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Star Legend
Windstar Cruises
Jan 31, 2028 - Feb 7, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 2, 2027 - Jan 9, 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
$786pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Mar 7, 2027 - Mar 14, 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
$670pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Emerald Princess
Princess Cruises
Jan 2, 2028 - Jan 16, 2028 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,363pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Sep 4, 2027 - Sep 11, 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
$705pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 20, 2028 - Mar 27, 2028 (7 Nights)
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
$2,443pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 13, 2027 - Feb 20, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$578pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Viking Sky
Viking
Dec 24, 2028 - Jan 3, 2029 (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

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
Dec 28, 2026 - Jan 13, 2027 (16 Nights)
San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$14,175pp
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!

Crown Princess
Princess Cruises
Jan 31, 2027 - Feb 14, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,324pp
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
Norwegian Prima
Norwegian Cruise Line
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$1,209pp
Jim's Onboard Credit
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