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Cruise Dates

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October 2026

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Regal Princess

Princess Cruises

Jan 30, 2028 - Feb 13, 2028 (14 Nights)

Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami

Average Starting Price

$1,289pp

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 Escape

Norwegian Cruise Line

Feb 12, 2027 - Feb 19, 2027 (7 Nights)

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

Average Starting Price

36% OFF

Mar 4, 2028 - Mar 12, 2028 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

Feb 14, 2027 - Feb 21, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Mar 19, 2027 - Apr 9, 2027 (21 Nights)

Rio de Janeiro, Brazil • Cruising the Amazon River • Alter Do Chao, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Santarem, Brazil • Cruising the Amazon River • Bridgetown, Barbados • St John's, Antigua • St. Thomas • Miami

Average Starting Price

Feb 7, 2027 - Feb 14, 2027 (7 Nights)

Miami • Nassau • St. Thomas • St John's, Antigua • Miami

Average Starting Price

30% OFF

Dec 12, 2026 - Dec 21, 2026 (9 Nights)

Miami • St. Thomas • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Feb 12, 2028 - Feb 23, 2028 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,854pp

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 Prima

Norwegian Cruise Line

Mar 21, 2027 - Mar 28, 2027 (7 Nights)

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

Average Starting Price

48% OFF

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

$1,537pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

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

Miami • St. Thomas • Samana, Dominican Republic • Nassau • Miami

Average Starting Price

$960pp

Jim's Onboard Credit

Norwegian Luna

Norwegian Cruise Line

Dec 19, 2027 - Dec 26, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami

Average Starting Price

$1,599pp

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!

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