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Wind Surf
Windstar Cruises
Nov 5, 2027 - Nov 28, 2027 (23 Nights)
Lisbon, Portugal • Funchal, Portugal • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$4,813pp
Jim's Onboard Credit
45% OFF
MSC Opera
MSC Cruises
Jul 30, 2027 - Aug 6, 2027 (7 Nights)
Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique
Average Starting Price
$1,367pp
Jim's Onboard Credit
52% OFF
MSC World Europa
MSC Cruises
Apr 11, 2027 - Apr 24, 2027 (13 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain
Average Starting Price
$699pp
Jim's Onboard Credit
48% OFF
MSC World Asia
MSC Cruises
Oct 30, 2027 - Nov 21, 2027 (22 Nights)
Marseille (Provence), France • Genoa (Portofino), Italy • Naples, Italy • Messina (Taormina), Italy • Valletta, Malta • Barcelona, Spain • Palma de Mallorca, Spain • Alicante, Spain • Malaga, Spain • Las Palmas (Gran Canaria), Spain • St John's, Antigua • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,444pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$731pp
Jim's Onboard Credit
9% OFF
Crystal Serenity
Crystal Cruises
Mar 10, 2028 - Mar 20, 2028 (10 Nights)
Fort Lauderdale • Grand Turk • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • St. Kitts • San Juan, Puerto Rico • Nassau • Fort Lauderdale
Average Starting Price
$5,110pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Nieuw Amsterdam
Holland America Line
Nov 29, 2026 - Dec 20, 2026 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,164pp
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 Prestige
Regent Seven Seas Cruises
Jan 29, 2029 - Feb 7, 2029 (9 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Miami
Average Starting Price
$6,899pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Dec 19, 2028 - Jan 11, 2029 (23 Nights)
Miami • Progreso, Mexico • Cozumel • Roatan, Honduras • Harvest Caye, Belize • George Town, Cayman Islands • Miami • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Castries, St. Lucia • St John's, Antigua • Tortola • Miami
Average Starting Price
$11,599pp
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!

Enchanted Princess
Princess Cruises
Feb 25, 2027 - Mar 7, 2027 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,774pp
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!

Grandeur of the Seas
Royal Caribbean
Jun 19, 2027 - Jun 26, 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
$796pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
Miami • Providenciales, Turks and Caicos Islands • Gustavia, St. Barts • St John's, Antigua • Road Bay, Anguilla • San Juan, Puerto Rico
Average Starting Price
$3,755pp
Jim's Onboard Credit
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