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Cruise Dates

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October 2026

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Emerald Princess

Princess Cruises

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Mar 27, 2027 - Apr 3, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida

Average Starting Price

27% OFF

Mar 25, 2028 - Apr 8, 2028 (14 Nights)

Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • Dominica • St. Kitts • St. Thomas • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore

Average Starting Price

Mar 1, 2028 - Mar 18, 2028 (17 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami • Cozumel • Roatan, Honduras • Harvest Caye, Belize • Costa Maya • Miami

Average Starting Price

Feb 13, 2027 - Feb 23, 2027 (10 Nights)

Miami • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Great Stirrup Cay • Miami

Average Starting Price

Jan 7, 2029 - Jan 19, 2029 (12 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama

Average Starting Price

20% OFF

Feb 5, 2027 - Feb 12, 2027 (7 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$3,320pp

Jim's Onboard Credit

29% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Mar 12, 2029 - Mar 22, 2029 (10 Nights)

Miami • Samana, Dominican Republic • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Tortola • Miami

Average Starting Price

Feb 12, 2027 - Feb 19, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Terre de Haut, Guadeloupe • Puerto Plata, Dominican Republic • Miami

Average Starting Price

47% OFF

Oct 17, 2027 - Oct 24, 2027 (7 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Miami

Average Starting Price

$546pp

Jim's Onboard Credit

Norwegian Epic

Norwegian Cruise Line

Dec 24, 2027 - Dec 31, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida

Average Starting Price

$1,239pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Rhapsody of the Seas

Royal Caribbean

Dec 31, 2027 - Jan 8, 2028 (8 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • St John's, Antigua • Kingstown, Saint Vincent Island, Saint Vincent • San Juan, Puerto Rico

Average Starting Price

$1,308pp

Jim's Onboard Credit

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