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Port: San Juan, Puerto Rico×
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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
$1,169pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Nov 18, 2028 - Nov 26, 2028 (8 Nights)
Fort Lauderdale • Grand Turk • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • San Juan, Puerto Rico
Average Starting Price
$875pp
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!

Valiant Lady
Virgin Voyages
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$1,533pp
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!

6% OFF
Carnival Magic
Carnival Cruise Line
Nov 28, 2026 - Dec 6, 2026 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$498pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

EXPLORA I
Explora Journeys
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami
Average Starting Price
$8,090pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 16, 2028 - Jan 23, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico
Average Starting Price
$679pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 14, 2027 - Nov 28, 2027 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$4,019pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 30, 2028 - Feb 6, 2028 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$731pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 13, 2027 - Jan 21, 2027 (8 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Terre de Haut, Guadeloupe • Grenada • Castries, St. Lucia • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$5,550pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
Miami • Providenciales, Turks and Caicos Islands • Gustavia, St. Barts • St John's, Antigua • Road Bay, Anguilla • San Juan, Puerto Rico
Average Starting Price
$3,545pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 27, 2028 - Apr 19, 2028 (23 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 • Lisbon, Portugal • Brest, France • Amsterdam, Netherlands
Average Starting Price
$4,211pp
Jim's Onboard Credit
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
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