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October 2026

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59% OFF

Carnival Magic

Carnival Cruise Line

Mar 6, 2027 - Mar 14, 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

$454pp

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!

50% OFF

MSC Opera

MSC Cruises

Oct 18, 2027 - Nov 1, 2027 (14 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic

Average Starting Price

Nov 20, 2027 - Dec 5, 2027 (15 Nights)

Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten

Average Starting Price

41% OFF

Feb 27, 2027 - Mar 7, 2027 (8 Nights)

Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Amber Cove, Dominican Republic • Miami

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

Mar 11, 2028 - Mar 18, 2028 (7 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

Dec 14, 2026 - Dec 23, 2026 (9 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Bimini • Miami

Average Starting Price

Feb 20, 2027 - Feb 27, 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

$568pp

Jim's Onboard Credit

FREE Specialty Dining Meal

EXPLORA III

Explora Journeys

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

Feb 25, 2027 - Mar 7, 2027 (10 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale

Average Starting Price

$1,774pp

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!

42% OFF

MSC World Europa

MSC Cruises

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

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain • Marseille (Provence), France • Genoa (Portofino), Italy • La Spezia, Italy • Rome (Civitavecchia), Italy • Palma de Mallorca, Spain

Average Starting Price

Nov 27, 2027 - Dec 11, 2027 (14 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados

Average Starting Price

$8,408pp

Jim's Onboard Credit

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