Tips for Trips, Vacation Planning

When is the Best Time to go to the Caribbean?

Collecting shells, Turks and Caicos

When you think of the Caribbean you think abundant sunshine, clear skies, and the perfect temperature. While it may be like that most of the time, there are times of the year that may not appeal to you. Do you enjoy crowds or no crowds? Do you like it to be hot or cooler? Do you absolutely need to get away in those winter months? Or do you want a great price on the hotel and flight? These are all questions you need to ask yourself prior to booking. Just like life you cannot have it all. Below, I will let you know when it’s the perfect time for you to go!

For me, I do not like crowds, I like it hot (so I won’t freeze when getting out of the ocean), I would prefer to get away in the winter months but not necessary (crazy, harsh Chicago winters), and I also like a good deal. Therefore the best time for me to go is end of winter season, before/after spring break, or middle of May-June for a better deal, plus its hot :). How did I come up with that? Keep reading!

Lets break it down.

$$$ will equal most expensive and $ will equal least expensive.

High Season: $$$

High season typically runs from mid December-mid April. Here you will find larger crowds and you will pay top dollar because of the high demand to escape the unforgiving winter. But, just because it is the Caribbean doesn’t mean they do not get affected by chilly winter temperatures. There is about a 10 degree temperature difference between Northern Caribbean spots and the Southern Caribbean. For example, in the Bahamas the average high could be 70 degrees while in Trinidad and Tobago the average will be 79 degrees.   Reservations for this time should be made well in advance. If you are the type of person who does not mind crowded places and doesn’t mind spending more money just to get away from the winter temps up north then this would be the time for you to go. I have gone on vacation during January and it is so very nice to get away from the cold winters of Chicago but that higher price to pay is not always nice.

To Summarize:

♦Milder temps

♦More expensive

♦Get to escape the cold winter

♦Rain is rare

Sunset on St.John


Shoulder Season: $$

Shoulder season starts mid April-May and also can include late October-November. There is less demand for hotels so you can expect to find a good deal. Shoulder season does not include Easter and spring break times, it revolves around it. What is also great about this season is it provides ideal conditions for snorkeling and diving. This is a time when water is calm, visibility is best, and marine life is active. Think of October and November like summer break for the locals and because of that some shops, restaurants, and resorts may be closed. Temperatures are almost perfect, little rainfall, and less crowds. I tend to head down to the Caribbean during this time and each time has been pleasant with no complaints. Although one time, out of the 10 years of traveling to the Caribbean, our last two days were straight rain 😦 but considering it only happened once I will have to consider it a fluke. I still love my islands!

To Summarize:

♦Great temperatures

♦Best time for snorkeling and diving

♦Good deals

♦Less crowded

♦Some resorts, shops, and restaurants close during October and November

st martin
No crowds!


Low Season: $$

Low season is June-August. During this time you can expect less crowds, can get a better deal on prices, and temperatures are in the mid-high 80’s with an average low in the 70s. This is a great time if you want a quiet and relaxed vacation. June is considered the rainiest month of the year. Nassau, Bahamas comes in first for highest total rainfall in the month of June at 8.6 inches of rain, followed by Havana, Cuba at 7.2 inches, and third place goes to Lamentin, Martinique with 6.7 inches of rain. Aruba, Bonaire, and Curacao win for the least amount of rainfall during June, all with totals less then 1 inch.

To Summarize:

♦Better deal for hotels

♦Hotter temps

♦Less crowded

♦June is rainy season



Hurricane Season:

Expect to find LOW prices during this time. I am sure can guess why. Hurricane season is technically June-November. But August is when to really see less than ideal weather. Also, September and October is usually the peak time for hurricanes. But not all Hurricanes treat the Caribbean the same. You want to know something interesting? Hurricanes do not like the equator and therefore tend to stay away from it. That is good news for the southeastern Caribbean! What is even better Aruba, Bonaire, Curacao, and Barbados are rarely affected by hurricanes. Alright! What is not so good is the southwestern and northeastern tend to have the most.

To summarize:

♦Will find best prices on hotels

♦Expect lots of humidity

♦Seas can be rough

♦Not crowded

I hope you have found your ideal time you would like to travel to the Caribbean. Let me know how it goes! If you have any other comments or suggestions on when the best time to go is, I would love to hear from you!

Happy Traveling!






Tips for Trips

Nonstop flights: Chicago to Caribbean

Crystal clear waters in Cayman Islands

Chicago to…?

O’hare international airport (ORD) is a major airport, so I think we Chicagoans are pretty lucky because we have access to most Caribbean islands. But not all those flight are non-stop. Here is a list of the nonstop flights from Chicago to the Caribbean islands.

These 6 locations offer nonstop flights year round! (order:shortest to longest)

1.Grand Cayman, Cayman Islands (4hrs)

2. Montego Bay, Jamaica (4hrs)

3. Nassau, Bahamas (4hrs)

4. San Juan, Puerto Rico (5hrs)

5. Punta Cana, Dominican Republic (5hrs)

6. Aruba (5hrs)

You are able to get non stop flights to St. Thomas, Sint Maarten, and Turks and Caicos but it is only during the winter season. Plan accordingly!

Tips for Trips

3 tips for flying in 2017

If you are looking for ways to save when traveling consider these tips:

1. Book approximately 8 weeks or 2 months before your departure.

I have heard this before and i think generally it holds true. I did apply this rule a few times in the past 2 years and I say it has worked for me. No hurt in trying!

2. Use an app geared toward traveling.

Hopper, Skyscanner, and Airfare Watchdog are just some examples of the apps out there. They are great tools to help you brainstorm your travel ideas. So far, I have only personally used Hopper and Skyscanner. Hopper is great for figuring out when the cheapest month/week to fly and it also gives you notifications when prices are about to rise or when to wait it out. However, I have found google flights to be a better resource when finding the cheapest flight. Sky scanner is cool because it compares prices to destinations all over the world. Or there is an option to pick a month and find the best deals for that month in destinations all over the world. Let me know if of any other apps and if they work well for you!

3. Fly out midweek

Flights seem to be cheaper when departing on a tuesday or wednesday and/or returning midweek. I can personally say this is true and I tend to use this route when traveling. Try it out!

“The Grid” over Chicago