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Cruise Dates

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October 2026

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Silver Ray

Silversea

Jan 5, 2027 - Jan 16, 2027 (11 Nights)

Miami • San Juan, Puerto Rico • St. John • St. Kitts • Deshaies, Guadeloupe • St John's, Antigua • Tortola • Miami

Average Starting Price

Jan 30, 2027 - Feb 6, 2027 (7 Nights)

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

Average Starting Price

$1,394pp

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!

Independence of the Seas

Royal Caribbean

Apr 4, 2027 - Apr 11, 2027 (7 Nights)

Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami

Average Starting Price

$602pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Celebrity Summit

Celebrity Cruises

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

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

Average Starting Price

Dec 5, 2027 - Dec 12, 2027 (7 Nights)

San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Roseau, Dominica • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Feb 13, 2027 - Feb 23, 2027 (10 Nights)

Miami • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Great Stirrup Cay • Miami

Average Starting Price

Dec 19, 2027 - Jan 2, 2028 (14 Nights)

Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami • Celebration Key • Amber Cove, Dominican Republic • Grand Turk • Miami

Average Starting Price

$2,323pp

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

Dec 19, 2027 - Jan 2, 2028 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale

Average Starting Price

$2,163pp

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!

Silver Nova

Silversea

Jan 6, 2027 - Jan 18, 2027 (12 Nights)

Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St. Kitts • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Bridgetown, Barbados

Average Starting Price

Nov 13, 2026 - Nov 20, 2026 (7 Nights)

Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Disney Castaway Cay, Bahamas • Fort Lauderdale

Average Starting Price

Jan 23, 2028 - Jan 30, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Ocean Cay • Miami

Average Starting Price

$3,915pp

Jim's Onboard Credit

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