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Valiant Lady
Virgin Voyages
Feb 20, 2027 - Feb 27, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,043pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Dec 4, 2027 - Dec 18, 2027 (14 Nights)
Miami • St. John • Saint Barthelemy, Gustavia • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • Little Bay, Montserrat • St John's, Antigua • Road Bay, Anguilla • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,653pp
Jim's Onboard Credit
Insignia
Oceania Cruises
Nov 24, 2026 - Dec 19, 2026 (25 Nights)
Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Cruising the Amazon River • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico • Nassau • Miami
Average Starting Price
$13,249pp
Jim's Onboard Credit
9% OFF
Crystal Grace
Crystal Cruises
Dec 11, 2028 - Dec 22, 2028 (11 Nights)
Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Roseau, Dominica • St John's, Antigua • Fort Lauderdale
Average Starting Price
$6,270pp
Jim's Onboard Credit
Silver Dawn
Silversea
Jan 25, 2028 - Feb 5, 2028 (11 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • Roseau, Dominica • Canouan, Saint Vincent and the Grenadines • Grenada • Willemstad, Curacao • Kralendijk, Bonaire • St. John • San Juan, Puerto Rico
Average Starting Price
$4,800pp
Jim's Onboard Credit
26% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Mar 20, 2028 - Apr 1, 2028 (12 Nights)
Miami • Cruising the Atlantic Ocean • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Atlantic Ocean cruising • Atlantic Ocean cruising • Miami
Average Starting Price
$8,599pp
Jim's Onboard Credit
9% OFF
Crystal Symphony
Crystal Cruises
Dec 10, 2027 - Dec 19, 2027 (9 Nights)
San Juan, Puerto Rico • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • Gustavia, St. Barts • Tortola • Fort Lauderdale
Average Starting Price
$3,660pp
Jim's Onboard Credit
31% OFF
Seven Seas Mariner
Regent Seven Seas Cruises
Nov 7, 2028 - Nov 17, 2028 (10 Nights)
Miami • Tortola • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • Miami
Average Starting Price
$6,549pp
Jim's Onboard Credit
Azamara Journey
Azamara
Nov 21, 2026 - Dec 5, 2026 (14 Nights)
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 • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Gustavia, St. Barts • San Juan, Puerto Rico
Average Starting Price
$5,089pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Feb 14, 2027 - Mar 6, 2027 (20 Nights)
Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • St. Thomas • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Scenic Cruising Soufriere Bay • Roseau, Dominica • Bridgetown, Barbados • Grenada • Scarborough (Tobago), Trinidad and Tobago • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Falmouth, Jamaica • Miami
Average Starting Price
$4,444pp
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!

Seabourn Ovation
Seabourn
Nov 20, 2026 - Nov 28, 2026 (8 Nights)
Miami • San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Roseau, Dominica • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$4,368pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Jan 24, 2028 - Feb 4, 2028 (11 Nights)
Fort Lauderdale • St. Thomas • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,791pp
Jim's Onboard Credit
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