Anguilla with Kids in Tow

We traveled to Anguilla and Nevis (check out our review on Nevis) for Josh’s 40th birthday in July of 2018. They are two incredibly different, but equally amazing islands. Although we thoroughly enjoyed our vacation, there were a few things we wished we had known ahead of time.

Anguilla is a British overseas territory and a part of the Leeward Islands. Anguilla’s currency is the East Caribbean dollar, but the US dollar is widely accepted and what we used while we were there. It is known for its powdery beaches and amazing food, so it was an easy choice for a birthday celebration!


Getting There

Coming from the West Coast, we were prepared for several airplanes and a good amount of travel time, but we didn’t anticipate how much travel it would actually be! It’s the little things that alone are not much, but they begin to add up after you’ve been on 3 airplanes to get there, and you still have hours before you reach the resort.

So we flew from California, had a short layover in Dallas, and continued on to Miami.  We had an overnight layover in Miami, which worked out OK, since we were able to visit with family for a few hours.  We stayed at the Four Seasons Miami for the night, which was very nice (see our separate review on the FS Miami).  The next day we flew from Miami to St Maarten.  While Anguilla has an airport, it is a small one that can only accommodate regional jets or larger private jets.  If you’re traveling by private jet or from Puerto Rico on a regional jet, for example, then fly directly to Anguilla.  Otherwise, your best bet is to fly to St Maarten.

Once we arrived in St Maarten, we took a taxi to the dock, where we cleared immigration for St Maarten.  We boarded a boat run by a company called Funtime Charters.  They were very professional and efficient.  They took our luggage at the airport and we didn’t have to worry about it until we got to the resort. Once the boat gets going, they have drinks on board that are complimentary, from water and juices to local beers and rum punch. The ride to Anguilla was approximately 30 minutes because the seas were a bit rough due to Tropical storm Beryl that was hanging around in the Atlantic at the time.

We cleared immigration in Anguilla, and then took a taxi to the resort.  It was a long two day journey, and it was totally worth it once we arrived at the resort! We arranged our transfers, taxi and boat, through the hotel to make things a bit easier, but it would definitely be simple enough to do it on the fly once you arrive in St Maarten.

Where We Stayed

We stayed at the Four Seasons Anguilla.  It had recently opened after refurbishment from the damage caused by Hurricane Irma. Have I already mentioned that we’re obsessed with the Four Seasons brand?! We loved them before we had children, but now that we visit FS hotels with kids, we have fallen in love with the brand all over again.  They just make life on the road with kids in tow so much easier!




Upon arrival, they escorted us to the lobby where they gave us cold towels and welcome drinks.  They even had juices in kids’ cups for the little ones. They checked us in and showed us to our room. We had an ocean-view studio room with two queen beds and a crib.  It had a nice balcony with a plunge pool, which I highly recommend with kids.  Our kids were in there daily, especially when it was too windy (because of the nearby storm) or raining to go to the beach or the resort pools. The resort provided a diaper disposal pail, baby toiletries (bubble bath, body wash, and body lotion) for the kids, and we had an array of delicious snacks to welcome us as well (fruit, cookies, candied dry fruit, water and local sodas).



The style of the resort is one of understated elegance, with white fabrics, wood and stone elements, and taupe colors throughout. It is located on the northwest side of the island, on a bluff that overlooks two of Anguilla’s most beautiful  beaches, Mead’s Bay and Barne’s Bay. Barnes’s Bay is more pristine and quiet, while Mead’s Bay has more action. The Four Season Sea Center is located on Mead’s Bay. There you have access to snorkeling gear, kayaks, paddle boards, and more.

Where We Dined

Many of the restaurants that we had read about and had been recommended to us were closed for refurbishment from the hurricane, so we were limited in our choices. However, the restaurants we experienced only confirmed Anguilla’s nickname as the “Culinary Capital of the Caribbean”! We enjoyed a delicious seafood dinner at Coba, which is on property at the Four Seasons.  It has a bluff top location with views of both Barnes Bay and Meads Bay.  It’s perfect for a sunset dinner.  Our dining experience, however, was at the family owned and operated “treehouse” restaurant called Veya. The laidback atmosphere paired with immaculate service and delicious food, made for an absolute culinary highlight! The lobster risotto there is just exquisite!

Overall Experience

Although our time in Anguilla was clouded (literally) with a looming Tropical storm, we made the most of it.  We thoroughly enjoyed the delicious seafood and tropical sauces that they pair with their dishes, The beaches were absolutely stunning, and the Four Seasons resort is a true gem of a resort.  I think the plunge pool on our balcony saved the day, since our kids were able to frolic and play there, despite the weather. We look forward to a return visit, where we will be able to enjoy some water activities and see more of this beautiful island.  In terms of what we wished we had known, well it is quite a journey to get there from the West Coast, so we will plan our time differently.  We will stay for a week, rather than the 4 days that we planned this time around.

15 response to Kid-Friendly Anguilla

  1. […]  We were fortunate enough to visit Nevis (along with Anguilla, see our review of Anguilla here) the past July for Josh’s 40th birthday.  We had not heard of Nevis before this trip, and we […]

  2. Alley says:

    Absolutely worth the travel time to see this beauty! Would love to go one day!!

  3. ania says:

    i love Four Season as well, and this place looks awesome

  4. Amanda says:

    This is beyond beautiful. I only dream of a trip like this 🙂

  5. Shel says:

    What a beautiful island! The beaches are phenomenal! And such a great place to celebrate a birthday.

  6. Dianne says:

    I’m so glad to read about your trip. This Four Seasons Resort has been on our radar. It’s a bummer when weather doesn’t turn out the way we wished.

  7. Gina says:

    This is so beautiful!! Would love to plan a trip here!

  8. Jamie says:

    What a dream! Beach destinations are our family’s favorite vacations! Pinning this for later!

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