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October 2026

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Vista

Oceania Cruises

Nov 25, 2026 - Dec 7, 2026 (12 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Tortola • Miami

Average Starting Price

Nov 28, 2027 - Dec 12, 2027 (14 Nights)

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

Average Starting Price

Jan 3, 2028 - Jan 15, 2028 (12 Nights)

Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • 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

Mar 27, 2027 - Apr 6, 2027 (10 Nights)

Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale

Average Starting Price

$874pp

Jim's Onboard Credit

Norwegian Pearl

Norwegian Cruise Line

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

Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Philadelphia

Average Starting Price

Mar 22, 2027 - Apr 2, 2027 (11 Nights)

Fort Lauderdale • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • Fort Lauderdale

Average Starting Price

Dec 1, 2027 - Dec 12, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,754pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Zuiderdam

Holland America Line

Apr 7, 2027 - Apr 17, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Miami

Average Starting Price

$2,004pp

Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Rhapsody of the Seas

Royal Caribbean

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

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

Average Starting Price

$1,079pp

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!

EXPLORA II

Explora Journeys

Jan 16, 2028 - Jan 23, 2028 (7 Nights)

San Juan, Puerto Rico • Bequia Island, Saint Vincent • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

Mar 21, 2027 - Mar 28, 2027 (7 Nights)

Miami • Nassau • St. Thomas • St John's, Antigua • Miami

Average Starting Price

$1,074pp

Jim's Onboard Credit

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