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Silver Spirit
Silversea
Feb 20, 2029 - Mar 4, 2029 (12 Nights)
Miami • San Juan del sur, Nicaragua • Gustavia, St. Barts • St John's, Antigua • Roseau, Dominica • St. Kitts • Road Bay, Anguilla • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$5,300pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$639pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$636pp
Jim's Onboard Credit
Vista
Oceania Cruises
Nov 13, 2028 - Nov 25, 2028 (12 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$4,899pp
Jim's Onboard Credit
9% OFF
Crystal Serenity
Crystal Cruises
Feb 12, 2028 - Mar 10, 2028 (27 Nights)
Fort Lauderdale • Tortola • Gustavia, St. Barts • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Santo Tomas de Castilla, Guatemala • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$12,610pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$713pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 12, 2027 - Jan 2, 2028 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$5,169pp
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!

Silver Nova
Silversea
Jan 13, 2029 - Jan 22, 2029 (9 Nights)
Fort Lauderdale • San Juan del sur, Nicaragua • St. Kitts • Gustavia, St. Barts • St John's, Antigua • Roseau, Dominica • Soufrier Bay, St. Lucia • Bridgetown, Barbados
Average Starting Price
$4,200pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
May 6, 2028 - May 13, 2028 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$2,085pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,192pp
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!

Rotterdam
Holland America Line
Feb 23, 2027 - Mar 16, 2027 (21 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 • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$3,989pp
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!

Rhapsody of the Seas
Royal Caribbean
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$757pp
Jim's Onboard Credit
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