Travel to the Caribbean

View of the Caribbean

Let's Travel to the Caribbean

Experience the ultimate tropical getaway in the Caribbean, where you can indulge in endless sunshine, pristine beaches, and crystal-clear waters. Whether you choose to relax at renowned beach resorts or venture off the beaten path for a secluded retreat, the Caribbean offers a myriad of options for the perfect vacation.


Featured Travel in the Caribbean

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Work with our Travel Advisors

Hotel Bookings

Let us find you the perfect hotel in the Caribbean!  Let us know your hotel needs… spa… private pool.  And don't forget the perks!

Custom Itineraries

Our professional travel advisors will work with you to build a personalized and customized itinerary in the Caribbean.


Personalized Travel

Our professional travel advisors at Live Well, Travel Often are great collaborators!  They want to know you and build you the prefect trip to the Caribbean!

When is the best time to visit the Caribbean?

When planning a trip to the Caribbean, it's important to consider the best time to visit. The Caribbean experiences a tropical climate, with warm temperatures and high humidity year-round. However, there are certain times of the year that are more popular for tourists and offer better weather conditions. The peak tourist season in the Caribbean is typically from December to April, when the weather is dry and temperatures are slightly cooler. This is also the time when prices for accommodations and flights tend to be higher. If you're looking to avoid the crowds and save some money, consider visiting during the shoulder seasons of May to June or September to November. During these times, you may experience some rain showers, but you'll also have the opportunity to enjoy lower prices and fewer tourists. Ultimately, the best time to visit the Caribbean depends on your preferences and priorities!  Let's chat and figure out when you should go!

What are the best places to visit in the Caribbean?

The Caribbean is made up of numerous islands, each with its own unique charm and attractions. Before planning your trip, it's important to decide on the best island for your interests. If you're looking for pristine beaches and luxury resorts, consider visiting islands like Barbados or St. Lucia. For a more adventurous experience, you might want to explore the volcanic landscapes of Dominica or hike through the rainforests of Grenada. If you're interested in history and culture, islands like Cuba or Puerto Rico offer a rich heritage and vibrant local communities. Additionally, some islands are known for their vibrant nightlife and party scene, such as Jamaica or the Dominican Republic. Our travel advisors will work with you to find one that aligns with your interests and preferences.