2025
Just next door to Blanchard's restaurant, Blanchard's Beach Shack is just as it sounds - a walk-up shack on the beach at Meads Bay serving delicious food. The mahi bites are a must and I'm told the chocolate chip cookies are as well, although they were sold out when we got there.
Blanchard's Beach Shack - Anguilla 2025
Day 4
Shoal Bay Beach
Zemi Beach House is located at the West end of Shoal Bay Beach. The beach is beautiful near the hotel, but as you walk further East, the white sand and crystal clear waters make up the most perfect looking beach I have seen.
Shoal Bay Beach - Anguilla 2025
Just a short walk along Shoal Bay Beach from our hotel is a small shack with outdoor seating and beach chairs. Sunday is funday at Gwen's with the scratch band playing in the afternoon. The food was decent and the rum punch was very strong!
Gwen's Reggae Bar - Anguilla 2025
Overall
For a purely beach vacation, Anguilla was absolutely perfect and had some of the most beautiful beaches I've ever seen. The island is small so there isn't a whole lot else to do - if you are more of an active person Sint Maarten has much more to offer and is just a 20 minute ferry (or 10 minute plane) ride away.
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