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Cruise Dates

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October 2026

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Explorer of the Seas

Royal Caribbean

Dec 28, 2026 - Jan 4, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Grand Bahama Island • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$1,959pp

Jim's Onboard Credit

FREE Specialty Dining Meal

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!

Celebrity Apex

Celebrity Cruises

Dec 28, 2027 - Jan 4, 2028 (7 Nights)

Port Canaveral (Orlando), Florida • Grand Turk • San Juan, Puerto Rico • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,981pp

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!

Norwegian Getaway

Norwegian Cruise Line

Dec 14, 2026 - Dec 22, 2026 (8 Nights)

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

Average Starting Price

31% OFF

Jan 27, 2029 - Feb 10, 2029 (14 Nights)

Galveston • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • Grenada • Fun Day at Sea • Fun Day at Sea • Montego Bay, Jamaica • Fun Day at Sea • Fun Day at Sea • Galveston

Average Starting Price

$1,321pp

Jim's Onboard Credit

Norwegian Gem

Norwegian Cruise Line

Nov 28, 2026 - Dec 10, 2026 (12 Nights)

Tampa • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Falmouth, Jamaica • George Town, Cayman Islands • Tampa

Average Starting Price

Oct 28, 2027 - Nov 6, 2027 (9 Nights)

New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

71% OFF

Nov 12, 2026 - Nov 22, 2026 (10 Nights)

Miami • St. Thomas • St. Kitts • Philipsburg, St. Maarten • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Dec 7, 2026 - Dec 16, 2026 (9 Nights)

Tampa • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Tampa

Average Starting Price

$961pp

Jim's Onboard Credit

FREE Specialty Dining Meal

26% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Dec 18, 2027 - Dec 28, 2027 (10 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • Roseau, Dominica • St John's, Antigua • Tortola • Miami

Average Starting Price

$8,349pp

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!

47% OFF