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32 Results

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A scenic beach in Montego Bay, Jamaica, with a long line of palm trees and resort hotels along the white sand, and a large school of fish visible in the clear blue water.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

17-night Tropical Sparkle & Holiday Cheer Cruise From Galveston, Texas

Galveston
Montego Bay
Ocho Rios
Punta Cana
San Juan
+6 more

Aboard

Seven Seas Splendor

From

Galveston, Texas

1 Sailing

Dec 11, 2026

1 Sailing

Dec 11, 2026

Published prices from

$11,999

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Lesser Antilles Journey Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Roseau
St. John's
Basseterre
+2 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Dec 19, 2026

1 Sailing

Dec 19, 2026

Published prices from

$11,799

per person*

taxes & fees included

A scenic shot of the stunning Seven Mile Beach in Grand Cayman, with a wide, sandy beach, calm turquoise water, and resorts with palm trees under a beautiful blue sky.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

14-night Caribbean Celebration Cruise From Tampa, Florida

Tampa
Grand Cayman (George Town)
Ocho Rios
Oranjestad
Willemstad
+6 more

Aboard

Seven Seas Mariner

From

Tampa, Florida

1 Sailing

Dec 21, 2026

1 Sailing

Dec 21, 2026

Published prices from

$12,399

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Caribbean Zephyr Cruise From Miami, Florida

Miami
St. Maarten (Philipsburg)
Pointe A Pitre
St. John's
Basseterre
+2 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Jan 10, 2027

1 Sailing

Jan 10, 2027

Published prices from

$24,049

per person*

taxes & fees included

An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

12-night Prestige Isles Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Basseterre
Roseau
Castries
+4 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Mar 5, 2027

1 Sailing

Mar 5, 2027

Published prices from

$12,149

per person*

taxes & fees included

Historic El Morro fortress overlooking the ocean in San Juan, Puerto Rico.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Tropical Passage Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Roseau
Bridgetown (Barbados)
Castries
+5 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Mar 20, 2027

1 Sailing

Mar 20, 2027

Published prices from

$7,399

per person*

taxes & fees included

A sunny view of the colorful waterfront of Willemstad, Curacao, with its iconic pastel-colored Dutch colonial buildings lining the Handelskade street and a ship docked in the port.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

15-night Cultural Currents Cruise From Miami, Florida

Miami
Roadtown
Gustavia
Fort de France
St. Vincent (Kingstown)
+6 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Mar 26, 2027

1 Sailing

Mar 26, 2027

Published prices from

$13,599

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Caribbean Mystique Cruise From San Juan, Puerto Rico

San Juan
Roadtown
Basseterre
St. John's
Gustavia
+6 more

Aboard

Seven Seas Prestige

From

San Juan, Puerto Rico

1 Sailing

Mar 30, 2027

1 Sailing

Mar 30, 2027

Published prices from

$7,099

per person*

taxes & fees included

Modern Panama City skyline with skyscrapers.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

14-night Carnival Of Caribbean Colors Cruise From Panama City, Panama

Panama City
Panama Canal
Cartagena (Colombia)
Santa Marta
Oranjestad
+9 more

Aboard

Seven Seas Grandeur

From

Panama City, Panama

1 Sailing

Mar 31, 2027

1 Sailing

Mar 31, 2027

Published prices from

$10,249

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Blissful BVI Cruise From Miami, Florida

Miami
Nassau
San Juan
St. Thomas (Charlotte Amalie)
St. John's
+3 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Apr 5, 2027

1 Sailing

Apr 5, 2027

Statue of Liberty and Manhattan skyline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

14-night Caribbean Compass Cruise From Miami, Florida

Miami
Old Bahama Channel
Oranjestad
Willemstad
Kralendijk
+6 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Apr 15, 2027

1 Sailing

Apr 15, 2027

Published prices from

$9,699

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Island Rendezvous Cruise From Miami, Florida

Miami
Bahamian Waters
Puerto Plata
San Juan
St. Thomas (Charlotte Amalie)
+4 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Nov 28, 2027

1 Sailing

Nov 28, 2027

Published prices from

$7,099

per person*

taxes & fees included

Miami skyline at dusk, showcasing vibrant colors and reflections shimmering in the water below.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

11-night Virgin Islands Voyage From Miami, Florida

Miami
Bahamian Waters
St. Thomas (Charlotte Amalie)
St. John's
Castries
+4 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Dec 7, 2027

1 Sailing

Dec 7, 2027

Published prices from

$8,499

per person*

taxes & fees included

A beautiful panoramic view of Roseau, Dominica, with a colorful town nestled between the deep blue Caribbean Sea and a backdrop of lush green, volcanic mountains.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Season To Cheer Cruise From Miami, Florida

Miami
Bahamian Waters
Puerto Plata
San Juan
Basseterre
+4 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Dec 18, 2027

1 Sailing

Dec 18, 2027

Published prices from

$8,349

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

25-night Ultimate Island Holiday Cruise From Miami, Florida

Miami
Bahamian Waters
Roadtown
St. Thomas (Charlotte Amalie)
St. Maarten (Philipsburg)
+18 more

Aboard

Seven Seas Voyager

From

Miami, Florida

1 Sailing

Dec 19, 2027

1 Sailing

Dec 19, 2027

Published prices from

$13,149

per person*

taxes & fees included

An aerial view of the vibrant marina and coastline of Pointe-à-Pitre, Guadeloupe, showing numerous boats docked in the harbor, surrounded by lush green hills and the turquoise Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night A Journey In Beauty Cruise From Miami, Florida

Miami
Bahamian Waters
Roadtown
Gustavia
St. Maarten (Philipsburg)
+6 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Jan 5, 2028

1 Sailing

Jan 5, 2028

Published prices from

$6,749

per person*

taxes & fees included

An aerial view of the colorful waterfront of St. John's, Antigua, with a long pier extending into the calm, blue sea and the town's charming buildings and marina in the background.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Bahamian Breeze Cruise From Miami, Florida

Miami
Bahamian Waters
St. Maarten (Philipsburg)
Basseterre
St. John's
+3 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Jan 7, 2028

1 Sailing

Jan 7, 2028

Published prices from

$7,749

per person*

taxes & fees included

A vibrant underwater scene with a large school of tropical fish swimming over a colorful coral reef in the clear, blue waters of the Bahamas.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Golden Caribbean Beaches Cruise From Miami, Florida

Miami
Bahamian Waters
Puerto Plata
San Juan
St. Maarten (Philipsburg)
+4 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Jan 17, 2028

1 Sailing

Jan 17, 2028

Published prices from

$8,149

per person*

taxes & fees included

Rocky beach and palm trees in Barbados.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

15-night Romance Of Roseau Cruise From Miami, Florida

Miami
Bahamian Waters
Roadtown
Roseau
Castries
+8 more

Aboard

Seven Seas Prestige

From

Miami, Florida

1 Sailing

Feb 16, 2028

1 Sailing

Feb 16, 2028

Published prices from

$13,049

per person*

taxes & fees included

A panoramic view of Gustavia, Saint Barthélemy, featuring a bay filled with luxury yachts and sailboats, framed by lush, green hillsides dotted with houses.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

12-night Calypso Currents Cruise From Miami, Florida

Miami
Puerto Plata
Cayo Levantado
San Juan
Gustavia
+5 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Mar 20, 2028

1 Sailing

Mar 20, 2028

Published prices from

$8,599

per person*

taxes & fees included

A tropical island scene in Cayo Levantado with white sandy beaches, turquoise water, palm trees, and colorful resort buildings, with visitors relaxing on the shore and boats anchored near the coastline.
Up to $500 FREE Onboard Credit*+ 3 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

27-night Springtime Atlantic Crossing Cruise From Miami, Florida

Miami
Puerto Plata
Cayo Levantado
San Juan
Gustavia
+12 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Mar 20, 2028

1 Sailing

Mar 20, 2028

Published prices from

$16,049

per person*

taxes & fees included

A vibrant panoramic view of Castries, St. Lucia, with colorful buildings nestled along the harbor and lush green hills in the background under a blue sky with white clouds.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Sapphire Archipelago Cruise From Miami, Florida

Miami
Roadtown
Pointe A Pitre
Castries
Roseau
+2 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Nov 7, 2028

1 Sailing

Nov 7, 2028

Published prices from

$6,549

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

12-night Tides & Traditions Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
Gustavia
St. John's
Pointe A Pitre
+4 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Nov 17, 2028

1 Sailing

Nov 17, 2028

Published prices from

$7,399

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

12-night Caribbean Quest Cruise From Miami, Florida

Miami
Roadtown
Basseterre
Oranjestad
Falmouth (Jamaica)
+3 more

Aboard

Seven Seas Mariner

From

Miami, Florida

1 Sailing

Nov 29, 2028

1 Sailing

Nov 29, 2028

Published prices from

$7,199

per person*

taxes & fees included

A stunning panoramic view of Road Town on Tortola, British Virgin Islands, showing the harbor filled with boats and a small town surrounded by lush green hills overlooking the Caribbean Sea.
Up to $500 FREE Onboard Credit*+ 2 more offers
TCW EXCLUSIVE
Regent Seven Seas Cruises.

10-night Steel Drum Serenade Cruise From Miami, Florida

Miami
St. Thomas (Charlotte Amalie)
St. John's
Castries
Gustavia
+2 more

Aboard

Seven Seas Grandeur

From

Miami, Florida

1 Sailing

Dec 3, 2028

1 Sailing

Dec 3, 2028

Published prices from

$6,849

per person*

taxes & fees included

    • Showing results 1 - 24 of 32

*Rates and offers are per person, in US Dollars, based on double occupancy, capacity controlled, subject to availability and confirmation, and may change without notice. Government taxes and fees are included. Rates and offers are available for select dates and categories only. Additional restrictions may apply. Call 1-800-377-9383 for full terms and conditions.