Explore the Possibilities with Your Kids

Yao Yao’s Top 10 Islands: #5 Anguilla

Yao Yao’s Top 10 Islands: #5 Anguilla

Yao Yao’s Top 10 Islands: #5 Anguilla


It’s not hard to imagine why Yao Yao loved Anguilla. But what makes it so special compared to all the other islands she’s been to?  The answer is not too hard to guess. . .

The trip was my brainchild, and it was a very last-minute decision. Like many parents, I have worked most of my adult life and always felt the pull between work and home. So time away with Jim and Yao Yao is sacrosanct, and anytime we can knit a few days together, we’re off!

I found myself in the enviable position of having more flexibility in my schedule than my husband and thought it would a great opportunity to spend time alone with Yao Yao. It’s something we do every few years, and I highly recommend it.

So, it was Spring Break, and I was looking for warm weather and relatively easy flights to and fro, trying to avoid anyplace where big groups and Disney-esque activities were prevalent. I also avoided places Jim had expressed a big desire to go to, to avoid tantrums and pouting because he was being left behind. After all, a little sensitivity is called for in these situations.

I was fortunate to secure a hotel at this late date, though I paid dearly for the flights. I had a guidebook, a few Anguilla travel articles, and several handouts we’d picked up at the airport. Turns out we didn’t need most of the information. We had one week of doing what we wanted, when we wanted, for as long as we wanted. And here’s what transpired . . .

Perhaps it was that it was just the two of us on this trip — no “adult” conversation to be saddled with, just the two of us to make critical decisions like: “Should we walk to dinner or drive?” “Wanna eat inside or out?” “Snorkeling or tubing?” Actually, the answers to those questions are what elevated this island to Yao Yao’s Top 10 Islands list.

With some dumb luck, our location turned out to be perfect. Though we eventually drove and walked much of the island, there were plenty of things to see and do “right in our own backyard.” This was an easy trip. This was a vacation.

Something else happened, too: I shifted out of my typical role and took on some of the activities and tasks Jim usually handles in his manliest fashion. He loves to drive in other countries, and to put it gently, he’s more . . . well, assertive behind the wheel than I am. (That’s putting the best possible face on it.) But I’m happy to sit back and let him figure out the new car, laws, and rules of the road. When I travel abroad for work, I typically grab a cab or have the luxury of a car service. So when we go to Asia or anywhere that I have to navigate difficult terrain (or contend with other cultures’ driver quirkiness), I’m happy to step aside and let Mr. Andretti take the wheel. This time, I took on that role of getting the two of us from point A to point B, all while trying to remember to stay on the left side of the road. This became one of the really silly things Yao Yao and I did together. At home, she was still sitting in the back seat — I called it “Driving Miss Yao Yao.” But in Anguilla, she sat up front, and became both navigator and “wing-man,” which caused mayhem and laughter as we repeated our mantra every five minutes: “To the left, to the left, to the left, left, left,” to the tune of “The William Tell Overture.”

I have a “bum” arm from an accident years ago, so I will often acquiesce to Jim if there is a water sport where Yao Yao wants parental accompaniment, especially if the water is really cold (under 86 degrees). I’m the camp photographer, and unless it’s like river rafting or another daylong activity, I slip into my photographer role. Well, with Dad toiling away in the salt mines, and Yao Yao wanting to go ocean tubing, I quickly raised my hand and said, “I’m in!” We had so much fun, and to Yao’s delight, I fell out of the tube, doing a lovely spread eagle dismount — something she still likes to remind me of. Thankfully, there are no photos!

Perhaps my lack of planning was part of the success of this trip, and why it ranks so high in Yao Yao’s estimation? No journal to write for her part, no massive reading on my part. Just a map, a car, and a carefree attitude, and off we went — and for a good part of it, she led the way… Footprints on Anguilla

Islands We Have Known & Loved

Harbour Island
St Martin
St Bart’s
St Vincent
Nova Scotia
Block Island
Martha’s Vineyard
Los Roques
Ile de Re

Venice Burano
Isola di San Michele
La Maddalena
Isola Maggiore

Hong Kong
Koh Tao
Koh Samui
Koh Samet


I realized how different it is traveling as a single parent. It’s much easier as Yao Yao has gotten older, but I remember taking her alone to St Bart’s and St. Martin, and my eyes and hands had to be on her 24/7. I would fall into bed exhausted and usually wake up to her staring at me, asking, “When’s breakfast?” Then it would start all over again. . . .

I have deep admiration to all you single mothers and fathers, not so much when you travel — that’s the easy stuff —but every morning, every day, and every evening. Amazing . . .


The first thing you should know is Anguilla is great place to bring kids. There are miles of beaches with families swimming, kids building sand castles, no loud music blaring or loud drunken tourists. The restaurants — even the fine dining ones — are more than accommodating to kids. Best of all, there were no malls or cruise ships ( at the time we went) so even with all the construction and luxury villas, it still feels like the Caribbean. It’s a small island, only 16 miles long and three miles wide, and the size gives you an opportunity to quickly get the lay of the land. The Valley, the island’s capital and home to many of the historical sights, like Wallblake House, a plantation home built in 1787, as well as the Airport and Blowing Point.   It’s well worth exploring.

Getting there:
Fly, Boat, Ferry and …  Here are some good resources for helping you get from wherever you are to Anguilla.
La Vue Anguilla 
How to get there…

Where to stay…

There are some lovely hotels and it really depends on what activities you’re interested in. I was sad to see a lot of construction going on when we were there, so I hope they don’t overdevelop.

The Viceroy is hip, sophisticated, modern, and chockablock with amenities like private cabanas. No, it’s not cheap, but it’s the Caribbean
Viceroy on Anguilla

Malliouhana Resort
Newly renovated. I haven’t been since it was renovated so will not opine on the design, but they have a ton of amenities and are well situated on the island.
Malliouhana Resort

Anacaona Hotel
This hotel is the bargain of the century. It’s well located, the people are lovely, and their beach is . . . well, it’s the same beach as the Viceroy’s, if you catch my drift. But when you compare the cost to some of the other hotels, you might just be able to look beyond the dated fixtures in the bathroom.
Anacaona Hotel on Anguilla

What and where to eat…

Okay, this is a tough one, as there are so many really good places to eat. I have been on other islands where you pay New York (or Paris) for faux French fare and I begin to wonder, why not embrace the island’s food traditions? Anguilla does. However if you want sushi, tacos, or burgers, you can have that, too!

Blanchard’s Beach Shack
The food is fresh and innovative, and the ambiance is pure fun — tables are right on the sand. It was always busy, and one afternoon, they were so busy that they stopped taking orders for 20 minutes. Oh well, guess we’ll just have to sit with our toes in the sand and mope!

Blanchards Restaurant
A bit more formal restaurant — the food is good, but Miss Yao Yao much preferred Blanchard’s Beach Shack.

Viceroy Lounge and Restaurants
There are five dining options at the Viceroy Hotel: Sunset Lounge, Coba Restaurant, Bamboo Bar and Grill, Aleta, and The Half Shell. The Sunset Lounge has sushi and appetizers and is perfect if you don’t feel like a long, protracted dinner. We really enjoyed the Bamboo Bar and Grill for lunch. The service is not fast, so with small kids, make sure you ask them to bring their meals first or order an appetizer to tide them over. I really thought the food was very good, and, more importantly, so did Yao Yao. I was surprised, as it’s more stylish and formal than many other eateries on the island. And yes, she wore a dress!

Now this was a surprise, and I don’t think we would have gone if Jim had been with us (he’s a Mexican food snoot). But I’m so glad we did! The food (way too much food) was really good.
Picante in Anguilla

The Sandbar
A great place for tapas and drinks, and it’s right on the beach. It’s not ideal for toddlers in the evening, because it gets busy with the bar crowd. I liked it right at sunset and it was just lively enough to feel like you weren’t eating with the Geriatric Crowd. The food is good and you sit right on a deck overlooking the beach. Yao Yao loved the food, but thought there wasn’t enough variety!

Straw Hat
I know a lot of people love this restaurant, but I was singularly unimpressed. But perhaps we hit an off night? ☹

Smokey’s at The Cove
This is a fun, casual beachside restaurant on the cove. It’s past a really sad looking group of horses for rent. Sit on the deck, play the beach games, and enjoy the beach fare. It’s pretty good, not fantastic food. I know many complain about the service, but frankly, where are they rushing off to?
Smokey’s in Anguilla

What to Do
Okay, here’s my first recommendation: Do nothing — nothing! Sit, watch the water, admire the shells, read a book, swim, and explore the reefs. Relax on a hammock. Take a stroll. You get the idea.

Swimming with the dolphins
Horseback riding
Day trips to other islands: St. Maarten, Nevis, and St. Bart’s
Bike riding
Cave tours
Museum tour
Salt water pond tour
Caves and trail tour
Art galleries tour

Other great resources
Frommers Fast Facts on Anguilla
Anguilla Beaches
Anguilla Travel & Leisure Article
Anguilla Afar Magazine

Glad I Could . . .
Yao Yao I could speak English on Anguilla and that did make things easier.
My mom let me pick the restaurants and that was really fun. I like the Viceroy chain of hotels, so we had dinner there twice and a really good lunch.
Samantha – take this time to spend with Yao Yao.

Favorite Restaurant
Yao Yao – Blanchard’s Beach Shack was my favorite place to eat because it’s fun, it’s on the beach, and they have a lot of variety, from lobster rolls to fish tacos. We could walk from our hotel and it’s casual, so I didn’t have to dress up.
Samantha –  This is a really tough one.  I would have to say Blanchards Beach Shack because Yao Yao loved it so much.

Random Act of Kindness
Yao Yao – Our hotel was so nice to us. They made me a mango smoothie when we were just sitting and reading. One night I wanted ice cream at Blanchard’s, but we were having a late dinner on the other side of the island. They let me get my ice cream and put it in their freezer, so I could eat it when I got back.
Samantha –  Yao Yao got up early one morning and got dressed for a beach run with me because she knew I was missing my work out!

Best Part of the Day
Yao Yao – walking on the beach in the morning with my mom.  There were no other people and we got to look at the foot prints of dogs, birds and other animals.
Samantha – We had a nice terrace so every evening we talked about our day, read or sketched and then called Jim. There is something magical that happens when you have your child all alone with long sunny days and leisurely evenings.


Really Liked . . .
Yao Yao Our beach was really nice and the water was warm enough for my mom to swim with me. It has sand dunes I could jump off, and you can also walk to the Viceroy hotel, which I really liked.
Samantha How effortless this trip was. We did not have one issue with weather, food, activities, or reservations. It was seamless.

Yao Yao – Swimming with the dolphins was so fun. They feel so different than I thought they would. They pulled me in the water and then two of the dolphins pushed my feet so I could actually stand up. But in a way I feel bad for them: It’s hard, because it was my highlight, but I felt bad because they didn’t have a choice and they were trapped.. We read about it when we got home. It’s complicated because I want to preserve sea life, but I also wanted to swim with the dolphins. I don’t think I would do it again, but I am glad I got to.
Samantha – Watching Yao Yao sitting on the hammock taking pictures of the butterflies with a huge smile on her face.

Best Idea
Yao Yao – My mom didn’t make me keep a journal. She usually makes me do one on every trip. I did take photographs of the lizards and dolphins.
Samantha  – Taking a walk every morning on the beach with Yao Yao. It was a great time to walk, with no distractions — and we typically had our run of the beach. We spent a fair amount of time following animal tracks!


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