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9% OFF
Crystal Symphony
Crystal Cruises
Dec 2, 2027 - Dec 10, 2027 (8 Nights)
Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Pointe-à-Pitre, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$3,750pp
Jim's Onboard Credit
49% OFF
MSC World America
MSC Cruises
Sep 25, 2027 - Oct 9, 2027 (14 Nights)
Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$1,571pp
Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Vision of the Seas
Royal Caribbean
Feb 13, 2028 - Feb 20, 2028 (7 Nights)
San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$780pp
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
$8,220pp
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!

Azamara Quest
Azamara
Dec 12, 2027 - Dec 27, 2027 (15 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 • Portsmouth, Dominica • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$4,089pp
Jim's Onboard Credit
Viking Sea
Viking
Nov 15, 2026 - Nov 25, 2026 (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
EXPLORA IV
Explora Journeys
Apr 29, 2028 - May 6, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Marigot Bay, St. Lucia • Miami
Average Starting Price
$3,485pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 20, 2028 - Feb 27, 2028 (7 Nights)
Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Celebration Key • Miami
Average Starting Price
$899pp
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
Dec 27, 2026 - Jan 3, 2027 (7 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
Average Starting Price
$4,613pp
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!

Sky Princess
Princess Cruises
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$699pp
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!

Rhapsody of the Seas
Royal Caribbean
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$900pp
Jim's Onboard Credit
43% OFF
Carnival Vista
Carnival Cruise Line
Jan 9, 2027 - Jan 17, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$762pp
Jim's Onboard Credit
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