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October 2026

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Eurodam

Holland America Line

Nov 28, 2026 - Dec 5, 2026 (7 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,139pp

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!

Vision of the Seas

Royal Caribbean

Jan 30, 2028 - Feb 6, 2028 (7 Nights)

San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Nov 30, 2028 - Dec 10, 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

Nov 24, 2028 - Dec 4, 2028 (10 Nights)

Average Starting Price

Feb 26, 2028 - Mar 4, 2028 (7 Nights)

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

Average Starting Price

Mar 25, 2028 - Apr 1, 2028 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

Apr 18, 2027 - Apr 25, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,500pp

Jim's Onboard Credit

FREE Specialty Dining Meal

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!

Rotterdam

Holland America Line

Mar 4, 2028 - Mar 18, 2028 (14 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Fort Lauderdale

Average Starting Price

$3,559pp

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!

58% OFF

Carnival Magic

Carnival Cruise Line

Jan 23, 2027 - Jan 31, 2027 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$435pp

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!

Norwegian Epic

Norwegian Cruise Line

Mar 24, 2028 - Mar 31, 2028 (7 Nights)

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

Average Starting Price

55% OFF

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

Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Miami

Average Starting Price

Jan 17, 2027 - Jan 31, 2027 (14 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • 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

$1,636pp

Jim's Onboard Credit

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