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Seabourn Ovation
Seabourn
Dec 18, 2027 - Dec 28, 2027 (10 Nights)
Bridgetown, Barbados • Grenada • Bequia Island, Saint Vincent • St. Pierre • Terre de Haut, Guadeloupe • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Road Bay, Anguilla • Philipsburg, St. Maarten
Average Starting Price
$7,383pp
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!

EXPLORA III
Explora Journeys
Nov 22, 2026 - Dec 6, 2026 (14 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Grand Turk • Miami
Average Starting Price
$7,995pp
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!

Enchanted Princess
Princess Cruises
Feb 5, 2027 - Feb 15, 2027 (10 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,999pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Mar 4, 2028 - Mar 11, 2028 (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
$788pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 14, 2028 - Dec 24, 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
45% OFF
MSC Meraviglia
MSC Cruises
Feb 13, 2027 - Feb 27, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Nassau • Ocean Cay • Grand Turk • Miami
Average Starting Price
$1,155pp
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!

Azamara Journey
Azamara
Dec 28, 2026 - Jan 14, 2027 (17 Nights)
Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Charlestown, Nevis • St. Croix • San Juan, Puerto Rico • St. John • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$5,419pp
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!

24% OFF
MSC World Europa
MSC Cruises
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,258pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Feb 26, 2028 - Mar 4, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
44% OFF
Carnival Magic
Carnival Cruise Line
Mar 11, 2028 - Mar 19, 2028 (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
$713pp
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!

Star Pride
Windstar Cruises
Jan 3, 2027 - Jan 17, 2027 (14 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • 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
$6,954pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$639pp
Jim's Onboard Credit
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