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Cruise Dates

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October 2026

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Silver Shadow

Silversea

Jan 10, 2027 - Jan 20, 2027 (10 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St John's, Antigua • Little Bay, Montserrat • Les Saintes, F.W.I. • St. Kitts • Trois Ilets, Martinique • Castries, St. Lucia • Grenada • Bridgetown, Barbados

Average Starting Price

Jan 6, 2028 - Jan 27, 2028 (21 Nights)

San Juan, Puerto Rico • Sail the Caribbean Sea • Bridgetown, Barbados • Sail the Atlantic Ocean • Iles du Salut (Ile Royale), French Guiana • Sail the Atlantic Ocean • Sail the Mouth of the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Sail the Amazon River • Sail the Amazon River • Belem, Brazil • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Jan 8, 2028 - Jan 18, 2028 (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

$4,299pp

Jim's Onboard Credit

Adventure of the Seas

Royal Caribbean

Feb 23, 2028 - Mar 3, 2028 (9 Nights)

Port Canaveral (Orlando), Florida • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

Mar 19, 2028 - Apr 4, 2028 (16 Nights)

Miami • San Juan, Puerto Rico • St John's, Antigua • Funchal, Portugal • Cadiz, Spain • Malaga, Spain • Barcelona, Spain

Average Starting Price

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

San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Grand Turk • Miami • Providenciales, Turks and Caicos Islands • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Bequia Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

$10,395pp

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!

9% OFF

Crystal Symphony

Crystal Cruises

Dec 28, 2027 - Jan 11, 2028 (14 Nights)

Fort Lauderdale • George Town, Cayman Islands • Montego Bay, Jamaica • La Romana, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • St John's, Antigua • St. Kitts • Tortola • Samana, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$7,030pp

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!

Azamara Journey

Azamara

Dec 18, 2026 - Jan 5, 2027 (18 Nights)

San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • Gustavia, St. Barts • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Scarborough (Tobago), Trinidad and Tobago • Mayreau Island, Saint Vincent and the Grenadines • Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Charlestown, Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

$5,729pp

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!

48% OFF