Caribbean Cruises 2026–2028 with Princess

Pick your path to paradise before it sails away. The Caribbean is all rhythm and color — steel drums in the streets, jerk chicken on the grill and warm, swimmable waters from sunrise on. With Princess, you sleep while we sail and wake up somewhere new, hopping from reefs and rainforests to quiet beaches and cobblestoned port towns — the good stuff without the stress.

Start planning: Browse all Caribbean cruises

Destinations: choose your Caribbean

Sail from these convenient ports

Why cruise the Caribbean with Princess?

What you’ll do: shore excursions and nightlife

Staterooms and suites: compare your options

Choose the right space for your style and budget, then explore ship‑specific details on each page:

Deals for 2026–2028

Getting there: airfare, hotels and transfers

Bonus: new‑guest onboard credit

Sign up for emails and get $50 onboard credit on your next cruise. Offer available only to new Princess guests who book a 2026–2028 cruise within 90 days of email sign‑up. Website Terms, Privacy Policy and Additional terms apply.

Helpful planning links

Cruises to the Caribbean FAQs

What are the major cruise ports within the Caribbean?
Princess itineraries visit a range of islands, but a few key ports form the heart of most Caribbean routes: St. Thomas, St. Maarten, Cozumel, Grand Turk, Aruba, Barbados, Roatán, Belize City and Nassau. These blend beaches, local culture and easy access to adventure. Common departure ports include Miami, Fort Lauderdale, Port Canaveral and San Juan.

Where do Princess Cruises’ ships dock in the Caribbean?
Princess docks close to the action in nearly every port so you can step off and explore quickly: - St. Thomas, U.S.V.I.: Havensight Pier or Crown Bay Marina, both near Charlotte Amalie. - St. Maarten: Dr. A.C. Wathey Cruise & Cargo Facility, about a mile from Philipsburg. - Grand Turk: Grand Turk Cruise Center, steps from the beach. - Nassau, Bahamas: Prince George Wharf, across from downtown. - Roatán, Honduras: Coxen Hole Town Center or Mahogany Bay. - Belize City, Belize: Ships anchor offshore; tenders to Belize Tourism Village. - Aruba: Oranjestad cruise terminal, near shops and dining. - Barbados: Bridgetown’s Deep Water Harbour, a short ride or walk to town. - Princess Cays, Bahamas: Ship tenders directly to the private island resort.

Do any cruises leave from the Caribbean?
Yes. In addition to U.S. departure ports, Princess offers itineraries that depart from San Juan, Puerto Rico — a convenient jumping‑off point for deeper Southern Caribbean exploration.

What is the best month to cruise around the Caribbean?
Most travelers favor the dry season, December–April, for sunny weather and mild temperatures. Expect higher prices and larger crowds during this peak window.

What month is the cheapest to go on a cruise?
Generally the wet season (May–November) offers the best values and more room ashore. Weather can be less predictable, and itineraries may adjust for tropical systems. Princess offers value year‑round with rotating promotions like Free 3rd & 4th Guests and last‑minute deals. See current offers on the deals and promotions page.

What is the weather like in the Caribbean?
Warm year‑round with average highs in the 80s (°F). Dry season brings lower humidity and sunshine; wet season brings brief showers and a higher chance of storms. Pack for heat and include a light rain layer.

What is some valuable advice when planning a cruise to the Caribbean?
Compare itineraries to decide between iconic hot spots and quieter islands. Book early for peak season. Pack versatile outfits for beaches, warm days and casual evenings. If you’re sailing in wet season, build in flexibility and consider travel insurance.

Do I need travel insurance for my Caribbean cruise?
Not required but strongly recommended — especially during wet season — to help cover trip interruptions, medical expenses and weather‑related changes.

Are hurricanes a concern on Caribbean cruises?
They can be from June to November. Cruise lines monitor storms closely and adjust routes as needed for safety.

Ready to plan?