Callahan's Travel Company
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British Virgin Islands

(20 offers included)
Cruising the Leeward Islands Marigot, Saint Martin to Marigot, Saint Martin
Departing on Apr 03, 2027 on the Emerald Azzurra
Nights: 7
Dates: Apr 03, 2027 through Apr 10, 2027
Itinerary:
Marigot, Saint Martin, Marigot, Saint Martin - Anguilla, Virgin Gorda – Norman Island, British Virgin Islands, Norman Island - Jost van Dyke, British Virgin Islands, Anegada, British Virgin Islands, Saba, Bonaire, Saint Eustatius and Saba – Gustavia, Saint Barthélemy, Gustavia, Saint Barthélemy, Marigot, Saint Martin
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
$4,990.00
(USD)
Per Person
Outside
$4,990.00
Cat: D
$712.86/Night
Balcony
$6,640.00
Cat: B
$948.57/Night
Suite
$9,840.00
Cat: T
$1,405.71/Night
Cultural Currents 20 nights on board Seven Seas Mariner
Departing on Mar 26, 2027 on the Seven Seas Mariner
Nights: 20
Dates: Mar 26, 2027 through Apr 15, 2027
Itinerary:
Miami, Nassau, Cruising The Straits Of Florida, Costa Maya, Harvest Caye, Roatan, Cruising The Caribbean Sea, Montego Bay, George Town, Cruising The Straits Of Florida, Miami, Nassau, Cruising The Atlantic Ocean, San Juan, Charlotte Amalie, St. John's, Gustavia, Tortola, Cruising The Atlantic Ocean, Miami
from
$11,999.00
(USD)
Per Person
Suite
$11,999.00
Cat: H
$599.95/Night
Azure Caribbean Roundtrip from Miami
Departing on Jan 05, 2026 on the Nautica
Nights: 12
Dates: Jan 05, 2026 through Jan 17, 2026
Ship: Nautica
Itinerary:
Miami, Willemstad, Oranjestad, Kralendijk, Castries, Pointe A Pitre, Jost Van Dyke, Miami
from
$3,499.00
(USD)
Per Person
Inside
$3,499.00
Cat: G
$291.58/Night
Outside
$3,849.00
Cat: D
$320.75/Night
Balcony
$5,199.00
Cat: B1
$433.25/Night
Departing on Aug 19, 2026 on the Norwegian Escape
Nights: 10
Dates: Aug 19, 2026 through Aug 29, 2026
Itinerary:
New York City, Ny, San Juan, Pr, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, ST THOMAS, VI, Tortola, British Virgin Islands, PUERTO PLATA, DOMINICAN REPUBLIC, New York City, Ny
Make every day a sun day during a Caribbean cruise on Norwegian Escape®. Hop on a bicycle for a fun-filled tour of the historic sites of Old San Juan, including Fort San Cristobal and Santa Catalina Palace. Then snorkel among colorful tropical fish and green sea turtles at Turtle Cove in St. Thomas. Uncover Puerto Plata’s local history at the 16th century Fortaleza San Felipe or embark on an off-roading adventure through lush jungle to swim in cascading mountain pools.
from
$1,946.23
(USD)
Per Person
Inside
$1,946.23
Cat: IF
$194.62/Night
Outside
$2,296.23
Cat: OB
$229.62/Night
Balcony
$2,596.23
Cat: BF
$259.62/Night
Suite
$2,886.23
Cat: MC
$288.62/Night
Departing on Oct 12, 2025 on the Grand Princess
Nights: 7
Dates: Oct 12, 2025 through Oct 19, 2025
Itinerary:
San Juan, Tortola, St Kitts, Dominica, Grenada, Barbados, San Juan
from
$455.00
(USD)
Per Person
Inside
$455.00
Cat: IF
$65.00/Night
Outside
$980.00
Cat: OW
$140.00/Night
Balcony
$1,295.00
Cat: B2
$185.00/Night
Suite
$3,610.00
Cat: S2
$515.71/Night
Golden Caribbean Strands Roundtrip from Miami
Departing on Feb 23, 2027 on the Marina
Nights: 10
Dates: Feb 23, 2027 through Mar 05, 2027
Ship: Marina
Itinerary:
Miami, San Juan, Basseterre, Philipsburg, Tortola, Puerto Plata, Great Stirrup Cay, Miami
from
$2,999.00
(USD)
Per Person
Inside
$2,999.00
Cat: G
$299.90/Night
Outside
$3,799.00
Cat: C
$379.90/Night
Balcony
$4,399.00
Cat: B4
$439.90/Night
Suite
$6,199.00
Cat: PH3
$619.90/Night
Departing on Nov 30, 2025 on the Star Pride
Nights: 13
Dates: Nov 30, 2025 through Dec 13, 2025
Ship: Star Pride
Itinerary:
San Juan, CRUZ BAY, ST. JOHN, Virgin Islands (U.S.), Gustavia, Basseterre, Philipsburg, St. Maarten, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, San Juan, Santo Domingo, Cartagena, San Blas, Panama, Colón
This is the kind of voyage where each day is postcard-perfect and no two are exactly alike. Get a champagne facial at BVI’s Jost Van Dyke’s Bubbly Pool with its effervescent fizz powered by the ocean, and trek through huge round granite boulders on Virgin Gorda, BVI to find The Baths, its eerie grottoes dancing with light from the turquoise water. Kayak through a bioluminescent bay near San Juan, your paddle drawing glowing patterns in the dark waters.
from
$4,099.00
(USD)
Per Person
Suite
$4,099.00
Cat: SP
$315.31/Night
Caribbean: Barbados, Antigua & St. Lucia Roundtrip from San Juan, Pr
Departing on Jan 11, 2026 on the Norwegian Epic
Nights: 7
Dates: Jan 11, 2026 through Jan 18, 2026
Itinerary:
San Juan, Pr, Tortola, British Virgin Islands, ST JOHNS ANTIGUA, Bridgetown, Barbados, ST LUCIA, SAINT LUCIA, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, ST THOMAS, VI, San Juan, Pr
Soak in the best of paradise on this round-trip cruise from San Juan on Norwegian Epic. In St. John’s, see the baroque towers of St. John's Cathedral and visit the historic Fort James and the Antigua Lighthouse. Stroll Bridgetown’s inviting beaches of Carlisle Bay or tour one of the popular rum factories.
from
$800.68
(USD)
Per Person
Inside
$800.68
Cat: IF
$114.38/Night
Balcony
$1,180.68
Cat: BX
$168.67/Night
Suite
$1,300.68
Cat: MC
$185.81/Night
Dates: May 03, 2022 through Oct 05, 2027
Location(s):
Tortola Island
See a historic century-old prison, catch scenic views from Fahie Hill and Sage Mountain and more on this cultural tour near Romney-Pier Park.
from
$70.00
(USD)
Per Person
Departing on Dec 13, 2025 on the Emerald Azzurra
Nights: 14
Dates: Dec 13, 2025 through Dec 27, 2025
Itinerary:
Saint John’s, Antigua, Antigua and Barbuda, Barbuda, Antigua and Barbuda, Îles des Saintes, Guadeloupe, Deshaies, Guadeloupe, Gustavia, Saint Barthélemy, Virgin Gorda, British Virgin Islands, Norman Island, British Virgin Islands, San Juan, Puerto Rico, Culebra Island & Vieques Island, Puerto Rico, St. John, U.S. Virgin Islands, Jost Van Dyke, British Virgin Islands, Philipsburg, Sint Maarten, Gustavia, Saint Barthélemy, Little Bay, Montserrat, St John’s, Antigua, Antigua and Barbuda
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
$14,760.00
(USD)
Per Person
Balcony
$14,760.00
Cat: A
$1,054.29/Night
Departing on Dec 18, 2026 on the Azamara Journey
Nights: 10
Dates: Dec 18, 2026 through Dec 28, 2026
Itinerary:
San Juan, Charlotte Amalie, St. Thomas, Virgin Gorda, St. John's, Antigua, Gustavia, Saint- Pierre, Port Elizabeth, Bequia, Scarborough, Tobago, Mayreau, Grenadines, Bridgetown
from
$2,319.00
(USD)
Per Person
Inside
$2,319.00
Cat: Z
$231.90/Night
Outside
$2,919.00
Cat: Y
$291.90/Night
Balcony
$3,719.00
Cat: X
$371.90/Night
Suite
$6,109.00
Cat: W
$610.90/Night
Departing on Jan 02, 2027 on the Valiant Lady
Nights: 7
Dates: Jan 02, 2027 through Jan 09, 2027
Ship: Valiant Lady
Itinerary:
San Juan, Tortola, Sailing, Bridgetown, Castries, St. John's, Philipsburg, San Juan
Set out from San Juan on this epic 7-night voyage to some of the Caribbean's most beautiful islands. Start in Road Town, the capital of Tortola in the British Virgin Islands, where you can visit local rum distilleries, or relax at Cane Garden Bay Beach. Then complete your whirlwind Caribbean tour by heading to Barbados, St. Lucia, Antigua, and St. Maarten.
from
$1,113.00
(USD)
Per Person
Inside
$1,113.00
Cat: IZ
$159.00/Night
Outside
$1,323.00
Cat: VZ
$189.00/Night
Balcony
$1,533.00
Cat: TZ
$219.00/Night
Suite
$4,515.00
Cat: SS
$645.00/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
$1,779.00
(USD)
Per Person
Inside
$1,779.00
Cat: Z
$254.14/Night
Outside
$2,329.00
Cat: Y
$332.71/Night
Balcony
$3,119.00
Cat: X
$445.57/Night
Suite
$4,749.00
Cat: W
$678.43/Night
Caribbean: Dominican Republic & St. Thomas Roundtrip from New York City, Ny
Departing on Jan 12, 2026 on the Norwegian Breakaway
Nights: 11
Dates: Jan 12, 2026 through Jan 23, 2026
Itinerary:
New York City, Ny, PUERTO PLATA, DOMINICAN REPUBLIC, San Juan, Pr, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, Tortola, British Virgin Islands, ST THOMAS, VI, New York City, Ny
Get ready to experience your own slice of paradise on this roundtrip cruise to The Caribbean aboard Norwegian Breakaway. In Puerto Plata, uncover the local history at the 16th century Fortaleza San Felipe or embark on a jungle adventure to see Damajagua’s Waterfalls. In San Juan, the second oldest city in the Americas, you’ll find a little bit of everything: beaches, city life and lush rainforests to explore.
from
$1,121.93
(USD)
Per Person
Inside
$1,121.93
Cat: IF
$101.99/Night
Outside
$1,451.93
Cat: OX
$131.99/Night
Balcony
$1,701.93
Cat: BF
$154.72/Night
Suite
$1,851.93
Cat: MB
$168.36/Night
Discover Eastern Caribbean & Grenadines Bridgetown to Sint Maarten
Departing on Jan 22, 2028 on the Emerald Sakara
Nights: 14
Dates: Jan 22, 2028 through Feb 05, 2028
Itinerary:
Bridgetown, Barbados, Bridgetown - Speightstown, Barbados, Kingstown - Bequia Island, Saint Vincent and the Grenadines, Bequia Island - Mayreau Island, Saint Vincent and the Grenadines, Mayreau Island - Union Island, Saint Vincent and the Grenadines, Union Island, Saint Vincent and the Grenadines, Union Island - Tobago Cays, Saint Vincent and the Grenadines, Bridgetown, Barbados, Soufrière, Saint Lucia, Îles des Saintes, Guadeloupe, St. John’s, Antigua and Barbuda, Charlestown, Saint Kitts and Nevis, Gustavia, Saint Barthélemy, Virgin Gorda, British Virgin Islands, Philipsburg, Sint Maarten
From French-Creole flavours to colonial landmarks and coastal hideaways, experience the authentic heart of the Caribbean.
from
$11,990.00
(USD)
Per Person
Outside
$11,990.00
Cat: D
$856.43/Night
Balcony
$15,490.00
Cat: B
$1,106.43/Night
Suite
$22,190.00
Cat: T
$1,585.00/Night
Departing on Feb 25, 2026 on the Enchanted Princess
Nights: 20
Dates: Feb 25, 2026 through Mar 17, 2026
Itinerary:
Fort Lauderdale, Princess Cays, St Thomas, Dominica, Barbados, Martinique, Antigua, Fort Lauderdale, Princess Cays, St Thomas, Antigua, St Maarten, St Kitts, Tortola, Fort Lauderdale
from
$3,248.00
(USD)
Per Person
Inside
$3,248.00
Cat: IF
$162.40/Night
Outside
$4,308.00
Cat: O6
$215.40/Night
Balcony
$4,283.00
Cat: BF
$214.15/Night
Suite
$4,868.00
Cat: MF
$243.40/Night
Departing on Jan 31, 2026 on the Wind Spirit
Nights: 7
Dates: Jan 31, 2026 through Feb 07, 2026
Ship: Wind Spirit
Itinerary:
Philipsburg, St. Maarten, St. John's, Road Bay, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, British Virgin Islands, Gustavia, Philipsburg, St. Maarten
Bask on remote beaches resplendent in natural beauty during this relaxing, unrushed, and uncrowded 7-day getaway to secluded Caribbean destinations Windstar specializes in. Board a private speedboat bound for Little Bay, Anguilla’s smallest and most private beach, then snorkel among flitting grunts, wrasses and snappers. Guide your own rigid inflatable boat (RIB) through Sir Francis Drake Waterway bays and isles around Jost Van Dyke.
from
$2,699.00
(USD)
Per Person
Outside
$2,699.00
Cat: B
$385.57/Night
Discover the Pearls of the Caribbean Bridgetown to Marigot, Saint Martin
Departing on Dec 06, 2026 on the Emerald Azzurra
Nights: 14
Dates: Dec 06, 2026 through Dec 20, 2026
Itinerary:
Bridgetown, Barbados, Soufrière, Saint Lucia, Îles des Saintes, Guadeloupe, Falmouth Harbour, Antigua and Barbuda, Charlestown-Cades Bay, Saint Kitts and Nevis, Gustavia, Saint Barthélemy, Prickly Pear Cays, Anguilla - Marigot, Saint Martin, Marigot, Saint Martin, Marigot, Saint Martin - Anguilla, Virgin Gorda – Norman Island, British Virgin Islands, Norman Island - Jost van Dyke, British Virgin Islands, Anegada, British Virgin Islands, Saba, Bonaire, Saint Eustatius and Saba – Gustavia, Saint Barthélemy, Gustavia, Saint Barthélemy, Marigot, Saint Martin
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
$15,180.00
(USD)
Per Person
Outside
$15,180.00
Cat: D
$1,084.29/Night
Balcony
$21,780.00
Cat: B
$1,555.71/Night
Suite
$34,580.00
Cat: T
$2,470.00/Night
Departing on Jan 09, 2027 on the Star Flyer
Nights: 7
Dates: Jan 09, 2027 through Jan 16, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Road Bay, Anguilla, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Gustavia, St. Barts, Philipsburg, St. Maarten
from
$2,010.00
(USD)
Per Person
Inside
$2,010.00
Cat: Category 6
$287.14/Night
Outside
$2,320.00
Cat: Category 5
$331.43/Night
Departing on Dec 26, 2026 on the Star Flyer
Nights: 7
Dates: Dec 26, 2026 through Jan 02, 2027
Ship: Star Flyer
Itinerary:
Philipsburg, St. Maarten, Gustavia, St. Barts, White Bay, Jost van Dyke (B.V.I.), Sopers Hole - Tortola, British Virgin Islands (BVI, Sailing Sir Francis Drake Channel, The Bight - Norman Island, British Virgin Islands, Spanish Town - Virgin Gorda, British Virgin Island, Beach, Captain's Best, British Virgin Islands (B.V, Basseterre, St. Kitts (morning), South Friars Bay - Beach, St. Kitts (afternoon), Road Bay, Anguilla, Philipsburg, St. Maarten
from
$2,210.00
(USD)
Per Person
Inside
$2,210.00
Cat: Category 6
$315.71/Night
Outside
$2,520.00
Cat: Category 5
$360.00/Night