Windswept Travel
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Barbados (16 offers included)

14-Day Southern Caribbean Adventurer
Roundtrip from San Juan
from $1,260.00 (USD)
Per Person
Nights: 14
Price Per Night:$90.00 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St Thomas, St Kitts, Dominica, Grenada, Barbados, San Juan, St Thomas, St Maarten, Antigua...
Other Categories Starting At:
Inside
$1,260.00
Cat: IF
Outside
$1,430.00
Cat: OZ
Balcony
$2,220.00
Cat: BF
Suite
$3,200.00
Cat: ME
14-Day Southern Caribbean Adventurer
Roundtrip from San Juan
from $1,367.00 (USD)
Per Person
Nights: 14
Price Per Night:$97.64 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St Thomas, St Maarten, Antigua, St Vincent, Barbados, San Juan, St. Croix, Dominica, St Lucia...
Other Categories Starting At:
Inside
$1,367.00
Cat: IF
Outside
$1,549.00
Cat: OZ
Balcony
$2,167.00
Cat: BF
Suite
$2,767.00
Cat: ME
from $3,999.00 (USD)
Per Person
+ $38.00 taxes/fees
Nights: 15
Ship: Wind Spirit
Price Per Night:$266.60 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, Basseterre, Gustavia, St. John's, Les Saintes, Roseau, Mayreau, Bridgetown, Basseterre, St. John's...
Discover less-traveled roads and concealed refuges throughout the Caribbean on this 14-day cruise that blends iconic destinations and little-known shorelines like a favorite beachside cocktail. Search for green sea turtles and watch iridescent fish flit among sunken freighter wreckage from the dry side of a porthole in a Gustavia-based, semi-submersible. Sail past St. Kitts uncrowded southeast shores before slipping silently beneath the surface to snorkel among exotic fish and colorful coral.
Other Categories Starting At:
Inside
N/A
Outside
$3,999.00
Cat: B
Balcony
N/A
Suite
N/A
20-Day Southern Caribbean Discovery
San Juan, Puerto Rico to Bridgetown, Barbados
from $9,009.00 (USD)
Per Person
+ $160.00 taxes/fees
Nights: 20
Price Per Night:$450.45 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, Aruba, Curacao, Bonaire, Trois Ilets, Roseau, Montserrat, Carambola Beach, Antigua, Tortola...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$9,009.00
Cat: V1
14-Day Southern Caribbean Adventurer
Roundtrip from San Juan
from $1,233.00 (USD)
Per Person
Nights: 14
Price Per Night:$88.07 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St Thomas, St Maarten, Antigua, St Vincent, Barbados, San Juan, St Thomas, St Maarten, Antigua...
Other Categories Starting At:
Inside
$1,233.00
Cat: IF
Outside
$1,395.00
Cat: OZ
Balcony
$2,223.00
Cat: BF
Suite
$2,683.00
Cat: ME
7-Day Southern Caribbean with Barbados
Roundtrip from San Juan
from $758.00 (USD)
Per Person
Nights: 7
Price Per Night:$108.29 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St. Croix, St Kitts, Guadeloupe (Pointe-A-Pitre), St Vincent, Barbados, San Juan
Other Categories Starting At:
Inside
$758.00
Cat: IF
Outside
$863.00
Cat: OZ
Balcony
$1,218.00
Cat: BF
Suite
$1,358.00
Cat: ME
from $6,560.00 (USD)
Per Person
Nights: 17
Ship: Explora II
Price Per Night:$385.88 (USD)
(based on double occupancy, for comparison only)
Itinerary: Barcelona, Tangier, Las Palmas de Gran Canaria, Bridgetown, Pointe-à-Pitre, St. John's (Antigua), Charlotte Amalie (Saint Thomas), Miami
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$6,560.00
Cat: OT1
from $6,499.00 (USD)
Per Person
+ $68.00 taxes/fees
Nights: 25
Ship: Wind Spirit
Price Per Night:$259.96 (USD)
(based on double occupancy, for comparison only)
Itinerary: Lisbon, Bridgetown, Bequia, Mayreau, St. George's, Kralendijk, Willemstad, Oranjestad, Cartagena, Colón
This is a voyage for those who want to see and do things out of the ordinary. Cross the Atlantic relishing your "me time" and arrive in the Southern Caribbean, which is usually the last part of the Caribbean that cruisers explore. Because these tend to be smaller and less developed than other Caribbean islands, they’re meant for the savvy traveler to discover plus, you’ll be here at a time just before most tourists arrive. These islands are filled with unique sights, attractions, and activities.
Other Categories Starting At:
Inside
N/A
Outside
$6,499.00
Cat: BX
Balcony
N/A
Suite
N/A
Nights: 16
Ship: Explora I
Price Per Night:$550.63 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Tobago/Scarborough, Martinique/Fort de France, St. John's (Antigua), St. Maarten/Philipsburg, Tortola/Road Town, Miami, New Year Fireworks SJU, Jost van Dyke, Deshaies...
Capture the party spirit with the joyful ring of steel drums from bustling Bridgetown to Tobago's colourful markets. Explore the delights of Martinique with its blend of French and Caribbean culture. We spend Christmas revelling in the sunny climes of Sint Maarten, then welcome the New Year admiring San Juan's glorious firework display before sailing to the British Virgin Islands and beyond, taking in the splendours of Guadeloupe, Martinique and St Kitts.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$8,810.00
Cat: OT1
7-Day Southern Caribbean with Barbados
Roundtrip from San Juan
from $798.00 (USD)
Per Person
Nights: 7
Price Per Night:$114.00 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St Thomas, St Maarten, Antigua, St Lucia, Barbados, San Juan
Other Categories Starting At:
Inside
$798.00
Cat: IF
Outside
$882.00
Cat: OZ
Balcony
$998.00
Cat: BF
Suite
$1,148.00
Cat: ME
Nights: 15
Ship: Explora II
Price Per Night:$470.00 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Charlotte Amalie (Saint Thomas), Jost van Dyke, St. John's (Antigua), Gustavia, San Juan, St. George's (Grenada), Bequia, Bridgetown, Martinique/Fort de France...
Beneath the brilliant sun, over the sparkling sea, we travel the tropics from Miami to Basseterre. En route, uncover the spectacular beaches of Jost van Dyke and the lively spirit of San Juan.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$7,050.00
Cat: OT1
7-Day Classic Caribbean Yacht Harbors
Bridgetown, Barbados to Philipsburg, Sint Maarten
from $4,376.00 (USD)
Per Person
+ $55.00 taxes/fees
Nights: 7
Price Per Night:$625.14 (USD)
(based on double occupancy, for comparison only)
Itinerary: Barbados, St Lucia, Montserrat, Antigua, Carambola Beach, Great Harbour, Jost Van Dyke, St Maarten
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$4,376.00
Cat: V1
7-Day Southern Caribbean with Barbados
Roundtrip from San Juan
from $648.00 (USD)
Per Person
Nights: 7
Price Per Night:$92.57 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St Maarten, Guadeloupe (Pointe-A-Pitre), Dominica, Grenada, Barbados, San Juan
Other Categories Starting At:
Inside
$648.00
Cat: IF
Outside
$728.00
Cat: OZ
Balcony
$1,048.00
Cat: BF
Suite
$1,248.00
Cat: ME
24-Day Atlantic Passage, Iberian Coast & France
Bridgetown, Barbados to Monte Carlo, Monaco
from $9,786.00 (USD)
Per Person
+ $130.00 taxes/fees
Nights: 24
Price Per Night:$407.75 (USD)
(based on double occupancy, for comparison only)
Itinerary: Barbados, Saint Pierre, Carambola Beach, Madeira, Lisbon, Leixoes (Porto), Cadiz, Malaga, Mahon, Port-Vendres...
Aboard The Yachts of Seabourn, the world is more intimate and more enchanting. Here, you’ll explore ports rarely visited by larger ships and meet people who are happy to show you around their hidden corner of the globe. With their unmatched sense of style, elegance and grace, The Yachts of Seabourn beckon you to travel beyond the bounds of the imagination. Aboard Seabourn, every desire is met promptly and with a welcoming smile. Whether it's a warm blanket and a cup of gourmet hot chocolate as you drift along the Norwegian Fjords or a relaxing neck massage poolside, you'll feel that you're a member of a very exclusive club.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$9,786.00
Cat: V3
from $5,199.00 (USD)
Per Person
+ $91.00 taxes/fees
Nights: 24
Ship: Wind Star
Price Per Night:$216.63 (USD)
(based on double occupancy, for comparison only)
Itinerary: Barcelona, Tarragona, Palma de Mallorca, Valencia, Cartagena, Málaga, Tangier, Lisbon, Bridgetown
Ideal for anyone seeking equal portions of relaxing time at sea and port visits, this transatlantic crossing features a combination of leisurely, uninterrupted sea crossing time balanced with the best ports in the Western Mediterranean. Spend time crossing the Atlantic and enjoying the romance of sailing as you make your way to your ultimate destination.
Other Categories Starting At:
Inside
N/A
Outside
$5,199.00
Cat: B
Balcony
N/A
Suite
N/A
from $2,720.00 (USD)
Per Person
Nights: 5
Ship: Explora I
Price Per Night:$544.00 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Saint John/Cruz Bay, Deshaies, Bridgetown
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$2,720.00
Cat: GT