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

Princess ships dock close to the action in nearly every port, so guests can step off and start exploring right away. Here’s where you’ll come ashore at some of the Caribbean’s most visited ports:

• St. Thomas, U.S. Virgin Islands: Ships dock at Havensight Pier or Crown Bay Marina, both a short ride from downtown Charlotte Amalie’s shops and cafés.
• St. Maarten: Ships berth at the Dr. A.C. Wathey Cruise & Cargo Facility, about a mile from Philipsburg’s colorful waterfront.

• Grand Turk, Turks & Caicos: The ship docks right at the Grand Turk Cruise Center, steps from the beach and within sight of the turquoise water.

• Nassau, Bahamas: Ships dock at Prince George Wharf, directly across from downtown Nassau’s straw market and colonial landmarks.

• Roatán, Honduras: Depending on the itinerary, you’ll dock at either Coxen Hole’s Town Center port or Mahogany Bay, both close to beaches and reef excursions.
• Belize City, Belize: Because the harbor is shallow, ships anchor offshore and tender guests to the Belize Tourism Village near downtown.
• Aruba: Ships dock at the cruise terminal in Oranjestad, steps from shopping, restaurants and the island’s pastel Dutch architecture.
• Barbados: Ships dock at Bridgetown’s Deep Water Harbour, a short drive or 20-minute walk to the city center.
• Princess Cays, Bahamas: Ships anchor offshore and tender guests directly onto Princess’ private island resort.

Yes. In addition to U.S. based departure ports for Caribbean cruises, Princess offers itineraries that depart directly from San Juan, Puerto Rico — a convenient jumping-off point for deeper exploration into the Southern Caribbean.

Most travelers favor the dry season, from December through April, for the sunniest weather and mild temperatures. But this peak season also means higher prices and larger crowds. If you’re after ideal weather and don’t mind sharing the beach, that’s your window.

Look to the wet season (May through November) for the best cruise deals. You’ll likely pay less and have more elbow room ashore. Just know the weather can be unpredictable, and some rerouting may happen if tropical systems pop up. However, Princess Cruises offers incredible value year-round with deals like Free 3rd & 4th guests, exciting last-minute cruise offers and rotating deals and promotions to help you make the most of your getaway.

Find your cruise deal: Princess Cruise Deals & Promotions & Last Minute Cruise Deals

The Caribbean stays warm year-round, with average highs in the 80s. The dry season brings sun and lower humidity, while the wet season includes more rain showers and a higher chance of storms. Pack for heat, but always bring a light rain layer just in case.

Compare different Caribbean cruise itineraries to decide if you want to hit the classic hot spots or venture to quieter islands. Book early for peak season, and pack versatile outfits that work for tropical heat, beaches and casual nightlife. If you're traveling during the wet season, build in flexibility and consider travel insurance.

It’s not required, but it’s strongly recommended — especially if you're cruising during the wet season when weather can get temperamental. Insurance can cover trip interruptions, medical expenses and those rare but real moments when a storm forces a change of plans.

They can be, particularly from June to November (which overlaps with the wet season). Cruise lines monitor storms closely and often adjust routes as needed for safety..