Vacation on a Boat in the Caribbean

Archived Q&A and Reviews


Sailing vacation in the Caribbean with grandparents & kids

June 2016

My inlaws are experienced sailors and have a dream of taking a family vacation next year with their children and grandchildren in the British Virgin Islands. At the moment, they are proposing a 40 ft catamaran for 10 people (3 couples, and 4 kids ages 4-10) for 10 days. The 4 kids would share a double cabin and 2 foward berths. Each couple would have their own double or queen berth. Has anyone done something like this with this many people/kids?

Recommendations for about boats, activities, days ashore, length of trip or just general advice? My spouse and my sibling-in-law grew up sailing/racing, but neither have done much in decades. Nobody in the group has ever done a trip like this with kids. smooth or stormy

I have been on such and adventure with small/young kids in the Caribbean and have to say you will have one of the best times of your life. A forty-foot catamaran is perfect. It's a much smoother sail than a sailboat.

Ten days is about right. Less and you are jet lagged, more and the magic wears off. My adventures have lasted from anywhere from 10 days to a month.

You didn't say what islands but it's a lot like driving across Europe. You will find things for the adults and kids to do. Depending on where you will be the islands are spaced a few hours sail apart so everything changes. One day you might be on a Dutch island, the next British, and the following day French.

Buy all of your food local on each island and get a taste how different everything can be.

Bring or make sure you have snorkeling equipment. There is always something to see or do.

BUT... remember you are on the open ocean help is not a 911 call away. Your life is in the hands of the captain of the ship. If you don’t have confidence I would hire a captain. A local captain knows where to go, what to do, the good beaches and will know what’s happening. (Weather, events and most importantly where the pirates are. - I'm not joking, there are modern day pirates.)

You will be on the open ocean and there are risks. Just so you know what you are getting into you might want to a listen to This American Life - 525 Call for Help May 9, 2014.

As they say in the story thousands of people every year do exactly what you are doing. Many with kids under one or two years of age. This is not a Disney vacation where everything is kid-proof. The only way you will have a wonderful time is if you trust your life and the life of your kids to the captain. If not hire a hire a captain.

Don't miss out on the trip. Do what it takes for you feel COMPLETELY safe otherwise you won't enjoy the adventure.


Non-hotel rental in the US Virgin Islands

May 2006

I will be traveling to the USVI for the month of August and would like to know if anyone can refer/recommend any non-hotel rental properties on St.John or St.Thomas. Thanks

I’ve been to the Caribbean many times, St. John’s /St Thomas/Tortola with kids, ranging from 2- 14. I found the best accommodations are bare boat rentals. A bare boat rental comes with a Captain and possible a mate. If you want meals you can arrange for a chef and wait staff. In my opinion it’s not as much fun, I love the local food. The kids love Cheese burgers in Paradise.

I think this is a lot safer for the kids then a hotel/vac rental. And you get a local the Captain, who knows the local scene. If you don’t like where you are, pull up anchor and in an hour or two you can be at another beach/bay or island. In my opinion this is the greatest. One thing that blew the kids minds were the night time swims. Dive in and the water lights up from the luminescent bacteria in the water. Something they have never forgotten.

One last thing, you didn’t list ages of your kids, but there are some incredible snorkeling spots. And be sure to take in a swim with the rays. Don’t’ forget your underwater camera