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cruising the caribbean

The Only Caribbean Vacation Itinerary You Need

The Caribbean, with its white sandy beaches and vibrant culture, is a dream destination for travelers seeking both fun and relaxation. With so many islands to explore and experiences to savor, planning the perfect Caribbean vacation itinerary can be overwhelming.


Because there’s so much to see, and so much of it is separated by water, we recommend a Caribbean catamaran charter. With catamaran charters, you can easily navigate the best the Caribbean has to offer and fit a lot into a 7-day trip.


So sit back and let us guide you through the only Caribbean vacation itinerary you need. And get ready for a magical experience.

Caribbean vacation itinerary

Our Caribbean Vacation Itinerary

The following Caribbean vacation itinerary is made for a seven-day experience. You can add days to any leg of this trip!


Day 1: Pick Up Your Chartered Catamaran

Your Caribbean vacation itinerary begins as you pick up your chartered catamaran. The beauty of this is that it can be anywhere that’s convenient for you.


If you have found cheap flights to Jamaica, you can bet you’ll find a boat waiting for you. Catamaran charter in the Caribbean is plentiful, and day one is all about getting set up.


Unless you’re going at it alone, you will receive a brief orientation and safety briefing from your captain. You’ll set sail, leaving the mainland behind and embarking on your unforgettable journey.


The first day is all about getting comfortable with your new home at sea, so don’t rush to visit anywhere in particular. Enjoy the breathtaking views, lounge around, and get to grips with your new home.

Caribbean vacation itinerary
St. Lucia

Day 2: Island Hop to St. Lucia

On day two, your catamaran will set sail for the enchanting island of St. Lucia. This is an ideal place to start because it’s situated between many other great islands.


Known for its stunning beaches and the iconic Piton Mountains, St. Lucia offers an array of activities for every type of traveler. Upon arrival, explore the colorful fishing villages and quaint towns that dot the island.


For the more adventurous, hike up Gros Piton for awe-inspiring views, or take a rejuvenating dip in the Sulphur Springs mud baths. Or, if you’re feeling like a sleep visit, just park up on the white sand beaches and spend a day sunbathing and swimming.


With the likes of Reduit Beach and Anse Chastanet, St Lucia has some of the best beaches in the Caribbean.

St. Vincent, Caribbean vacation itinerary
St. Vincent

Day 3: Venture to St. Vincent and the Grenadines

As your journey continues, our Caribbean vacation itinerary takes you to St. Vincent and the Grenadines, which is a collection of thirty-two stunning islands and cays that promise to enchant even the most seasoned traveler.


Arriving in Kingstown, the capital of St. Vincent, explore the lively markets, historic churches, and charming cobblestone streets that give this city its unique character.


Then, embark on an island-hopping adventure through the idyllic Grenadines. This is your chance to get a little lost and stumble upon some smaller, hidden gems.


Though, if you have time left on day three, you could visit Bequia. This is where you can stroll through the seaside town of Port Elizabeth and make your way to the breathtaking Tobago Cays.


This is also a good spot for snorkeling, diving, and swimming with sea turtles.

Barbados, Caribbean vacation itinerary

Day 4: Barbados is a must-see

On day four of this Caribbean vacation itinerary, you’ll set sail for the sun-swept shores of Barbados. There are so many sailing destinations in the Caribbean, but this eastern Caribbean island is brimming with culture, history, and natural beauty.


It’s one of the best-known islands, and not just because Rihanna owns a property there.


Begin your day in the capital city of Bridgetown, exploring the colorful colonial architecture, bustling markets, and the UNESCO World Heritage site of the historic Garrison area. From here, head to the picturesque west coast of Barbados, where you’ll find idyllic sandy beaches perfect for swimming and sunbathing.


Don’t forget to sample the local cuisine, such as flying fish and cou-cou, before retiring to your catamaran for a peaceful night under the stars.

relaxing on catamaran

Day 5: Spend a day relaxing at sea

After four days of island exploration, day five of this Caribbean vacation itinerary is all about relaxation and rejuvenation. It’s time to slow down and savor the simple pleasures of life at sea.


You may be tired from all the walking around and indulging in so many strong cultures, so it’s time for some isolation.


Unwind on the deck with a good book, sunbathe under the Caribbean sun, or take a leisurely dip in the crystal-clear waters. If you’ve gone all out on your vacation, your onboard chef will prepare a delicious lunch that is a homage to the local cuisine.


Otherwise, prepare yourself a little picnic with some drinks.


In the evening, gather with your friends and family for a fun-filled game night or simply relax and watch the sunset paint the sky.


Day 6: Go Snorkeling and observe the marine life

On day six, it’s time to dive beneath the surface and discover the vibrant underwater world of the Caribbean. Head to a nearby coral reef, where you’ll have the opportunity to snorkel or scuba dive, exploring the colorful marine life that calls these waters home.


Swim alongside sea turtles, admire schools of tropical fish, and marvel at the intricate coral formations that make up this delicate ecosystem. These can be the moments that you really remember, as the feeling of freedom sweeps you away and you become one with the sea life – if not for a brief moment.


Day 7: Head back to Drop Off Your Catamaran

On the final day of your adventure, it’s time to say goodbye to your home at sea and the friends you’ve made along the way. As you sail back to the marina to drop off your catamaran, take the time to reflect on the incredible memories you’ve created.


Take some final photographs of your boat and surroundings and thank your captain. Day seven is all about doing whatever you want to do on your final day after you hand over the keys.

Caribbean vacation itinerary

Safety Tips

While this Caribbean vacation itinerary is undoubtedly filled with excitement and adventure, it’s essential to keep safety in mind. Always follow your captain’s instructions and adhere to safety guidelines when onboard the catamaran.


When exploring the islands, remain aware of your surroundings and practice common sense. Use reef-safe sunscreen to protect both your skin and the delicate marine ecosystem, and stay hydrated by drinking plenty of water.


Alternatives to Sailing

If sailing isn’t your preferred mode of transportation, don’t worry—there are plenty of alternatives for exploring the Caribbean. Consider booking a small group tour or island-hopping by plane or ferry to experience the best of the region.


Many islands also offer all-inclusive resorts, providing a luxurious and hassle-free vacation experience. Whilst this will mean you only see a limited amount of the Caribbean, you will be assured of a relaxing time.


Final Word

This seven-day Caribbean vacation itinerary offers the perfect balance of adventure, relaxation, and cultural immersion. Whether you’re snorkeling through vibrant coral reefs, hiking up lush mountain peaks, or simply indulging in the local cuisine, you’re sure to create memories that will last a lifetime.


If you’re looking for a slow-paced itinerary, simply take your favorite three days above and double them up. For example, spend two days in St. Lucia, two days in Barbados, and two days anchored at sea. There are so many Caribbean destinations that you can’t go wrong.


No matter how many days you spend on your tropical adventure, this Caribbean vacation itinerary is a perfect way to find inspiration.

Christa Thompson

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