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Cruise Dates

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October 2026

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Silver Spirit

Silversea

Jan 30, 2029 - Feb 11, 2029 (12 Nights)

Miami • San Juan del sur, Nicaragua • Road Bay, Anguilla • St. Kitts • Roseau, Dominica • St John's, Antigua • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Miami

Average Starting Price

48% OFF

Dec 12, 2027 - Dec 26, 2027 (14 Nights)

Miami • Ocean Cay • Puerto Plata, Dominican Republic • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Jan 5, 2027 - Jan 16, 2027 (11 Nights)

Miami • San Juan, Puerto Rico • St. John • St. Kitts • Deshaies, Guadeloupe • St John's, Antigua • Tortola • Miami

Average Starting Price

Jan 20, 2027 - Feb 5, 2027 (16 Nights)

Miami • Ocho Rios, Jamaica • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Belize City • Key West, Florida • Miami • Puerto Plata, Dominican Republic • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

Jan 29, 2028 - Feb 5, 2028 (7 Nights)

Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

Feb 7, 2028 - Feb 17, 2028 (10 Nights)

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

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

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

San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

25% OFF

Nov 11, 2026 - Nov 25, 2026 (14 Nights)

Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Miami

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

19% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Dec 19, 2026 - Dec 29, 2026 (10 Nights)

Miami • St. Thomas • St John's, Antigua • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami

Average Starting Price

$11,799pp

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!

Celebrity Eclipse

Celebrity Cruises

Dec 14, 2027 - Dec 23, 2027 (9 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$860pp

Jim's Onboard Credit

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