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Cruise Dates

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October 2026

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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

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

Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Dec 5, 2027 - Dec 19, 2027 (14 Nights)

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

Average Starting Price

38% OFF

Jan 8, 2028 - Jan 16, 2028 (8 Nights)

Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida

Average Starting Price

Apr 4, 2027 - Apr 14, 2027 (10 Nights)

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

Average Starting Price

$1,101pp

Jim's Onboard Credit

FREE Specialty Dining Meal

30% OFF

Vista

Oceania Cruises

Dec 21, 2026 - Dec 28, 2026 (7 Nights)

Miami • Tortola • St. Thomas • Nassau • Miami

Average Starting Price

$3,045pp

Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Scarlet Lady

Virgin Voyages

Mar 11, 2028 - Mar 18, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Fort-De-France, Martinique • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

43% OFF

Mar 8, 2027 - Mar 18, 2027 (10 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • St. Kitts • St. Lucia • St John's, Antigua • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

Apr 23, 2028 - Apr 29, 2028 (6 Nights)

Fort Lauderdale • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Mar 10, 2029 - Mar 25, 2029 (15 Nights)

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

Average Starting Price

$2,434pp

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 IV

Explora Journeys

Mar 4, 2028 - Mar 11, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Key West, Florida • Ocean Cay • Miami

Average Starting Price

Nov 24, 2026 - Dec 3, 2026 (9 Nights)

Fort Lauderdale • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • St. Thomas • Fort Lauderdale

Average Starting Price

$1,186pp

Jim's Onboard Credit

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