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Scarlet Lady
Virgin Voyages
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Eurodam
Holland America Line
Feb 27, 2027 - Mar 9, 2027 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,989pp
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!

27% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 24, 2028 - Mar 5, 2028 (10 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$6,849pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 4, 2028 - Dec 14, 2028 (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
$3,799pp
Jim's Onboard Credit
Viking Vesta
Viking
Dec 8, 2028 - Dec 21, 2028 (13 Nights)
Barcelona, Spain • Sail the Mediterranean Sea • Sail the Atlantic Ocean • Funchal, Portugal • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Philipsburg, St. Maarten • Sail the Caribbean Sea • Sail the Caribbean Sea • Fort Lauderdale
Average Starting Price
$2,999pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Feb 20, 2028 - Feb 27, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$781pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Oct 30, 2027 - Nov 6, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$997pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 14, 2027 - Feb 28, 2027 (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
$1,428pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Nov 30, 2027 - Dec 14, 2027 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,899pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$5,103pp
Jim's Onboard Credit
Silver Shadow
Silversea
Dec 16, 2028 - Dec 23, 2028 (7 Nights)
San Juan del sur, Nicaragua • Virgin Gorda, British Virgin Islands • St John's, Antigua • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Charlestown, Nevis • Gustavia, St. Barts • San Juan del sur, Nicaragua
Average Starting Price
$3,700pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Mar 4, 2028 - Mar 11, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,037pp
Jim's Onboard Credit
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