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Cruise Dates

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October 2026

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Norwegian Bliss

Norwegian Cruise Line

Jan 4, 2027 - Jan 16, 2027 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan

Average Starting Price

Dec 12, 2026 - Jan 2, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,604pp

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!

Regal Princess

Princess Cruises

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

Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$669pp

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!

Star Princess

Princess Cruises

Dec 30, 2028 - Jan 6, 2029 (7 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$1,225pp

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!

Emerald Princess

Princess Cruises

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

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

Average Starting Price

Dec 28, 2028 - Jan 7, 2029 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Martinique • Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico

Average Starting Price

$1,650pp

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!

Celebrity Xcel

Celebrity Cruises

Nov 8, 2026 - Nov 15, 2026 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Dec 13, 2026 - Dec 27, 2026 (14 Nights)

Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami

Average Starting Price

Dec 12, 2026 - Dec 19, 2026 (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

59% OFF

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 - Nov 28, 2027 (8 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

Average Starting Price

$3,028pp

Jim's Onboard Credit

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