Have questions? We're here.
Couple snorkeling in the tropical waters of the Caribbean

Top Caribbean Tours & Trips in 2023

Travel made your way
Talk with an expert
Build your ideal Caribbean trip. Call 1.406.541.2677
Start Planning My Trip
Adventure Life's travel specialists have handpicked these Caribbean vacation packages for 2023, so you can experience the region like never before. Take a cruise to the Bahamas, St. Lucia, Antigua, St. Barths, British Virgin Islands, Bridgetown, Soufriere, Gustavia, Terre-de-Haut, and Cabrits, or choose from any of the 40 top-rated  Caribbean tours listed below. The most popular things to do in the Caribbean in 2023 are scuba divingkayaking, small ship cruises, snorkeling, small ship sailing, wildlife viewing, and hiking. Our trips to the Caribbean in 2023 range in price from $1,499 to $83,499 for adventures of 5 to 99 days. Contact one of Adventure Life's expert Caribbean trip planners for help curating your dream Caribbean holiday package. 
Filter (40 Results)
  • Start Date
    OR, More specific start
  • Length
    to
  • Price
    to
  • Activity Level
  • Experiences
  • Activities
  • Ship
  • Destinations
    • Caribbean
Mountains by the ocean in St Lucia
$4,755
EXPLORE

On the Sunny Side of Life

Philipsburg Roundtrip - 8 Day Itinerary aboard Sea Cloud
  • Visit the port town of Philipsburg
  • Experience St. Barthélemy
  • Explore the town of Terre-de-Haut
  • Tour around Dominica
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, 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 vibrant, …
Cruise Details
0
White Sand Beach in Barbados
$2,420
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 Cruises, 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
Relax in the sunny squares of historic Savannah
$5,599
EXPLORE

Boston, MA to Nassau, Bahamas

Boston - Nassau - 16 Day Itinerary aboard Ocean Voyager
  • Learn Boston's history
  • Wander through historic Baltimore
  • Experience Southern hospitality
  • Explore Charleston's architecture
Starts/ Ends in:
Boston / Nassau
Activities:
Archaeological Site Visits, Small Ship Cruises, Urban Exploration, Village Visits
Activity Level:
Relaxed
Sail on this 16-day itinerary cruising the seaboard from bustling Boston to beachy Nassau aboard Ocean Voyager. With stops in Baltimore, Charleston, West Palm Beach, and more, this journey has been handcrafted to sample the Eastern cities of the United States as you head to your final destination …
Cruise Details
0
Dock going out into the crystal blue ocean
$2,460
EXPLORE

Classic Yachtsman Caribbean

Antigua to Barbados - 8 Day Itinerary aboard Royal Clipper
  • Enjoy Grenada's unique aromas
  • Discover Falmouth Harbour, Antigua
  • Enjoy the beach in ÎIes des Saintes
  • Explore lush St. Lucia Island
Starts/ Ends in:
St. John's / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing
Activity Level:
Relaxed
Swim and snorkel amidst the beautiful, pristine waters of the Caribbean Sea on this 8-day expedition aboard Royal Clipper. Sail away from your everyday life and find tropical bliss in the islands. From the stunning drama of the spectacular Pitons at St. Luciato the captivating charm of Les Saintes, …
Cruise Details
0
Pelicans hanging out in the ocean
$10,880
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
Stroll along the beautiful beaches of the Caribbean
$7,495
EXPLORE

Front Row Seat at the Famous Bucket Regatta

Round-trip Philipsburg - 11 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 Cruises, 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 vibrant, …
Cruise Details
0
Stroll along the beautiful beaches of the Caribbean
$6,785
EXPLORE

Windjammer Rendezvous in the Lesser Antilles

Philipsburg Roundtrip - 12 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 Cruises, 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 vibrant, …
Cruise Details
0
Gatun Lock of the Panama Canal
$4,370
EXPLORE

Panama to Antigua

15 Day Itinerary aboard Royal Clipper
  • Transit the historic Panama Canal
  • Enjoy Grenada's unique aromas
  • Discover Dutch colonial Curacao
  • Swim in paradise in Bonaire
Activities:
Small Ship Cruises, Small Ship Sailing, 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
Tropical Caribbean Beach in Martinique
$2,460
EXPLORE

Windward Islands Christmas Cruise

8 Day Itinerary aboard Royal Clipper
  • Discover lush St. Lucia Island
  • Enjoy Trafalgar Falls
  • Visit Falmouth Harbour, Antigua
  • View sophisticated Martinique
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
The 439-foot Royal Clipper is the ultimate sea-going experience for sail cruising enthusiasts, combining the grandeur, adventure, and tradition of sailing with the superior service, amenities, and accommodations of the finest modern yacht. Swim and snorkel in the Caribbean Sea's pristine …
Cruise Details
0
Pink beach huts in the Caribbean
$2,420
EXPLORE

Windward Islands

8 Day Itinerary aboard Royal Clipper
  • Explore beaches in Barbados
  • See lush island of St. Lucia
  • Discover Falmouth Harbour, Antigua
  • Visit sophisticated Martinique
Starts/ Ends in:
Bridgetown / Bridgetown
Activities:
Small Ship Cruises, Small Ship Sailing, 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
Tropical waterfall and turquoise pool in lush forest
$2,360
EXPLORE

Treasure Islands

8 Day Itinerary aboard Star Flyer
  • Visit Virgin Gorda's famous “Baths”
  • Enjoy the lifestyle of Soper's Hole
  • Walk the streets of Basseterre
  • Relax on famous St. Barts
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Small Ship Sailing, Snorkeling
Activity Level:
Relaxed
Set a course for the Treasure Islands and the French Riviera of the Caribbean. Discover a treasure trove of breathtaking beaches, old forts, and seaside villages waiting for you. Starting at St Martin, makeyour way to the super-chic St Barths, historic Antigua, and lush Iles des Saintes, Dominica, …
Cruise Details
0
Beautiful beach in Dominica
$2,360
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:
Small Ship Cruises, Small Ship Sailing, 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
Picturesque Cuba
$10,295
EXPLORE

Christmas Cuban Style

Santo Domingo to Havana - 15 Day Itinerary aboard Sea Cloud II
  • Explore vibrant Santo Domingo
  • Swim and snorkel at Maria la Gorda
  • Soak in the culture of Cuba
  • Stroll through historic Havana
Starts/ Ends in:
Santo Domingo / Havana
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Board Sea Cloud II for this 15-day cruise from Santo Domingo to Havana. Depart from Santo Domingo in the Dominican Republic, the oldest continuously inhabited city in the New World. Visit Port Antonio, Jamaica, once the banana capital of the world.See some of the highlights of Cuba, including …
Cruise Details
0
Cuba homes in Havana
$7,295
EXPLORE

The incomparable temperament of Cuba

Havana to Cienfuegos - 13 Day Itinerary aboard Sea Cloud II
  • Stroll the Malecon in Havana
  • Snorkel and swim at Maria la Gorda
  • Explore beautiful Cienfuegos
  • Visit film sets in Jamaica
Starts/ Ends in:
Havana / Cienfuegos
Activities:
Small Ship Cruises, Snorkeling, Village Visits
Activity Level:
Relaxed
Experience the incomparable charm of Cuba's colonial heritage paired with Jamaica's relaxed and romantic beach flair onthis 13-day cruise from Havana to Cienfuegos aboard Sea Cloud II. Stroll down the famed Malecon promenade in Havana and soak in the distinctive spirit of the city. Snorkel …
Cruise Details
0
Iconic cars in Havana, Cuba
$7,365
EXPLORE

The Rousing Rhythms of Cuba

Havana to Santo Domingo - 11 Day Itinerary aboard Sea Cloud II
  • Stroll down the Malecon
  • Snorkel and swim at Maria La Gorda
  • Visit banana farms in Jamaica
  • Marvel at historic Santo Domingo
  • Appreciate Cuban music culture
Starts/ Ends in:
Havana / Santo Domingo
Activities:
Small Ship Cruises, Snorkeling
Activity Level:
Relaxed
Warm hospitality, eventful history and lively musical tradition make Cuba and Jamaica two dream destinations in the Caribbean. As different as the two islands are –here, culture, beach and nature go perfectly hand in hand and fit under one hat. Board Sea Cloud II for this 11-day cruise from …
Cruise Details
0
Mountains by the ocean in St Lucia
$3,840
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 Cruises, 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
Enjoy a ride around the islands.
$1,499
EXPLORE

Bahamas Sailing Adventure

7 Day Itinerary aboard Liberty Clipper
  • Explore the Out Islands
  • Learn how to sail and steer
  • Encounter unique wildlife
  • Kayak, snorkel, or paddle board
Starts/ Ends in:
Nassau / Nassau
Activities:
Kayaking, Sailing Schooner, Snorkeling, Stand Up Paddle Board, Wildlife Viewing
Activity Level:
Relaxed
Set sail for new horizons on a barefoot 7-day cruise in the Bahamas. On the 125-foot schooner, the tall ship Liberty Clipper, explore the Out Islands of the Bahamas from this majestic windjammer. Be welcomed aboard by expert crew who are there for your safety and enjoyment. From qualified Captains …
Cruise Details
0
Learn about the history of the Caribbean
$8,085
EXPLORE

Superyachts Meet at the Bucket Regatta

Caribbean: Round-trip Philipsb - 13-113 Day Itinerary aboard Sea Cloud II
  • Discover beautiful islands
  • See St Barths' luxurious lifestyle
  • Observe incredible sunsets
  • Discover The Baths at Virgin Gorda
Starts/ Ends in:
Philipsburg / Philipsburg
Activities:
Small Ship Cruises, Snorkeling, Spa Relaxation
Activity Level:
Relaxed
Experience the blue waters of the wonderful Caribbean on this 13-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 buildings and friendly …
Cruise Details
0
1-18 of 40 Results

Caribbean Travel Guide

Favorite Caribbean All Trips

Top Caribbean Travel Destinations

Caribbean Trips by Departure Date

Top Experiences in Caribbean

Caribbean Trips by Duration

Caribbean Trips by Activity

More Reasons

Why Travel With Adventure Life

All News

Recognized By