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Cruise Dates

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October 2026

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Norwegian Prima

Norwegian Cruise Line

Feb 5, 2028 - Feb 12, 2028 (7 Nights)

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

Average Starting Price

Apr 9, 2028 - Apr 16, 2028 (7 Nights)

Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami

Average Starting Price

$919pp

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!

Rotterdam

Holland America Line

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!

Norwegian Escape

Norwegian Cruise Line

Sep 17, 2028 - Sep 24, 2028 (7 Nights)

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

Average Starting Price

53% OFF

Dec 18, 2026 - Dec 26, 2026 (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

$586pp

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!

Celebrity Apex

Celebrity Cruises

Dec 5, 2026 - Dec 12, 2026 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida

Average Starting Price

Nov 18, 2028 - Nov 25, 2028 (7 Nights)

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

Average Starting Price

$925pp

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!

Celebrity Xcel

Celebrity Cruises

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

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

Average Starting Price

$2,152pp

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!

Harmony of the Seas

Royal Caribbean

Jan 22, 2028 - Jan 29, 2028 (7 Nights)

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

Average Starting Price

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

$1,600pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Norwegian Aqua

Norwegian Cruise Line

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

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

Average Starting Price

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

Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida

Average Starting Price

$2,565pp

Jim's Onboard Credit

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