

7-night Southern Caribbean Cruise
Aboard
Brilliance of the Seas
From
San Juan, Puerto Rico
13 Sailings
Dec 14, 2025 - Apr 12, 2026
Published prices from
$841
per person*
taxes & fees included
Cruising the Southern Caribbean replaces your stresses with sandy beaches, sunny days, and clear waters.

4.9/5 ⭐Google 600+ Reviews | A+ Better Business Bureau




Aboard
Brilliance of the Seas
From
San Juan, Puerto Rico
13 Sailings
Dec 14, 2025 - Apr 12, 2026
Published prices from
per person*
taxes & fees included


Aboard
Rotterdam
From
Fort Lauderdale, Florida
4 Sailings
Jan 9 - Mar 13, 2026
Published prices from
per person*
taxes & fees included


Aboard
Celebrity Ascent
From
Fort Lauderdale, Florida
21 Sailings
Dec 12, 2025 - Apr 7, 2028
Published prices from
per person*
taxes & fees included


Aboard
Azamara Journey
From
San Juan, Puerto Rico
3 Sailings
Nov 7 - Dec 5, 2026
Published prices from
per person*
taxes & fees included


Aboard
Queen Elizabeth
From
Miami, Florida
14 Sailings
Dec 30, 2025 - Nov 26, 2026
Published prices from
per person*
taxes & fees included


Aboard
Star Pride
From
San Juan, Puerto Rico
5 Sailings
Nov 15, 2026 - Jan 10, 2027
Published prices from
per person*
taxes & fees included


Aboard
Seabourn Ovation
From
Bridgetown, Barbados
12 Sailings
Jan 10, 2026 - Mar 13, 2027
Published prices from
per person*
taxes & fees included


Aboard
Seven Seas Grandeur
From
Miami, Florida
1 Sailing
Dec 8, 2027
Published prices from
per person*
taxes & fees included

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Overview
Of all the islands in the Caribbean, those in the South are a bit more exclusive. Further away from the coast of the U.S., a cruise to the Southern Caribbean sometimes requires a flight to one of the islands, like Puerto Rico or Aruba, or an extended sailing.
However, once you get to the Southern Caribbean, with its white sand beaches and warm weather, you’ll feel like you're in paradise.
From hot springs to waterfalls, you can let the gorgeous and therapeutic waters of the Southern Caribbean cascade down your shoulders or delight your senses. Explore tropical island paradises filled with vibrant butterflies, ostriches, and grab a snorkel to discover underwater life, or immerse yourself in intriguing culture.
Relax and be inspired by the natural beauty of the Southern Caribbean.

Explore the forts and old buildings that make up Old San Juan, the historical heart of Puerto Rico. This walled Spanish city was sought after by the British and the French, and while here, you can uncover its historical significance for yourself.

Visit the oldest known rum distillery, Mount Gay Rum in Barbados, and be sure to savor your free sample after the tour. Puerto Rico is also home to the Bacardi distillery, which offers tours as well.

The constantly warm waters of the Southern Caribbean make snorkeling, windsurfing, and heading out on a catamaran simply marvelous. Check out the shipwreck sites off the coast of Aruba.

Be one with nature by exploring one of the many rainforests on these islands. Hike El Yunque in Puerto Rico. In Dominica, you can take a tram through the rainforest. If you’re feeling adventurous in St. Lucia, get on the zip line.

Get lucky at one of the many casinos on several of the islands, especially Aruba, where many of them are open 24 hours a day and are decorated with stunning chandeliers.