Discover videos and articles of our Caribbean sailing experiences from the Dominican Republic down to Trinidad broken down by country or location. Each article/video offers information on passage planning, what the journey is like, entrances to anchorages and marinas, and things to do at each location.
For a bit of variety and lessons about what boat life is truly like we’ve also showcased various boat high and lowlights.
If you’re planning a sailing adventure up or down the Caribbean island chain, watching these videos will provide you with helpful tips on what to do, what not to do in addition to providing you with a good feel for each area.
There’s a menu on the right if you ever want to jump over to another country. And if you’re not sure whether you want to sail in the Caribbean or the Mediterranean, read my article 25 Differences – The Caribbean or The Mediterranean.
Sailing Experiences on the Leeward Islands
Sail with us from Turks and Caicos to Samana in the Dominican Republic. View our passage plan, experience what it’s like to anchor off a deserted island in the pitch black, and find out how to put a staysail up.
Simon will explain how we monitor boats in the area over AIS using our plotter. Check out some humpback whales that breach and slap their tails. Find out why we had to divert to the Dominican Republic rather than sailing on to Puerto Rico. You’ll also see what can go wrong with a genoa halyard and how to replace one halyard with another.
Finally, discover where a suspected fuel leak came from and take a tour of the lovely Puerto Bahia Marina.
Check It Out ===> Dominican Republic
Sailing Across The Mona Passage
If you fail to plan for sailing across the Mona Passage, the waterway between the Dominican Republic and Puerto Rico, you might find yourself in some majorly harsh sea conditions. I’m talking about big swells, big waves, and big winds. You can also throw in a few potential thunderstorms too! This is must know-before-you-go information.
Check It Out ===> Sailing Across The Mona Passage
Sail Puerto Rico
After waiting for an appropriate weather window, we managed to motor across the Mona Passage and arrive safely in Marina Pescaderia. Making your way along the south coast of Puerto Rico is not a quick passage. Many boaters wake at first light or before and get to the next anchorage before noon when the seas start to get unruly.
On our recent trip to mainland Puerto Rico, we spent several weeks visiting six locations by boat including two marinas and four anchorages along the south coast. And by car, we traveled the east coast, west coast and a bit of the north to visit the capital city, San Juan. We also dropped anchor in two spots in the Spanish Virgin Islands (owned by Puerto Rico) but the mainland and the islands seemed worlds apart.
Check It Out ===> Sail Puerto Rico – Summary
US Virgin Islands
In this video, we take you to four anchorages on the US Virgin Island of St John and we’ll also take you to meet a sea lion named, Omar, on the US Virgin Island of St Thomas. The anchorages include Cruz Bay (Honeymoon Beach), Francis Bay, Leinster Bay, and the hurricane hole outside of Coral Bay.
Check It Out ===> St John, US Virgin Islands
The British Virgin Islands
In these Caribbean sailing videos, we’re going to show you some of the best anchorages in the British Virgin Islands. We’ll show you Spanish Town on Virgin Gorda, the famous geological attraction called The Baths. Then we’ll sail over to Leverick Bay to catch a pirate singing show. We’ll also give you a tour of the Leverick Bay Resort and Marina. Britican’s Captain, Simon, will do a drive-by of Bitter End and Saba Rock – two massive sailor hang-outs that were destroyed in hurricanes.
In part two, you’ll get to check out Trellis Bay, Tortolla, and then head over to the capital city, Road Town. We anchor at Peter Island and hang out for quite a while in Cane Garden Bay. A bunch of cruisers hikes Sage Mountain – an excursion well worth the time.
Finally, we fill up with fuel from Nanny Key Marina and head to Spanish Wells to book out before we leave for Saba.
Check It Out ===>British Virgin Islands
|THE BRITICAN EXPERIENCE - A LIFE CHANGING WEEK-LONG LIVEABOARD EXPERIENCE|
|Spend one week with Britican to give the liveaboard life a test drive. Learn about sailing, anchoring, maneuvering in marina's, docking, provisioning, cooking, maintaining, troubleshooting AND checking out all the white sandy beaches, snorkeling over the fish-filled reef and testing out exotic tropical drinks. You create the itinerary. Discover how we can help you to get out sailing and enjoying the lifestyle sooner rather than later. Find out more here. Click here for more information.|
If you’re looking for white sandy beaches, a diversity of food, wonderfully welcoming people, a history you can grasp, and an absence of over-the-top tourist attractions put Anguilla on your countries to sail to list.
Being the most northerly Leeward Island in the Caribbean, Anguilla is the last stop, heading north, before hitting the Virgin Islands.
Check It Out ===>Anguilla
Ever wonder what sailing to the Caribbean Island of Saba might be like? Heck, have you ever heard of the tiny 5 miles long Dutch island of Saba? Join us on our journey to experience a very lumpy sea and our struggles to pick up a mooring ball in the pitch black. Find out what to do when water is flowing into your bilge. And most impressively, experience the sheer pleasure of waking up next to an indescribably beautiful view (that you didn’t know was there)!
We’ll also take you for a bus tour of the island in addition to climbing to the very top of Mount Scenery, Saba’s volcano AND we’ll show you the world’s smallest commercial runway. It might make you realize that sailing to Saba is probably a better choice than flying.
Check It Out ===>Saba
Just as hurricane season had arrived we decided to take a spontaneous 2-day/night sail up to St Martin from Bequia in the Grenadines. We had friends in St Martin that we really wanted to see. After looking at the weather and checking out our passage planning software we discovered that we could make it all the way up to St Martin’s within 48 hours. That’s a two day non-stop passage passing 11 countries/islands. See what the passage was like.
Check It Out ===> St Martin
Tintamarre Island, St Martin
Have you ever heard of Tintamarre Island just off St Martin? It’s deserted! How often do you spend time on a tropical deserted island? Do you know what it’s like? One of the major benefits of being a cruiser is being able to hang out in places that ‘normal’ people never see.
We spent time with two other family cruiser boats anchored off of Tintamarre Island. The island, located next to St Martin in the Caribbean, is deserted but was once inhabited. Watch the video to get a glimpse of this must-see island.
Check It Out ===> Tintamarre
St Kitts and Nevis – Caribbean Sailing
In this video, we’ll take you from Saba, past St. Eustatius and down to St Kitts and Nevis. Find out what tasks Simon does at 5 am in the morning, experience a very bumpy ride, learn all about booking in and out of St Kitts and Nevis, see what cruisers get up to in St Kitts & Nevis, check out St Christophe Marina, climb a volcano, visit a fort, and much more.
Check It Out ===>St Kitts & Nevis
The big appeal to sailing Montserrat was to check out the abandoned (or should I say demolished?) city of Plymouth. That’s what Caribbean sailing is all about! Why was it demolished? Montserrat’s volcano became active and blew it’s top. And the activity started in 1995 and has been going since then. Get our passage plan, see where you can anchor and take a tour of the island.
Check It Out ===>Montserrat
Check out our passage plan from Montserrat sailing Antigua. Sit back and take a tour of one of our favorite Caribbean islands.
Check It Out ===>Antigua
After our quick visit to Antigua, we sailed south to Guadeloupe with our two buddy boats, Pura Vida and Rondo. On our trip, we anchored in Deshaies, stopped off at the Jacques Cousteau’s Marine Park on Pigeon Island for a snorkel, and then went onto Les Saintes.
Watch the video to see some sailing, fishing, snorkeling, the Green Flash, kids on a boat, waterfalls, and much more. And make sure to scroll down to get links to resources mentioned in the video.
Check It Out ===>Guadeloupe
Carry on below to head into the Winward Islands.
Caribbean Sailing Experiences on the Windward Islands
What’s life on a boat like for cruisers? There’s some passage planning, heavy winds, a major squall, sushi, swimming, pot luck, fishing, socializing – you know, all the things you do when you live on a boat. In this video, Simon will show you our passage plan from Guadeloupe to Dominica in addition to clips from our sail.
Check It Out ===>Dominica
And to experience our first visit to Domina with a hike to the Boiling Lake, trips to the sulfur spa’s, our anchorage in Roseau and Portsmouth, traveling up the Indian River, visiting waterfalls and plantations and much more, watch our two-part video series and read our extensive article about the beauty of Dominica.
Check It Out ===>Dominica – Sightseeing
Check out what it’s like to visit Martinique with boat buddies!
Also, if you’re interested in why you should visit a French Caribbean Island, read this: 8 Reasons To Sail To A French Caribbean Island
Check It Out ===>Martinique
And go for our first sightseeing visit to Martinique – we managed to get there in time for Carnival! We didn’t like Martinique the first time. Find out why by watching our video/reading our article.
Check It Out ===>Martinique Sightseeing
Take a tour if St Lucia by sailboat and foot. In this video, you’ll see Rodney Bay, the marina and surrounding area, Marigot Bay, The Pitons by water and up on top, natural baths, and much more. It’s one of our older videos but if you want a good grasp of what you’ll find in St Lucia, it’s worth a watch. Also, we offer a written review of the Rodney Bay Marina.
Check It Out ===> St Lucia
Check It Out ===> Rodney Bay Marina Review
On our Caribbean sailing visit to St Vincent, we checked into Chateaubelair on the northwest side of the island. Then we sailed down to Cumberland Bay and anchored with our stern facing the shore – an anchor heading out to sea and a line tided to the shore. What were our overall thoughts on the island and the people? Watch the video to find out.
Check It Out ===>St Vincent & The Grenadines
Bequia – Caribbean Sailing
Bequia St Vincent is a sailing cruiser dream stop. If you ask any cruiser what their favorite spot is in the southern Caribbean, Bequia is usually high on the list, if not top of the list.
In this video, we’ll show you our passage plan from St Vincent to Bequia. There’s an example of what it looks like when an anchor drags. Additionally, there are some sights of Bequia including the town, some beaches, and a walk across the island.
Our captain, Simon, will explain the process of repairing the black caulk on our teak deck, we’ll show you the liveaboard cruiser hang out, what our 8-year-old daughter Sienna gets up to on a daily basis (does she have a social life?!), a crazily insane rainstorm, and a small bug issue. Discover what boat life is like in Bequia!
Check It Out ===>Bequia
Also, check out our first visit to Bequia. We did a video and long article on the beautiful island and since then we keep coming back!
Check It Out ===>Bequia – Our First Visit
Mustique, also known as Billionaire’s Island, is a private island owned by the Mustique Company. The island is a beautiful stop for sailors but it does come at a price. Is it worth the money to possibly run into the likes of Mick Jagger, Tommy Hilfiger or Raquel Welch? The last time we stopped in Mustique (2020), we were sat at a table right next to Bono from U2!
Check It Out ===> Mustique
Tobago Cays – Prior to visiting St Vincent and the Grenadines not only did I not know they existed but I was completely blown away that places of such unspoiled beauty even existed. Tobago Cays is not to be missed. Watch the video and ready the article.
Check It Out ===>Tobago Cays
Watch this video on Union Island, St Vincent Grenadines to enjoy a ride around Chatham Bay, get close to a pelican, witness one flipper races, meet a man with a machete, experience a walk across the island to the main town, get an interesting fact about the Grenadines, take in a 360-degree view of Chatham bay, travel from Chatham Bay to Clifton and get a little dingy tour of the Clifton anchorage.
Check It Out ===>Union Island
One of our favorite Caribbean sailing destinations. The people make a living from fishing, boat building, and farming. No large cruise ships or tourist boats descend upon the quiet island making it more authentic than most. The video below showcases our very first visit to Carriacou. Since the video, we’ve been back at least 10 more times.
We’ve taken a land trip checking out every corner of the island, tested out other anchorages, and discovered Grenada’s largest gem – Sandy Island. Sandy is a wildlife reserve so the fish are protected. The reef is AMAZING. It’s like swimming in an aquarium.
Check It Out ===> Carriacou
Both Grenada and Trinidad & Tobago are popular hurricane season destinations. By June 1st cruisers either headway up the north coast of American or way down to the bottom of the Caribbean. We’ve spent two hurricane season in Grenada and find it to be an excellent destination. Not only do hurricanes usually miss the island, but there are also loads of reasons to enjoy the beautiful country. We also have a favorite marina we stop in at. La Phare Bleu Marina is not to be missed.
Furthermore, the Grenada Carnival is our favorite Carnival in the Caribbean. Watch our short video to find out why: Grenada Carnival.
Check It Out ===> Grenada
Check It Out ===> La Phare Bleu Marina
Trinidad And Tobago
Sail with us from Grenada to Trinidad and Tobago and back again. Explore the main commercial port, Chaguaramas, and Peke’s Boatyard. Get a feel for what it’s like to have your boat in and out of the water. If you ever plan on going to Trinidad for hurricane season or for boat work this five-part series will prove to be very helpful. Not only can you check out the facilities but you’ll gain a deep understanding of what it’s actually like to be in Trinidad.
Check It Out ===>Trinidad and Tobago
|THE BRITICAN EXPERIENCE - A WEEK-LONG BLUEWATER CRUISING EXPERIENCE|
|Julia joined us for a week with her two beautiful children. She had no set of objectives. Her aim was to get an experience. And boy did she! Never having sailed before she took to the helm on day one and never looked back. Julia experience the thrill of sailing, the peacefulness of a quiet anchor, and the deliciousness of a lobster BBBQ on the beach. If you'd like to experience what it's truly like to live and cruise on a bluewater sailboat, come join us for a week. Check out our availability here: Click here for more information.|
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