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5 English Caribbean Islands to Add to Your List {Featuring Windstar}

The Caribbean is beautiful! Pair that with a small boat, luxury cruise line, and it ends up being the perfect combination. My husband and I spent 11 lovely days wandering around the sea, and this post focuses on the 5 English Caribbean islands we visited along the way.

Although this post is sponsored in partnership with Windstar Cruises, all opinions and views are my own. I took my first cruise on the Mediterranean Sea with Windstar 8 years ago, and I had an equally fabulous time on my second journey and truly love this cruise line.

English Caribbean Islands Windstar Cruises | Hill City Bride Destination Wedding Travel Blog

My husband and I spent 11 days on board the Star Pride exploring the Gems of the Leeward Islands. Our cruise was a time of visiting 8 Caribbean islands with 2 restful days at sea.

HERE’S A PEEK AT OUR FULL ITINERARY WITH WINDSTAR CRUISES.

Day 1 – Depart from Old San Juan, Puerto Rico

Day 2 – At Sea

Day 3 – Basseterre, St. Kitts

Day 4 – Gustavia, St. BarthelemyWindstar Cruises Gems of the Leeward Islands Route

Day 5 – St. John’s, Antigua & Barbuda

Day 6 – Les Saintes, Guadeloupe

Day 7 – Pigeon Island, St. Lucia

Day 8 – St. Georges, Grenada

Day 9 – Bequia, St. Vincent Grenadines

Day 10 – Anse Mitan, Martinique

Day 11 – At Sea

Day 12 – Disembark in Old San Juan, Puerto Rico

Above, the bolded islands are the English islands I will be focusing on in this post. 

I can’t even begin to describe what a wonderful trip my husband and I had on our Windstar Cruises adventure! If you missed my post on the French islands, be sure to check it out here. We actually visited 8 islands – 5 English and 3 French – so I’m focusing on the English Caribbean islands. There is so much to say about each one!

DAY 3 – BASSETERRE, ST. KITTS

  • Anchored at 8am, Departed at 10pm

  • Mode of Transportation – ATV

  • Highlights – Wingfield Estate, Caribelle Batik, Brimstone Hill Fortress, Black Rock Beach, Outlying Beaches

Our first cruise stop was at St. Kitts – one of the English Caribbean islands – and I can’t tell you how excited we were to go out and explore! The order of business after we got off of the ship was to find a rental of some sort, and we decided on a stable SUV. The port talk the evening before (Windstar does a list of island highlights each night for the next day, which is so nice!) had my mind spinning about what there was to see, and we couldn’t wait to explore. The first place we stumbled upon was Wingfield Estate, famous for batik and a former facility for producing sugar cane. The rainforest area was lovely, and it was interesting to learn a bit about the making of batik patterns and see the fabric drying in the sun.

Traveling the English Caribbean Islands - Windstar Cruise - St. Kitts | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Kitts | Hill City Bride Wedding Travel Blog Virginia

Our next stop was Brimstone Hill Fortress, which offered such lovely views and photo ops.

I am a sucker for fortresses for that very reason! Plus, the history is usually interesting. One thing about renting an ATV was that it offered us the opportunity to spend as much or as little time as we wanted at each stop. I would highly recommend stopping by this fort if you are in St. Kitts. Such a pretty place!

Traveling the English Caribbean Islands - Windstar Cruise - St. Kitts | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Kitts | Hill City Bride Wedding Travel Blog Virginia

We also made our way around to the beach with the black rocks.

I was expecting to walk on a beach peppered with black stones, but instead, there were large rocks all around. It was a beautiful site!

One semi-upsetting thing of note. At this stop, there were a few merchants selling food and handmade wares. There was also a guy with a small monkey who wanted people to pay him to have their photo taken with the monkey (who was wearing a diaper). I didn’t want to touch the monkey or have my photo taken with it, but the man basically forced us to do so (we didn’t pay him and told him he didn’t want to have our photo taken…etc.). All of that to say that you may need to watch out and be a bit forceful with your “no” on this one of the English Caribbean islands if you don’t want to purchase something.

Since our boat didn’t leave until 10pm, we had time to peruse the island a bit.

One thing I loved – and a very special memory I have – was being able to explore some of the beaches at our leisure.

The photo with the pebbles shows a beach that we explored that had the most lovely rocks. They were all different colors, and I brought a few home with me. We enjoyed a time of swimming and relaxing at some of the beaches around St. Kitts. We also took a peek at St. George’s Anglican Church in Basseterre before we headed back onto the ship. This was definitely one of our favorite English Caribbean Islands!

Traveling the English Caribbean Islands - Windstar Cruise - St. Kitts | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Kitts | Hill City Bride Wedding Travel Blog Virginia

DAY 5 – ST. JOHN’S, ANTIGUA & BARBUDA

  • Anchored at 8am, Departed at 10pm

  • Mode of Transportation – Car

  • Highlights – Betty’s Hope, Nelson’s Dockyard, Beaches, Sunset

For our trek in Antigua, we decided to rent a car, which ended up being a smart decision! We grabbed a map and started wandering – we had certain items on our list but knew that the beaches and the ocean were a part of our must-sees for the day. We started out at Betty’s Hope, which is a location with sugar mills dating back to the late 1600s. The goats at Betty’s Hope made me laugh a bit – they were as interested in us as we were them!

Traveling the English Caribbean Islands - Windstar Cruise - Antigua | Hill City Bride Wedding Travel Blog Virginia

Next, we headed to various points along the ocean.

The views were lovely, and it was interesting how the salt water wore away the rock. I photographed tiny succulent plants taking up residence on the rocks. So cute! We visited a beach with beautiful clear water, which was perfect for snorkeling. One thing I adore about Windstar Cruises is that they allow each of their passengers to sign out a snorkeling set for the duration of the cruise. Very convenient!

After our time at the beach, we headed to Nelson’s Dockyard.

I have to admit that we were a bit disappointed at first when we got to Nelson’s Dockyard. We didn’t fully understand what it was all about before we got there, but it is actually a historic site that is a working dockyard. They have taken the old buildings and have shops and restaurants inside, which is interesting, but we were looking for the normal views that forts afford. So, we headed to the other part of the parks system, called Shirley Heights, and the view was SPECTACULAR! The first photo below is one of my favorites from our time on the English Caribbean islands.

The rest of the time we spent perusing the rainforest and finding beaches with our rental car.

Due to our late departure, we found a fun restaurant and had a freshly caught meal. The evening sunset was beautiful, and we watched it while we were sitting on the beach. How romantic!

Traveling the English Caribbean Islands - Windstar Cruise - Antigua | Hill City Bride Wedding Travel Blog Virginia

DAY 7 – PIGEON ISLAND, ST. LUCIA

  • Anchored 8am, Departed 5pm

  • Mode of Transportation – walking

  • Highlights – Zip Lining Excursion, Windstar Beach Party, Fort Rodney

This is the one stop where we decided that instead of wandering on our own, we booked an excursion with Windstar. There were several opportunities along the way for zip lining, and we thought that the rainforests in St. Lucia would be the best for our tastes. We had such a fun time! Everything was organized perfectly – we had transport to and from the zip lining location, and we learned a bit about the history of St. Lucia along the way.

Our time zip lining in St. Lucia was so exciting. The lines were fast, and we had a guide with us helping to take photos and instruct us along the way. We felt perfectly safe, and the views from up high were so lovely. You can tell below that we had a lot of fun, lol! Tip: closed toed shoes and a shirt with sleeves are a must!

Traveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog Virginia

After zip lining, we enjoyed time on the beach with Windstar and headed up to Fort Rodney, which was close by.

I didn’t snap any photos of our beach party, but this was the day where Windstar took dinner to the shore. During the day bubble cabanas with lounge chairs were set up for everyone to enjoy the beach. You could also waterski and enjoy other water sports at the beach – all organized by Windstar. So fun! Then, our dinner had the casual feel of a barbeque.

Of course, we headed up to the nearby fort, which was within walking distance. The views were so pretty, and I even snapped a photo of the Star Pride anchored in the harbor. We were lucky enough to find other travelers at the top who took a photo of us – one of my favorites from the trip!

All in all, we had a lovely day on this one of the English Caribbean islands. With everything taken care of by Windstar, we were able to relax and have a day where we didn’t have to think about what to explore.

Traveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - St. Lucia | Hill City Bride Wedding Travel Blog Virginia

DAY 8 – ST. GEORGES – GRENADA

  • Docked at 8am, Departed at 10pm

  • Mode of Transportation – scooter

  • Highlights – exploring the island and town, cats (lol!), and Annadale Falls

I’m going to go ahead and admit that this was a frustrating day for us as we found this one of the English Caribbean islands really hard to navigate. I think part of the frustration was that we were on a scooter, which obviously doesn’t offer the stability of an ATV or car. It rained a bit, so we rode the scooter in the rain. To top that off, the roadways were difficult. There were no names to the roads, and one main road would look like another, so it was hard to tell where we were going even though I had a map in hand constantly (which is hard to read with the wind and trying to hold on while on a scooter!). I just needed to get that information out before I went on about the island itself.

The coastline in Grenada was really pretty near the port, so we definitely enjoyed our time walking around. There are also a few shops and museums in the town. I was really happy to find a few friendly kitties at the place that rented us the scooter.

Traveling the English Caribbean Islands - Windstar Cruise - Grenada | Hill City Bride Wedding Travel Blog Virginia

Traveling the English Caribbean Islands - Windstar Cruise - Grenada | Hill City Bride Wedding Travel Blog Virginia

We also visited the Underwater Sculpture Park.

The map did come in handy to find this park! And when we got there, a tour boat was waiting to take people out to where the statues were. Basically, statues are submerged underwater, which help to attract reef life to the area. You can either stay on top of the water and use a snorkel to look down below, or you can try to swim down. I was determined to swim down and touch one, and I definitely felt the pressure on my ears. I was really glad that we were able to visit the park. If you are curious about what is below the surface (as I didn’t have an underwater camera), just take a peek here.

We also wanted to see a waterfall, so we headed to Annadale Falls.

Again, it was a bit difficult to find, but we were glad that we found it. The falls were pretty, and the sound of the falling water was so serene and relaxing.

The last few photos are of a fort that was near the port, and you will spot the Star Pride docked in the harbor.

Traveling the English Caribbean Islands - Windstar Cruise - Grenada | Hill City Bride Wedding Travel Blog Virginia

DAY 9 – BEQUIA, ST. VINCENT GRENADINES

  • Anchored at 8am, Departed at 5pm

  • Mode of Transportation – walking

  • Highlights – Fort Hamilton, Princess Margaret Beach

We really enjoyed our time on this one of the English Caribbean islands. Everything was within walking distance, and the water was so clear! Fort Hamilton was a short walk, and it afforded lovely views of the harbor and the Star Pride.

I had just watched the first season of The Crown, and I was so excited that the beach was named after Princess Margaret! The island has constructed a convenient walkway from the town to the beach, and Princess Margaret Beach was perfect for relaxing and swimming. Be sure to take note of the directional sign below. It was so colorful, and the distances were real – everything on Bequia was within walking distance. We had a nice, relaxing day!

Traveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog VirginiaTraveling the English Caribbean Islands - Windstar Cruise - Bequia | Hill City Bride Wedding Travel Blog Virginia

Are you ready to head to the English Caribbean islands?

I would highly recommend it! And our favorite way to do so was to go along with Windstar Cruises. If you want to see the other 3 islands we visited – the French ones – just click here. One thing I loved about our journey was the variety that each of the islands offers. It was one of our favorite trips with long-lasting memories.

Happy travels!

  • Eileen M Loya - What an exciting island hopping experience! I have never been on a cruise before. I hope to have a chance to do so. Thanks for sharing your photos!

  • Happy and Busy - I’ve never been to the Caribbean. Thank you for sharing this. I will use this for future reference and hope to get there someday!

  • Carmen Rene - The Brimstone Hill Fortress views are beautiful and the St Johns architectures are amazing, I’ve never been to the Caribbean but I’ll surely save this post, thank you for sharing.

  • MELANIE EDJOURIAN - Oh wow this looks amazing. I’ve never been on a cruise before but this makes me rethink. The pictures you were able to take are lovely. What an amazing experience.

  • Mommy Sigrid - Sighh…the Caribbean has always beckoned to me when I was growing up. But now that I am in my 40s, it’s becoming farther and farther away. Who knows? God might just give me a miracle. 😀

  • Sreekar - Wow. Great picture first off! Loved the beaches, they do look absolutely stunning. Wanderlust quotient 100/100 Would dearly love to check out Bequia!

  • kimberly c - I love the caribbean and have only been there one time to the Bahamas. It was also on a cruise ship (nothing better). This (especially the ocean) brought back so many memories. Need to go back soon. Nothing prettier than the water there and nature. Your trip looked like a great fun time. The way it should be!

  • Kristina - this looks like such a beautiful trip, it’s making me want to go right now! I’d love to do a cruise around the Caribbean!

    K x

  • Monidipa - This looks such an amazing place to spend a holiday. I love the sea and beaches, reading the whole post gave me goosebumps. I would love to cruise around Caribbean. Thanks for sharing your lovely adventure. Great pics.!!

  • Elizabeth O - What an incredible time it looks like you had. I love the idea of cruises as you get to explore so many different places!

  • Geraline Batarra - I have never been but definitely a must visit place to see and to explore, I will definitely add this to my bucket list.

  • Nidhi Fouzdar - Blogs about travel motivates me to work hard so that I can afford to explore all these amazingly beautiful places on my own <3 Definitely you had a great time

  • Happy and Busy - I love your journey! I also wanted to go to the Caribbean Islands someday. I will use this as a guide. Thank you!

  • Matt - Wow, so amazing photos and great suggestions, That St. George’s Anglican Church really took me by surprise, looks like it’s been taken right out of middle England, would not imagine seeing something like that in the Carribean.

  • Azlin Bloor - Everything looks just so beautiful! I can just imagine myself on any of these islands, it’s perfect for everyone, whether it’s the newlywed or not! Your images show them off so well!

  • Tawnya - I’m so jealous looking at your pictures! I’ve been on a couple cruises but never in the Caribbean. It seems like a cruise might be the best way to see the Caribbean because you stop in so many places. Looks like you had a wonderful trip!

  • My Teen Guide - Visiting the Caribbean islands has always been a dream for me. It has been sitting on my bucket list for the longest time. Seeing your photos fueled my wanderlust for the place! I have to sit down and talk to my husband about this. We have to pull our efforts and resources together to make a dream trip to the Caribbean islands the soonest time!

  • Jelena - The Caribbean looks beautiful! I love this kind of vacation when you go around several places and you can enjoy both nature and architecture.

  • Kemi - So beautiful and I’m so jelly! I’ve only been to Cuba and Cayman Islands and so want to do more French and even Dutch isles. I’ve never been on a cruise before so it should be fun. I’ll look into Windstar for my first time cruising. Gorgeous pics, btw!

  • Clarice Lao / Camping for Women - We’re planning to take another trip to celebrate our 5th anniversary. We’re a bit undecided if we’re off to Europe or the Caribbean but after reading your post — I am now leaning towards enjoying these islands. Thank you for sharing and your photos are great.

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