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Cruise Dates

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October 2026

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49% OFF

MSC Seashore

MSC Cruises

Dec 18, 2027 - Jan 2, 2028 (15 Nights)

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

Average Starting Price

$2,180pp

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!

Icon of the Seas

Royal Caribbean

Apr 24, 2027 - May 1, 2027 (7 Nights)

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

Average Starting Price

$1,473pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Viking Sky

Viking

Feb 7, 2028 - Feb 17, 2028 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

Dec 3, 2027 - Dec 18, 2027 (15 Nights)

Lisbon, Portugal • Gibraltar • Philipsburg, St. Maarten • San Juan, Puerto Rico • Miami

Average Starting Price

Feb 4, 2028 - Feb 14, 2028 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • St. Thomas • Fort Lauderdale

Average Starting Price

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

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

37% OFF

Dec 18, 2027 - Dec 26, 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

$956pp

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

Dec 19, 2027 - Jan 2, 2028 (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 • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$1,613pp

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!