Where’s Wilson: John’s Favorite & Least Favorite Beach Vacations

Where's Wilson, The Newest ICLEF Blog

In the newest Where’s Wilson post, our ICLEF travel expert, John Wilson explores his favorite and least favorite Caribbean beach vacations. Sit back, enjoy and learn from the travel master.

Beach Vacations: Caribbean, Mexico and Central America
By John Wilson 

My first trip to the “islands” was over spring break my sophomore year at Indiana. IU sponsored a trip to Freeport in the Bahamas. My friends and now lawyers, Jack O’Bryan and Pete Huse, had the money to go on the trip. I only had my tax refund check of $250. I hitched a ride to Florida and got deck passage from Miami to Freeport on a cruise ship for $25 round trip. My friends let me (and a few others) stay in their room. I was lucky. I got to sleep under the table. Those sleeping on the open floor got stepped on. I had so much fun; I did the same thing the next year on the IU trip to Nassau.

Over the years I have upgraded accommodations, but when the days get short and gray and it snows on Veteran’s Day, thoughts turn to beach vacations. I have now traveled to over forty islands and other destinations in the Caribbean, Mexico and Central America. I have developed some favorites and not so favorites. If you agree with all, you are clearly my twin separated at birth (for better or worse). More likely you will disagree with some, agree with others, but hopefully the thoughts will help you enjoy better beach vacations.

First, why the Caribbean – rather than Florida or other places in the States? i have been asked that many times. Outside the States is not right for everybody. My neighbor went to Mexico once, got a small case of Montezuma’s Revenge (traveler’s diarrhea) and hasn’t traveled outside the States since. But, Jimmy Buffet only has one song about Miami and a bunch about the islands.

Sunset on the Caribbean Islands

In the islands and the east coast of Mexico and Belize, the water is a beautiful color of blue and the sand is white like few other places. To me, the different cultures, language, food (fresh local fish), music, lifestyle, and pace are all interesting. There are local beers and unique drinks in almost every location. Lots of times, you don’t have to drive a car the entire trip. Not only can the local people be interesting, but you can meet people from all over the world who travel to these destinations.

While weather can be variable in Florida in the winter months, it’s hard to argue with the weather in the Caribbean, Mexico and Central America from December to May, especially the islands. The surrounding water moderates the air temperature so days run in the 80’s and nights in the 70’s, every day and night. Hurricane season technically goes into December, but problems are very rare that month. Be careful about going to the Bahamas in the winter as Freeport is farther north than Ft. Lauderdale, and can be cool for swimming into the spring.

Least Favorite Trips

How bad can it be? The definition of a least favorite trip to these areas is one that I would only do for free.

Atlantis, Paradise Island, Nassau, Bahamas – One should not be in an elevator on a beach vacation. Atlantis is expensive, not known for good or friendly service, has no real Bahamian feel and the pool area is so crowded you have to do that, “go down at 8:00 a.m. and put a towel on your chair to reserve it” thing. If you need to go to Paradise Island, try The one and only Ocean Club. A classic upscale and old school hotel with a shuttle to the casino. You might meet Wayne Gretsky there. I did. There are also casinos in Aruba, Puerto Rico, The Dominican Republic, St. Croix, St. Maarten, Curacao and Bonaire. I like Curacao. It has great snorkeling, even right off the beaches.

Cancun – More elevators and the tourist zone is not real. In the 1960’s the Mexican government did a study of the area, found it had the best weather and beaches and started building hotels.* You can find good accommodations at reasonable prices and good service. Cancun is a great place to land on your way in and out out of town when going to areas that, to me, are more interesting than Cancun.

Take a look at Isla Mujeres. It’s literally in view of Cancun, but a world away. When Cancun shut down waiting for the government to organize a clean up after hurricane Wilma, the residents on Isla were each given a bucket and mop. They cleaned up and opened the island. Even with ongoing development, Isla has a village feel. Try the mom and pop restaurants on the beach under the tents. They have fresh, local Red Snapper that is addictive.

The sand, sea and weather continues down the coast, the Mayan Riviera, and into Belize. Originally, Playa del Carmen, forty miles south of Cancun, was a fishing village and ferry stop. Playa has gone from 25,000 people when we started going there to over 250,000 now. Dogs don’t sleep in the main street anymore and they have a Ruth’s Chris. It still has some of the old feel and can be navigated on foot. Accommodations range from basic to luxurious. There are numerous small communities along the coast also. Take a look at Akumal or the area south of the Mayan ruins of Tulum.

St. Thomas, Virgin Islands – What a shame. It’s an island of natural beauty which is marred by congestion and man made and man laid litter. In Charlotte Amalie, the main city, multiple cruise ships disgorge way more tourists than the town and the island can handle. Vendors are aggressive. Generally, food is generic. There is a taxi consortium that makes travel around the island expensive. If you need to stay in St. Thomas, as we do for an upcoming trip to the British Virgin Islands, there are some good B&B’s. Or look in the Red Hook area and at Secret Harbour Resort which gets consistently good reviews.

Large Cruise Ships – In my opinion, the islands are too small to accommodate all the folks coming off these ships. Generally, there are not a lot of sights on a given island. Those sights are overly crowded when the ships come in. I would rather stay at a small resort and have a thirty second walk to the beach, than pack up my stuff, leave the ship, take a taxi, go to a beach for a few hours and repeat the process to get back to the ship. if you want to go on a cruise, try a small line or windjammer type ship with fewer passengers that can go to small, low visitor islands like St. Vincent and Carriacou in the Grenadines.

Some All-Inclusives – All-Inclusives are also included in my most favorite vacations and family vacation comments to follow. Nobody said this would be easy. I suggest taking a close look at the location and reviews of food. When looking at reviews on line, especially for all-inclusives, because they tend to be the places first time travelers go, make sure their “best vacation ever” is not their only vacation ever. Food tends to be good for breakfast, okay for lunch and then dinner may be pretty boring, especially if you are going to be there for a week. Look for a location that allows you to get off the reservation. For example, Montego Bay in Jamaica is not a favorite place for me to be offsite, but Negril in Jamaica is.

Most Favorite Trips

Sailing in the British Virgin Islands – All the best of the Caribbean. Sun, sand, sea and interesting people along the way. if you wear a golf shirt to one of the small island restaurants instead of a t-shirt, you may be overdressed. The bar may be a self-serve honor bar, and dinner is likely to be a freshly caught lobster or fish. You can go “bare-boat” if you are a licensed skipper, or hire a captain. While hardcore sailors go for the traditional monohull boats, trust me, get a catamaran. Smoother sailing and much more room which is particularly nice if you get some rain. The Moorings out of Road Town, Tortola is a good operation for renting a boat. Favorite of favorites: The Soggy Dollar Bar, White Bay, Jost Van Dyke Island. The picture below was taken from the Soggy Dollar bar.

White Sandy Beach, Hopkins, Belize

There are some upscale and elegant island resorts in the BVI which are worth a look if that is your preference. They are also good for those who want to be in the area but suffer from seasickness to the degree they cannot sail in these relatively smooth waters. Look at Cooper Island Beach Club, for upscale casual and for even more upscale casual, Peter Island. Off the chart upscale casual? Try Richard Branson’s Necker Island where for only $60,000 per night, you and twenty six of your best friends, my wife and I, can enjoy his private island.

Swept Away, Negril, Jamaica – It’s an all-inclusive. Nobody said this would be easy. So why Swept Away when all inclusive are on my list to avoid? First, Negril itself has all the components I like for a beach vacation, including facing the west so there are great sunsets. The resort is on Seven Mile Beach (which is five miles long) and great for beach walks to work up a thirst. We have enjoyed Negril when staying at other accommodations.

At Swept Away, the atrium rooms that we like are one or two stories. No building in Negril is “taller than a palm tree”. Each of these rooms has a patio with a hammock and is great for the included room service breakfast.

Catamarans Outside Soggy Dollar Bar, Jost Van Dyke Island


Swept Away Atrium rooms include porch hammock and free room service breakfast

No phone or TV. The staff is very gracious and friendly. All the food is good/excellent with several different places and styles to dine. Entertainment nightly ranges from good to excellent. For better or worse, couples only and no children. It has a sports orientation, with a lap pool, basketball, spa, fitness and weight complex and all the water sports. For example, an individual half hour tennis lesson with a pro is included each day. Finally, in addition to bars on the beach and elsewhere, it has a self-serve Red Stripe beer tap on the beach.

Belize – For your first trip to Belize, go to Ambergris Caye. You fly into Belize City from the States and then catch a puddle jumper for a half hour flight to the Caye. There is no real terminal at the airport at Ambergris Caye. The security fence for the airport is a two foot tall white picket fence. Depending on where you stay, you may be able to walk directly to your accommodations. Just remember that roller bags don’t work so well in the sand. There are many choices for rooms ranging from luxurious to not. Pull up Trip Advisor or a similar site and find what you like. I would suggest you stay closer to town, but there are water taxis that ply the coast or you can rent golf carts or bikes if you are farther out. This is a great location for scuba and snorkeling, including swimming with manta rays and sharks (nurse, not white). Belize is the former British Honduras. English is the official language. The beaches are not broad but they go for miles north and south if you like a good beach walk. Very friendly folks. World class sport fishing. Take a side trip or even spend a night on adjacent Caye Caulker. If you go to Ambergis Caye and want to move on to more Belize adventures, let me know and I’ll make some more recommendations. (Take a look at Beaches and Dreams in Hopkins, Belize.)

Harbour Island, Family Islands, Bahamas – Harbour Island is four miles long and 500 yards wide. It has the most beautiful beach I have seen. The sand is light pink, and the sea is multiple colors of blue and green. Most of its restaurants are so small that you make a reservation at noon so the owners can purchase the fish and other food for the evening. Sitting at a beach bar one day, I asked the bartender for a recommendation on where to go to dinner. He directed me to a fellow sitting at the bar. He recommended Harbour Rocks. I asked him if it was any good. He said he thought it was. I asked the bartender to make me a reservation. The fellow at the bar said he would do it. And, he said he would join us. Of course, he was the owner. He was right. It was good. He invited another couple to join us for dinner. They were sailing through the Bahamas on a catamaran that was twenty feet long and only had a trampoline for them to stay on, no undercover berth. It was a great night and we sailed with them the next day. Harbour Island also has all levels of accommodations. Look at not only Trip Advisor, but also Airbnb and VRBO for other interesting rentals. If you like the small islands of the Bahamas, also check out Marsh Harbour and the Abacos.

Final Thoughts

Costa Rica – is particularly good for adventurous families as it offers kayaking, (ocean and river), zip lining, hiking, fishing, surfing and more. For adults and children too, look at Witch’s Rock Surf Camp. It has a one week package that includes your room, 1 1/2 hours of in water surfing lesson and 1/2 out of water lessons a day, plus breakfast at a very reasonable price. The staff, both surfing and restaurant/bar are the best. We wanted to play cards one night in the open air bar. They didn’t have any cards, so the bartender rode her bike to her apartment to get us some. If you go, ask for Flash as your instructor. Tell him Poppi sent you.

The spring break trip for your high school senior – Do not go the Nassau, Freeport or Cancun route for the reasons discussed above. Also, not only is it too easy to get in trouble with alcohol, drugs and worse there, some people there are too interested in helping your kids do it. I suggest you find a stand alone all inclusive, say south of Playa del Carmen, the farther in the jungle and away from a city the better. There is plenty to do and the kids can be pretty much on their own. By not being able to get off the property, they are much less likely to get into too much trouble. We had a plan where not every child’s parent had to go on the trip, but no more than three children per adult and each child had a designated adult.

Next up: The Olympics and Sochi.

*When development was started on January 23, 1970, Isla Cancún had only three residents, caretakers of the coconut plantation of Don José de Jesús Lima Gutiérrez, who lived on Isla Mujeres, and there were only 117 people living in nearby Puerto Juarez, a fishing village and military base.

Photographs may not be used without permission. Photographs © John Wilson, 2013. 


This is one of an ongoing series of travel discussions by John Wilson, retired lawyer and trust banker. John was motivated to start this series when he realized that his travel bio was more extensive and interesting than his legal credentials for doing ICLEF talks. He has traveled to forty-five states, over sixty countries and all continents except Antarctica.

If you have travel questions or tips of your own that you would like to suggest please contact ICLEF’s travel expert, John Wilson, by Clicking Here.

ICLEF • Indiana Continuing Legal Education Forum, Indianapolis, IN

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