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Cruise Dates

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October 2026

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Caribbean Princess

Princess Cruises

Jan 28, 2029 - Feb 11, 2029 (14 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

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

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$670pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Emerald Princess

Princess Cruises

Jan 16, 2028 - Jan 23, 2028 (7 Nights)

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

Average Starting Price

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

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

55% OFF

Feb 20, 2027 - Feb 28, 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

$505pp

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!

Azamara Quest

Azamara

Nov 28, 2027 - Dec 12, 2027 (14 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • 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

Average Starting Price

48% OFF

Mar 11, 2028 - Mar 25, 2028 (14 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami

Average Starting Price

$1,827pp

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!

Viking Sea

Viking

Nov 25, 2026 - Dec 5, 2026 (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

Jan 3, 2029 - Jan 13, 2029 (10 Nights)

Average Starting Price

Feb 19, 2028 - Feb 26, 2028 (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

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!

43% OFF

Carnival Celebration

Carnival Cruise Line

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

Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Miami

Average Starting Price

$671pp

Jim's Onboard Credit

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