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Freedom of the Seas
Royal Caribbean
Mar 25, 2027 - Mar 29, 2027 (4 Nights)
Miami • Grand Turk • Miami
Average Starting Price
$663pp
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!

48% OFF
MSC World Atlantic
MSC Cruises
Jan 29, 2028 - Feb 12, 2028 (14 Nights)
Port Canaveral (Orlando), Florida • Ocean Cay • Puerto Plata, Dominican Republic • Grand Turk • Nassau • Port Canaveral (Orlando), Florida • Ocean Cay • Costa Maya • Cozumel • Nassau • Port Canaveral (Orlando), Florida
Average Starting Price
$1,802pp
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!

Enchanted Princess
Princess Cruises
Dec 23, 2028 - Jan 2, 2029 (10 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
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!

Caribbean Princess
Princess Cruises
Feb 4, 2029 - Feb 11, 2029 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$925pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,098pp
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!

Silver Ray
Silversea
May 29, 2027 - Jun 8, 2027 (10 Nights)
Rome, Italy • Porto Santo Stefano • Florence/Pisa • Florence/Pisa • Portofino, Italy • Toulon, France • Ajaccio, France • Monte Carlo, Monaco • Monte Carlo, Monaco • Barcelona, Spain
Average Starting Price
$11,700pp
Jim's Onboard Credit
MSC Magnifica
MSC Cruises
Jan 7, 2027 - May 8, 2027 (121 Nights)
Barcelona, Spain • Gibraltar • Casablanca, Morocco • Mindelo, Cape Verde • Salvador, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Buenos Aires, Argentina • Buenos Aires, Argentina • Puerto Madryn, Argentina • Port Stanley, Falkland Islands • Ushuaia, Argentina • Ushuaia, Argentina • Puerto Montt, Chile • Valparaíso, Chile • Valparaíso, Chile • Hanga Roa (Rapa Nui), Chile • Bounty Bay Passage, Pitcaim • Papeete, French Polynesia • Papeete, French Polynesia • Moorea, French Polynesia • Aitutake, Aruntanga • Avatiu, Rarotonga, Cook Islands • Bay of Islands, New Zealand • Auckland, New Zealand • Tauranga, New Zealand • Christchurch, Lyttelton, New Zealand • Port Chalmers, New Zealand • Cruising Milford Sound • Hobart (Tasmania), Australia • Hobart (Tasmania), Australia • Sydney, Australia • Sydney, Australia • Noumea, New Caledonia • Luganville, Espirutu Santo • Apia, Samoa • International Dateline • Honolulu • Honolulu • Los Angeles • Cabo San Lucas • Puntarenas, Costa Rica • Balbao, Panama • Panama Canal, Panama • Panama Canal, Panama • La Romana, Dominican Republic • Tortola • Philipsburg, St. Maarten • Las Palmas (Gran Canaria), Spain • Ibiza, Spain • Naples, Italy • Rome (Civitavecchia), Italy • Genoa (Portofino), Italy • Marseille (Provence), France • Tarragona, Spain
Average Starting Price
$30,439pp
Jim's Onboard Credit
45% OFF
MSC Seashore
MSC Cruises
Jun 24, 2027 - Jun 27, 2027 (3 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$487pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 28, 2028 - Mar 21, 2028 (22 Nights)
San Juan, Puerto Rico • Funchal, Portugal • Casablanca, Morocco • Lisbon, Portugal • Cadiz, Spain • Gibraltar • Malaga, Spain • Almeria, Spain • Cartagena, Spain • Palma de Mallorca, Spain • Barcelona, Spain
Average Starting Price
$4,800pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 16, 2028 - Jan 23, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico
Average Starting Price
$679pp
Jim's Onboard Credit
47% OFF
MSC Poesia
MSC Cruises
Jan 23, 2028 - Feb 3, 2028 (11 Nights)
Miami • Montego Bay, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami
Average Starting Price
$1,073pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Dec 20, 2026 - Jan 4, 2027 (15 Nights)
San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Great Harbor Jost Van Dyke, British Virgin Islands • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$12,280pp
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!

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