How to Plan an Affordable Caribbean Island Vacation
Clear-to-the-bottom water. Swaying palm trees begging for you to plop down with your beach blanket and a good book underneath. Candy-colored buildings lined up along the brilliant white sand. Sound magical? It might be time to plan a Caribbean vacation!
Island-hopping on a Caribbean cruise is the most cost-effective way to explore this remarkable region. Instead of spending money on individual flights, hotels, and accommodations, a cruise offers the opportunity to visit many islands in one seamless trip.
For example, with a single 14-day itinerary, you can explore up to seven unique Caribbean destinations, including Puerto Rico, Barbados, Curaçao, and the serene shores of our private island, RelaxAway, Half Moon Cay™.
With convenient departures from Ft. Lauderdale or Miami, you’ll save both time and money on international flights and overnight stays.
When to Go: Cruise During Shoulder Season
What’s the cheapest month to go to the Caribbean? For the best value, consider cruising during the “shoulder season” — specifically early December and mid-April. Book a Caribbean cruise vacation that falls outside of major holidays and spring break, so you’ll enjoy lower prices, a less crowded feel, and the same stunning scenery!
Ready to Plan Your Caribbean Island Vacation? Browse itineraries and deals.
Holland America’s Caribbean cruises run from October through April with January and February as the peak months. Choosing an off-peak departure means you’ll save on your fare and have island beaches all to yourself.
5 Steps to Snagging a Caribbean Cruise Vacation Deal
Step 1: Book Early & Save on Amenities
Reserving your spot on board at least a year out gives you access to lower fares and the most coveted staterooms and suites, as well as the Have It All Early Booking Bonus.
Step 2: Choose a Shorter Caribbean Cruise
If you’re short on time or budget, opt for a 7-day Caribbean cruise that visits high-value destinations such as RelaxAway, Half Moon Cay™, Grand Turk, or Cozumel.
- Explore 7-day Caribbean cruises
Step 3: Travel During the Caribbean’s Shoulder Season
Cruise in October, April, or early December for the best fares.
Step 4: Select the “Have It All” Fare
Upgrade your base cruise fare to our Have It All premium package and receive our best amenities for only $60 per person, per day.
Have It All Includes:
- Surf Wi-Fi
- Signature Beverage Package
- Up to Three Nights’ Specialty Dining
- Up to US$300 Shore Excursion Credit
Step 5: Sign Up for Deals
Sign up for our email newsletter or check the deals page regularly for the latest sales, Top 10 Cruises of the Week (featuring the week’s 10 lowest fares), and exclusive private offers.
Promotions change frequently, and early access often means big savings. Check out the current Travel by Sea promotion!
Affordable Cruises From Convenient Ports
Avoid the cost of international flights by sailing from Ft. Lauderdale or Miami, our convenient Caribbean departure ports.
Want to book airfare at the same time as you cruise? Once you have booked your cruise, use FlightEase®, our flight booking tool, to secure competitively priced, flexible airfare options.
Bonus Tip for Spontaneous Sojourners: Sail Standby
If you have a flexible schedule and love a good deal, Holland America’s Standby Program may offer outstanding last-minute savings on your Caribbean vacation.
How it works:
- Sign up for a standby sailing
- Get notified if a stateroom becomes available 2–7 days before departure
- Cruise at an unbeatable fare
Learn More About the Caribbean
Curious to learn more about our Caribbean and Bahamas cruises? Discover more about our Caribbean cruise destinations and explore cruises to the Bahamas.
