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Regal Princess
Princess Cruises
Dec 26, 2026 - Jan 9, 2027 (14 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Grand Turk • Fort Lauderdale • Celebration Key • Grand Turk • Nassau • Fort Lauderdale
Average Starting Price
$1,229pp
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!

Rhapsody of the Seas
Royal Caribbean
Nov 28, 2026 - Dec 5, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$620pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$2,134pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

Enchanted Princess
Princess Cruises
Jan 2, 2029 - Jan 13, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,450pp
Jim's Onboard Credit
42% OFF
MSC Opera
MSC Cruises
May 28, 2027 - Jun 4, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique
Average Starting Price
$1,047pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • Bridgetown, Barbados • St. Lucia • Tortola • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$839pp
Jim's Onboard Credit
30% OFF
MSC World Europa
MSC Cruises
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$929pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$3,638pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 12, 2028 - Feb 26, 2028 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$10,208pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 25, 2029 - Mar 11, 2029 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,974pp
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!

Rhapsody of the Seas
Royal Caribbean
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$794pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Star of the Seas
Royal Caribbean
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,277pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

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