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Star of the Seas
Royal Caribbean
Feb 20, 2028 - Feb 27, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,648pp
Jim's Onboard Credit
CBT Exclusive
$$$ Savings

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!

Celebrity Apex
Celebrity Cruises
Apr 1, 2028 - Apr 8, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,092pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 5, 2028 - Feb 12, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,189pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 4, 2027 - Feb 14, 2027 (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
$6,799pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 7, 2028 - Feb 21, 2028 (14 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Nov 10, 2026 - Nov 21, 2026 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,969pp
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!

Star Princess
Princess Cruises
Dec 30, 2028 - Jan 13, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,344pp
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!

Norwegian Bliss
Norwegian Cruise Line
Nov 29, 2026 - Dec 11, 2026 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Tortola • Manhattan
Average Starting Price
$1,529pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami
Average Starting Price
$1,646pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 16, 2028 - Jan 30, 2028 (14 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami
Average Starting Price
$1,138pp
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!

Emerald Princess
Princess Cruises
Jan 16, 2028 - Jan 30, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,308pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Mar 17, 2028 - Mar 27, 2028 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,730pp
Jim's Onboard Credit
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