Have questions? We're here.
Clear waters of the Caribbean sea

All Caribbean Tours

Travel made your way
Talk with an expert
Customize any aspect of your Caribbean trip. 1.406.541.2677
Help Me Plan My Trip
Talk with an expert Ask a Question
Filter & Sort (88 Results)
Show Filter

37-54 of 88 Results
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Caribbean
St George's Harbor - Grenada
$1,599
Save $500
EXPLORE

Grenada Round Trip

7 Day Itinerary aboard Mandalay
  • Rise early & search for marine life
  • Snorkel in crystal-clear waters
  • Enjoy views of the night
  • Learn to raise the ship's sails
Starts/ Ends in:
Grenada / Grenada
Activities:
Sailing Schooner, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Sail through turquoise waters, watch for marine life, and relax on white sand beaches as you escape to these remote islands. This fabulous 7-day voyage offers you an authentic sailing experience giving you the chance to learn how to raise the sails, take a turn at the helm, or just relax on deck! …
Cruise Details
Play on the famously beautiful beaches of St. Barth's
$11,895
EXPLORE

Caribbean: Round-trip Philipsburg

16 Day Itinerary aboard Sea Cloud
  • Snorkel the famed Virgin Gorda
  • See luxurious St. Barthelemy
  • Explore the culture of Grenada
  • Admire beautiful St. Lucia
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Explore the best of the Caribbean on this round-trip cruise from Philipsburg aboard the Sea Cloud sailing ship. From the charming Dutch Colonial port town of Philipsburg, make your way to the British Virgin Islands. Snorkel the famed baths, or simply relax on the white sandy beaches before sailing …
Cruise Details
Explore the famous rock formations of the baths
$7,275
EXPLORE

Bridgetown to Philipsburg

11 Day Itinerary aboard Sea Cloud
  • Snorkel the waters of Virgin Gorda
  • Watch for stunning sunsets
  • Hike beautiful St. Lucia
  • Explore luxurious St. Barthelemy
Starts/ Ends in:
Bridgetown / Philipsburg
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Cruise across the beautiful Caribbean aboard the Sea Cloud. Sail from Bridgetown to Philipsburg, with stops in Soufriere on St. Lucia, Cabrits on Dominica, Gustavia on St. Barthelemy, and more. Snorkel the clear waters of the Baths on Virgin Gorda, hike lush forests for views from the pitons of St. …
Cruise Details
Wander through historic St. Lucia
$7,985
EXPLORE

Philipsburg to Bridgetown

11 Day Itinerary aboard Sea Cloud
  • See glitzy St. Barths
  • Snorkel the waters of Virgin Gorda
  • Watch stunning sunsets
  • Hike the pitons of St. Lucia
Starts/ Ends in:
Philipsburg / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 11-day cruise from Philipsburg to Bridgetown. As you sail, visit the charming port cities and remote coves of Gustavia, Virgin Gorda, Bequia, and more. The Caribbean is a vibrant, lively region of colorful islands and friendly locals. …
Cruise Details
Enjoy the natural beauty of the Caribbean
$7,975
EXPLORE

Caribbean: Bridgetown to Santo Domingo

10 Day Itinerary aboard Sea Cloud II
  • Hike the pitons of St. Lucia
  • Enjoy luxury in Gustavia
  • Swim and snorkel at Virgin Gorda
  • Explore vibrant Santo Domingo
Starts/ Ends in:
Bridgetown / Santo Domingo
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Join Sea Cloud II on this relaxing cruise sailing across the Caribbean. Begin your journey in colorful Bridgetown, Barbados, with its sunny beaches and preserved historic districts. Sail to Port Elizabeth and experience its relaxed lifestyle, or perhaps visit the nearby sea turtle sanctuary. On St. …
Cruise Details
Enjoy the beautiful blue Caribbean
$6,445
EXPLORE

Philipsburg to Bridgetown

9 Day Itinerary aboard Sea Cloud
  • Enjoy the ÎIes des Saintes
  • Watch incredible sunsets
  • Visit Cabrits National Park
  • Discover Antigua
Starts/ Ends in:
Philipsburg / Bridgetown
Activities:
Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 9-day round-trip cruise from Barbados. As you sail, visit the charming port cities and remote coves of Cabrits, Gustavia, Antigua and more. The Caribbean is a vibrant, lively region of colorful islands and friendly locals. Fall in love …
Cruise Details
Admire the locals on your Virgin Islands cruise
$3,499
EXPLORE

Bridgetown to Bridgetown

9 Day Itinerary aboard SeaDream I
  • Explore unspoiled Canouan Island
  • Visit Union Island
  • Snorkel at Tobago Cays
  • Discover Mayreau
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Kayaking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Discover the many facets of the Caribbean on this exclusive 9-day expedition. Observe reefs, fish, coral, and other aquatic life. Board a lovely catamaran that takes you on an exclusive sail-away to the beautiful Tobago Keys for a morning of swimming, snorkeling, and sunning.Discover an intimate …
Cruise Details
Bicycle on Cuban street
$3,885
EXPLORE

Cuba Cycling Tour

Quintessential Cuba - 8 Day Itinerary
  • Cycle through western Cuba
  • Visit Hemingway's former home
  • Ride through Cuba's tobacco fields
  • Explore Havana on foot
Activities:
Biking, Hiking, Land
Activity Level:
Relaxed
Cuba creates legends and imbues folklore. Everyday items such as a rolled cigar, a glass of rum spiked with sugarcane juice, a colorful classic car become more—gain a near-mythical status and a story that endured in the American consciousness even when Cuba’s doors were closed. Join …
Tour Details
Bridgetown, Barbados
$3,299
EXPLORE

Bridgetown to Marigot

8 Day Itinerary aboard SeaDream I
  • Discover Mayreau
  • Enjoy a horseback ride on Nevis
  • Snorkel at St. Barts
  • Hike the lush island Nevis
Starts/ Ends in:
Bridgetown / Marigot
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Explore the Caribbean Sea on this 8-day voyage starting in Bridgetown, aUNESCO Heritage Sites itself. You will be given time to visit spectacular places like Charlestown where you can enjoy a thrilling but comfortable horseback ride through the rolling countryside passing many natural and …
Cruise Details
The Southeast Peninsula of Saint Kitts with Nevis in the Background
$3,299
EXPLORE

San Juan to Charlotte Amalie via Antilles

8 Day Itinerary aboard SeaDream II
  • Enjoy the canopy at Tortola Island
  • Dive along the coast of St. Barths
  • Explore Tortola Island
  • Visit the beaches of St. Thomas
Starts/ Ends in:
San Juan / Charlotte Amalie
Activities:
Scuba Diving, Small Ship Cruise
Activity Level:
Relaxed
Sail through the Caribbean on this 8-day cruise beginning in Puerto Rico and ends in St. Thomas. As you cruise the blue waters, admire the vast horizon and shallow reef system, disembarking almost daily to explore the most charming coastal villages. Learn about the fascinating history of the region …
Cruise Details
Green sea turtle swimming
$3,399
EXPLORE

Charlotte Amalie to San Juan

8 Day Itinerary aboard SeaDream I
  • Visit beautiful St. John Island
  • Enjoy scenic Saba Island
  • Discover Soper's Hole, Tortola
  • Hike & snorkel at Norman Island
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Fall in love with the crystal waters and islands of the Caribbean on this 8-day Virgin Islands and Puerto Rico cruise. Begin in Charlotte Amalie and make your way for the sheltered coves and small towns of Cruz Bay, North Sound, Gustavia, and more. As you explore the island paradise of the …
Cruise Details
Islands of the Caribbean
$2,999
EXPLORE

Bridgetown to Marigot: Wine Voyage

8 Day Itinerary aboard SeaDream I
  • Enjoy a horseback ride on Nevis
  • Snorkel at St. Barts
  • Hike the lush island Nevis
  • Discover Bridgetown's beaches
Starts/ Ends in:
Bridgetown / Marigot
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Designed to enhance both your culinary and yachting experience, explore the flavors and history from some of the world's most renowned wineries while relaxing aboard the luxurious SeaDream I. Join exclusive wine tastings and a dinner consisting of a specially curated menu complemented with top …
Cruise Details
Soak in the sun in colorful Marigot
$2,999
EXPLORE

Marigot to Bridgetown

8 Day Itinerary aboard SeaDream I
  • Discover the underwater world
  • Enjoy the stunning St. Lucia
  • Fish at Marigot
  • Enjoy the glamour of St. Barts
Starts/ Ends in:
Marigot / Bridgetown
Activities:
Biking, Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Enjoy a little bit of everything on this amazing 8-day cruise, starting at Saint Martin and sailing to beautiful Barbados. Visit the famous jet-set island of St.Barts, well known for its charming streets, glamorous cafes and restaurants, and luxurious white sand beaches. Explorethe capital of …
Cruise Details
Unspoiled beaches and pristine coves in the Caribbean
$2,999
EXPLORE

Round-trip San Juan

8 Day Itinerary aboard SeaDream II
  • Visit the Puerto Rican capital
  • Snorkel at Trunk Bay
  • Explore Tortola by land rover
  • Zip line at South Friar's Bay
Starts/ Ends in:
San Juan / San Juan
Activities:
Hiking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Relish in the beauty and culture of the Caribbean on this 8-day voyage aboard the SeaDream II. Depart from San Juan, Puerto Rico, and set sail for St. John Island, the "most virgin" of the U.S. Virgin Islands. Visit the Caribbean paradise of Saba and the treasured destination of St. …
Cruise Details
Deep blue waters await you on your Caribbean cruise
$3,299
EXPLORE

Charlotte Amalie to San Juan via St. Barts

7 Day Itinerary aboard SeaDream I
  • Visit beautiful St. John Island
  • Enjoy scenic Saba Island
  • Discover Soper's Hole, Tortola
  • Hike & snorkel at Norman Island
Starts/ Ends in:
Charlotte Amalie / San Juan
Activities:
Hiking, Scuba Diving, Small Ship Cruise, Snorkeling, Wildlife Viewing
Activity Level:
Relaxed
Fall in love with the crystal waters and islands of the Caribbean on this 7-day Virgin Islands and Puerto Rico cruise. Begin in Charlotte Amalie and make your way for the sheltered coves and small towns of Cruz Bay, North Sound, Gustavia, and more. As you explore the island paradise of the …
Cruise Details
Relax on the beaches of the Caribbean
$11,225
EXPLORE

Caribbean: Round-trip Philipsburg

11 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 11-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
Take in the sights, sounds, and colors of Barbados
$4,900
EXPLORE

Bridgetown to Bridgetown

11 Day Itinerary aboard Silver Whisper
  • Enjoy unspoiled Bequia Island
  • Admire the slopes of St. Kitts
  • Explore white sandy shores
  • Discover bustling Port of Spain
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Hiking, Scuba Diving, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
When Bing Crosby sang "White Christmas," perhaps he meant the powdery sand of the Caribbean! Swap eggnog for rum punch, roast turkey for freshly grilled lobster and cold snowy days for long, sunny ones … but there’s no need to completely forget the holiday season: with the …
Cruise Details
Pink beach huts in the Caribbean
$3,960
Savings
EXPLORE

Bridgetown to Fort Lauderdale (Florida)

10 Day Itinerary aboard Silver Whisper
  • Relax on Jost Van Dyke's beaches
  • Visit Les Saintes
  • Tour Port Elizabeth on Bequia
  • Admire Mayreau Island
Starts/ Ends in:
Bridgetown / Fort Lauderdale
Activities:
Biking, Kayaking, Small Ship Cruise, Snorkeling
Activity Level:
Relaxed
Discover the Caribbean on this 10-day sailing adventure from Bridgetown to Fort Lauderdale, Florida. Visit the colorful small cities and the exceptional beaches this archipelago is famous for as you sit back and relax while sailing through one of the most exclusive regions in the world aboard the …
Cruise Details
37-54 of 88 Results

Caribbean Travel Guide

Favorite Caribbean Tours & Cruises

Why Travel With Adventure Life

More Reasons

Recognized By

All News