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Silver Shadow
Silversea
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St John's, Antigua • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$5,100pp
Jim's Onboard Credit
Crystal Symphony
Crystal Cruises
Mar 20, 2027 - Apr 12, 2027 (23 Nights)
Fort Lauderdale • San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • Santa Cruz de la Palma, Spain • Santa Cruz de Tenerife, Spain • Canary Islands • San Sebastian (La Gomera), Canary Islands, Spain • Arrecife (Lanzarote), Spain • Funchal, Portugal • Funchal, Portugal • Agadir, Morocco • Casablanca, Morocco • Cadiz, Spain • Portimão, Portugal • Lisbon, Portugal
Average Starting Price
$10,600pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Dec 20, 2026 - Jan 5, 2027 (16 Nights)
Miami • San Juan, Puerto Rico • Road Bay, Anguilla • St. Kitts • Marigot Bay, St. Martin, French West Indies • Terre de Haut, Guadeloupe • Fort-De-France, Martinique • Rodney Bay, Saint Lucia • Roseau, Dominica • Little Bay, Montserrat • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$11,163pp
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!

59% OFF
Carnival Magic
Carnival Cruise Line
Apr 17, 2027 - Apr 25, 2027 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$464pp
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!

Viking Sea
Viking
Feb 24, 2027 - Mar 6, 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
EXPLORA IV
Explora Journeys
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
San Juan, Puerto Rico • Gustavia, St. Barts • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Ocean Cay • Miami
Average Starting Price
$3,455pp
Jim's Onboard Credit
Silver Dawn
Silversea
Feb 24, 2028 - Mar 3, 2028 (8 Nights)
San Juan, Puerto Rico • St. Kitts • Gustavia, St. Barts • Deshaies, Guadeloupe • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$4,000pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Feb 19, 2027 - Mar 7, 2027 (16 Nights)
Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • Road Bay, Anguilla • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$12,375pp
Jim's Onboard Credit
Viking Sky
Viking
Feb 7, 2028 - Feb 17, 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
$4,299pp
Jim's Onboard Credit
Symphony of the Seas
Royal Caribbean
Mar 25, 2028 - Apr 2, 2028 (8 Nights)
Fort Lauderdale • Nassau • San Juan, Puerto Rico • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,248pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Jan 20, 2027 - Feb 5, 2027 (16 Nights)
Miami • Ocho Rios, Jamaica • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • Belize City • Key West, Florida • Miami • Puerto Plata, Dominican Republic • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$9,185pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Mar 26, 2028 - Apr 2, 2028 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • St John's, Antigua • Fort Lauderdale
Average Starting Price
$2,299pp
Jim's Onboard Credit
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