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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
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
Viking Sea
Viking
Dec 10, 2028 - Dec 20, 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
$3,799pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 14, 2027 - Feb 28, 2027 (14 Nights)
Fort Lauderdale • Celebration Key • Grand Turk • Nassau • Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$1,449pp
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!

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
$674pp
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!

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
$4,228pp
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 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
$788pp
Jim's Onboard Credit
45% 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
$707pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Dec 30, 2028 - Jan 13, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,344pp
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!

63% OFF
MSC World America
MSC Cruises
Nov 28, 2026 - Dec 5, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$468pp
Jim's Onboard Credit

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

Crown Princess
Princess Cruises
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$989pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,009pp
Jim's Onboard Credit
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