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October 2026

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Rotterdam

Holland America Line

Nov 10, 2026 - Nov 21, 2026 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,969pp

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

Mar 6, 2027 - Mar 16, 2027 (10 Nights)

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • St. Croix • Miami

Average Starting Price

$1,024pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Celebrity Constellation

Celebrity Cruises

Mar 6, 2027 - Mar 13, 2027 (7 Nights)

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

Average Starting Price

Dec 22, 2026 - Jan 5, 2027 (14 Nights)

Fort Lauderdale • Key West, Florida • Oranjestad, Aruba • Charlotteville, Tobago • Grenada • Bridgetown, Barbados • Castries, St. Lucia • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,664pp

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!

Grandeur of the Seas

Royal Caribbean

Aug 21, 2027 - Aug 28, 2027 (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 5, 2027 - Jan 21, 2027 (16 Nights)

Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Mar 19, 2027 - Mar 29, 2027 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale

Average Starting Price

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

San Juan, Puerto Rico • Oranjestad, Aruba • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 27, 2027 - Jan 6, 2028 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

$3,599pp

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!

Azamara Quest

Azamara

Dec 5, 2027 - Dec 19, 2027 (14 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

Dec 29, 2027 - Jan 8, 2028 (10 Nights)

Average Starting Price

$3,799pp

Jim's Onboard Credit

28% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Jan 27, 2028 - Feb 5, 2028 (9 Nights)

Miami • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Philipsburg, St. Maarten • Miami

Average Starting Price

$6,499pp

Jim's Onboard Credit

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