There are over 7,000 islands in the Caribbean, of which only 2% are inhabited. One of the best ways to get a taste of a bunch of islands is going on a Caribbean island-hopping cruise.

On our recent classic Caribbean cruise with Windstar Cruises, we visited 7 islands in 1 week. Most Caribbean cruises depart from Florida but our Windstar cruise departed from St. Maarten. This gave us the option to do a little more Caribbean island hopping on and after our cruise.

Each day we’d wake up in a different port to explore a new island. We had an epic week at sea on the Wind Surf cruise ship, here is what our week of Caribbean island hopping looked like.

Caribbean Island Hopping With Windstar Cruises

St Maarten

Our Windstar cruise started and ended in Philipsburg, St. Maarten. We arrived late in the evening and spent the night at Mercure St Martin. The next morning we headed to the port to board our ship the Wind Surf.

We basically just dropped our bags and jumped in a shuttle to Maho Beach for $16 per person round trip. One of the best things to do in St Maarten is head to Maho Beach and watch the planes land. We knew we wanted to spend the afternoon on the beach watching the planes literally land right above our heads and feel the jet blast when they take off.

Make sure to visit Sunset Beach Bar on Maho Beach and check the surfboard with all the arrival times. However, the board doesn’t have all of the flights. If you have access to the internet, the best schedule you can find here at the official SXM airport arrivals page.

Keep in mind the planes often land ahead of schedule, and of course sometimes behind. We probably watched at least 20 planes land. In between landings we hung out at the bar, the drink prices were reasonable at Maho Beach, $4 a beer and $9 daiquiris but happy hour is 2 for 1.

We suggest spending at least one night in Phillipsburg either before or after your Caribbean cruise. There are several excursions in St. Maarten (click here for a whole bunch bookable online) including some day trips to nearby islands.

Anguilla Day TripPrickly Pear Sailing Day TripSaba Day TripSt. Barts Sailing & Snorkeling

St. Maarten is also a great place to catch a ferry to other nearby Caribbean islands. We jumped on an Anguilla ferry and spent 5 nights continuing our Caribbean island-hopping adventure. If you happen to really enjoy St. Barts you can catch a ferry from St. Maarten to St. Barts, make sure to check out some of the best beaches in St Barts.

St. Maarten to Anguilla  ferry schedule and book online hereSt. Maarten to St. Barts ferry schedule and book online here

After our cruise, we took the ferry to Anguilla and spent 5 nights at CeBlue Villas. If you do head to Anguilla we highly suggest renting a car in Anguilla it’s the best way to explore the island.

We spent most of our days driving to all the different beaches on the island, eating at the best restaurants in Anguilla, relaxing in our private pool, but our favorite day was spent on Sandy Island where we had the best lobster of our lives. There a ton to do and see in Anguilla.


If you love walking on the beach for miles and miles head to Barbuda. Barbuda has crazy clear water and pink sand beaches that are actually pink! We only spent 5 hours on Barbuda but we literally walked the beach the entire time.

The beaches are deserted we only say one little place that appeared to maybe have some cold beers. There was only one offshore excursion in Barbuda to the Frigate Bird Sanctuary. Which is the world’s largest frigate birds nesting with 2,500+ birds. We did see tons of Frigatebirds but we weren’t bird watching, we were watching out for them when flying our drone. We were after gorgeous aerial shots of Barbuda like this.

NOTE: You can take a ferry from Barbuda to Antigua.


Dominica is known as the nature island in the Caribbean complete with lush rainforest, volcano peaks, hot springs, waterfalls, snorkeling, and much more.

We spent the day hiking in the Morne Trois Pitons National Park. We were high up in the rainforest crossing several rivers with spectacular views (when it’s not raining). There are over 300 miles of hiking trails in Dominica we hope to get back to do some more hiking in Dominica.

NOTE: You can take a ferry from Dominica to Guadeloupe, Martinique, and St. Lucia. 

Our home for the week the Wind Surf anchored in St Lucia.

St. Lucia 

There are tons of offshore excursions in St. Lucia but if you prefer to chill on the beach Windstar sets up a beach BBQ on Pigeon Island. They transform the beach into their own private club for the day complete with beach chairs, umbrella drinks, water sports, jerk chicken, and much more.

We booked a half-day private car to explore the island and got back to Pigeon Island just in time for lunch.

We loved our time in St Lucia and returned a year later and spent a week on the island at Sandals La Toc & Sandals St Lucian Grande. The two properties are way different, make sure to pick the best Sandals Resort for you. We preferred Sandals St. Lucian Grande.

When we were on Pigeon Island we could see the overwater bungalows at Sandals St. Lucian Grande. We were in awe and 3 weeks later we returned to St. Lucia and had the opportunity to stay in them!

We also didn’t have a chance to visit the Piton’s during our cruise so on our return trip we went on Pitons sunset & snorkel cruise. There are also Martinique day trips from St. Lucia, click here for details.

NOTE: You can take a ferry from St. Lucia to  Martinique, Dominica, and St. Lucia.

Les Saintes, Guadeloupe

Guadeloupe surprised us the most. We didn’t know much about the island, but we now know we’ll be going back. We spent the day out on a boat exploring the Les Saintes islands. Gorgeous beaches and volcanic hillsides. The water reminded us of our favorite islands, El Nido in the Philippines.

NOTE: You can take a ferry from Guadeloupe to Dominica, Martinique, and St. Lucia.

St. Kitts

Basseterre is often referred to as one of the prettiest Caribbean’s capital cities. So we made sure to save a few hours to explore the city. Adam went diving in St. Kitts in the morning while I was being pampered at the spa on the Wind Surf. There are often port day specials in the spa and I highly recommend getting a massage.

NOTE: You can take a ferry from St. Kitts to Nevis.

St. Barts

St. Barts is where the rich & famous come to play. The marina is full of million-dollar yachts and the shopping is top-notch (don’t forget your wallet). We spent the morning on a catamaran tour around St. Barts with a great snorkeling & beach stop at one of the best beaches in St Barts.

After snorkeling, we took the tender into Gustavia. We highly suggest renting a car to explore the island, this is the most affordable option to see most of the island. We opted to walk over to St. Jeans Bay, which was only 20 minutes from Gustavia.

Along the way we literally had the planes landing over our heads just like in St. Maarten at Maho Beach. However, the planes here have a very tricky landing! We recommend walking to the intersection to watch it in front of the runway.

NOTE: You can take a ferry from St. Barts to St. Maarten, click here for schedule & rates. 

Pin me for later!

We had an amazing time on our Windstar cruise and in one week of Caribbean island hopping we covered 7 islands (6 new to us). If you aren’t sure what island you’d like to spend a week vacation at, consider going on a Caribbean cruise first to get an idea of what some islands are like. We now have a few more islands on our bucket list we can’t wait to get back to. 

Thank you to Windstar Cruise Line for hosting us on such an epic Caribbean cruise! As always all opinions are our own.

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