• Overview
  • Trip Outline
  • Trip Includes
  • Trip Excludes
  • Booking
  • FAQ

Island hopping adventure in the Caribbean

Leave the ordinary behind and step into a world of vibrant culture, breathtaking scenery, and unforgettable experiences with our 14-day Caribbean Island Hopping Adventure, exclusively designed by Dagron Tours. Instead of spending endless hours planning, let us handle the details so you can focus on soaking up the best of the Caribbean.

Here's what you'll experience: 

Over 14 sun-soaked days, you’ll journey through eight stunning destinations: Barbados, Trinidad and Tobago, St. Lucia, Dominica, Grenada, Antigua, and the Dominican Republic.

  • Feel the sand between your toes on idyllic beaches where the sun kisses your skin.
  • Wander through lush rainforests and uncover nature’s most awe-inspiring secrets.
  • Swim alongside sea turtles and discover colourful marine life in crystal-clear waters.
  • Savour the flavours of the Caribbean, from Trinidad’s spicy curries to St. Lucia’s fresh seafood feasts.

Each island offers its own unique charm, blending adventure, relaxation, and vibrant culture into a seamless journey you’ll cherish forever.

Why choose Dagron Tours?

Booking with Dagron Tours means letting go of the stress of planning and embracing an expertly crafted experience. From flights to accommodations, we take care of everything to make your trip as smooth as possible. You deserve a holiday where every detail is handled.

  • Exclusive local experiences: Go beyond the guidebooks with activities curated for authenticity and excitement.
  • Effortless logistics: Enjoy round-trip airport transfers and seamless connections between destinations.
  • Small group intimacy: Start your adventure with as few as two travellers, ensuring a personalised experience.

What’s included?

We’ve designed this adventure with comfort and convenience in mind:

  • Economy-class flights between each island, so you can travel with ease.
  • Handpicked accommodations at top-rated hotels known for their comfort and Caribbean charm.
  • Round-trip airport transfers ensure a hassle-free journey from start to finish.

Imagine immersing yourself in the colours, sounds, and tastes of the Caribbean without lifting a finger to plan. Dagron Tours will guide you through an unforgettable journey filled with adventure, relaxation, and moments that will stay with you forever.

Ready to answer paradise’s call?

Book your spot today and make the Caribbean your next great story. With limited availability, there’s no better time to start your island-hopping adventure. Let Dagron Tours take you there.


This 14-day island-hopping adventure will take you on a journey through the colourful world of this beautiful region, with its rich culture and delicious food. You'll experience the diverse accents and lovely people who make up this fantastic place. So don't forget your sunscreen and camera because this experience will blow you away!

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2025 Caribbean Island Hopping: Available Dates
April - June (Shoulder Season) September - November (Shoulder Season)
April 11 - April 24 September 12 - September 25
April 18 - May 1 September 19 - October 2
April 25 - May 8 September 26 - October 9
May 2 - May 15 October 3 - October 16
May 9 - May 22 October 10 - October 23
May 16 - May 29 October 17 - October 30
May 23 - June 5 October 24 - November 6
May 30 - June 12 October 31 - November 13
June 6 - June 19 November 7 - November 20
June 13 - June 26 November 14 - November 27
June 20 - July 3 November 21 - December 4
June 27 - July 10 November 28 - December 11

Why These Dates Are the Best Times to Visit

The April to June and September to November periods fall within the Caribbean’s shoulder season—a time when you can enjoy the perfect balance of pleasant weather, fewer crowds, and better value. These dates have been carefully selected to give you an unforgettable experience without the challenges of peak-season travel.

April to June (Shoulder Season):

This period marks the end of the dry season in the Caribbean, offering sunny days, minimal rain, and warm waters perfect for snorkeling and beach days. With fewer tourists, you’ll have a more tranquil experience at iconic attractions like St. Lucia’s Pitons or Tobago’s Pigeon Point Heritage Park.

September to November (Shoulder Season):

During this time, the Caribbean enters its late summer season, with cooler breezes and occasional rains that keep the landscapes lush and vibrant. This is also a great time for budget-conscious travellers, as flights and accommodations are more affordable, and you’ll have fewer crowds at the region’s must-see spots.

Itineraries

Day 1: Friday

Arrive Bridgetown, Barbados

  • Morning: Arrive at Bridgetown, Barbados. Transfer to your hotel upon arrival.
  • Afternoon: Enjoy a Jolly Roger’s Cruise along the Caribbean’s blue waters. Relax with sunshine, rum punch, and reggae music.
  • Evening: Head to Oistins Fish Fry for a lively dinner experience featuring local seafood and entertainment.

Meals: Dinner
Overnight Stay: 3* Hotel in Bridgetown

Day 2: Saturday

Full-Day Island Tour

  • Morning: Explore top attractions, including:
    • Barbados Museum
    • Pelican Village
    • St. John's Parish Church
    • Welchman Hall Gully
    • Harrison's Cave.
  • Afternoon: Visit Gun Hill Signal Station and Flower Forest, enjoying stunning views and lush tropical surroundings.

Meals: Breakfast
Overnight Stay: Rostrevor Hotel or similar

Day 3: Sunday

Flight to Grenada & Island Tour

  • Morning: Check out of your hotel and enjoy free time for relaxation or last-minute shopping.
  • Afternoon: Transfer to the airport for your 6:15 PM flight to Grenada.
  • Evening: Upon arrival in Grenada, transfer to your hotel.

Meals: Breakfast
Overnight Stay: Radisson Beach Resort Grand Anse or similar

Day 4: Monday

Full-Day Grenada Island Tour

  • Morning: Start at Grand Anse Craft and Spice Market, then visit Grenada National Museum and Market Square in St. George's.
  • Afternoon: Explore Grand Etang National Park, enjoy lunch, then visit Annandale Waterfalls and River Antoine Rum Distillery.
  • Evening: Relax on the sandy shores of Grand Anse Beach.

Meals: Breakfast, Lunch
Overnight Stay: Radisson Beach Resort Grand Anse

Day 5: Tuesday

Flight to Trinidad and City Tour

  • Morning: Take the 8:55 AM flight to Trinidad. Upon arrival, explore Port of Spain, including:
    • Queen's Park Savannah and the Magnificent Seven.
    • National Museum and Art Gallery.
  • Afternoon: Visit the Royal Botanic Gardens and local markets. End the day at Woodford Square and the Red House.

Meals: Breakfast
Overnight Stay: 3* Hotel in Port of Spain

Day 6: Wednesday

Maracas Bay Adventure

  • Morning: Drive to Maracas Bay via scenic mountain roads. Spend the day relaxing on golden sands or swimming in turquoise waters.
  • Lunch: Try the famous Bake and Shark from beachside vendors.
  • Afternoon: Optional hiking trails for panoramic views.
  • Evening: Return to your hotel.

Meals: Breakfast
Overnight Stay: Kapok Hotel or similar

Day 7: Thursday

Flight to Tobago and Island Tour

A day to discover the heart of Tobago

Your day begins with an early morning pickup from your hotel in Port of Spain. You'll catch the 8:05 am flight to Tobago, arriving just 25 minutes later—enough time for a short, scenic journey to the island’s warm embrace.

Start your day at Crown Point

Once you land, your adventure begins with a tour of Crown Point, a lively area known for its welcoming energy and stunning beaches. It’s the perfect introduction to the relaxed and vibrant spirit of Tobago.

  • Morning: Fly to Tobago at 8:05 AM. Begin with a tour of Crown Point, then head to Pigeon Point Heritage Park for a glass-bottom boat tour and snorkeling.
  • Afternoon: Visit Fort King George and enjoy local cuisine for lunch.
  • Evening: Transfer to your hotel and relax.

Meals: Breakfast, Dinner
Overnight Stay: Bacolet Beach Club or similar

8: Friday

Tobago West Coast, Depart for St Lucia

  • Morning: Explore Castara Bay, Arnos Vale Nature Trail, or Mt. Irvine Bay.
  • Afternoon: Transfer to the airport for your evening flight to St. Lucia.
  • Evening: Arrive at Hewanorra International Airport (UVF). Transfer to Rodney Bay and settle into your hotel.

Meals: Breakfast
Overnight Stay: Bay Gardens Marina Haven Hotel

Day 9 : Saturday

Discovering the magic of St. Lucia

  • Morning: Explore Soufrière, including:
    • Sulfur Springs for a therapeutic mud bath.
    • Tet Paul Nature Trail for stunning views of the Pitons.
  • Afternoon: Visit Fond Doux Estate and Toraille Waterfall.
  • Evening: Return to Rodney Bay to enjoy its nightlife and dining options.

Meals: Breakfast, Lunch
Overnight Stay: Bay Gardens Marina Haven Hotel

Day 10: Sunday

Day Trip to Dominica

  • Morning: Take the Express des Îles ferry to Dominica (~2 hours). Explore:
    • Emerald Pool or Trafalgar Falls for lush nature trails.
  • Afternoon: Visit Morne Trois Pitons National Park and enjoy lunch in Roseau.
  • Evening: Return to St. Lucia by ferry.

Meals: Breakfast, Lunch
Overnight Stay: Bay Gardens Marina Haven Hotel

Day 11: Monday

Antigua Arrival and City Tour

  • Morning: Take a morning flight to Antigua. Check into your hotel.
  • Afternoon: Visit:
    • St. John's Cathedral
    • Devil's Bridge
    • Public market and cultural sites.

Meals: Breakfast, Lunch
Overnight Stay: 3* Hotel in Antigua

Day 12: Tuesday

Barbuda Day Trip & Evening transfer to Santo Domingo

  • Morning: Take the ferry to Barbuda (~90 minutes). Explore:
    • Pink Sand Beach: A serene spot for snorkeling and swimming.
    • Frigate Bird Sanctuary: Witness one of the largest bird colonies in the Caribbean.
  • Afternoon: Enjoy a freshly prepared seafood lunch before returning to Antigua.

Late Afternoon:

  • Transfer to the airport for your 4:00 PM flight to Santo Domingo.

Evening: Arrive in Santo Domingo at 5:10 PM. Transfer to your hotel and settle in. Take a quiet evening to relax or explore nearby restaurants for dinner.

Meals: Breakfast
Overnight Stay: Hispaniola Hotel & Casino Santo Domingo

Day 13: Tuesday

Santo Domingo Exploration, Dominican Republic

  • Morning: Explore the Colonial Zone, a UNESCO World Heritage Site:

    • Cathedral of Santa Maria la Menor: The first cathedral in the Americas.
    • Columbus Alcazar: A beautiful palace built for Diego Columbus.
    • Atarazana Street: Stroll through this historic area filled with boutique shops and art galleries.
  • Afternoon: Visit the Casas Reales Museum to learn about Santo Domingo’s colonial history. Optionally, explore the lush underground lakes at Los Tres Ojos (The Three Eyes National Park).

  • Evening: Enjoy a farewell dinner at a local Dominican restaurant to end your journey.

Meals: Breakfast
Overnight Stay: Hispaniola Hotel & Casino Santo Domingo

Day 14: Thursday

Departure

  • Morning: Transfer to the airport for your flight home or onward journey.

Meals: Breakfast

Accommodation, internal flights, transfers between airports and hotels, listed hotels and hotel taxes, activities as described and admission charges where applicable, river and land transfers, listed, lodges with full board and other meals as indicated. Local guides, local beverages.

International airfare, airport/departure taxes, gratuities, optional excursions, travel insurance.

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