Simpson Bay Cruises
Cruises that visit Caribbean: Saint Martin: Simpson Bay
7 Night - West Indies Explorer Cruise
Starting in Bridgetown, Barbados, Port Elizabeth VC, Bequia, Mayreau, Soufriere Bay, Terre De Haut, Iles des Saintes, Philipsburg, Simpson Bay, Gustavia, St Johns AG
2026 Sails: Nov 28, More...7 Night - Spanish & British Caribbean Delight Cruise
Starting in San Juan, Culebra, Esperanza, Vieques Island, St John VI (Cruz Bay), US Virgin Islands, Philipsburg, Simpson Bay, Gustavia, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, Charlotte Amalie, St Thomas
2026 Sails: Dec 12, More...
7 Night - St. Barths & Caribbean Gems Cruise
Starting in Charlotte Amalie, St Thomas, Philipsburg, Simpson Bay, Gustavia, Falmouth Bay, Charlestown, Nevis, Spanish Town, Virgin Gorda, Norman Island, White Bay, Jost van Dyke, San Juan
2026 Sails: Dec 12, More...7 Night - Tropical New Year's Ii Explorer Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Philipsburg, Simpson Bay, Gustavia, Norman Island, Charlotte Amalie, St Thomas
2026 Sails: Dec 27, More...7 Night - Best of British Virgin Isles & St. Barths Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Sandy Ground, Gustavia, Philipsburg, Simpson Bay, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, San Juan
2027 Sails: Jan 16, Mar 27, More...7 Night - Best of British Virgin Isles & St. Barths Cruise
Starting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Sandy Ground, Gustavia, Philipsburg, Simpson Bay, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, San Juan
2027 Sails: Apr 10, More...7 Night - Cruise Roundtrip from San Juan
Starting in San Juan, Gustavia, South Friars Bay, Charlestown, Nevis, Philipsburg, Simpson Bay, White Bay, Jost van Dyke, San Juan
2028 Sails: Nov 18, More...9 Night - Cruise Roundtrip from St Thomas (Charlotte Amalie)
Starting in Charlotte Amalie, St Thomas, Gustavia, Philipsburg, Simpson Bay, Sandy Ground, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, White Bay, Jost van Dyke, St John VI (Cruz Bay), US Virgin Islands, Charlotte Amalie, St Thomas
2028 Sails: Dec 29, More...
Cruises that visit Caribbean: Saint Martin: Simpson Bay
Click on a cruise ship itinerary that visits Simpson Bay (below) and select a sail date to receive competing cruise quotes. To search all cruise itineraries (not just Simpson Bay), please visit: Cruise Search or try our Virtual Cruise Advisor™.
7 Night - West Indies Explorer CruiseStarting in Bridgetown, Barbados, Port Elizabeth VC, Bequia, Mayreau, Soufriere Bay, Terre De Haut, Iles des Saintes, Philipsburg, Simpson Bay, Gustavia, St Johns AG
2026 Sails: Nov 28, More...
7 Night - Spanish & British Caribbean Delight CruiseStarting in San Juan, Culebra, Esperanza, Vieques Island, St John VI (Cruz Bay), US Virgin Islands, Philipsburg, Simpson Bay, Gustavia, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, Charlotte Amalie, St Thomas
2026 Sails: Dec 12, More...
7 Night - St. Barths & Caribbean Gems CruiseStarting in Charlotte Amalie, St Thomas, Philipsburg, Simpson Bay, Gustavia, Falmouth Bay, Charlestown, Nevis, Spanish Town, Virgin Gorda, Norman Island, White Bay, Jost van Dyke, San Juan
2026 Sails: Dec 12, More...
7 Night - Tropical New Year's Ii Explorer CruiseStarting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Philipsburg, Simpson Bay, Gustavia, Norman Island, Charlotte Amalie, St Thomas
2026 Sails: Dec 27, More...
7 Night - Best of British Virgin Isles & St. Barths CruiseStarting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Sandy Ground, Gustavia, Philipsburg, Simpson Bay, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, San Juan
2027 Sails: Jan 16, Mar 27, More...
7 Night - Best of British Virgin Isles & St. Barths CruiseStarting in San Juan, St John VI (Cruz Bay), US Virgin Islands, Sandy Ground, Gustavia, Philipsburg, Simpson Bay, White Bay, Jost van Dyke, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, San Juan
2027 Sails: Apr 10, More...
7 Night - Cruise Roundtrip from San JuanStarting in San Juan, Gustavia, South Friars Bay, Charlestown, Nevis, Philipsburg, Simpson Bay, White Bay, Jost van Dyke, San Juan
2028 Sails: Nov 18, More...
9 Night - Cruise Roundtrip from St Thomas (Charlotte Amalie)Starting in Charlotte Amalie, St Thomas, Gustavia, Philipsburg, Simpson Bay, Sandy Ground, Spanish Town, Virgin Gorda, Leverick Bay, Virgin Gorda, White Bay, Jost van Dyke, St John VI (Cruz Bay), US Virgin Islands, Charlotte Amalie, St Thomas
2028 Sails: Dec 29, More...
