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Rhapsody of the Seas
Royal Caribbean
Feb 19, 2028 - Feb 26, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$868pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Feb 13, 2027 - Feb 20, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,353pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Scarlet Lady
Virgin Voyages
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$10,174pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 24, 2027 - Feb 7, 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 • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,522pp
Jim's Onboard Credit
Silver Shadow
Silversea
Dec 7, 2028 - Dec 16, 2028 (9 Nights)
San Juan del sur, Nicaragua • Charlestown, Nevis • Philipsburg, St. Maarten • Les Saintes, F.W.I. • Roseau, Dominica • Trois Ilets, Martinique • Gustavia, St. Barts • St John's, Antigua • Soper's Hole, Tortola • San Juan del sur, Nicaragua
Average Starting Price
$4,200pp
Jim's Onboard Credit
Eurodam
Holland America Line
Mar 15, 2028 - Apr 1, 2028 (17 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Grand Turk • Amber Cove, Dominican Republic • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,239pp
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!

Harmony of the Seas
Royal Caribbean
Mar 27, 2027 - Apr 3, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,046pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Vision of the Seas
Royal Caribbean
Jan 10, 2027 - Jan 17, 2027 (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
$509pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Star of the Seas
Royal Caribbean
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,703pp
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!

Norwegian Prima
Norwegian Cruise Line
Feb 21, 2027 - Feb 28, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,099pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 14, 2028 - Feb 28, 2028 (14 Nights)
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 • 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
Average Starting Price
$4,154pp
Jim's Onboard Credit
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