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Crown Princess
Princess Cruises
Mar 7, 2027 - Mar 21, 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 • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,641pp
Jim's Onboard Credit
Eurodam
Holland America Line
Jan 2, 2028 - Jan 22, 2028 (20 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Montego Bay, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,714pp
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!

41% OFF
MSC Meraviglia
MSC Cruises
Feb 27, 2027 - Mar 7, 2027 (8 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$717pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Feb 22, 2029 - Mar 8, 2029 (14 Nights)
Miami • Cruising the Atlantic Ocean • Cruising the Atlantic Ocean • St. Thomas • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • Miami
Average Starting Price
$7,199pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 6, 2027 - Nov 21, 2027 (15 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$4,319pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Aug 14, 2027 - Aug 21, 2027 (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
$777pp
Jim's Onboard Credit
28% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 7, 2028 - Jan 17, 2028 (10 Nights)
Miami • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$7,749pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 23, 2027 - Mar 6, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,269pp
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!

Brilliant Lady
Virgin Voyages
Dec 28, 2026 - Jan 7, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Tortola • St John's, Antigua • Bimini • Miami
Average Starting Price
$1,690pp
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!

Adventure of the Seas
Royal Caribbean
Feb 9, 2028 - Feb 18, 2028 (9 Nights)
Port Canaveral (Orlando), Florida • Basseterre, St. Kitts and Nevis • Bridgetown, Barbados • St John's, Antigua • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,196pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Mar 19, 2027 - Mar 29, 2027 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,530pp
Jim's Onboard Credit
Silver Nova
Silversea
Jan 31, 2028 - Feb 11, 2028 (11 Nights)
Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Miami
Average Starting Price
$6,300pp
Jim's Onboard Credit
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