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Crown Princess
Princess Cruises
Feb 28, 2027 - Mar 14, 2027 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,296pp
Jim's Onboard Credit
54% OFF
MSC World America
MSC Cruises
May 1, 2027 - May 15, 2027 (14 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami • Roatan, Honduras • Costa Maya • Cozumel • Ocean Cay • Miami
Average Starting Price
$1,341pp
Jim's Onboard Credit

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

Rotterdam
Holland America Line
Feb 23, 2027 - Mar 16, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$3,989pp
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!

Grandeur of the Seas
Royal Caribbean
Aug 14, 2027 - Aug 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$777pp
Jim's Onboard Credit
27% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 29, 2029 - Feb 7, 2029 (9 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Miami
Average Starting Price
$6,899pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Mar 14, 2027 - Mar 28, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Cozumel • Belize City • Roatan, Honduras • Fort Lauderdale
Average Starting Price
$1,468pp
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
Feb 20, 2027 - Feb 27, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,043pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 21, 2027 - Dec 5, 2027 (14 Nights)
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 • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$3,329pp
Jim's Onboard Credit
36% OFF
Carnival Festivale
Carnival Cruise Line
Oct 30, 2027 - Nov 7, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$989pp
Jim's Onboard Credit
Symphony of the Seas
Royal Caribbean
Jan 29, 2028 - Feb 6, 2028 (8 Nights)
Fort Lauderdale • Nassau • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,134pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Feb 20, 2027 - Feb 27, 2027 (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
$699pp
Jim's Onboard Credit
3% OFF
Carnival Celebration
Carnival Cruise Line
Mar 28, 2027 - Apr 5, 2027 (8 Nights)
Miami • Celebration Key • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Miami
Average Starting Price
$811pp
Jim's Onboard Credit
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