Travel Files: Anguilla

Sharing our Anguilla travel guide along with all the details on our recent visit! Includes where to stay, best places to eat and what to do in Anguilla, plus much more!

A few weeks ago, Kurtis and I traveled to Anguilla for vacation in celebration of our 15 year anniversary (only four years late). We had initially planned to visit in 2020 prior to the pandemic but then obviously had to adjust our plans. With other factors, including our move across the country, we were finally able to visit the beautiful island of Anguilla in late February. Today I’m going to share our Anguilla travel guide which includes all of the highlights as well as tips and favorites from our vacation. You can also check out my Instagram Highlight from the trip, as well, which includes additional video footage, photos, and more!

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Where is Anguilla?

Most people I talked to pre-trip had never heard of Anguilla! So before I jump into our trip details, I thought I’d share a bit about where Anguilla is located and what it is known for.

Anguilla is a British Overseas Territory located in the Eastern Caribbean, part of the Lesser Antilles archipelago. It lies to the east of Puerto Rico and the Virgin Islands and directly north of St. Maarten.

Known for its stunningly beautiful beaches, turquoise waters, and vibrant coral reefs, Anguilla is a popular destination for travelers seeking a tranquil and luxurious getaway. The island boasts a flat, low-lying landscape of limestone and coral, offering breathtaking panoramic views and a serene atmosphere. Its capital, The Valley, is the heart of the island’s cultural and economic activities. Anguilla’s location makes it a unique blend of rich British heritage and captivating Caribbean charm, attracting visitors from around the world to experience its natural beauty, exquisite cuisine, and warm, welcoming community.

How To Get to Anguilla

We found that getting directly to Anguilla wasn’t as simple as just booking a flight if you have certain dates in mind. Several airlines only fly in and out once a week during the dates we looked at (late February/early March).

However, travel was still relatively easy. Our preferred airline is Delta, so we booked a flight from our home airport, Panama City Beach (ECP) to Atlanta. From Atlanta, we then flew directly to St. Maarten which is very close to Anguilla.

Once we arrived, we arranged water transport (a 20-30 minute boat ride depending on weather and water conditions) from the airport directly to our hotel. This was all a service offered through our hotel’s concierge. Although there are other vendors that offer this service, we opted to book directly through our hotel for simplicity so I didn’t research other options further (just know that there are some). In the future, I would likely just book this myself, since it was a rather straightforward process.

On our arrival day, it was raining when we arrived at the water taxi station, so they delayed departure by about 30 minutes so keep in mind delays are possible. Most of the vendors offer hourly trips back and forth between St. Maarten and Anguilla.

Other forms of transport include helicopter or airplane if you don’t love the idea of going by water. But we found it to be very enjoyable, even when the water was more rough. The photo below was on our return trip when we opted to sit up on the bow of the boat. But most seating is covered on the boats we saw!

Where To Stay in Anguilla

In terms of trip planning, we put the most effort into deciding which resort we wanted to stay at. In my prior research back in 2019 and 2020, I had narrowed it down to Four Seasons, Belmond Cap Juluca and Malliouhana.

As we re-started our planning efforts, these three appeared to still be ideal in terms of what we were looking for. After several polls on Instagram, I received similar responses. However, I did hear that Malliouhana recently changed ownership (no longer an Auberge Resorts Collection property) and a few told me it was just not the same. I’m guessing just some transition pains so may no longer be an issue.

We ultimately narrowed it to Four Seasons and Belmond Cap Juluca. Funny enough, Kurtis and I each had a final different choice. But, when we found that Cap Juluca is in a bay that tends to be windy this time of year, we both knew Four Seasons was the right choice for us. One of the reasons we left Nebraska is because we hate the wind so badly, so we didn’t want to purposely plan a vacation to a windy spot. I honestly think any of these options would have been heavenly, but wanted to share how we ultimately landed on Four Seasons.

We made a point of visiting the other two hotels we considered, and we’d recommend doing the same if you visit Anguilla! These certainly aren’t the only options on the island either.

Four Seasons Anguilla

The Four Seasons Anguilla is a rather large property, but we found it fairly easy to navigate and to walk around.

The message I received most on Instagram was about our room type and where it was located.

We booked the Deluxe Ocean View Suite which was in the building directly behind the central pool (shown above). The hotel was offering “buy five nights, get the sixth free” so we took advantage of it. We actually thought this would be too long for a beach vacation, but it was the perfect amount of time!

The room included a bedroom, living room area, and a small kitchenette closet space with a mini fridge, sink and microwave. It also had a powder bath in addition to the en suite. The balcony had a hot tub but we didn’t use the space much due to the mosquitos (I talk more about this in the tips section). Kurtis was able to spend a few mornings out on the balcony with his coffee though! The views were beautiful!

The hotel had three pools, which included one adults-only pool near the Sunset Lounge (below photo on the right). Like most resorts I’ve visited recently, people are out bright and early trying to reserve chairs. However, we found that if you didn’t have a preference on which pool you wanted to sit at, you could always find a lounge chair!

We ate at all of the onsite restaurants and enjoyed them all! I expand upon two of those in the food section below. They all had excellent food and service!

I won’t expand on all of the amenities, as their website does a great job of explaining them. But Kurtis also found the gym very well equipped, and he enjoyed getting his 3-5 mile walks in on the property each morning.

The grounds of the property were very well-maintained and the staff couldn’t have been nicer or more helpful.

Such a great property with even better people! We were very happy with our stay here!

Things to Do in Anguilla

Leading up to our visit to Anguilla, we knew we wanted to keep our vacation rather low-key and not have an action-packed agenda. However, we knew we’d want to spend a handful of days off property to explore the island! But keep in mind, it’s also a really great island if you’re just looking to relax and unwind.

Here are a few of the things we did, along with recommendations on activities we wanted to do but didn’t have time for.

Rent a MOKE to Tour the Island

We rented a MOKE through MOKE Anguilla, via the concierge at the Four Seasons. However it sounds like they work with multiple resorts on the island. It was a super easy process. You can reserve a half day or full day MOKE, and then pick up and drop off is at the hotel. It did require anyone driving to get a local driver’s license, but that essentially meant Kurtis showing his Florida license, filling out a form, and paying a $20 fee. This is also required if you get a rental car, so keep that in mind.

We toured most of the paved parts of the island, and even took a handful of dirt roads that made it onto Google Maps. We quickly found that many of the dirt roads aren’t frequently traveled and are very rutted, steep, and/or vegetation has quickly grown back in. So definitely take these roads at your own risk, and ensure you have plenty of water and full cell service/map access should you need it. It was hot on the northeast side of the island, and we even saw quite a few cacti. We made it as far as Captain’s Bay (photos below) before turning back to head back to the hotel.

We opted to do a full-day rental for one day. This allowed us to pick it up at the main entrance of our hotel and then come and go as we wished. We then just brought it back that evening after dinner, but the rental allowed us to have it all night if we chose. We realized after changing for dinner, we didn’t fit quite as well inside once we had the top on 😉

Although they weren’t the comfiest to ride around in, the MOKEs were such a fun way to see the island!

Visit The Arch

A quick MOKE ride away from the Four Seasons, our first stop in our MOKE was the Arch. We arrived fairly early in the morning (around 9:30 or so) and only saw one other couple the 30 minutes or so we were there. Having grown up in Utah and visiting Arches National Park multiple times, this is one of the smaller arches I’ve seen. But it is still very beautiful and worth a visit! There are a few little trails around and you can look out over the water from several angles since this is near the Western tip of the island.

We walked around (including out on the path that allows you to stand over the arch) and watched the iguanas. It’s a quick trip (that does require some slightly rough, dirt roads) but we’re glad we checked it out!

Visit the Various Beaches of Anguilla

Since our hotel had beach accommodations, we mostly visited the other beaches of Anguilla for drinks or lunch. But, outside of Captain’s Bay which was mostly lava rock, we found that most beaches had very soft sand, with little to no vegetation in the water.

Spend A Few Hours (Or A Day) At A Beach Bar

There are several well-known beach bars on the island. We received a bunch of recommendations to try Elvis Beach Bar, Sunshine Shack, and Dune Preserve (specifically “Sunday School” with Bankie). They’re essentially beachside restaurants and bars that also have lounge chairs, tables, and more. By mid-day, they can be rather lively and tend to have more of a party atmosphere.

The first beach bar we went to was Elvis Beach Bar mid-way through our MOKE day. It sits in an area called Sandy Ground and is a beautiful little bay. It’s a really fun spot with great music so we hung out for an hour or so and ordered nachos and drinks before continuing our journey. It was a very casual, toes-in-sand vibe, and also had lounge chairs you could use to sit oceanside.

We spent several hours one day at Sunshine Shack. We had actually tried to visit the day prior while we had the MOKE, but we didn’t arrive until later in the afternoon and it was packed. There was a line for seating and chairs, so we decided to just come back the next day when we could arrive earlier!

We came back the next day and arrived around 11:30. They are known for their ribs and barbecue, so at others’ recommendations, we ordered our food right when we arrived, and the food was delivered to our beach chairs around 1 or so once it was all smoked.

The beach is so beautiful and there are plenty of lounge chairs and umbrellas if you arrive early. So we enjoyed the waters and the beautiful views out to St. Maarten!

Other Recommendations for Things to Do In Anguilla

Following are some other recommendations I received from several of you as well as those that follow me on Instagram! Unfortunately we didn’t have enough days on our trip to try everything, but these activities all came highly recommended:

• Take a boat to Sandy Island – perhaps the most recommended activity we received. We had planned to go our last full day on the island, but the winds were 20-30 mph so we decided a pool day was a better fit. But we’d love to visit some day!
• Take a boat to Scilly Cay – eat fresh grilled lobster they catch and cook on site
• Visit St. Bart’s or St. Maarten via boat or air – it’s on the opposite side of St. Maarten
• Book a sunset sail with Tradition Sailing
• Bar hop the beach bars on Sandy Ground (this is where Elvis Beach Bar is that I mention above)

Admittedly, we didn’t receive any recommendations to eat here. But I knew I wanted to visit Malliouhana at some point on our trip, so we booked a night here for dinner. We first grabbed a drink at Bar Soleil which had breathtaking views and was located near their chic pool.

Celested is located just off the lobby and below Bar Soleil in the covered patio shown above. I recognized a lot of Serena & Lily pieces and textiles at the restaurant, and the views were gorgeous! We were the only people at the restaurant until we were nearly finished. They had a band playing and sat us right in front of it, so it was a tiny bit awkward to be the only ones clapping and watching them. The food and service were good – I wouldn’t say exceptional on either front. But still a very enjoyable evening.

Although it wasn’t necessarily a meal I’d prioritize if you don’t have time, I would still absolutely visit the hotel for a drink and to look around if you love beautiful decor and grounds like I do!

Other Recommendations on Where to Eat In Anguilla

Following are other recommendations on the best places to eat in Anguilla that we didn’t have time to visit:

• Straw Hat – make a reservation for a beachfront table. Multiple rave reviews about the tuna flatbread. A great option for either lunch or dinner.
• Jacala – make a reservation for a beachfront table
• Ocean Echo – Best rum punch on the island. Great for a casual pizza or salad. Multiple recommendations for their calypso wings, as well.
• Dune Preserve – A reggae beach bar near Sunshine Shack. Several people said they love “Sunday School” with Bankie but we didn’t have a full Sunday on the island to check it out.
• Dolce Vita – Beachfront tables at sunset come highly recommended at this Italian restaurant.

How to Get Around Anguilla

Anguilla isn’t super large by any means, however, there are definitely areas you’ll want to see that are more than a walk away. When we found out we could book MOKEs through our hotel, I really didn’t have any desire to travel around any other way!

The island is a British territory, so if you decide to drive a car or other form of transportation, just remember it’s on the “other” side of the road 🙂 Taxis are plentiful, though, so there’s really no need to drive on your own if you’d rather not mess with it.

On the day we didnt’ have the MOKE, we would use a taxi service. The taxis all appear to be locally owned and operated by the driver, so whenever one would drop us off, we’d grab their card and then call them to pick us up for our return trip. We didn’t realize we’d use the taxis as frequently as we did, so we were definitely short on cash. From our hotel, one average most fares were $20-25 each way + tip basically anywhere it seemed we went. So the expense definitely adds up! But we only used them a handful of times at dinner and one day to get to Sunshine Shack.

What To Wear In Anguilla

During the days, I was dressed very casually. Usually shorts and a tee or tank top, or a swimsuit coverup, depending upon our activity planned. In the evenings, I wore a sundress most nights. Regardless of where we went, I feel like there were some tourists that were more casual and others that were dressier. Definitely a “wear what you’re comfortable in” situation is appropriate at most spots, but most were what I’d consider resort casual.

Following are some of the items I packed for Anguilla. I splurged on a few of the dresses that I knew I could wear again for his company trip next month as well as here at home. All sources are listed below image.

SOURCES: Embroidered Dress | Raffia Block Heel Sandals | Aviator Sunglasses | All-Weather Gold Bangles – shown at the Four Seasons Anguilla

SOURCES: Mule Heel Raffia Sandals | Puffy Strap Heels | Raffia Strap Sandals | Slide Sandals | Raffia Mules | Striped Rug

SOURCES: Block Print Dress | Beaded Hoop Earrings | Raffia Block Heel Sandals | Aviator Sunglasses | Waterproof Gold Bangles – shown at the Four Seasons Anguilla

SOURCES: Linen Blend Beach Shirt | Straw Hat | Lip Balm (rose) | Gold Waterproof Bangles | Swim Shorts | Raffia Strap Sandals – shown at the Four Seasons Anguilla

SOURCES: Floral Linen Shirtdress (also here) | Beaded Hoop Earrings | Aviator Sunglasses | Braided Raffia Heels (similar here and here) – shown at Malliouhana

SOURCES: Tank Top | “Teal Blue 3” Sarong | Flip Flops – shown at the Four Seasons Anguilla

SOURCES: Striped Ruffle Collar Top | White Slim Boyfriend Jeans | Raffia Block Heel Sandals | Lantern Net Earrings | Gold Waterproof Bangles – shown at Blanchard’s

SOURCES: Striped Linen Dress | Raffia Block Heel Sandals | Aviator Sunglasses | White Resin Coral Earrings | Bracelet Set – shown at the Four Seasons Anguilla

Following are some additional clothes, swimsuits, shoes and accessories I packed for our Anguilla trip! Tap any of the images below to learn more about each item shown:

A Few Final Tips & Thoughts For Those Traveling to Anguilla

Following are a few final tips and thoughts if you plan to travel to Anguilla any time soon.

• We found that most people on the island eat late and most of the restaurants don’t open until 6:00 PM! We typically love to eat before 6:00 so it was fairly easy for us to snag a reservation around sunset (we were there before the time change). Most restaurants strongly encourage reservations so keep that in mind!
• There are several grocery stores on the island. We found it helpful to buy some extra soda, alcohol and bottled water to keep in our room. The mini bar rates were pretty outrageous ($8 cans of Diet Coke??) and the grocery stores were very reasonable. Most prices were listed in the Eastern Caribbean Dollar (XCD) but the one we stopped in converted it to USD prior to running our credit card.
• Speaking of cash/currency, there wasn’t anywhere we went on the island that didn’t accept the American dollar. Everything from the grocery store to taxi drivers to restaurants, etc. they all took the dollar (and prices at most restaurants were listed in USD). In our experience, it wasn’t necessary to have any XCD on hand!
• There were so many mosquitos on the island around dusk. Kurtis only knows that because he was with me. Ha! The first day we sat on our balcony, I had no less than a dozen bites. We realized our hotel thankfully had bug spray in the room, but I’d plan to pack some if you’re sensitive to their bites. I came home with probably 40 (mostly from the first day and then two times I forgot to spray), Kurtis came home with zero. Definitely worth packing your favorite deterrent, or bringing someone along whose blood they like better 😉
• Don’t let the weather forecast upset you! Much like Florida, rain can appear in the weather forecast most days, but sometimes it was on other areas of the island, other times it rained for 10 minutes. Regardless, you’re still in paradise so make the most of it!
• As of time of posting, note that the St. Maarten airport is under massive renovation. This meant delays at arrival (they could only accept one airplane at a time) as well as checking in. Also note that they had very limited seating and food options – including restaurants running out of food despite lines that were 30+ minutes long. Just plan accordingly and you’ll be fine!

That concludes our Anguilla travel guide! Feel free to leave any questions or comments with other recommendations so others can check it out as well! We can’t say enough good things about the island, the people, the food and the beauty of Anguilla. We highly recommend adding it to your bucket list and we hope we can return again some day!

Additional Travel Guides You May Enjoy

Following are even more travel guides and travel journals I’ve written over the years that you may enjoy. Tap any of the titles to read the full article.

• Mediterranean Cruise Tips, Highlights and Recap
• Rome & The Amalfi Coast – Kurtis’ 40th birthday trip
• Things To Do in Kauai
• Sailing The British Virgin Islands
• Southern Caribbean Cruise
• Our Napa Itinerary
• Montage Laguna Beach & Southern California
• Travel Files: Ireland & London
• Travel Files: Munich, Austria, and Venice

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