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Cruise Dates

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October 2026

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Rhapsody of the Seas

Royal Caribbean

Jan 22, 2028 - Jan 29, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Jan 2, 2028 - Jan 8, 2028 (6 Nights)

San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Aug 14, 2027 - Aug 21, 2027 (7 Nights)

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

Average Starting Price

$777pp

Jim's Onboard Credit

Norwegian Bliss

Norwegian Cruise Line

Jan 26, 2028 - Feb 7, 2028 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan

Average Starting Price

Feb 28, 2027 - Mar 7, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$651pp

Jim's Onboard Credit

27% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Jan 29, 2029 - Feb 7, 2029 (9 Nights)

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

Average Starting Price

48% OFF

Nov 5, 2027 - Nov 27, 2027 (22 Nights)

Barcelona, Spain • Palma de Mallorca, Spain • Alicante, Spain • Malaga, Spain • Las Palmas (Gran Canaria), Spain • St John's, Antigua • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique

Average Starting Price

Dec 28, 2026 - Jan 7, 2027 (10 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Tortola • Miami

Average Starting Price

$6,499pp

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!

Star of the Seas

Royal Caribbean

Oct 31, 2027 - Nov 7, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,354pp

Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!