Overland Express Travel
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St. Lucia (19 offers included)

11-Day Eastern Caribbean Wayfarer
Roundtrip from Fort Lauderdale, Florida, US
from $1,459.00 (USD)
Per Person
+ $245.00 taxes/fees
Eurodam
Holland America Line logo
More offers from Holland America Line
Nights: 11
Ship: Eurodam
Price Per Night:$132.64 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Florida, US, Days At Sea, St. Thomas, U.S.V.I., Basseterre, St Kitts and Nevis, Roseau, Dominica, Castries, Saint Lucia, St. Johns, Antigua and Barbuda, Philipsburg, Sint Maarten, Days At Sea, Half Moon Cay, Bahamas...
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Inside
$1,459.00
Cat: N
Outside
$1,629.00
Cat: HH
Balcony
$2,239.00
Cat: VH
Suite
$2,959.00
Cat: SZ
More Details Contact Us
Radiant Island Dawns
Miami to Bridgetown
from $3,499.00 (USD)
Per Person
Offer Image
Oceania Cruises logo
More offers from Oceania Cruises
Nights: 12
Ship: Insignia
Price Per Night:$291.58 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Oranjestad, Willemstad, Port Of Spain, St. George's, Castries, Kingstown, Roseau, Fort-De-France, Bridgetown
Other Categories Starting At:
Inside
$3,499.00
Cat: G
Outside
$3,849.00
Cat: D
Balcony
$5,099.00
Cat: B2
Suite
$6,599.00
Cat: PH3
More Details Contact Us
Saint (Isles) & Seas of the Caribbean
from $697.00 (USD)
Per Person
+ $1,276.00 taxes/fees
Tortola
Virgin Voyages logo
More offers from Virgin Voyages
Nights: 7
Price Per Night:$99.57 (USD)
(based on double occupancy, for comparison only)
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.
Other Categories Starting At:
Inside
$697.00
Cat: IN
Outside
$755.00
Cat: VW
Balcony
$1,575.00
Cat: TL
Suite
$3,392.00
Cat: SAB
More Details Contact Us
Transatlantic Crossing and Caribbean Celebration, 22 Nights
from $4,599.00 (USD)
Per Person
+ $242.36 taxes/fees
Queen Mary 2
Cunard Line logo
More offers from Cunard Line
Nights: 22
Ship: Queen Mary 2
Price Per Night:$209.05 (USD)
(based on double occupancy, for comparison only)
Itinerary: New York, New York, Amber Cove,Dominican Republic, Tortola, B.V.I., Dominica, Dominica, Barbados, Barbados, St Lucia, Saint Lucia, St. Kitts, ST Kitts/Nevis, New York, New York, London (Southampton), England
Join in the festive fun and games on board as you celebrate Christmas in the Caribbean sunshine. Then, enjoy a New Year’s Eve to remember, counting down to midnight as you sail toward New York.
Other Categories Starting At:
Inside
$4,599.00
Cat: IF
Outside
$6,199.00
Cat: EF
Balcony
$6,399.00
Cat: DF
Suite
$14,299.00
Cat: P2
More Details Contact Us
Caribbean & Central America Cruise
Bridgetown to Bridgetown
from $9,300.00 (USD)
Per Person
Offer Image
Silversea Cruises logo
More offers from Silversea Cruises
Nights: 14
Price Per Night:$664.29 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Castries, St George's, Day at sea, Philipsburg, St. Maarten, St. Thomas, Basseterre, St. Kitts, St. John's, Roseau, Bequia...
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Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$9,300.00
Cat: PA
More Details Contact Us
JEWELS OF THE WINDWARD ISLANDS
from $2,399.00 (USD)
Per Person
+ $219.00 taxes/fees
Wind Spirit Tahiti
Windstar Cruises logo
More offers from Windstar Cruises
Nights: 7
Ship: Wind Spirit
Price Per Night:$342.71 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Pigeon Island, The Pitons, Castries, Kingstown, Mayreau, St. George's, Bequia, Bridgetown
This is the Caribbean of days gone by – deep blue waters, quiet coves and tropical islands dotted with powdery beaches and lush green hillsides. Sail from the rugged natural beauty of St. Lucia to little-known isles that are off the tourist radar. From colorful Bequia and Mayreau in St. Vincent & the Grenadines to the open-air markets of exotic St. George’s, you’ll discover a part of the Caribbean that remains authentic and unspoiled.
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Inside
N/A
Outside
$2,399.00
Cat: B
Balcony
N/A
Suite
N/A
More Details Contact Us
Caribbean & Central America Cruise
Philipsburg to Philipsburg
from $6,100.00 (USD)
Per Person
Offer Image
Silversea Cruises logo
More offers from Silversea Cruises
Nights: 7
Price Per Night:$871.43 (USD)
(based on double occupancy, for comparison only)
Itinerary: Philipsburg, St. Maarten, St. John's, St. Thomas, Little Bay, Montserrat, Castries, Mayreau, Les Saintes, Philipsburg, St. Maarten
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Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$6,100.00
Cat: VI
More Details Contact Us
Amazonian & Tropical Song
Roundtrip from Miami
from $10,399.00 (USD)
Per Person
Offer Image
Oceania Cruises logo
More offers from Oceania Cruises
Nights: 44
Ship: Nautica
Price Per Night:$236.34 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Cruising The Atlantic Ocean, St. John's, Castries, St. George's, Port Of Spain, Cruising The Atlantic Ocean, Macapa, Santarem (Amazon River), Boca Da Valeria (Amazon River)...
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Inside
N/A
Outside
$10,399.00
Cat: C2
Balcony
$14,799.00
Cat: A3
Suite
$20,099.00
Cat: PH2
More Details Contact Us
STAR COLLECTOR: CARIBBEAN EXPLORATIONS
from $4,099.00 (USD)
Per Person
+ $273.00 taxes/fees
Wind Spirit Tahiti
Windstar Cruises logo
More offers from Windstar Cruises
Nights: 14
Ship: Wind Spirit
Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)
Itinerary: St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, St. Maarten, Jost Van Dyke, Great Harbour, Soper's Hole...
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
Other Categories Starting At:
Inside
N/A
Outside
$4,099.00
Cat: B
Balcony
N/A
Suite
N/A
More Details Contact Us
STAR COLLECTOR: CARIBBEAN EXPLORATIONS
from $4,099.00 (USD)
Per Person
+ $273.00 taxes/fees
Wind Spirit Tahiti
Windstar Cruises logo
More offers from Windstar Cruises
Nights: 14
Ship: Wind Spirit
Price Per Night:$292.79 (USD)
(based on double occupancy, for comparison only)
Itinerary: St. Maarten, Jost Van Dyke, Great Harbour, Soper's Hole, Jost Van Dyke, Great Harbour, Virgin Gorda / Prickly Pear, Gustavia, Road Bay, Falmouth Harbour, St. Maarten, Charlestown...
Skip the usual Caribbean cruise stops and discover the small harbors, overlooked havens and most remote secrets among the Leeward Islands. Whether you’re looking for hidden shops, sampling new cuisine or seeking a local place to sip rum cocktails over the melodic beat of steel drums, this highly personalized adventure is an intimate opportunity to familiarize yourself with the lesser-known charms of Les Saintes, Anse Mitan, Pigeon Island and much more.
Other Categories Starting At:
Inside
N/A
Outside
$4,099.00
Cat: B
Balcony
N/A
Suite
N/A
More Details Contact Us
Classic Caribbean
St. Maarten to St. Maarten
from $2,299.00 (USD)
Per Person
+ $126.00 taxes/fees
Wind Surf Capri
Windstar Cruises logo
More offers from Windstar Cruises
Nights: 7
Ship: Wind Surf
Price Per Night:$328.43 (USD)
(based on double occupancy, for comparison only)
Itinerary: St. Maarten, Charlestown, Roseau, Pigeon Island, Les Saintes, Gustavia, Basseterre, St. Maarten
From the stunning drama of the Pitons to the captivating charm of Les Saintes. From hidden coves and secret beaches to exotic markets and lively cafés. Discover the best of this region with one single Caribbean cruise. Sandy beaches, turquoise waters, lush mountains, and beautiful waterfalls blend with the music, tastes, and joie de vivre unique to the Caribbean life.
Other Categories Starting At:
Inside
N/A
Outside
$2,299.00
Cat: B
Balcony
N/A
Suite
$5,399.00
Cat: OS
More Details Contact Us
Eastern Caribbean, 35 Nights
from $4,449.00 (USD)
Per Person
+ $176.85 taxes/fees
Queen Victoria
Cunard Line logo
More offers from Cunard Line
Nights: 35
Price Per Night:$127.11 (USD)
(based on double occupancy, for comparison only)
Itinerary: London (Southampton), England, Madeira, Portugal, Barbados, Barbados, St Lucia, Saint Lucia, Grenada, Grenada, St. Vincent, St. Vincent/Grenadines, Curacao, Antilles, Aruba, Aruba, Dominica, Dominica, Antigua...
This roundtrip Caribbean voyage from Southampton is the perfect way to escape the January blues. Enjoy an enviable start to 2026, soaking up the sun on some of the world’s best white-sand beaches.
Other Categories Starting At:
Inside
$4,449.00
Cat: IE
Outside
$6,699.00
Cat: FC
Balcony
$7,399.00
Cat: BF
Suite
$17,999.00
Cat: P2
More Details Contact Us
18-Day Eastern & Western Caribbean: Leeward Islands & Mexico
Roundtrip from Miami, Florida, US
from $3,489.00 (USD)
Per Person
+ $440.00 taxes/fees
Zuiderdam
Holland America Line logo
More offers from Holland America Line
Nights: 18
Ship: Zuiderdam
Price Per Night:$193.83 (USD)
(based on double occupancy, for comparison only)
Itinerary: Miami, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Other Categories Starting At:
Inside
$3,489.00
Cat: N
Outside
$3,989.00
Cat: HH
Balcony
$4,889.00
Cat: VH
Suite
$6,789.00
Cat: SZ
More Details Contact Us
Ladera
from $822.33 (USD)
Per Person
Ladera
Pleasant Holidays logo
More offers from Pleasant Holidays
Nights: 3
Price Per Night:$274.11 (USD)
(based on double occupancy, for comparison only)
Location(s): St. Lucia
Once part of Rabot Estate, one of Soufrière's oldest cocoa plantations, this authentic and luxurious open-air hotel is surrounded by a lush hillside of mango trees.
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21-Day Eastern Caribbean Wayfarer / Western Explorer
Roundtrip from Fort Lauderdale, Florida, US
from $3,419.00 (USD)
Per Person
+ $503.00 taxes/fees
Eurodam
Holland America Line logo
More offers from Holland America Line
Nights: 21
Ship: Eurodam
Price Per Night:$162.81 (USD)
(based on double occupancy, for comparison only)
Itinerary: Fort Lauderdale, Florida, US, Days At Sea, Philipsburg, Sint Maarten, St. Johns, Antigua and Barbuda, Castries, Saint Lucia, Roseau, Dominica, Basseterre, St Kitts and Nevis, St. Thomas, U.S.V.I., Days At Sea, Half Moon Cay, Bahamas...
Other Categories Starting At:
Inside
$3,419.00
Cat: N
Outside
$3,779.00
Cat: HH
Balcony
$5,039.00
Cat: VH
Suite
$7,109.00
Cat: SZ
More Details Contact Us
14-Day Exotic Caribbean In Depth
Roundtrip from Bridgetown, Barbados
from $7,824.00 (USD)
Per Person
+ $335.00 taxes/fees
Seabourn Ovation
Seabourn Cruise Line logo
More offers from Seabourn Cruise Line
Nights: 14
Price Per Night:$558.86 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Barbados, Castries, Saint Lucia, Pointe-a-pitre, St. Johns, Antigua and Barbuda, Great Harbour, Jost Van Dyke, Carambola Beach, Philipsburg, Sint Maarten, Frenchmans Cay, Carambola Beach, Fort-De-France, Martinique...
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
$7,824.00
Cat: V1
More Details Contact Us
STAR COLLECTOR: LOVELY LEEWARDS
from $4,199.00 (USD)
Per Person
+ $344.00 taxes/fees
Star Pride New York
Windstar Cruises logo
More offers from Windstar Cruises
Nights: 14
Ship: Star Pride
Price Per Night:$299.93 (USD)
(based on double occupancy, for comparison only)
Itinerary: San Juan, St. George's, Bequia, Pigeon Island, Les Saintes, St. Maarten, San Juan, St. Thomas, St. Maarten, Basseterre...
Whether you’re passionate about swimming among rarely seen undersea wildlife or the intricate cultures and intertwined European histories of the Windward Islands, this 2-week cruise offers the best combinations of charm, island heritage and natural beauty. Shop unique designer apparel in St. Barts, where you’ll discover a fashionable confluence of high-end brands normally associated with places like Madison Avenue, but displayed in an ambiance that’s anything but intimidating.
Other Categories Starting At:
Inside
N/A
Outside
N/A
Balcony
N/A
Suite
$4,199.00
Cat: S
More Details Contact Us
7-Day Classic Caribbean Yacht Harbors
Bridgetown, Barbados to Philipsburg, Sint Maarten
from $3,489.00 (USD)
Per Person
+ $165.00 taxes/fees
Seabourn Ovation
Seabourn Cruise Line logo
More offers from Seabourn Cruise Line
Nights: 7
Price Per Night:$498.43 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Barbados, Castries, Saint Lucia, Montserrat, St. Johns, Antigua and Barbuda, Carambola Beach, Great Harbour, Jost Van Dyke, Philipsburg, Sint 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
$3,489.00
Cat: V1
More Details Contact Us
21-Day Lesser Antilles In Depth
Roundtrip from Bridgetown, Barbados
from $8,264.00 (USD)
Per Person
+ $405.00 taxes/fees
Seabourn Ovation
Seabourn Cruise Line logo
More offers from Seabourn Cruise Line
Nights: 21
Price Per Night:$393.52 (USD)
(based on double occupancy, for comparison only)
Itinerary: Bridgetown, Barbados, Port Elizabeth, Bequia, St. Vincent and the Grenadines, Roseau, Dominica, Carambola Beach, Oranjestad, Aruba, Kralendijk, Bonaire, Willemstad, Curacao, , Bridgetown, Barbados, Castries, Saint Lucia...
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
$8,264.00
Cat: V1
More Details Contact Us