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Viking Sky
Viking
Jan 13, 2029 - Feb 3, 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
$12,299pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Nov 29, 2026 - Dec 13, 2026 (14 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Grand Turk • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Gustavia, St. Barts • San Juan, Puerto Rico
Average Starting Price
$9,485pp
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!

Star Pride
Windstar Cruises
Mar 30, 2027 - Apr 15, 2027 (16 Nights)
San Juan, Puerto Rico • Lisbon, Portugal • London (City), England
Average Starting Price
$2,760pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 7, 2027 - Feb 14, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$681pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Apr 29, 2028 - May 6, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Pointe-à-Pitre, Guadeloupe • St. Kitts • Marigot Bay, St. Martin, French West Indies • Miami
Average Starting Price
$3,755pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 29, 2028 - Feb 5, 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
$833pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 8, 2028 - Jan 15, 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
$1,219pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 16, 2027 - Jan 23, 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
$726pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 16, 2028 - Feb 26, 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
$4,499pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 24, 2028 - Feb 7, 2028 (14 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 • 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
$4,014pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 27, 2027 - Jan 3, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$1,180pp
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!

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