How to Find Your Perfect Caribbean Cruise | A Planning Guide

Dream of Sun, Sand and Turquoise Water? Your Caribbean Cruise Awaits.

Expert planning for your perfect island-hopping adventure.
From Family fun to romantic escapes, we handle every detail.

Cruise ship sailing in the Caribbean ocean

Why a Caribbean Cruise?

The Caribbean really does have something for everyone. Whether this is your first cruise, traveling with kids or even organizing a group trip, the Caribbean just hits on so many levels.

What makes it special? Each islands has it’s own personality. You have Jamaica with it’s incredible food and music, the Bahama’s with it’s blue water, Aruba with some of the nicest people you will meet and so much more. Plus, you can snorkel and dive over shipwrecks, visit real life forts used by pirates, shop duty-free and of course sit under a palapa on a beach and completely Disconnect.

The Caribbean is easy which why it works for everyone. You can visit almost every island with no language barriers at all, the weather is pretty much reliable and comfortable. Families love the variety of activities at their finger tips from swimming with stingrays and pigs, visiting distilleries and breweries or taking in some cultural foodie tours. Couples can find romance and adventure all on one stop!

Not to mention you can wake up in a different country every couple of days too. How cool is that!

Traveling with Little Ones?

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Eastern, Western or Southern: Where to Go?

Most Caribbean Cruise Lines durations sail an average of 5 to 8 nights and focus on these
3 major Caribbean Regions for guests to explore and enjoy.

Eastern Caribbean

Best For
Beaches and Shopping

Travelers seeking the world’s most picture-perfect beaches, extensive duty-free shopping for jewelry and luxury goods, and a more leisurely, sun-and-sand-focused vacation.

Visit st. maarten

visit st. thomas

visit san juan p.r.

Western

Best For
Adventure and Ruins

Active travelers and history buffs who want to snorkel or dive on world-class reefs, explore ancient Mayan ruins, and enjoy eco-adventures like zip-lining or cave tubing.

Visit cozumel

visit jamaica

visit the cayman’s

Southern

Best For
Exotic and Unique

Veteran cruisers and culture seekers wanting to explore less-traveled ports, a vibrant mosaic of European influences, and unique, exotic island landscapes.

visit aruba

visit bonaire

visit Curaçao

The Best Cruise Lines for the Caribbean

Each cruise line is remarkably different. There really is a cruise line for
everyone. We work with our clients to match their travel style to the cruise
line that best fits their need.

Cruise Line	Luxury Level	Family Friendly	Couples/Romance	Waterparks	Budget Friendly	All-Inclusive	Overall Rating
Royal Caribbean	★★★☆☆ Mid-Range	★★★★★ Excellent	★★★☆☆ Good	✓	★★★☆☆ Moderate	✗	★★★★☆ Very Good
Virgin Voyages	★★★★☆ Premium	✗ Adults Only	★★★★★ Excellent	✗	★★★☆☆ Moderate	★★★★☆ Mostly	★★★★☆ Very Good
Silversea	★★★★★ Ultra-Luxury	★★☆☆☆ Limited	★★★★★ Excellent	✗	✗ Expensive	★★★★★ Full	★★★★★ Exceptional
Carnival	★★☆☆☆ Value	★★★★★ Excellent	★★☆☆☆ Limited	✓	★★★★★ Excellent	✗	★★★☆☆ Good
Princess Cruises	★★★☆☆ Premium	★★★★☆ Very Good	★★★★☆ Very Good	✗	★★★☆☆ Moderate	✗	★★★★☆ Very Good
Regent Seven Seas	★★★★★ Ultra-Luxury	★★☆☆☆ Limited	★★★★★ Excellent	✗	✗ Expensive	★★★★★ Full	★★★★★ Exceptional
Norwegian (NCL)	★★★☆☆ Mid-Range	★★★★★ Excellent	★★★☆☆ Good	✓	★★★☆☆ Moderate	✗	★★★★☆ Very Good
Celebrity	★★★★☆ Premium	★★★☆☆ Good	★★★★★ Excellent	✗	★★☆☆☆ Higher End	✗	★★★★☆ Very Good
Seabourn	★★★★★ Ultra-Luxury	✗ Adults Only	★★★★★ Excellent	✗	✗ Expensive	★★★★★ Full	★★★★★ Exceptional
Disney	★★★★☆ Premium	★★★★★ Best in Class	★★★☆☆ Good	✓	★★☆☆☆ Premium Priced	✗	★★★★★ Exceptional
MSC	★★★☆☆ Mid-Range	★★★★☆ Very Good	★★★☆☆ Good	✓	★★★★☆ Very Good	✗	★★★☆☆ Good

Your Common Caribbean Questions Answered

Do I need a Passport to Cruise to the Caribbean?

Although I highly encourage all my clients to have a passport, if you are embarking on a Closed Loop Cruise, you do not need a passport. A closed loop cruise is a cruise that starts and Ends in the SAME U.S. port ( Florida, Texas, Virginia, Boston, Etc ). The Western Hemisphere Travel Initiative details this rule and states “U.S. citizens can often board a closed-loop cruise with proof of citizenship, such as an original or certified copy of their birth certificate, and a government-issued photo ID, like a driver’s license.” Again I would strongly suggest to ALWAYS Cruise with a passport.

When is the best time to cruise the Caribbean?

The Caribbean’s beautiful and stable weather makes it an ideal cruise destination nearly year-round. However, travelers should be mindful of the Atlantic hurricane season, which officially runs from June 1st to November 30th, with peak activity typically from mid-August through October.

Even a distant hurricane can create rough seas and a bumpy ride. If a storm directly threatens the itinerary, cruise lines will prioritize safety by altering the ship’s course. This can lead to changes in the planned ports of call or, in rare cases, visiting a port that has been damaged by a previous storm. While cruise lines are experts at avoiding storms, flexibility is key when traveling during this season.

What is included in the cruise fare?

Your cruise fare is designed to be a fantastic value, covering all the essentials for a memorable vacation. While the exact inclusions can vary, especially with modern booking options, here is a general guide to what you can typically expect.

Almost Always Included in the Standard Cruise Fare:

Your Stateroom: Your private cabin accommodation for the duration of the cruise, including a stateroom attendant who provides daily service.
Meals in Complimentary Venues: All meals (breakfast, lunch, and dinner) in the ship’s main dining rooms, the buffet, and several other casual eateries like a poolside grill or pizza parlor.
Basic Beverages: Standard beverages like tap water, iced tea, basic coffee, hot tea, and select juices (usually available at the buffet) are included.
Onboard Activities & Entertainment: Access to most of the ship’s features, including swimming pools, hot tubs, the fitness center, live theater shows, comedy clubs, and live music venues.
Port Fees, Taxes & Duties: These government and port-assessed charges are included in the final price you pay for your cruise.

Typically Costs Extra:

Specialty Restaurants: Premium dining venues, such as a steakhouse, sushi bar, or Italian bistro, carry an extra charge per person or per item.
Alcoholic & Premium Beverages: Alcoholic drinks, soda, specialty coffees (lattes, cappuccinos), bottled water, and fresh-squeezed juices are not included in the base fare and are charged to your onboard account. Drink packages are often available for purchase.
Shore Excursions: Tours and activities you choose to do in port are an additional cost.
Daily Gratuities: Most cruise lines automatically add a daily service charge or gratuity to your onboard account to recognize the service of the crew.
Onboard Services: Items like Wi-Fi packages, spa and salon treatments, casino play, professional photos, and shopping are all extra.

The Most Important Detail: Check Your Specific Booking

Many cruise lines now offer tiered pricing or “all-inclusive” style packages (e.g., packages that bundle a drink package, Wi-Fi, and gratuities). The specific amenities included in your vacation depend entirely on the fare you purchased.
For the definitive list of what your cruise includes, it is essential to review your booking confirmation or log into your cruise planner on the cruise line’s website. This will show exactly which package you have and what perks come with it.

Ready to Plan the Perfect Getaway?

With a better understanding of your cruise options, you are ready for the exciting next step: planning your voyage. We specialize in matching travelers to the perfect ship and itinerary that aligns with their vision.

Let’s discuss your thoughts and finalize a vacation that checks every box.
For additional planning resources, including packing guides and essential first-timer information, please visit our
Cruises page HERE.

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