Families flock to the Caribbean for great deals in summer
Snorkeling is a fun activity with kids

Families flock to the Caribbean for great deals in summer

In summer, you’ll find cheaper air fares to the Caribbean than in winter, too, which will enable you to experience more far-flung locales. Look for deals in the Bahamas, for example, that include free airfare from Nassau to the outer islands. But be forewarned that especially if you plan to travel in August or September, a tropical storm might rain on your parade.

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Families can enjoy sailing and racing on island of Anguilla
Sailboats ready for racing at the Anguilla Youth Sailing Club

Families can enjoy sailing and racing on island of Anguilla

Sail racing is the island of Anguilla’s national sport dating back to the early days of the 20th century when Anguillan men on their way back from working in sugar cane fields in the Dominican Republic would race their schooners home. In fact, the unique design of the racing boats here evolved from fishing boats that would fish as much as 40 miles off shoe

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On Anguilla, a couple aim to make a Caribbean destination affordable
Anacona Hotel Anguilla

On Anguilla, a couple aim to make a Caribbean destination affordable

The Ricketts want their little hotel and villa business to show people that Anguilla is not only for those who can afford five-star luxury. The hotel also serves as the island’s unofficial cultural center. In fact, the restaurant is crowded the night we visit with locals and visitors alike for the weekly dance performance that tells the story of Anguilla.

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Families welcome for sun and fun on the tiny island of Anguilla
Farming on stilts in the hydroponic garden at CuisinArt Resort Anguilla

Families welcome for sun and fun on the tiny island of Anguilla

Locals are quick to tell you Anguilla, a British territory, isn’t only about the beaches, though their motto is “tranquility wrapped in blue.” “I have lived in Anguilla for 20 years and the thing that never changes is the people,” says children’s book author Jo-Anne Mason, originally from Brooklyn.

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Spread the word: you can find affordable family vacation spots in the Caribbean
Anacona Hotel Anguilla

Spread the word: you can find affordable family vacation spots in the Caribbean

Sue and Robin Ricketts started Anguilla’s flourishing villa business—ideal for multigenerational families and now manage some 80 villas on the island from the most luxurious ($1,000,000 a week) to totally affordable (a few thousand). Now they also run the boutique 27-room Anacona where rooms can be as low as $150 a night and all kinds of special programs—tennis, sailing, wellness, biking, yoga, art…...

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In Anguilla everybody sails, especially the kids
Sailboats ready for racing at the Anguilla Youth Sailing Club

In Anguilla everybody sails, especially the kids

The Anguilla Youth Sailing Club that teaches local as well as visiting kids to sail (look for programs through the Viceroy Hotel and others) “Kids really rally round the boat racing…we start to teach them at age four,” says Paul Koeniger, who oversees the youth sailing club.

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A day well spent at the stunning new Viceroy Anguilla
Sunset from the infinity pool at the Viceroy Anguilla

A day well spent at the stunning new Viceroy Anguilla

We spent the afternoon at the stunning Viceroy Resort down the road from where we are staying that employs 600 people for their 166 rooms. Did I mention the five-bedroom villas that rent for as much as $17,500 a night?

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Time for a little relaxation and indulgence at the CuisinArt Anguilla
Serving up spiny lobsters at the CuisinArt Anguilla

Time for a little relaxation and indulgence at the CuisinArt Anguilla

At the CuisinArt Resort in Anguila. I indulged in a facial (anti-aging of course) and a soak in the “healing waters” pool that offers a combination, I’m told, of mineral sea salt and fresh water that is supposed to help my aching knee.

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Five days in Anguilla on a best girlfriends getaway
The mile long beach at the CuisinArt Anguilla

Five days in Anguilla on a best girlfriends getaway

We’re here on a girlfriends’ getaway ensconced in a huge three-bedroom villa with its own pool, kitchen, and beach. I’m sitting aside the pool and hear the crashing waves as I write this. Did I mention the mile-long beach?

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