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October 2026

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Nieuw Statendam

Holland America Line

Mar 21, 2027 - Apr 4, 2027 (14 Nights)

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

Average Starting Price

$2,709pp

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!

31% OFF

Carnival Miracle

Carnival Cruise Line

Jan 15, 2028 - Jan 27, 2028 (12 Nights)

Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Croix • St John's, Antigua • Martinique • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore

Average Starting Price

$1,322pp

Jim's Onboard Credit

59% OFF

Margaritaville at Sea Beachcomber

Margaritaville at Sea

Mar 20, 2027 - Mar 27, 2027 (7 Nights)

Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$799pp

Jim's Onboard Credit

29% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 20, 2027 - Mar 30, 2027 (10 Nights)

Miami • St. Thomas • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • St John's, Antigua • Tortola • San Juan, Puerto Rico

Average Starting Price

Dec 7, 2027 - Dec 17, 2027 (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

Dec 4, 2027 - Dec 13, 2027 (9 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St. Thomas • Miami

Average Starting Price

$5,285pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 13, 2027 - Nov 20, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Lucia • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Oct 16, 2027 - Oct 23, 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

Aug 15, 2027 - Aug 22, 2027 (7 Nights)

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

Average Starting Price

$1,602pp

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!

Harmony of the Seas

Royal Caribbean

Sep 4, 2027 - Sep 11, 2027 (7 Nights)

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

Average Starting Price

Dec 9, 2027 - Dec 19, 2027 (10 Nights)

Average Starting Price

$3,799pp

Jim's Onboard Credit

Norwegian Aqua

Norwegian Cruise Line

Aug 22, 2027 - Aug 29, 2027 (7 Nights)

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

Average Starting Price

$1,029pp

Jim's Onboard Credit

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