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The Caribbean
This 2026, for one time only, we’ll be exploring for two weeks the most off the grid countries in the Caribbean! This Expedition is the best way to visit these 8 countries: St Kitts, St Vincent, Antigua, Dominica, St Lucia, Grenada, Barbados and Trinidad & Tobago and will aim to vist some of the most remote regions like Sint Marteen, Bequia,Tobago and Barbuda. Using the most efficient flight schedule to maximize time in each island, during the most ideal season and together with the best travel family you could hope for to share this Caribbean adventure.
Join us for an adventure of a lifetime as we explore the hidden gems, pristine beaches and rich culture of this tropical paradise.
- Trip dates: January 20th - February 1st 2026
- 13 days
- 12 nights
itinerary
Day 1: Saint Kitts and Nevis
- We will start in the beautiful island of Saint Kitts. After checking into your hotel, take some time to explore the vibrant capital city, Basseterre. Welcome Dinner and enjoy a leisurely dinner at a seaside restaurant as you watch the sunset over the Caribbean Sea.
Day 2: Saint Kitts – Sint Maarten – Antigua
- Our day starts with a morning flight to St. Maarten*. We take a brief tour of the island, known for its lively atmosphere and the famous plane-landing beach. In the afternoon, we catch a flight to Antigua. *(The visit to Sint Maarten is subject to flight connections).
Day 3: Antigua and Barbuda
- We will take a day trip to the stunning island of Barbuda. Known for its pink sand beaches. Barbuda offers a tranquil escape from the hustle and bustle. Spend the day relaxing on the beach or snorkeling in the clear waters, and exploring the natural beauty of the island. Return to Antigua in the evening.
Day 4: Antigua to Dominica
- We will visit Antigua in the morning and then we fly to Dominica in the afternoon and prepare to explore one of the Caribbean’s most untouched islands.
Day 5: Dominica
- We will take a trip to the famous Waterfalls in the island and visit Morne Trois Pitons National Park, a UNESCO World Heritage Site. If you’re up for the challenge, you can also hike to the world-famous Boiling Lake.
Day 6: Dominica to Saint Lucia
- Today, we fly to Saint Lucia in the morning and spend the day exploring the island: Pigeon Island National Park for some history and breathtaking views. And we end the day with a sunset beach visit.
Day 7: Saint Lucia to Barbados
- Catch a afternoon flight to Barbados and begin your exploration of this lively island where we will discover the charm of Bridgetown.
Day 8: Barbados
- We will enjoy a full day in Barbados, starting with some relaxation on its beautiful beaches and we will visit some of the island landmarks.
Day 9: Barbados to Saint Vincent
- In the morning, we will visit any landmarks missed on previous days in Barbados. Then, in the afternoon, we will take a flight to Saint Vincent. If there is time, we can take a stroll through the capital, Kingstown.
Day 10: Saint Vincent to Grenada
- If the weather is in our favor, we will take a boat or ferry to Bequia to explore this island, which is part of the Grenadines. Then, after an evening flight to Grenada, we will begin our adventure on the “Spice Isle.”
Day 11: Grenada
- We will spend the day discovering Grenada’s unique attractions, exploring the colorful capital, St. George’s, and learn about the island’s history at Fort George.
Day 12: Grenada to Tobago
- Early flight to Trinidad in the morning, followed by a short flight to Tobago. Upon arrival, explore the charming town of Scarborough and relax. Enjoy the evening with some local music and cuisine.
Day 13: Trinidad and Tobago
- The expedition ends after breakfast with a flight return to Trinidad (Port of Spain) and you can stay longer in Trinidad or If you are interested in visiting the Guianas in South America, please let us know as we will work on an Add-On for Guiana and Suriname.
Disclaimer: While Wander Expeditions prioritizes visiting every listed Caribbean country, please note that flexibility is necessary due to factors like Force Majeure, weather, or flight cancellations. You must be prepared to accept this flexibility and acknowledge that we cannot be held responsible for delays and alterations in the schedule, or for expenses incurred as a result of any such circumstances.
Included
Not included
Accomodation
Shared Twin Rooms in Hotels (3*) or local guest houses.Transport
Private vehicles and fuel.Activities
We will cover activities on the islands unless otherwise stated.The Best Travel Fam!
The best travel family to do this region with.Flight booking and assistance
Flights aren't included but we will provide you with the exact schedule of flights to book, and assist you on how to book the cheapest alternative available.
January 20th – February 1st 2026
Our Selection Process takes only 10 minutes and it helps us create the best travel family!
FAQ
HOW DO I GET A VISA FOR THESE COUNTRIES?
We will visit Saint Kitts and Nevis, Sint Maarten (the Dutch side of the island of Saint Martin, Antigua and Barbuda, Dominica, Saint Lucia, Barbados, Saint Vincent, Grenada, Trinidad and Tobago. Most of these are visa free for most nationalities but some nationalities could require a visa for some of the countries.
Please note that due to connecting flights, you will need to be allowed to enter US and European territory.
WHAT'S THE BEST WAY TO GET THERE?
Wander Expedition does not handle flight bookings on your behalf and is not ultimately responsible for your flight connection. However, we can provide guidance and support as you research the best options for your journey.
Our Expedition will start in Saint Kitts that you can fly from Miami, New York, Puerto Rico or Santo Domingo (Dominican Republic) and Flying out from Trinidad that you can connect with US, Panama or Amsterdam in Europe.
WHAT HAPPENS IF ONE OF THE FLIGHTS IS CANCELLED? THERE IS A BACK UP PLAN?
Connecting the islands in the Caribbean can be challenging, but we have been working on the best logistics. We will advise you on the exact flights that you need to buy for the expedition. However, weather conditions can affect the flights, which is why we will ask you to leave a buffer before leaving Trinidad, the last destination, just to make sure any unforeseen circumstances can be accommodated. We have also included a couple of buffer days during the expedition to try to accomodate any disruption.
Our plan is to visit all the listed countries and islands on this itinerary, and the expedition will cover 13 days and 12 nights. However, while Wander Expeditions prioritizes visiting every listed Caribbean country on the itinerary, please note that flexibility is necessary due to factors like Force Majeure, weather, or flight cancellations. You must be prepared to accept this flexibility and acknowledge that we cannot be held responsible for delays and alterations in the schedule, or for additional expenses incurred as a result of any such circumstances.
WHO IS THIS EXPEDITION FOR?
This Expedition is designed for everyone seeking a fun time, an exploration of off-the-beaten-path destinations, the opportunity to make new travel friends, and create unforgettable travel stories. We crafted this itinerary to visit the most remote countries of the Caribbean and making it the perfect unique off-the-grid adventure.
If you are planning to visit every country, this is the best way to slice the Caribbean Islands, a region that has hard logistics and that is hard to do solo!
ARE THE FLIGHTS BETWEEN ISLANDS INCLUDED?
Wander Expeditions is facilitating the logistics, hotels, and activities in the itinerary. In this expedition, you will be responsible for purchasing the connecting flights between the different countries and islands. We have crafted a detailed itinerary and will provide you with the exact flights that you need to buy.
DISCLAIMER
While Wander Expeditions prioritizes visiting visiting every listed Caribbean country on this itinerary, please note that flexibility is necessary due to factors like Force Majeure, weather, or flight cancellations. You must be prepared to accept this flexibility and acknowledge that we cannot be held responsible for delays and alterations in the schedule, or for additional expenses incurred as a result of any such circumstances.
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