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October 2026

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49% OFF

MSC World America

MSC Cruises

Sep 11, 2027 - Sep 25, 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

$1,541pp

Jim's Onboard Credit

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

Rhapsody of the Seas

Royal Caribbean

Feb 13, 2027 - Feb 20, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$550pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Viking Sky

Viking

Jan 3, 2029 - Jan 13, 2029 (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

Feb 26, 2028 - Mar 11, 2028 (14 Nights)

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

Average Starting Price

$3,559pp

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 II

Explora Journeys

Mar 19, 2028 - Apr 11, 2028 (23 Nights)

Miami • San Juan, Puerto Rico • St John's, Antigua • Funchal, Portugal • Cadiz, Spain • Malaga, Spain • Barcelona, Spain • St Tropez, France • Monte Carlo, Monaco • Livorno, Italy • Rome (Civitavecchia), Italy • Mahon, Spain • Barcelona, Spain

Average Starting Price

Nov 14, 2026 - Nov 21, 2026 (7 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

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

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

Average Starting Price

$901pp

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!

Crystal Serenity

Crystal Cruises

Nov 23, 2026 - Nov 27, 2026 (4 Nights)

Fort Lauderdale • Nassau • Samana, Dominican Republic • San Juan, Puerto Rico

Average Starting Price

Jan 31, 2027 - Feb 7, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Feb 26, 2028 - Mar 4, 2028 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Mar 29, 2028 - Apr 7, 2028 (9 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Port Canaveral (Orlando), Florida

Average Starting Price

58% OFF

Jan 23, 2027 - Jan 31, 2027 (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

$435pp

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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