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Star Legend
Windstar Cruises
Dec 20, 2027 - Jan 3, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,504pp
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!

EXPLORA III
Explora Journeys
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!

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
Seabourn Ovation
Seabourn
Nov 21, 2026 - Dec 5, 2026 (14 Nights)
San Juan, Puerto Rico • St. Barthelemy, F.W.I • St. Kitts • Les Trois-Îlets • Port Elizabeth, South Africa • Kralendijk, Bonaire • Oranjestad, Aruba • Willemstad, Curacao • Rodney Bay, Saint Lucia • Dominica • Terre de Haut, Guadeloupe • Road Bay, Anguilla • San Juan, Puerto Rico
Average Starting Price
$6,684pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Nov 21, 2027 - Nov 28, 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
$619pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
San Juan, Puerto Rico • Gustavia, St. Barts • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Ocean Cay • Miami
Average Starting Price
$3,990pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 21, 2027 - Nov 28, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$714pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Nov 21, 2027 - Nov 28, 2027 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 24, 2027 - Dec 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$1,079pp
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!

Celebrity Constellation
Celebrity Cruises
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$713pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
May 13, 2028 - May 19, 2028 (6 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Disney Lookout Cay at Lighthouse Point, Bahamas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,612pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Mar 19, 2027 - Mar 27, 2027 (8 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$952pp
Jim's Onboard Credit
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