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October 2026

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Adventure of the Seas

Royal Caribbean

Jan 26, 2028 - Feb 4, 2028 (9 Nights)

Port Canaveral (Orlando), Florida • Basseterre, St. Kitts and Nevis • Fort-De-France, Martinique • St John's, Antigua • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

Nov 15, 2026 - Nov 25, 2026 (10 Nights)

Miami • Philipsburg, St. Maarten • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bimini • Miami

Average Starting Price

Nov 6, 2027 - Nov 21, 2027 (15 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 • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

Sep 25, 2027 - Oct 2, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

Mar 29, 2027 - Apr 9, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Feb 23, 2027 - Mar 16, 2027 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale

Average Starting Price

$3,989pp

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 Xcel

Celebrity Cruises

Feb 28, 2027 - Mar 7, 2027 (7 Nights)

Miami • Nassau • St. Thomas • St John's, Antigua • Miami

Average Starting Price

Dec 17, 2027 - Dec 27, 2027 (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 20, 2028 - Jan 31, 2028 (11 Nights)

Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • St. Kitts • Gustavia, St. Barts • St John's, Antigua • St. John • Miami

Average Starting Price

Feb 7, 2027 - Feb 19, 2027 (12 Nights)

Miami • San Juan, Puerto Rico • St. John • St. Kitts • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Roseau, Dominica • Fort-De-France, Martinique • Bequia Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

Dec 19, 2027 - Dec 29, 2027 (10 Nights)

Average Starting Price

$3,599pp

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!

Sirena

Oceania Cruises

Dec 10, 2027 - Dec 22, 2027 (12 Nights)

Miami • Nassau • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St. Thomas • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami

Average Starting Price

$3,499pp

Jim's Onboard Credit

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