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Cruise Dates

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October 2026

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46% OFF

MSC Meraviglia

MSC Cruises

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

Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Nassau • Miami

Average Starting Price

$1,265pp

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!

Coral Princess

Princess Cruises

Dec 21, 2028 - Jan 4, 2029 (14 Nights)

Fort Lauderdale • St. Thomas • St John's, Antigua • St. Kitts • Dominica • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Grand Turk • Fort Lauderdale

Average Starting Price

$2,125pp

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!

Rotterdam

Holland America Line

Jan 15, 2028 - Jan 29, 2028 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,419pp

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!

58% OFF

Carnival Venezia

Carnival Cruise Line

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

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

Average Starting Price

$444pp

Jim's Onboard Credit

Norwegian Getaway

Norwegian Cruise Line

Nov 16, 2026 - Nov 23, 2026 (7 Nights)

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

Average Starting Price

$419pp

Jim's Onboard Credit

Norwegian Escape

Norwegian Cruise Line

Mar 12, 2027 - Mar 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

$719pp

Jim's Onboard Credit

28% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Dec 30, 2028 - Jan 9, 2029 (10 Nights)

Miami • St. Thomas • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Tortola • Miami

Average Starting Price

$7,599pp

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!

Crown Princess

Princess Cruises

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

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

Average Starting Price

Dec 14, 2026 - Dec 23, 2026 (9 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Bimini • Miami

Average Starting Price

Sep 26, 2027 - Oct 3, 2027 (7 Nights)

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

Average Starting Price

$1,486pp

Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!