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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
Viking Sea
Viking
Jan 25, 2027 - Feb 4, 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
42% OFF
MSC Opera
MSC Cruises
Aug 13, 2027 - Aug 20, 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
$1,117pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,338pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$4,768pp
Jim's Onboard Credit
Viking Sky
Viking
Nov 14, 2028 - Nov 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
Insignia
Oceania Cruises
Nov 9, 2026 - Dec 19, 2026 (40 Nights)
Lisbon, Portugal • Arrecife (Lanzarote), Spain • Las Palmas (Gran Canaria), Spain • Santa Cruz de la Palma, Spain • San Juan, Puerto Rico • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Cruising the Amazon River • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico • Nassau • Miami
Average Starting Price
$24,699pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Mar 23, 2027 - Apr 6, 2027 (14 Nights)
Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,918pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
Philipsburg, St. Maarten • St John's, Antigua • Gustavia, St. Barts • 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 • Charlestown, Nevis • Philipsburg, St. Maarten
Average Starting Price
$3,028pp
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 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
Feb 6, 2027 - Feb 13, 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
$608pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Grandeur of the Seas
Royal Caribbean
Nov 6, 2027 - Nov 13, 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
$798pp
Jim's Onboard Credit
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