Windswept Travel
✆: 954-424-8733 / 866-433-8249
✉:

British Virgin Islands

(19 offers included)
Departing on Dec 12, 2026 on the Azamara Journey
Nights: 16
Dates: Dec 12, 2026 through Dec 28, 2026
Itinerary:
Bridgetown, Castries, Roseau, Basseterre, St.Kitts, Charlestown, Nevis, Philipsburg, San Juan, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua, Gustavia, Saint- Pierre, Port Elizabeth, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown
from
$4,179.00
(USD)
Per Person
Inside
$4,179.00
Cat: 12
$261.19/Night
Outside
$5,159.00
Cat: 08
$322.44/Night
Balcony
$6,689.00
Cat: V3
$418.06/Night
Suite
$10,289.00
Cat: N2
$643.06/Night
Departing on Nov 30, 2026 on the Emerald Sakara
Nights: 13
Dates: Nov 30, 2026 through Dec 13, 2026
Itinerary:
Miami, Florida, USA, Nassau, Bahamas, Emerald Bay, Exuma's, Bahamas, San Salvador Island, Bahamas, Gordon's Beach, Long Island, Bahamas, Grand Turk, Turks & Caicos Islands, San Juan, Puerto Rico, Cruz Bay, Saint John, US Virgin Islands, Nevis, Saint Kitts and Nevis, Falmouth Harbour, Antigua and Barbuda, Gustavia, Saint Barthélemy, Prickly Pear Cays, Virgin Gorda, British Virgin Islands, Saint Thomas, US Virgin Islands
Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.
from
$14,580.00
(USD)
Per Person
Outside
$14,580.00
Cat: D
$1,121.54/Night
Balcony
$20,680.00
Cat: B
$1,590.77/Night
Suite
$32,580.00
Cat: T
$2,506.15/Night
Departing on Dec 29, 2025 on the Explora I
Nights: 8
Dates: Dec 29, 2025 through Jan 06, 2026
Ship: Explora I
Itinerary:
Miami, New Year Fireworks SJU, Jost van Dyke, Deshaies, Bridgetown, Martinique/Fort de France, Basseterre, San Juan
from
$5,120.00
(USD)
Per Person
Suite
$5,120.00
Cat: OT1
$640.00/Night
Departing on Dec 05, 2026 on the Azamara Journey
Nights: 7
Dates: Dec 05, 2026 through Dec 12, 2026
Itinerary:
San Juan, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Saint George's, Grenada, Scarborough, Tobago, Bridgetown
from
$1,709.00
(USD)
Per Person
Inside
$1,709.00
Cat: Z
$244.14/Night
Outside
$2,239.00
Cat: Y
$319.86/Night
Balcony
$2,989.00
Cat: X
$427.00/Night
Suite
$4,499.00
Cat: W
$642.71/Night
Caribbean & Central America Cruise Bridgetown to San Juan
Departing on Jan 20, 2027 on the Silver Shadow
Nights: 10
Dates: Jan 20, 2027 through Jan 30, 2027
Itinerary:
Bridgetown, Bequia, Castries, Trois Ilets, Roseau, Les Saintes, Little Bay, Montserrat, Basseterre, St. Kitts, Gustavia, St Barthelemy, Jost Van Dyke (British Virgin Islands), San Juan
from
$6,400.00
(USD)
Per Person
Suite
$6,400.00
Cat: VI
$640.00/Night
Caribbean & Central America Cruise San Juan to Bridgetown
Departing on Jan 10, 2027 on the Silver Shadow
Nights: 10
Dates: Jan 10, 2027 through Jan 20, 2027
Itinerary:
San Juan, Jost Van Dyke (British Virgin Islands), Gustavia, St Barthelemy, St. John's, Little Bay, Montserrat, Les Saintes, Basseterre, St. Kitts, Trois Ilets, Castries, St George's, Bridgetown
from
$6,400.00
(USD)
Per Person
Suite
$6,400.00
Cat: VI
$640.00/Night
Departing on Mar 22, 2026 on the Grand Princess
Nights: 14
Dates: Mar 22, 2026 through Apr 05, 2026
Itinerary:
San Juan, St Thomas, St Maarten, Antigua, Dominica, Barbados, San Juan, St Maarten, Dominica, Grenada, Barbados, Tortola, San Juan
from
$1,182.00
(USD)
Per Person
Inside
$1,182.00
Cat: IF
$84.43/Night
Outside
$1,282.00
Cat: OZ
$91.57/Night
Balcony
$2,112.00
Cat: BF
$150.86/Night
Suite
$2,837.00
Cat: ME
$202.64/Night
Departing on Nov 07, 2026 on the Azamara Journey
Nights: 7
Dates: Nov 07, 2026 through Nov 14, 2026
Itinerary:
San Juan, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Saint George's, Grenada, Scarborough, Tobago, Bridgetown
from
$1,799.00
(USD)
Per Person
Inside
$1,799.00
Cat: Z
$257.00/Night
Outside
$2,349.00
Cat: Y
$335.57/Night
Balcony
$3,139.00
Cat: X
$448.43/Night
Suite
$4,679.00
Cat: W
$668.43/Night
Departing on Feb 01, 2027 on the Norwegian Bliss
Nights: 12
Dates: Feb 01, 2027 through Feb 13, 2027
Itinerary:
New York City, Ny, PUERTO PLATA, DOMINICAN REPUBLIC, San Juan, Pr, ST THOMAS, VI, Tortola, British Virgin Islands, Basseterre, Saint Kitts - Nevis, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, New York City, Ny
Set sail on a spectacular 12-day round-trip sailing from New York to the Caribbean with Norwegian. In Puerto Plata, visit Fortaleza San Felipe, which was built in the 16th century or head to the Amber Museum, which is filled with a unique collection of valuable Dominican amber. Wander San Juan's picturesque cobblestone streets, plazas and chapels, all reflecting its rich Spanish heritage. And on the island of St. Thomas, witness Charlotte Amalie's breathtaking harbor - once home to pirates but still full of many treasures today.
from
$1,477.50
(USD)
Per Person
Inside
$1,477.50
Cat: IF
$123.13/Night
Outside
$1,877.50
Cat: OB
$156.46/Night
Balcony
$2,127.50
Cat: BF
$177.29/Night
Suite
$2,427.50
Cat: MC
$202.29/Night
Departing on Jan 17, 2026 on the Emerald Azzurra
Nights: 14
Dates: Jan 17, 2026 through Jan 31, 2026
Itinerary:
San Juan, Puerto Rico, Culebra Island & Vieques Island, Puerto Rico, St John, U.S. Virgin Islands - Jost Van Dyke, British Virgin Islands, Norman Island, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthélemy, Little Bay, Montserrat, St John’s, Antigua, Gustavia, Saint Barthélemy, Îles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Barbuda, Antigua and Barbuda, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico
Embark on an unforgettable Caribbean voyage exploring pristine beaches and coral reefs, island-hopping through diverse cultures, where the warmth of the locals will enhance your luxury yacht adventure.
from
$16,780.00
(USD)
Per Person
Outside
$16,780.00
Cat: D
$1,198.57/Night
Balcony
$21,980.00
Cat: B
$1,570.00/Night
Suite
$37,600.00
Cat: T
$2,685.71/Night
Departing on Nov 16, 2025 on the Norwegian Aqua
Nights: 7
Dates: Nov 16, 2025 through Nov 23, 2025
Itinerary:
Miami, Fl, PUERTO PLATA, DOMINICAN REPUBLIC, ST THOMAS, VI, Tortola, British Virgin Islands, Great Stirrup Cay, Bahamas, Miami, Fl
Make New Waves on board the all-new Norwegian Aqua™, the latest evolution of our innovative Prima Class. Sail from sunny Miami to the Dominican Republic, where you can catch spectacular views at the top of Pico Isabel de Torres Mountain. Find natural treasures in St. Thomas and Tortola, home to pirate legends and amazing coastal cuisine. Then splash the day away at Great Stirrup Cay, Norwegian’s very own private island where you can relax on the beach, grab a cocktail or even ride a zipline.
from
$992.91
(USD)
Per Person
Inside
$992.91
Cat: IF
$141.84/Night
Outside
$1,152.91
Cat: OB
$164.70/Night
Balcony
$1,572.91
Cat: BF
$224.70/Night
Suite
$1,912.91
Cat: MB
$273.27/Night
Seattle To Miami, 40 Nights (Q626B) Seattle, Washington to Miami, FL, USA
Departing on Sep 17, 2026 on the Queen Elizabeth
Nights: 40
Dates: Sep 17, 2026 through Oct 27, 2026
Itinerary:
Seattle, Washington, Ketchikan, Alaska, Juneau, Alaska, Tracy Arm, Alaska, Victoria, BC, Canada, Seattle, Washington, Los Angeles, California, Cabo San Lucas, Mexico, Puerto Quetzal, Guatemala, Fuerte Amador (tours to PanamaCity), Panama, Panama Canal, Panama, Curacao, Antilles, Aruba, Aruba, Miami, FL, USA, San Juan, Puerto Rico, Antigua, St Lucia, Saint Lucia, Barbados, Barbados, St. Maarten, Netherlands Antilles, Tortola, B.V.I., Miami, FL, USA
Spend 40 nights on Queen Elizabeth enjoying all the experiences on board when you’re not exploring the sights and sounds that await in Alaska, North America, Central America, and the Caribbean.
from
$3,699.00
(USD)
Per Person
Inside
$3,699.00
Cat: IF
$92.48/Night
Outside
$4,461.00
Cat: FC
$111.53/Night
Balcony
$4,920.00
Cat: CB
$123.00/Night
Suite
$13,470.00
Cat: P2
$336.75/Night
Departing on Mar 11, 2026 on the Explora II
Nights: 7
Dates: Mar 11, 2026 through Mar 18, 2026
Ship: Explora II
Itinerary:
San Juan, Road Bay, St. John's (Antigua), St. Maarten/Philipsburg, Spanish Town (Virgin Gorda), Miami
from
$3,690.00
(USD)
Per Person
Suite
$3,690.00
Cat: OT1
$527.14/Night
Leeward Isles Serenade Roundtrip from Tampa
Departing on Mar 03, 2026 on the Insignia
Nights: 15
Dates: Mar 03, 2026 through Mar 18, 2026
Ship: Insignia
Itinerary:
Tampa, San Juan, Charlotte Amalie, Philipsburg, St. John's, Roseau, Basseterre, Frederiksted, Tortola, Tampa
from
$4,999.00
(USD)
Per Person
Inside
$4,999.00
Cat: G
$333.27/Night
Outside
$5,699.00
Cat: D
$379.93/Night
Balcony
$7,499.00
Cat: B2
$499.93/Night
Dates: May 03, 2022 through Nov 13, 2027
Location(s):
Tortola Island
Trek to Virgin Gorda to explore the oversized granite boulders of The Baths, its maze-like trail and Devil's Bay on this Romney-Pier Park tour.
from
$196.00
(USD)
Per Person
Yucatan & Leeward Seafarer Roundtrip from Miami
Departing on Jan 04, 2026 on the Allura
Nights: 24
Dates: Jan 04, 2026 through Jan 28, 2026
Ship: Allura
Itinerary:
Miami, Costa Maya, Cozumel, Belize City, Santo Tomas, Roatan, Montego Bay, George Town, Key West, Miami, San Juan, Tortola, Frederiksted, Basseterre, Pointe A Pitre, St. John's, Charlotte Amalie, Miami
from
$11,299.00
(USD)
Per Person
Balcony
$11,299.00
Cat: A3
$470.79/Night
Departing on Dec 22, 2025 on the Explora II
Nights: 14
Dates: Dec 22, 2025 through Jan 05, 2026
Ship: Explora II
Itinerary:
Miami, Ocean Cay, Charlotte Amalie (Saint Thomas), Spanish Town (Virgin Gorda), Marigot, San Juan, Road Bay, New Year Fireworks SJU, Saint John/Cruz Bay, New Year Fireworks SJU, Puerto Plata, Dominican Republic, Key West, Miami
Season's greetings harmonise with warm island paradise and stress-free strolls on beaches of shimmering white sand. Relish sun-kissed relaxation aboard EXPLORA II as you gracefully traverse the turquoise waves. At Ocean Cay Marine Reserve, indulge in seaside massages and, in St Martin, sip delicious cocktails. Welcome the New Year with firework-bright Puerto Rico skies and weave through glorious island views to Florida's golden shores.
from
$9,735.00
(USD)
Per Person
Suite
$9,735.00
Cat: OT1
$695.36/Night
14-Day Exotic Caribbean Isles Roundtrip from Barbados
Departing on Mar 21, 2026 on the Seabourn Ovation
Nights: 14
Dates: Mar 21, 2026 through Apr 04, 2026
Itinerary:
Barbados, St Lucia, Montserrat, Antigua, Carambola Beach, Great Harbour, Jost Van Dyke, St Maarten, Frenchman's Cay, Carambola Beach, Saint Pierre, Port Elizabeth, Grenada, Barbados
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.
from
$7,398.00
(USD)
Per Person
Suite
$7,398.00
Cat: V3
$528.43/Night
Departing on Nov 21, 2026 on the Azamara Journey
Nights: 7
Dates: Nov 21, 2026 through Nov 28, 2026
Itinerary:
San Juan, Virgin Gorda, St. John's, Antigua, Saint- Pierre, Port Elizabeth, Bequia, Saint George's, Grenada, Scarborough, Tobago, Bridgetown
from
$2,039.00
(USD)
Per Person
Inside
$2,039.00
Cat: Z
$291.29/Night
Outside
$2,669.00
Cat: Y
$381.29/Night
Balcony
$3,419.00
Cat: X
$488.43/Night
Suite
$5,309.00
Cat: W
$758.43/Night