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October 2026

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59% OFF

Carnival Magic

Carnival Cruise Line

Apr 17, 2027 - Apr 25, 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

$464pp

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!

48% OFF

MSC Seashore

MSC Cruises

Dec 12, 2027 - Dec 26, 2027 (14 Nights)

Miami • Ocean Cay • Puerto Plata, Dominican Republic • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Mar 25, 2028 - Apr 2, 2028 (8 Nights)

Fort Lauderdale • Nassau • San Juan, Puerto Rico • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Feb 8, 2027 - Feb 18, 2027 (10 Nights)

Miami • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami

Average Starting Price

Jan 10, 2028 - Jan 24, 2028 (14 Nights)

San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Jan 16, 2027 - Jan 23, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

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

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

Average Starting Price

Jan 3, 2027 - Jan 14, 2027 (11 Nights)

Cape Liberty • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • Cape Liberty

Average Starting Price

$1,393pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Regal Princess

Princess Cruises

Dec 19, 2027 - Jan 2, 2028 (14 Nights)

Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami • Celebration Key • Amber Cove, Dominican Republic • Grand Turk • Miami

Average Starting Price

$2,323pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

43% OFF

Carnival Vista

Carnival Cruise Line

Jan 9, 2027 - Jan 17, 2027 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Grand Bahama Island • Port Canaveral (Orlando), Florida

Average Starting Price

Apr 2, 2028 - Apr 9, 2028 (7 Nights)

Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

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

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami

Average Starting Price

$6,195pp

Jim's Onboard Credit

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