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Icon of the Seas
Royal Caribbean
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,206pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Luna
Norwegian Cruise Line
Feb 13, 2028 - Feb 20, 2028 (7 Nights)
Miami • Great Stirrup Cay • St. Thomas • Tortola • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,229pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,338pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Fort-De-France, Martinique • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • San Juan, Puerto Rico
Average Starting Price
$598pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Eurodam
Holland America Line
Nov 28, 2026 - Dec 12, 2026 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$2,204pp
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!

Viking Sea
Viking
Dec 5, 2026 - Dec 15, 2026 (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
$5,299pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St. Croix • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$553pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Star of the Seas
Royal Caribbean
Nov 14, 2027 - Nov 21, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,589pp
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!

Hero of the Seas
Royal Caribbean
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$2,047pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 10, 2027 - Jan 24, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,676pp
Jim's Onboard Credit
45% OFF
Carnival Celebration
Carnival Cruise Line
Feb 6, 2028 - Feb 13, 2028 (7 Nights)
Miami • Celebration Key • Fun Day at Sea • Fun Day at Sea • St. Thomas • Amber Cove, Dominican Republic • Fun Day at Sea • Miami
Average Starting Price
$598pp
Jim's Onboard Credit
45% OFF
MSC Meraviglia
MSC Cruises
Jan 16, 2027 - Jan 30, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Puerto Plata, Dominican Republic • Miami • Nassau • Ocean Cay • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,055pp
Jim's Onboard Credit
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