Kelly Durham

The Caribbean Contessa

My interests are definitely people and travel! I am a major Type A personality! I left my job practicing law two years ago, so that I could eliminate some of the stress and finally be able to place my family at the very top of priority list! That was the best decision I ever made! I now run a relatively stress-free homebased internet business, making more money than I was practicing law! Go figure! My legal, political and real estate careers have taken me to the Caribbean quite frequently over the years. As a result, I am known on the internet as "The Caribbean Contessa". I send out a free weekly ezine, entitled, "The Island Lover's Guide to the Caribbean" sharing the information I obtain while visiting the islands! I feel very blessed to have the life I have. Although I have always worked extremely hard to get where I am, I also truly believe in the power of "The Secret", and I concentrate on living my life that way each and every day. I would love to converse with people who have visited any of the Caribbean Islands, and I would like to compare notes on the pros and cons of both vacationing and residing in the islands. I would like to hear your thoughts about the restaurants, resorts, transportation, etc.





Travel Blog Posts



Many first-time cruisers experience some anxiety! I remember that feeling very well! I remember asking myself: "What should I expect? What is expected of me? Where do I go? How do I keep all of this paperwork straight?" Well, trust me, you can relax! It looks so much more difficult than it really is! I am going to take you through the steps of your first full day on the ship! There really is a routine that is followed on every cruise, and if you are aware of the routine, you are going to look like a pro! Once your cruise is booked, all of your documents will arrive in a rather thick packet in the mail. Don't panic. It looks much worse than it is! Please do read everything thoroughly, but a once over on ... read more




Oh my, my, my! What a wonderful summer this is! So far, the weather has been just as gorgeous in Kentucky as it has been in the Caribbean! We have many beautiful lakes and mountains to explore, but I still have to constantly have my fix of palm trees and magnificent beaches! Not to mention-my sinus and allergy issues completely disappear in the Caribbean! It's so wonderful to be able to breathe! : ) We just returned from Anguilla, and, as usual, I have tons of awesome information to share with you! There is no way I will be able to squeeze everything into one issue, so you will get at least two issues out of this island! Anguilla, which rhymes with "vanilla', and means "eel" because of the eel shape of the island, used to ... read more



The Caribbean Contessa icon
The Caribbean Contessa
October 1st 2006

Montserrat, at 12 miles long and almost 7 miles wide, was once known as a 'haven of tranquility'. The island was most appropriately named "the Emerald isle of the Caribbean ". It was a slice of the old Caribbean with a smattering of beaches and hotels, and a lush, mountainous interior that invited exploration. The island's peaceful surroundings were shattered by the devastating eruption of the Soufriere (French for sulfur) Volcano, known by locals as Chance's Peak, in 1995. As ash, rocks, and lava rained down from the newly reactivated volcano, two-thirds of the population of 12,000, the entire southern portion of the island, was evacuated. In 1997, the increased volcanic activity destroyed the abandoned capital, Plymouth . At the present time, volcanologists constantly monitor the activity, and though they can predict the activity, they have ... read more



Published: October 1st 2006Central America Caribbean » Antigua & Barbuda » Barbuda
The Caribbean Contessa icon
The Caribbean Contessa
October 1st 2006

“Antigua--a different beach for every day of the year!” We just finished up with all of the Derby activities here in Louisville, Kentucky, and what an exciting week it was! With all of the air shows, fireworks celebrations, galas, parades, brunches, lunches, dinners and tastings, I am thrilled to sit still for a few moments and provide you with more awesome information on Antigua! Speaking of special events, April and May are very exciting times in Antigua as well! The Antigua Classic Yacht Regatta was held April 19-24th! Mark your calendar, because the 2008 Regatta will be held April 18th-23rd. What an event! The Regatta has maintained a steady growth since its 1988 birth with 7 boats. It now hosts between 50 and 60 yachts every year and enjoys a wonderful variety of competitors including ... read more



The Caribbean Contessa icon
The Caribbean Contessa
October 1st 2006

I'm thrilled about the subject-matter of this entry of what I call my "Island Lover's Guide to the Caribbean", because this is one of my all-time favorites--Antigua! In fact, I have so much awesome information that I want to share with you about this Caribbean hot spot, I'm probably going to break this down into a couple of entries! Even though most of my initial visits to the islands were during my days as a lawyer/lobbyist and considered "working trips", I quickly learned that each island has its own particular style. Now that I travel mainly for the purpose of experiencing what each island has to offer, I can tell you that the only way to get a real feel for the islands and their varied landscapes, exotic flora, bustling waterfront towns, and friendly laid-back ... read more






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