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Vision of the Seas
Royal Caribbean
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Fort-De-France, Martinique • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • San Juan, Puerto Rico
Average Starting Price
$549pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Grandeur of the Seas
Royal Caribbean
Jul 10, 2027 - Jul 17, 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
$909pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 27, 2028 - Apr 3, 2028 (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
$2,411pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 30, 2028 - Jan 9, 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
$4,499pp
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
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
Silver Shadow
Silversea
Feb 3, 2029 - Feb 10, 2029 (7 Nights)
San Juan del sur, Nicaragua • St. John • St John's, Antigua • Road Bay, Anguilla • St. Kitts • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan del sur, Nicaragua
Average Starting Price
$3,900pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 17, 2027 - Jan 24, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,029pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Fort-De-France, Martinique • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 5, 2028 - Feb 12, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,189pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 21, 2028 - Mar 13, 2028 (21 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 • Funchal, Portugal • Casablanca, Morocco • Lisbon, Portugal
Average Starting Price
$4,271pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Nov 20, 2026 - Nov 28, 2026 (8 Nights)
San Juan, Puerto Rico • St. Thomas • Willemstad, Curacao • Oranjestad, Aruba • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$952pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$994pp
Jim's Onboard Credit
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