5 Steps to Plan Your Perfect First Trip to Caribbean

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Planning your first Caribbean vacation is an exciting experience. However, there are a lot of misconceptions about the Caribbean, and each country is different from those surrounding it.

To get the most out of your vacation, you’ll want to walk in prepared and knowledgeable about what to expect. Here are five must-follow steps to planning your perfect first trip to the Caribbean. 

Choose Your Destination

The Caribbean has over 7000 islands and 26 countries. While this is a relatively small area compared to the rest of the world, there’s plenty of diversity along those shores. Choosing your destination is the first step in planning your first trip.

First, consider your lifestyle when choosing a destination. If you’re adventurous and want to spend time hiking and exploring the natural surroundings of your island, choose a place like Jamaica or Grenada. If you dream of privacy and relaxation, try finding a perfect villa on Turks and Caicos or Aruba. 

Once you do some research and find the island or archipelago that’s right for you, you can start to get into the details of your trip.

Choose The Right Dates

The Caribbean tourist season runs in alignment with the North American winter, generally spanning from the December holidays until the end of April. If you plan on heading to the Caribbean during that timeframe, aim to plan your trip at least eight months in advance to get your first pick for accommodations and travel times.

During the tourist season, you can expect beaches to be busier and prices to be higher. Planning a trip for the fringe months, like November, can help you avoid the influx of fellow visitors. Just be mindful that the rainy season stretches from June into November, which could (literally) put a damper on your trip.

Learn About the Local Culture

Don’t make the classic first-time visitor of thinking that all islands in the Caribbean are the same. This beautiful escape is a melting pot of numerous cultures and languages. Some islands speak French while others speak Dutch, Spanish, English, etc.

Treat every island you visit in the Caribbean as a local country. Take time to learn about your destination and what to expect, from the lifestyle pace to the local culinary dishes to the local history and lore.

Plan Your Activities Ahead of Time

There are a lot of incredible things to see and do across the many islands of the Caribbean. Planning your activities ahead of time will help you get the best providers and have the experiences you want. 

Give yourself time to research the events you’re interested in trying and find a reliable guide or tour facilitator. If you have questions, go through the local tourism office to see who they recommend to ensure you get the best experience possible. 

Pack and Prepare

When it’s time to head away on vacation, the two areas of your focus will be packing appropriately and ensuring you have the right documentation in place. Each country within the Caribbean will have different requirements and limitations— look at each destination you’ll be visiting to determine whether you need a passport or visa.

When packing for a Caribbean vacation, layers and sun protection are key. Bring light sweaters for the cooler evenings and supportive sneakers for island adventures. Things like sunscreen, bug spray, SPF lip balm, hats, sunglasses, and after-sun care are must-haves for a happy, safe Caribbean vacation.

With these five steps, you’ll be able to build a fantastic itinerary for your first trip to the Caribbean.

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About Author

Kelly Lewis is the founder of Go! Girl Guides, the Women's Travel Fest and Damesly. She's an optimist, an adventurer, an author and works to help women travel the world.

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