The days are getting longer, kids are out of school and you been saving those vacation days since the holidays so you can get away from your annoying coworker who talks about how cute her dogs are everyday. The thought of going on a vacation, sitting on the beach with sand between your toes, clear blue seas and sipping a fruity beverage with an umbrella in it is amazing but the idea of planning that trip isn’t so much fun. Trip planning can be a headache, especially when you’re the one in the family who has to plan it. So many things one must consider, how long, who is going, where to? Maybe the most important part of this process is how much money am I trying to spend? We all aren’t Jay Z and Beyonce who can afford to rent a yacht off the coast of St. Barts for a few weeks, we have to think a smaller scale but you can still enjoy the many wonders of the Caribbean without taking a second mortgage on the house. I’ll give you a few pointers to have a great trip and it is reasonably affordable.

The Caribbean islands are islands that border or are surrounded by the Caribbean Sea, many were claimed by European countries after the voyages of Christopher Columbus, and sometimes they are called the West Indies which was used by all European nations to describe the territories they acquired in the Americas. That’s one of the reasons you will find a large European influence in the Caribbean as well as people speaking Spanish, French, German and Dutch on the islands, also many Europeans live in the Caribbean but enough with the history lesson my inner nerd is starting to come out. I personally have been to the Caribbean several times on vacations, Puerto Rico, Mexico, Dominican Republic and Jamaica so I can speak from experience that it’s possible to enjoy a vacation in paradise without breaking the bank.



Puerto Rico

The Caribbean is full of resorts all up and down the coast of their sandy white beaches, Sandals, Couples, Iberostar, St. Regis, Four Seasons the list goes on and on. These resorts offer everything from pools right outside your room, private butlers, endless drinks but these premium amenities come with a premium price tag. I’ve stayed in a Couples resort and believe being waited on hand and foot is something I got used to really quick, I’ve also stayed amongst the locals and that was just as an enjoyable experience as staying in a 4-5 star resort. There are many condos and beach homes all over the Caribbean, many are owned as a second home or vacation home. Most people who own these properties rent them out short term and long term to people wanted to visit the area, many sites offer these homes at very reasonable rates. Sites such as Flip key, Home Away, Vacation Renter by Owner all have properties just about anywhere in the world you can think of. I rented a condo in Punta Cana, Dominican Republic for me and my wife for 6 days at a rate of $50 a day, no it wasn’t in the slums it was an area of the city with brand new condos being developed and two blocks from Bavaro beach which is 20 miles of pristine Dominican coast line.

Many times when you stay at a resort you are in a secluded area with just other tourists but by renting a condo in the city, you get to see what is going on in that city. The official language in the Dominican Republic is Spanish, many locals don’t speak any English so the language barrier could be a problem but most of the business owners speak English. Also by staying in the city I was about to found out where the locals hung out and eat at the local restaurants, getting authentic cuisine. I was lucky enough to befriend a Haitian taxi driver while we were there and he was my unofficial tour guide showing me all the best places to get some great Dominican food. When I went to Puerto Rico I did stay at a resort for a friend’s wedding but the first night there was the only time we ate food at the resort during the 5 days we were there. I rented a car and drove around exploring and eating the local food, we found a nice mom and pop restaurant not far from where we stayed with some of best Arroz con pollo and plantains I have ever ate and only for a few dollars. Puerto Rico has a great food truck scene as well, you just have to be a lil bit adventurous while you’re on vacation, most people in the Caribbean are very laid back and friendly, if you ask them for a recommendation on where to eat they will guide you in the right direction.

If a resort is what you desire, many will let you pay in installments if you don’t want to foot the bill all at once and it gives you time to save some money before you take you trip, most require full payment within 30 days of arrival but you can book your dates at many resorts up to two years in advance. If you are able to book your trip in one payment, booking the resort and flight together can save you hundreds of dollars. The resort sites often let you reserve flight and resorts together, as well as many travel sites such as Expedia, Orbitz, Travelocity and one of my favorites Cheap Caribbean. The Internet is maybe the most useful tool you have when you want to travel, endless resources are at your fingertips, Trip Advisor is my go to site when I’m deciding on a destination. They have real reviews not those fake company websites saying how wonderful there hotels are, these are from people who have been to these hotels, restaurants, sites and many advice columns with people more than willing to answer any question you may have.

Time of year also plays a part in the price of going to the Caribbean; there is a high season and low season. In the Caribbean the high season is considered the wintertime, Thanksgiving to New Years rates tend to be higher and Spring Break. This is also when my Europeans travel and Americans living on the East Coast trying to escape the cold weather. The rates tend to go down in the summer, I know that seems backwards but this is hurricane season from June 1st til November 30th, don’t let that scare you away, you can get some really great prices traveling during these months. I had one of my trips delayed a day because of a hurricane but I was still able to go and enjoy my trip. If you do book a trip during hurricane season or any trip be sure to invest in some travel insurance just in case some unforeseen emergency occurs you can be reimbursed for your trip and get that money so you can go at another time. Resorts usually will refund your money but airlines will only give you credit if you have to cancel then charge a booking fee for changed dates so it’s best just to get travel insurance so that is one less worry that you have.




Finally don’t be afraid to book your own trip, travel agents offer a great service but that comes with a price they have to earn a living too. Like I said earlier take advantage of the internet, don’t let it intimidate you, yes there are thousands of travel sites and blogs but find one you like, like this blog (smile) and let that be your go to for information. The world is a big place and it’s waiting to be discovered, so get out there enjoy it so you can make all your friends jealous with your stories of world travel and adventure.