Have questions? We're here.
Vivid blue waters of the Caribbean

Windward Islands Trips in 2022

Travel made your way
Talk with an expert
Customize any aspect of your Caribbean trip. 1.406.541.2677
Help Me Plan My Trip
Filter (21 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Windward Islands
White Sand Beach in Barbados
$1,580
Savings
EXPLORE

Grenadine Islands

8 Day Itinerary aboard Royal Clipper
  • Visit one island in Grenadines
  • Smell the aroma of Grenada
  • Walk and swim at Marigot Bay
  • Taste the spicy Creole cooking
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join the Royal Clipper on this 8-day cruise through theGrenadine Islands. Embark on an interesting adventure, visiting towns full of contrasts,Bridgetown, Barbados. Then, call on one of the islands of Grenadine, for a blissful, laid-back beach day.From the horseshoe-shaped Carenage at St. …
Cruise Details
0
Bright blue waters of the Caribbean
$1,360
Savings
EXPLORE

Grenadine Islands

7 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Take in Grenada's unique aromas
  • Discover Tobago Cays
  • View Bequia's waterfront
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Sailing Schooner, Snorkeling
Activity Level:
Relaxed
Experience tropical life with a refined twist on this incredible 7-day cruise aboard the tall ship Royal Clipper. Lush mountains, rain forests, volcanic crater lakes, mangroves, beautiful beaches, and delicate coral reefs are hallmarks of this coveted destination. Enjoy a wonderful journey of …
Cruise Details
0
Pelicans hanging out in the ocean
$9,870
EXPLORE

Sailing the Caribbean

8 Day Itinerary aboard Sea Cloud
  • Experience a 4-masted, 30-sail ship
  • Sail into lesser-known ports
  • Explore wildlife, culture, and sea
  • Enjoy the relaxed Caribbean pace
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Stand on deck as Sea Cloud’s 30 white sails fill with wind, and measure the passage of time by a distant island’s approach on the horizon.Join thisextraordinary and historic yacht for an 8-day voyage that brings you into lesser-known ports of the "Old Caribbean" and offers the …
Cruise Details
0
Caribbean beach bar
$5,395
EXPLORE

Caribbean: Round-trip Bridgetown via Bequia

8 Day Itinerary aboard Sea Cloud
  • Explore the Argyle Waterfall
  • Discover Grenada Island
  • Swim in the Tobago Cays
  • Visit Old Hegg Turtle Sanctuary
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Sailing Schooner, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 8-day round-trip cruise from Barbados. As you sail, visit the charming port cities and remote coves of Tobago Cays, Soufriere, Cabrits, and more. The Caribbean is a vibrant, lively region of colorful buildings and friendly locals. Fall …
Cruise Details
0
Mountains by the ocean in St Lucia
$3,620
Save $600
EXPLORE

Pearls of the Caribbean

Roundtrip Fort-de-France - 9 Day Itinerary aboard Le Dumont-d'Urville
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Observe marine animals
  • Enjoy the beach on Mayreau Island
Starts/ Ends in:
Fort de France / Fort de France
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Take this opportunity to explore the enchanting islands in the Caribbean Sea. Join Le Dumont-d'Urville on this 9-day cruise combining long, white-sand beaches and the laid-back Creole way of life. Discover the UNESCO-listed sites in Saint Lucia and the historic center of Bridgetown and its …
Cruise Details
0
Take a leisurely stroll through beautiful Bridgetown
$3,299
EXPLORE

Bridgetown to Bridgetown

8 Day Itinerary aboard SeaDream I
  • Admire Mayreau's beauty
  • Snorkel at Tobago Cays
  • Explore Bridgetown
  • Relax and enjoy luxurious amenities
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
Feel the unique charm of the Caribbean Islands on this 8-day voyage. Delight yourself in European influence and the ideal weather of this region as you cruise round-trip out of Bridgetown, Barbados. Enjoy playing from the water sports marina as the ship anchors off on different ports. Visit …
Cruise Details
0
Take the time to explore St. Lucia
$3,399
EXPLORE

Bridgetown Roundtrip

8 Day Itinerary aboard SeaDream I
  • Visit Union Island
  • Discover Mayreau
  • Swim and snorkel at Tobago Cays
  • Explore Bridgetown's beaches
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
The natural beauty of the Caribbean, with miles of beaches, private coves, and brilliant turquoise water is brought to life with the casual luxury of the SeaDream I. This 8-day Bridgetown roundtrip cruise is designed to highlight the Caribbean's colorful sightseeing, wonderful dining and …
Cruise Details
0
Vivid blue waters of the Caribbean
$2,999
EXPLORE

Bridgetown to Bridgetown

7 Day Itinerary aboard SeaDream I
  • Explore Bridgetown
  • Relax and enjoy luxurious amenities
  • Snorkel at Tobago Cays
  • Admire Mayreau's beauty
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling, Village Visit
Activity Level:
Relaxed
The natural beauty of the Caribbean, with miles of beaches, private coves, and brilliant turquoise water is brought to life with the casual luxury of the SeaDream I. This 7-day Bridgetown roundtrip cruise is designed to highlight the Caribbean's colorful sightseeing, wonderful dining, and …
Cruise Details
0
Gatun Lock of the Panama Canal
$3,500
Savings
EXPLORE

Panama Canal: Barbados to Panama

15 Day Itinerary aboard Royal Clipper
  • Explore Bridgetown, Barbados
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Transit the historic Panama Canal
Starts/ Ends in:
Bridgetown / Balboa
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Royal Clipper takes you to the seas for a stunning adventure packed with incredible experiences starting at the charming port town of Bridgetown, Barbados. Scour the streets of the UNESCO-listed cities of Cartagena de Indias, Colombia, and Willemstad, Curaçao. Swim in the protected, …
Cruise Details
0
Spot monkeys in the rainforest canopy
$13,680
Savings
EXPLORE

Fortaleza to Bridgetown

22 Day Itinerary aboard Silver Wind
  • Visit the Forte do Castelo in Belem
  • Marvel at Giant Water Lilies
  • Tour the city of Georgetown
  • Observe wildlife
Starts/ Ends in:
Fortaleza / Bridgetown
Activities:
Local Market, Small Ship Cruise, Urban Exploration, Wildlife Viewing
Activity Level:
Relaxed
Travel north from Fortaleza all the way to the Caribbean, taking in some spectacular sights – and sites – along the way. Everything you could possibly want from Brazil is on this voyage – Zodiac expeditions into the mighty Amazon jungle, gastronomic excellence, unprecedented …
Cruise Details
0
Beautiful beach in Dominica
$1,520
Savings
EXPLORE

Leeward Islands

8 Day Itinerary aboard Star Flyer
  • Visit Dominica Island
  • Snorkel at Iles des Saintes
  • Sail across Rivière Salée
  • Enjoy Gustavia's unique charm
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
With an island for every taste, the Caribbean is the ultimate place for relaxation. Explore the world-famous white sands and turquoise water throughout the Caribbean Sea. With more than 5,000 islands and cays spread across this amazing region, there’s a lot of paradise to see. Best of all, …
Cruise Details
0
Pink beach huts in the Caribbean
$1,580
Savings
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore lush St. Lucia Island
  • Hike to Trafalgar Falls
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
For connoisseurs of sail cruising, the 439-foot Royal Clipper offers the ultimate sea-going experience, balancing the grandeur, adventure and tradition of sailing with the superb service, amenities, and accommodations of the finest modern yacht. Swim and snorkel amidst the beautiful, pristine …
Cruise Details
0
Evening light on the canoes
$26,340
EXPLORE

Wild South America: The Guianas to Brazil

23 Day Itinerary aboard National Geographic Explorer
  • Spot incredible wildlife
  • Explore historic cities
  • Enjoy live musical performances
  • See Kaieteur Falls
Starts/ Ends in:
Port of Spain / Salvador
Activities:
Archaeological Sites, Wildlife Viewing
Activity Level:
Relaxed
Extraordinary diversity and a dazzling array of points of interest await on this exploration through five countries, two legendary rivers, and a host of places few people ever see. Experience fascinating ecosystems from riverine to jungle to urban, within dramatic natural settings. Spot tropical …
Cruise Details
0
Mountains by the ocean in St Lucia
$5,220
EXPLORE

Panama, Colombia & Caribbean Islands

Colón - Fort-de-France - 13 Day Itinerary aboard Le Champlain
  • Sail through the Central America.
  • See San Blas, Bonaire & Grenadines
  • Experience swim and snorkel.
  • Learn traditions of the Kuna people
  • Dive with an experienced instructor
Starts/ Ends in:
Colon / Fort de France
Activities:
Archaeological Sites, Land & Sea, Scuba Diving, Snorkeling, Spa & Relaxing, Village Visit
Activity Level:
Relaxed
Cruise between Central America and the West Indies, discovering the natural treasures of the Caribbean Sea and its many cultural influences. Your journey in Central America continues with an all-new port of call in the magnificent Portobelo Bay, in a region imbued with the traditions of Congo …
Cruise Details
0
Soufrière Bay, Saint Lucia
$3,620
EXPLORE

Pearls of the Caribbean: Bridgetown Roundtrip

Bridgetown Rountrip - 9 Day Itinerary aboard Le Dumont-d'Urville
  • See UNESCO World Heritage Sites
  • Visit the Grenadine Islands
  • Experience long white-sand beaches
  • Enjoy the beach on Mayreau Island
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Discover a true picture-postcard of the West Indies: long white-sand beaches, colorful seabeds, and the easy Creole way of life. Board Le Dumont-d’Urville inBarbadosat the port ofBridgetown, whose UNESCO-listed historical center shows the extent of the British colonial presence, and head for …
Cruise Details
0
Bright blue waters of the Caribbean
$4,140
Savings
EXPLORE

Bridgetown to Fort Lauderdale

9 Day Itinerary aboard Silver Wind
  • See Conception Island's wildlife
  • Visit Devil’s Bay National Park
  • Marvel at Barbuda's frigatebirds
  • Dip in the hot springs of Roseau
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Experience the Caribbean as never before during this 9-day cruise from Bridgetown to Fort Lauderdale. Spend time relaxing on white sandy beaches and enjoying coral reefs and the warm, clear waters of islands such as Dominica, St. Vincent and Antigua. But the Caribbean is so much more: tiny, off the …
Cruise Details
0
Stroll along the beautiful beaches of the Caribbean
$6,165
EXPLORE

Caribbean: Round-trip Philipsburg

9 Day Itinerary aboard Sea Cloud
  • Visit the port town of Philipsburg
  • Discover the stunning White Bay
  • Explore the famous ‘Love City’ Cruz
  • Experience St. Barthélemy
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Delight yourself with deep volcanic lakes, dense rainforests, waterfalls, and small river courses that form the primordial backdrop of the island’s sugar cane fields and spice plantations. The scent of cloves, cinnamon, and nutmeg hang in the air wherever you go. Admire the Caribbean's …
Cruise Details
0
Relax on the beaches of the Caribbean
$5,530
EXPLORE

Caribbean: Round-trip Philipsburg

10 Day Itinerary aboard Sea Cloud
  • Snorkel the British Virgin Islands
  • See luxurious St. Barths
  • Watch stunning sunsets
  • Explore charming Soufriere
Starts/ Ends in:
Philipsburg / Gustavia
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 10-day round-trip cruise from Philipsburg in St. Maarten. As you sail, visit the charming port cities and remote coves of Gustavia, Virgin Gorda and more. The Caribbean is a vibrant, lively region of colorful islands and friendly locals. …
Cruise Details
0
1-18 of 21 Results

Caribbean Travel Guide

Favorite Caribbean Tours & Cruises

Top Windward Islands Travel Destinations

Windward Islands Trips by Departure Date

Windward Islands Trips by Duration

More Reasons

Why Travel With Adventure Life

All News

Recognized By