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EXPLORA I
Explora Journeys
Dec 27, 2026 - Jan 11, 2027 (15 Nights)
Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Great Harbor Jost Van Dyke, British Virgin Islands • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami
Average Starting Price
$15,520pp
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!

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
Brilliant Lady
Virgin Voyages
Jan 11, 2027 - Jan 21, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami
Average Starting Price
$1,090pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Mar 7, 2027 - Mar 17, 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
$1,124pp
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!

EXPLORA II
Explora Journeys
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Macapa, , Brazil • Tobago • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$6,850pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 22, 2027 - Jan 2, 2028 (11 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$3,034pp
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!

42% OFF
MSC Opera
MSC Cruises
Oct 29, 2027 - Nov 5, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique
Average Starting Price
$1,117pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Aug 7, 2027 - Aug 14, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$828pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$588pp
Jim's Onboard Credit
FREE Specialty Dining Meal
EXPLORA III
Explora Journeys
Jan 13, 2027 - Jan 29, 2027 (16 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$11,600pp
Jim's Onboard Credit
49% OFF
MSC World Europa
MSC Cruises
Apr 10, 2027 - Apr 24, 2027 (14 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain
Average Starting Price
$829pp
Jim's Onboard Credit
Viking Vesta
Viking
Dec 14, 2027 - Dec 27, 2027 (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
$2,699pp
Jim's Onboard Credit
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