250-886-8825

Roberta Westwood
Cruise & Vacation Consultant

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  • Adults (25+)
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109 Cruises

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  • 7-Night Caribbean Cruise

    7-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Dec 21, 2019
    Returns: Sat, Dec 28, 2019
    Depart – San Juan, Puerto Rico
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Iles des Saintes (Saintes Islands), France
    • Pigeon Island, Saint Lucia
    • Saint George's, Grenada
    • Port Elizabeth, Bequia, Saint Vincent and the Grenadines
    • At Sea
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Philipsburg (St. Maarten), Netherlands Antilles - Iles des Saintes (Saintes Islands), France - Pigeon Island, Saint Lucia - Saint George's, Grenada - Port Elizabeth, Bequia- At Sea - San Juan, Puerto Rico
    from
    $3,176* CAD
    *restrictions apply


  • 14-Night Caribbean Cruise

    14-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Dec 21, 2019
    Returns: Sat, Jan 4, 2020
    Depart – San Juan, Puerto Rico
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Iles des Saintes (Saintes Islands), France
    • Pigeon Island, Saint Lucia
    • Saint George's, Grenada
    • Port Elizabeth, Bequia, Saint Vincent and the Grenadines
    • At Sea
    • San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Gustavia, St Bartelemy, France
    • Little Bay, Montserrat
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Philipsburg (St. Maarten), Netherlands Antilles - Iles des Saintes (Saintes Islands), France - Pigeon Island, Saint Lucia - Saint George's, Grenada - Port Elizabeth, Bequia- At Sea - San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Gustavia, St Bartelemy- Little Bay, Montserrat - Philipsburg (St. Maarten), Netherlands Antilles - Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico
    from
    $5,558* CAD
    *restrictions apply
  • 7-Night Caribbean Cruise

    7-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Dec 28, 2019
    Returns: Sat, Jan 4, 2020
    Depart – San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Gustavia, St Bartelemy, France
    • Little Bay, Montserrat
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Gustavia, St Bartelemy- Little Bay, Montserrat - Philipsburg (St. Maarten), Netherlands Antilles - Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico
    from
    $5,823* CAD
    *restrictions apply
  • 14-Night Caribbean Cruise

    14-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Dec 28, 2019
    Returns: Sat, Jan 11, 2020
    Depart – San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Gustavia, St Bartelemy, France
    • Little Bay, Montserrat
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    • San Juan, Puerto Rico
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Iles des Saintes (Saintes Islands), France
    • Port Elizabeth, Bequia, Saint Vincent and the Grenadines
    • Pigeon Island, Saint Lucia
    • Saint George's, Grenada
    • At Sea
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Gustavia, St Bartelemy- Little Bay, Montserrat - Philipsburg (St. Maarten), Netherlands Antilles - Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico - Philipsburg (St. Maarten), Netherlands Antilles - Iles des Saintes (Saintes Islands), France - Port Elizabeth, Bequia- Pigeon Island, Saint Lucia - Saint George's, Grenada - At Sea - San Juan, Puerto Rico
    from
    $7,676* CAD
    *restrictions apply
  • 14-Night Caribbean Cruise

    14-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Jan 4, 2020
    Returns: Sat, Jan 18, 2020
    Depart – San Juan, Puerto Rico
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Iles des Saintes (Saintes Islands), France
    • Port Elizabeth, Bequia, Saint Vincent and the Grenadines
    • Pigeon Island, Saint Lucia
    • Saint George's, Grenada
    • At Sea
    • San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Gustavia, St Bartelemy, France
    • Little Bay, Montserrat
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Philipsburg (St. Maarten), Netherlands Antilles - Iles des Saintes (Saintes Islands), France - Port Elizabeth, Bequia- Pigeon Island, Saint Lucia - Saint George's, Grenada - At Sea - San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Gustavia, St Bartelemy- Little Bay, Montserrat - Philipsburg (St. Maarten), Netherlands Antilles - Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico
    from
    $6,882* CAD
    *restrictions apply
  • 7-Night Caribbean Cruise

    7-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Jan 11, 2020
    Returns: Sat, Jan 18, 2020
    Depart – San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Gustavia, St Bartelemy, France
    • Little Bay, Montserrat
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Gustavia, St Bartelemy- Little Bay, Montserrat - Philipsburg (St. Maarten), Netherlands Antilles - Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico
    from
    $4,367* CAD
    *restrictions apply
  • 14-Night Caribbean Cruise

    14-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Jan 11, 2020
    Returns: Sat, Jan 25, 2020
    Depart – San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Gustavia, St Bartelemy, France
    • Little Bay, Montserrat
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    • San Juan, Puerto Rico
    • At Sea
    • Port Elizabeth, Bequia, Saint Vincent and the Grenadines
    • Saint George's, Grenada
    • Pigeon Island, Saint Lucia
    • Iles des Saintes (Saintes Islands), France
    • Philipsburg (St. Maarten), Netherlands Antilles
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Gustavia, St Bartelemy- Little Bay, Montserrat - Philipsburg (St. Maarten), Netherlands Antilles - Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico - At Sea - Port Elizabeth, Bequia- Saint George's, Grenada - Pigeon Island, Saint Lucia - Iles des Saintes (Saintes Islands), France - Philipsburg (St. Maarten), Netherlands Antilles - San Juan, Puerto Rico
    from
    $6,750* CAD
    *restrictions apply
  • 14-Night Caribbean Cruise

    14-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Jan 18, 2020
    Returns: Sat, Feb 1, 2020
    Depart – San Juan, Puerto Rico
    • At Sea
    • Port Elizabeth, Bequia, Saint Vincent and the Grenadines
    • Saint George's, Grenada
    • Pigeon Island, Saint Lucia
    • Iles des Saintes (Saintes Islands), France
    • Philipsburg (St. Maarten), Netherlands Antilles
    • San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Little Bay, Montserrat
    • Gustavia, St Bartelemy, France
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - At Sea - Port Elizabeth, Bequia- Saint George's, Grenada - Pigeon Island, Saint Lucia - Iles des Saintes (Saintes Islands), France - Philipsburg (St. Maarten), Netherlands Antilles - San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Philipsburg (St. Maarten), Netherlands Antilles - Little Bay, Montserrat - Gustavia, St Bartelemy- Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico
    from
    $7,544* CAD
    *restrictions apply
  • 7-Night Caribbean Cruise

    7-Night Caribbean Cruise
    Windstar Cruises
    Star Legend
    Depart: Sat, Jan 25, 2020
    Returns: Sat, Feb 1, 2020
    Depart – San Juan, Puerto Rico
    • Charlotte Amalie, US Virgin Islands
    • Philipsburg (St. Maarten), Netherlands Antilles
    • Little Bay, Montserrat
    • Gustavia, St Bartelemy, France
    • Jost van Dyke, British Virgin Islands
    • Virgin Gorda, British Virgin Islands
    Returns – San Juan, Puerto Rico
    San Juan, Puerto Rico - Charlotte Amalie, US Virgin Islands - Philipsburg (St. Maarten), Netherlands Antilles - Little Bay, Montserrat - Gustavia, St Bartelemy- Jost van Dyke, British Virgin Islands - Virgin Gorda, British Virgin Islands - San Juan, Puerto Rico
    from
    $4,764* CAD
    *restrictions apply
  • 12-Night Western Mediterranean Europe Cruise

    12-Night Western Mediterranean Europe Cruise
    Windstar Cruises
    Star Legend
    Depart: Fri, Sep 25, 2020
    Returns: Wed, Oct 7, 2020
    Depart – Lisbon, Portugal
    • Lisbon, Portugal
    • Lisbon, Portugal
    • Lisbon, Portugal
    • Lisbon, Portugal
    • Lisbon, Portugal
    • Portimao, Portugal
    • Cadiz, Spain
    • Malaga, Spain
    • Gibraltar, Gibraltar
    • Almeria, Spain
    • At Sea
    • Palma de Mallorca, Spain
    Returns – Barcelona, Spain
    Lisbon, Portugal - Lisbon, Portugal - Lisbon, Portugal - Lisbon, Portugal - Lisbon, Portugal - Lisbon, Portugal - Portimao, Portugal - Cadiz, Spain - Malaga, Spain - Gibraltar, Gibraltar - Almeria, Spain - At Sea - Palma de Mallorca, Spain - Barcelona, Spain
    from
    $9,264* CAD
    *restrictions apply

Terms & Conditions

† CAD price displayed for reference only using exchange rate of the day (Estimated exchange rate of 1 USD = 1.3236 CAD as of Aug 14, 2019). Price are approximate and are subject to change. Cruise must be booked in US dollars and all payments must be made in US dollars.

*Expedia Extras offers are per stateroom (unless otherwise stated) on select sailings, based on double occupancy, apply to new bookings only, are not combinable with any other offer, are capacity controlled and may be withdrawn without notice. Certain restrictions may apply. For full terms and conditions, click the specific Expedia Extra offer or contact your Expedia CruiseShipCenters Vacation Consultant.

Prices are per person (based on 2 passengers in the same stateroom), cruise only in CAD dollars. Airfare, transfers, taxes, fees and port expenses are additional (unless otherwise stated). Prices vary by ship, stateroom type and sailing date. Prices and offers are subject to availability and change without notice, and are capacity controlled. Fuel supplement may apply. Expedia CruiseShipCenters is not responsible for errors that may occur due to the transfer of information from selected third parties, technical error, or human error.

Our default sort order is based on a number of relevant factors such as cruise line rating, ship rating, price per day, origin rating, destination rating, length of cruise, and booking window.

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Roberta Westwood
Cruise & Vacation Consultant
Navigators Club - Platinum