from
$4,144.00
(USD)
Per Person
+ $235.00 taxes/fees
Nights:
20
Ship:
Zuiderdam
Price Per Night:$207.20 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, Relaxaway Half Moon Cay, San Juan, St Thomas, Tortola, St Maarten, Antigua, Scenic Cruising Soufriere Bay, St Lucia, Roseau, Barbados, Grenada, Scarborough, Bonaire, Aruba, Curacao, Falmouth, Miami
Other Categories Starting At:
Inside
$4,144.00
Cat: N
Cat: N
Outside
$5,044.00
Cat: HH
Cat: HH
Balcony
$5,894.00
Cat: VH
Cat: VH
Suite
$8,744.00
Cat: SZ
Cat: SZ
Category N - Flash Special: Book by Sunday 10/26/2025
from
$2,170.15
(USD)
Per Person
Nights:
11
Ship:
Norwegian Pearl
Price Per Night:$197.29 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
PHILADELPHIA, PA, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, ST THOMAS, VI, Tortola, British Virgin Islands, San Juan, Pr, PUERTO PLATA, DOMINICAN REPUBLIC, PHILADELPHIA, PA
Set out on a captivating 11-day sailing from Philadelphia, leaving behind the East Coast skyline for the sunlit allure of the Caribbean. Stop at St. Thomas, where blue waters invite you to snorkel at Magens Bay, explore the charming boutiques of Charlotte Amalie, or simply immerse yourself in the island’s relaxed ambiance. Next, discover the green hills and hidden beaches of Road Town, Tortola - hike up Sage Mountain for sweeping views or trace the coastline by boat.
Other Categories Starting At:
Inside
$2,170.15
Cat: IF
Cat: IF
Outside
$2,570.15
Cat: OK
Cat: OK
Balcony
$3,220.15
Cat: BF
Cat: BF
Suite
$3,820.15
Cat: MB
Cat: MB
from
$1,393.00
(USD)
Per Person
Nights:
7
Ship:
Valiant Lady
Price Per Night:$199.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
San Juan, Philipsburg, St. Maarten, Basseterre, St. John's, Castries, Sailing, Tortola, San Juan
This 7-night idyllic journey departs from San Juan and docks the next day in St. Maarten. From there you'll head to St. Kitts followed by St. Johns in Antigua - the quintessential paradise lover's paradise - where you'll discover the epitome of a tropical haven. From there you'll dock in St. Lucia, then spend a day sailing to the British Virgin Islands before finally returning to San Juan.
Other Categories Starting At:
Inside
$1,393.00
Cat: IZ
Cat: IZ
Outside
$1,603.00
Cat: VZ
Cat: VZ
Balcony
$1,813.00
Cat: TZ
Cat: TZ
Suite
$4,830.00
Cat: SS
Cat: SS
from
$7,999.00
(USD)
Per Person
Nights:
19
Ship:
Allura
Price Per Night:$421.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, Oranjestad, Willemstad, Kralendijk, St. George's, Castries, Gustavia, Tortola, Miami, Costa Maya, Belize City, Roatan, Cozumel, Miami
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
$7,999.00
Cat: A3
Cat: A3
Suite
N/A
from
$915.87
(USD)
Per Person
Nights:
7
Ship:
Norwegian Breakaway
Price Per Night:$130.84 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
San Juan, Pr, Tortola, British Virgin Islands, Basseterre, Saint Kitts - Nevis, Bridgetown, Barbados, ST LUCIA, SAINT LUCIA, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, ST THOMAS, VI, San Juan, Pr
Sail away from San Juan for seven days of pure island enchantment, where each port beckons with promise and charm. Start in Road Town, Tortola, where lush hills and secret coves await - dive into crystal waters where you might see a gentle sea turtle or journey inland to the mystical Baths, where giant granite boulders create hidden grottos.
Other Categories Starting At:
Inside
$915.87
Cat: IF
Cat: IF
Outside
$1,115.87
Cat: OB
Cat: OB
Balcony
$1,315.87
Cat: BF
Cat: BF
Suite
$1,465.87
Cat: MB
Cat: MB
from
$7,995.00
(USD)
Per Person
Nights:
10
Ship:
Emerald Sakara
Price Per Night:$799.50 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Philipsburg, Sint Marteen, Norman Island, British Virgin Islands, Virgin Gorda, British Virgin Islands, Gustavia, Saint Barthélemy, Charlestown, Saint Kitts and Nevis, St. John’s, Antigua and Barbuda, Îles des Saintes, Guadeloupe, Soufrière, Saint Lucia, Bequia Island, Saint Vincent and the Grenadines, Tobago Cays, Saint Vincent and the Grenadines, Bridgetown, Barbados
From capital cities with vibrant cultures to hidden caves, hot springs and island gems, this unforgettable cruise is yours to discover.
Other Categories Starting At:
Inside
N/A
Outside
$7,995.00
Cat: D
Cat: D
Balcony
$10,495.00
Cat: B
Cat: B
Suite
$15,295.00
Cat: T
Cat: T
from
$4,950.00
(USD)
Per Person
Nights:
9
Ship:
Explora I
Price Per Night:$550.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, Puerto Plata, Dominican Republic, Cayo Levantado, Dominican Republic, San Juan, Charlotte Amalie (Saint Thomas), Spanish Town (Virgin Gorda), Miami
Experience sounds, sights and tastes of Miami, then explore the pirate history of San Andrés, with its patchwork coconut groves and rocky beauty. After jungle adventures in Puerto Limon, relax in the lush tropical surroundings of Gatun Lake and marvel at man-made wonder of the Panama Canal.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$4,950.00
Cat: OT1
Cat: OT1
from
$69.00
(USD)
Per Person
Location(s):
Tortola Island
Enjoy a scenic drive in Road Town, get panoramic views from Sky World, and swim in Cane Garden Bay on this beach tour near Romney-Pier Park.
from
$1,489.00
(USD)
Per Person
Nights:
10
Ship:
Brilliant Lady
Price Per Night:$148.90 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, Florida, Sailing, Philipsburg, St. Maarten, Tortola, St. Croix, San Juan, Puerto Plata, Sailing, Beach Club at Bimini, Miami, Florida
Sail two days from Miami to the stunning beaches and immaculate vibes of Philipsburg, St. Maarten, followed by the enchanting rainforests and impressive wildlife of Tortola, British Virgin Islands. Awake the next day in St. Croix followed by San Juan and then the silver coasts of Puerto Plata, Dominican Republic. Sail another day to the brilliant Beach Club at Bimini before returning to Miami.
Other Categories Starting At:
Inside
$1,489.00
Cat: IN
Cat: IN
Outside
$1,590.00
Cat: VZ
Cat: VZ
Balcony
$1,990.00
Cat: TZ
Cat: TZ
Suite
$6,100.00
Cat: SS
Cat: SS
from
$6,244.00
(USD)
Per Person
+ $360.00 taxes/fees
Nights:
32
Ship:
Zuiderdam
Price Per Night:$195.13 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, St Maarten, Antigua, St Lucia, Roseau, St Kitts, St Thomas, Half Moon Cay, Miami, Half Moon Cay, Amber Cove, San Juan, St Kitts, Tortola, St Maarten, Antigua, Martinique, Barbados, Grenada, Scarborough, Aruba, Curacao, Ocho Rios, Grand Cayman, Cozumel, Miami
Other Categories Starting At:
Inside
$6,244.00
Cat: N
Cat: N
Outside
$6,714.00
Cat: HH
Cat: HH
Balcony
$8,144.00
Cat: VH
Cat: VH
Suite
$12,774.00
Cat: SS
Cat: SS
Category N - Flash Special: Book by Sunday 10/26/2025
from
$5,970.00
(USD)
Per Person
Nights:
7
Ship:
Emerald Kaia
Price Per Night:$852.86 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
San Juan, Puerto Rico, Vieques Island, Puerto Rico, St. John, U.S. Virgin Islands - Jost Van Dyke, British Virgin Islands, Jost Van Dyke, British Virgin Islands, Philipsburg, Sint Maarten - Gustavia, Saint Barthélemy, Gustavia, Saint Barthélemy, Little Bay, Montserrat - St. John’s, Antigua, Antigua and Barbuda, St. John’s, Antigua, Antigua and Barbuda
Immerse yourself in stunning landscapes, vibrant cultures, and luxurious serenity on a journey through the Caribbeans idyllic hideaways.
Other Categories Starting At:
Inside
N/A
Outside
$5,970.00
Cat: D
Cat: D
Balcony
N/A
Suite
$7,795.00
Cat: B
Cat: B
from
$1,219.00
(USD)
Per Person
Nights:
12
Ship:
Azamara Onward
Price Per Night:$101.58 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, Florida, San Juan, Philipsburg, St. John's, Antigua, Basseterre, St.Kitts, Charlestown, Nevis, Virgin Gorda, Miami, Florida
Other Categories Starting At:
Inside
$1,219.00
Cat: Z
Cat: Z
Outside
$1,629.00
Cat: Y
Cat: Y
Balcony
N/A
Suite
N/A
from
$5,486.75
(USD)
Per Person
Nights:
15
Ship:
Explora II
Price Per Night:$365.78 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
San Juan, Road Bay, St. John's (Antigua), St. Maarten/Philipsburg, Spanish Town (Virgin Gorda), Miami, Charlotte Amalie (Saint Thomas), Terre-de-Haut, Bridgetown, Martinique/Fort de France, Basseterre, San Juan
Sapphire shorelines and emerald hilltops dazzle under the Caribbean sun on our exploration from the paradise of Road Bay through St John's striking shoreline to the patchwork peaks of Phillipsburg. Gentle winds escort us onwards to the heritage of Spanish Town, the rhythms of Miami and heart-shaped, heart-stopping Magen's Bay in St Thomas. Pause to browse through pretty French-influenced markets in Terre-de-Haut and Fort-de-France, then watch the sunrise sparkle over lively St Kitts.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$5,486.75
Cat: OT2
Cat: OT2
Virtuoso Voyages Hosted Benefits
Exclusive Benefits
from
$5,800.00
(USD)
Per Person
Nights:
10
Ship:
Silver Shadow
Price Per Night:$580.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, Fl, Day at sea, San Juan, St John, Gustavia, St Barthelemy, Basseterre, St. Kitts, Jost Van Dyke (British Virgin Islands), Day at sea, Miami, Fl
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$5,800.00
Cat: VI
Cat: VI
from
$3,499.00
(USD)
Per Person
Nights:
12
Ship:
Nautica
Price Per Night:$291.58 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Miami, Willemstad, Oranjestad, Kralendijk, Castries, Pointe A Pitre, Jost Van Dyke, Miami
Other Categories Starting At:
Inside
$3,499.00
Cat: G
Cat: G
Outside
$3,849.00
Cat: D
Cat: D
Balcony
N/A
Suite
N/A
from
$3,899.00
(USD)
Per Person
Nights:
7
Ship:
Wind Spirit
Price Per Night:$557.00 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
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.
Other Categories Starting At:
Inside
N/A
Outside
$3,899.00
Cat: A
Cat: A
Balcony
N/A
Suite
N/A
from
$1,150.93
(USD)
Per Person
Nights:
12
Ship:
Norwegian Gem
Price Per Night:$95.91 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
JACKSONVILLE, FLORIDA, FL, Grand Bahama Island, Bahamas, Great Stirrup Cay, Bahamas, PUERTO PLATA, DOMINICAN REPUBLIC, Tortola, British Virgin Islands, PHILIPSBURG ST MAARTEN, NETHERLAND ANTILLES, Basseterre, Saint Kitts - Nevis, ST THOMAS, VI, San Juan, Pr, JACKSONVILLE, FLORIDA, FL
Other Categories Starting At:
Inside
$1,150.93
Cat: IF
Cat: IF
Outside
$1,220.93
Cat: OK
Cat: OK
Balcony
$2,130.93
Cat: BF
Cat: BF
Suite
$2,300.93
Cat: MB
Cat: MB
from
$4,700.00
(USD)
Per Person
Nights:
7
Ship:
Silver Shadow
Price Per Night:$671.43 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
San Juan, St John, Little Bay, Montserrat, St. John's, Gustavia, St Barthelemy, Basseterre, St. Kitts, Jost Van Dyke (British Virgin Islands), San Juan
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$4,700.00
Cat: VI
Cat: VI
from
$2,039.00
(USD)
Per Person
+ $150.00 taxes/fees
Nights:
9
Ship:
Nieuw Amsterdam
Price Per Night:$226.56 (USD)
(based on double occupancy, for comparison only)
(based on double occupancy, for comparison only)
Itinerary:
Fort Lauderdale, Antigua, St Thomas, Tortola, San Juan, Relaxaway Half Moon Cay, Fort Lauderdale
Other Categories Starting At:
Inside
$2,039.00
Cat: N
Cat: N
Outside
$2,289.00
Cat: HH
Cat: HH
Balcony
$2,589.00
Cat: VH
Cat: VH
Suite
$4,089.00
Cat: SZ
Cat: SZ
Category N - Flash Special: Book by Sunday 10/26/2025
