Our Trip to Anguilla

We just returned from four days in gorgeous Anguilla, and today I’ll share with you all of the details.  We were in town for some business that we were able to piggy back on top of a friends wedding, so I’ll share with you how we got there, where we stayed, and everything you need to know about traveling to Anguilla!

Getting to Anguilla from Miami

We are located in South Florida, so Miami was the only option for traveling to Anguilla.  American Airlines takes a jet that’s operated by American Eagle, meaning it’s a smaller aircraft.  When you travel to an island of only 15,000 people, you usually get an aircraft like this.  The slow season shows only one flight, but during high season as it is right now in January, they have two daily flights both to and from Anguilla.

Upon boarding our flight we found many familiar faces and found out there was another wedding at where we stayed, the Four Seasons Anguilla, and barely any other people on the flight were engaging in either of the two weddings, so that tells you how quaint the island is!

Clearing Customs and Exiting the Airport

Upon arrival, the Four Seasons had a sign for us and immediately directed us to a waiting van where they added the $35 fee to our room. That was definitely a nice touch.  Customs and immigration were very easy. They asked our trip dates, where we were staying, stamped our passports, and let us in.  Easy, peasy.

I will say, the Anguilla airport is TINY!  It’s something that you have to see to believe.  It’s very primitive and run down, and the funny thing is that there are more private jets than commercial airlines.  In fact, there is only ONE GATE at the airport!  I simply can’t make this up. It’s quite eye opening for a place with so much beauty and wealth.

Things to Do in Anguilla

We found the island gorgeous and perfect for a beach escape, but other than the usual Caribbean stuff like parasailing, snorkeling, going out on a boat to explore, and seeing caves, there aren’t many things to do in Anguilla.  Check out that link with all the options, as we made a pretty big list of things you can do on that page.

We spent time cruising around the island on what’s called a “Moke.”  It’s a 1950’s looking car that allows you to tool around the island and see things in a very relaxed vehicle.  It’s almost like a golf cart that goes much faster.  I rented it for $140 and was issued a 72 hour drivers license with that rental.

moke rentals anguilla
We saw the entire country in half a day thanks to this guy!

We also did plenty of hanging on the beach at Mead’s Bay.  It’s gorgeous!  The Half Shell Bar, which is part of the Four Seasons, is a great casual vibe that services the beach as well as their small outdoor (covered) patio deck.  It’s a great place to catch amazing scenery and the crystal clear blue waters that make Anguilla special.

Dining Options

You won’t find a ton of dining options outside of the big resorts in Anguilla.  There are some, but on a limited four day itinerary with a lot of Anguilla wedding events to be a party of we were unable to explore as much as we would normally do.

crayfish risotto

Salt, which is located at the Four Seasons, offers an expansive menu for all meals, including a large brunch buffet and a great dinner. My Crayfish Risotto is pictured above. It’s very scenic.

salt anguilla
We had a great backdrop at Salt!

Here is a photo of the breakfast area at Salt.

anguilla four seasons salt restaurant

Is Anguilla Expensive?

Yes, it’s very expensive.  Most of the Caribbean islands are this way, but I found this to be on the upper echelon of prices.  Even Grand Cayman felt a little cheaper, but at these levels, you can’t really go on a budget because you get what you pay for.

The one exception was the great beach bar called The Falcon Nest we found while tooling around in the Moke.  The ice cold Corona beers were only $4!

Falcon Nest
$4 Coronas!

All in all, this trip was more about the wedding than anything.  While it wasn’t our wedding and I’m not one to post other people’s pics online without asking, I can say it was very lavish, well organized, and fun!  I’ll post pics once they share them online – so bookmark this page and come back if you want to see those.

It was at the Savi Beach Club adjacent to the Four Seasons Hotel and it was to the nines!  Bottles of Dom P champagne flowed and the dancing went until 2 in the morning!

Would We Go Back to Anguilla?

Absolutely. In fact, we’d recommend renting a villa at the Four Seasons and will probably opt for that next time.  The lobby bar is lively at the hotel, but we are more adventurous in the likes of hitting the town and finding some vibrance, so if having limited options like one lobby bar open late night and only a couple places to eat on property, Anguilla may not be for you.  We had dozens of friends to share the experience with and catch up with, so that made the trip for us.  It’s peaceful, stunning, has a great gym, spa, and fitness facility.  You really can’t go wrong here.  Now, I’m still liking the abundance of fun that the Ritz in Grand Cayman offers, but that place is very special to us as that’s where we got engaged and I’ve been visiting the Caymans since the 1990’s.

Leaving Anguilla and Departure Tax

When you leave Anguilla, make sure you are there early enough for your flight, but don’t plan on being there three hours early or you may lose your mind.  We were two hours early and didn’t really expect there to be only a tiny room with 7 tables and five bar stools to hang out at before you are asked to go to the one gate.  Yes, the one gate!

You’ll have to show your passport and pay a $28 departure tax prior to going through security and to your gate, so keep that in mind. You can’t miss it, as it’s in the center of the area and that’s where they will issue your boarding pass.  The boarding passes were NOT available on the American Airlines App, so I have to assume that’s just how they operate things in Anguilla.


I can say that this was a very successful and fun trip!  I’d never thought of going to Anguilla, but I’m glad we did, and we made many memories there – most importantly – sharing our friends very special day.

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Tim Schmidt is a 20+ year Entrepreneur and Digital Marketer. A Fort Lauderdale-based "Digital Nomad," he enjoys traveling as much as possible with family and friends. AllWorld is his escape to document all of his adventures, including being a hardcore "foodie." He has property in Costa Rica and visits several times each year and is happy to offer his expert advice for planning your trip.

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