Seabourn Ovation Sailing Dates and Sailing Calendar

For more information, prices, and detailed day-by-day Seabourn Ovation itineraries, please click one of the Seabourn Ovation sailing dates below.

Get FREE Price Alerts

Subscribe to our weekly cruise deals email and enjoy FREE price change alerts and updates for this cruise and others like it.

We promise to protect your privacy and personal data. You can review our privacy policy here.

Sail Date

Itinerary Name and Ports

Duration

Save to Favorites

Priced From(per person)

Nov 20, 2026

(Friday)

8 Night Southern Caribbean Gems Cruise

From Miami, Florida to Bridgetown, Barbados

Ports: Miami, San Juan, Great Harbour, Carambola Beach, Roseau, Port Elizabeth, Bridgetown

8 Nights

Add to Favorites
Compare Favorites
$3,439

Suite (double occupancy)

Includes taxes & feesLearn More
Nov 20, 2026

(Friday)

15 Night Southern Caribbean in Depth Cruise

From Miami, Florida to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Miami, San Juan, Great Harbour, Carambola Beach, Roseau, Port Elizabeth, Bridgetown, Rodney Bay, Little Bay, St John's, Carambola Beach, Spanish Town, Philipsburg (St. Maarten)

Special Promotions
15 Nights

Add to Favorites
Compare Favorites
$5,919

Suite (double occupancy)

Includes taxes & feesLearn More
Nov 28, 2026

(Saturday)

7 Night Classic Caribbean Yacht Harbors Cruise

From Bridgetown, Barbados to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Bridgetown, Rodney Bay, Little Bay, St John's, Carambola Beach, Spanish Town, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$3,119

Suite (double occupancy)

Includes taxes & feesLearn More
Nov 28, 2026

(Saturday)

14 Night Exotic Caribbean In Depth Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Rodney Bay, Little Bay, St John's, Carambola Beach, Spanish Town, Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

14 Nights

Add to Favorites
Compare Favorites
$4,959

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 5, 2026

(Saturday)

7 Night Yachtsmans Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

7 Nights

Add to Favorites
Compare Favorites
$2,639

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 5, 2026

(Saturday)

14 Night Yachtsmans Caribbean in Depth Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown, Carambola Beach, Terre de Haut, Saint-Pierre Martinique France, Roseau, Rodney Bay, Bridgetown

14 Nights

Add to Favorites
Compare Favorites
$4,719

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 12, 2026

(Saturday)

7 Night Caribbean Gems Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Carambola Beach, Terre de Haut, Saint-Pierre Martinique France, Roseau, Rodney Bay, Bridgetown

7 Nights

Add to Favorites
Compare Favorites
$2,879

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 19, 2026

(Saturday)

7 Night Classic Caribbean Yacht Harbors Cruise

From Bridgetown, Barbados to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$2,959

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 19, 2026

(Saturday)

14 Night Exotic Caribbean In Depth Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

14 Nights

Add to Favorites
Compare Favorites
$6,879

Suite (double occupancy)

Includes taxes & feesLearn More
Dec 26, 2026

(Saturday)

7 Night Yachtsmans Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

7 Nights

Add to Favorites
Compare Favorites
$4,639

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 2, 2027

(Saturday)

7 Night Treasures of Aruba Bonaire and Curacao Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Rodney Bay, Willemstad (Curacao), Oranjestad, Bonaire, Bridgetown

7 Nights

Add to Favorites
Compare Favorites
$3,799

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 9, 2027

(Saturday)

7 Night Classic Caribbean Yacht Harbors Cruise

From Bridgetown, Barbados to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$4,299

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 9, 2027

(Saturday)

14 Night Exotic Caribbean In Depth Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

14 Nights

Add to Favorites
Compare Favorites
$7,599

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 16, 2027

(Saturday)

7 Night Yachtsmans Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

7 Nights

Add to Favorites
Compare Favorites
$5,599

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 16, 2027

(Saturday)

14 Night Caribbean Gems In Depth Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten)

14 Nights

Add to Favorites
Compare Favorites
$8,719

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 23, 2027

(Saturday)

7 Night Classic Caribbean Yacht Harbors Cruise

From Bridgetown, Barbados to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$6,499

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 23, 2027

(Saturday)

14 Night Exotic Caribbean In Depth Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

14 Nights

Add to Favorites
Compare Favorites
$8,559

Suite (double occupancy)

Includes taxes & feesLearn More
Jan 30, 2027

(Saturday)

7 Night Yachtsmans Caribbean Cruise

From Philipsburg (St. Maarten), Netherlands Antilles to Bridgetown, Barbados

Ports: Philipsburg (St. Maarten), Frenchman's Cay, Carambola Beach, Trois Ilets, Port Elizabeth, St George's, Bridgetown

7 Nights

Add to Favorites
Compare Favorites
$3,759

Suite (double occupancy)

Includes taxes & feesLearn More
Feb 6, 2027

(Saturday)

7 Night Caribbean Gems Cruise

From Bridgetown, Barbados to Bridgetown, Barbados

Ports: Bridgetown, Carambola Beach, Saint-Pierre Martinique France, Roseau, Terre de Haut, Rodney Bay, Bridgetown

7 Nights

Add to Favorites
Compare Favorites
$4,719

Suite (double occupancy)

Includes taxes & feesLearn More
Feb 13, 2027

(Saturday)

7 Night Classic Caribbean Yacht Harbors Cruise

From Bridgetown, Barbados to Philipsburg (St. Maarten), Netherlands Antilles

Ports: Bridgetown, Castries, Little Bay, St John's, Carambola Beach, Great Harbour, Philipsburg (St. Maarten)

7 Nights

Add to Favorites
Compare Favorites
$4,079

Suite (double occupancy)

Includes taxes & feesLearn More

Browse Seabourn Ovation Itineraries by Month ▼

Overlay Title