How to Prepare/Organize for a Caribbean Cruise

Caribbean Cruise

From the Desk of Clearissa Coward’s Command Center/Divinely Organized   

How to Prepare/Organize for a Caribbean Cruise
“You can’t always wait for the perfect time  to travel.  Sometimes, we have to dare to do it because life is too short to wonder.”
The Travel Diva
Travel is fun and exciting; however, if a trip is not planned correctly, it can be a disaster or at least stressful. Vacations should never be stressful.  For the purpose of this article, we are going to go through the steps of preparing for a Southern Caribbean cruise for two, November 26 – December 3, 2017. Yes, you read the dates correctly. We are planning over a year in advance and there are several reasons to plan that far in advance for a seven-day cruise. This particular cruise will depart from San Juan, PR, which is yet another reason to plan ahead, and our ports of call are San Juan, St. Thomas, USVI, Barbados, St. Lucia, St. Kitts, WI, and St. Maarten, NA. We are excited. With that said, let’s begin the process and explore “how to prepare/organize for a Caribbean cruise.”

Consult with an Expert

  • I do not advise booking this type of trip yourself.
  • I do advise hiring a travel agent. I know you’re thinking, hiring a travel agent will cost you. Well, it might, but it will cost you less to hire a travel agent or a travel specialist than it will to make mistakes or schedule flights and departure dates incorrectly or to not make the proper arrangements. Trust me when I tell you, a good travel agent will take the guess work out of your cruise and give you an organized, step-by-step trip itinerary that will be well worth the extra few dollars you pay.
  • One of the best reasons for hiring a travel agent would be the ability to plan for a trip a year and a half in advance. That’s right, they get all of the early bird deals before the rest of us and if you book through an agent, you will generally be allowed to pay for the vacation over that year and a half time period. Now it doesn’t get any better than that. Especially if you are taking a 5-star vacation on a 3-star budget.
  • Build a relationship with your travel agent. Once your agent gets to know the travel dreams for you and your family, s/he will keep you abreast of specials and great travel deals that only an agent can provide.
  • Get on your travel agent’s mailing list. You will be surprised at the great information an agent can provide for you. From the price of a passport (we will discuss this later) to the best times to travel in certain areas of the country and even the world. I realize you can Google almost anything, but a travel agent will remove all of the guesswork from your trip. Your agent will make the arrangements and you can relax and make memories.
Caribbean Cruise

Plan Ahead

  • I like it best when we can plan a vacation without disrupting anything in our household, that works best for us.
  • Could we pay for a cruise out right? Yes, we could but why not take advantage of a payment plan? We do and it’s wonderful.
  • Having all of this time to plan also affords me the opportunity to save our spending money as well. A few years ago, I began saving my change. I never/or very rarely spend change. I have a hiding place where I dump all of my change and the last time I cashed it in, I had over $800.00 and that was 10 months of saving. Not a bad haul for a few months of saving change…right?


  • Once we decided to book the cruise, I created a folder on my computer to store all correspondence from our travel agent. Having all of her correspondence in one place makes it easy for me to refer back to any instructions and or tips that she will send throughout the year (another great reason to have an agent).
  • If you do not already, designate a place to begin placing all things related to the cruise, i.e. passports, flight information, etc. Make sure to have the necessary paperwork for “all” travelers in one place. The worst thing to happen would be for one of you not to have the necessary paperwork when the time to travel is near.
  • Although you have an agent, begin doing a little research on your own. It’s good to know what to expect at each port. It is also nice to take a virtual tour of the cruise ship. You can now see the cabins and common areas of the ships and take virtual tours of the amenities. It’s fun to do and helps you to get familiar with what will be your surroundings for seven days at sea.
Caribbean Cruise


  • Now is a great time to begin prepping your budget.
  • Prepare for excursions, gratuities, and drinks. Cruises are not all inclusive and you will be responsible for any alcoholic beverages you consume.
  • Also, if you’re like me, you should also prepare for any shopping you will do. I always like to bring back t-shirts and other gift items as well as some things for me. 🙂

These are just a few tips for getting prepared to take a 7-day cruise. There will be lots more to do and preparations to make. Stay tuned for our next post. We will discuss passports and other important documents you should have available. You can never begin pulling paperwork together too soon.

Do you need a travel agent, I am blessed to have two and I am now friends with both agents. Each agent provides a different type and style of service and both are really passionate about what they do.

If you want the best prices for an all-inclusive vacation or a 7-day cruise like the one we are planning or specifications for an island wedding? If so, visit who provided the travel quote for this week’s article.

See you soon with the next installment of this series. Do you have a special trip planned or need help planning your next adventure? Follow along and get some good tips during this series and leave your travel tips in the comments section.

Organization touches every aspect of your life…including travel.

Caribbean Cruise
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10 thoughts on “How to Prepare/Organize for a Caribbean Cruise

  1. Jenna @ A Savory Feast says:

    I would LOVE to be preparing for a caribbean cruise right now! We had hoped to take one before I hit the cutoff since I’m pregnant right now. I guess I just need to start planning for a cruise after the baby is born!

  2. Clearissa Coward says:

    Hi Jenna. First congratulations on the new baby!!! How wonderful. But why not begin planning for a cruise after the baby is born. What a great gift to you and your hubby. And besides, you will be amazed at how much fun the planning can be. Relax and enjoy the remainder of your pregnancy and plan away. Wishing you a peaceful delivery and a healthy and happy baby.

  3. Clearissa Coward says:

    Hi Tianna,

    Thanks for reading along. I hope the tips will help you plan a cruise for you. Thanks for the congrats but I am in no way going to have a baby. Oh Noooooooooo!!! Not me. 🙂

  4. Keesha Metcalfe says:

    You are giving me ideas Clearissa! A Caribbean cruise is an excellent vacation idea. I may just take your suggestion and do this. Why not? I sure deserve it!

  5. Clearissa Coward says:

    Hi Keesha. Thank you for reading along. Yes, indeed you do deserve a Caribbean cruise. In my opinion, everyone deserves to be in the Caribbean. 🙂 Go ahead…start planning.

  6. Rhonda Gales says:

    The cruise sounds wonderful. I don’t cruise since I acquired motion sickness on my last cruise to the Bahamas, but these are great tips for anyone who does.

  7. Clearissa Coward says:

    Hi Rhonda. Thank you for reading along. I am so sorry to hear that you developed motion sickness. I love to cruise. It is so relaxing to me. I hope I never develop motion sickness. Thank you for the compliment. It means a lot, especially from someone who no longer cruises.

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