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Cruise Dates

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October 2026

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Norwegian Pearl

Norwegian Cruise Line

Jan 3, 2028 - Jan 15, 2028 (12 Nights)

Philadelphia • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia

Average Starting Price

Mar 6, 2027 - Mar 13, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Tortola • San Juan, Puerto Rico

Average Starting Price

Jan 8, 2028 - Jan 22, 2028 (14 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Fort Lauderdale

Average Starting Price

$3,229pp

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!

Celebrity Constellation

Celebrity Cruises

Mar 6, 2027 - Mar 13, 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

Nov 8, 2027 - Nov 15, 2027 (7 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

Average Starting Price

Feb 6, 2027 - Feb 16, 2027 (10 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Little Bay, Montserrat • Les Saintes, F.W.I. • Roseau, Dominica • Trois Ilets, Martinique • Castries, St. Lucia • Grenada • Bridgetown, Barbados

Average Starting Price

48% OFF

Oct 23, 2027 - Nov 6, 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

$1,621pp

Jim's Onboard Credit

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

Grandeur of the Seas

Royal Caribbean

Jul 24, 2027 - Jul 31, 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

Nov 6, 2027 - Nov 14, 2027 (8 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • 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

Mar 14, 2027 - Mar 21, 2027 (7 Nights)

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

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!

Norwegian Dawn

Norwegian Cruise Line

Jan 28, 2028 - Feb 7, 2028 (10 Nights)

Jacksonville • Grand Bahama Island • Great Stirrup Cay • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Tortola • San Juan, Puerto Rico • Jacksonville

Average Starting Price

Dec 30, 2027 - Jan 6, 2028 (7 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale

Average Starting Price

$2,234pp

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!

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