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Vision of the Seas
Royal Caribbean
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$765pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • 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
Average Starting Price
$10,524pp
Jim's Onboard Credit
Silver Shadow
Silversea
Mar 20, 2029 - Apr 3, 2029 (14 Nights)
San Juan del sur, Nicaragua • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • Santa Cruz de la Palma, Spain • Barcelona, Spain
Average Starting Price
$4,100pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 2, 2027 - Jan 9, 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
$648pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Prima
Norwegian Cruise Line
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,239pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 27, 2028 - Mar 12, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • 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
$1,738pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 8, 2029 - Mar 1, 2029 (21 Nights)
San Juan, Puerto Rico • Sail the Caribbean Sea • Bridgetown, Barbados • Sail the Atlantic Ocean • Iles du Salut (Ile Royale), French Guiana • Sail the Atlantic Ocean • Sail the Mouth of the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Sail the Amazon River • Sail the Amazon River • Belem, Brazil • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$12,499pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 24, 2027 - Jan 31, 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
$574pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Star Pride
Windstar Cruises
Nov 8, 2026 - Nov 15, 2026 (7 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$3,461pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Nov 20, 2027 - Nov 27, 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
$888pp
Jim's Onboard Credit
Silver Shadow
Silversea
Dec 23, 2028 - Dec 30, 2028 (7 Nights)
San Juan del sur, Nicaragua • St. John • St John's, Antigua • Charlestown, Nevis • Philipsburg, St. Maarten • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • San Juan del sur, Nicaragua
Average Starting Price
$4,300pp
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!

Rhapsody of the Seas
Royal Caribbean
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$508pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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