Six Beach Bars You Should Visit While Cruising The Caribbean

By: Charter, Cruising Tips, Destinations

Once the anchor is set and the boat is secure there is nothing like the sound of the dinghy getting prepared for the quick trip to the beach bar. You know what I’m talking about, the little grass shack on that picture postcard beach where the drinks flow as easily as the sailing stories do.

What do you seek out in a beach bar? Do you need food and drink, do you need cocktails and a view or do you just need a bartender that loves to talk?

Check out a few of our favorite Beach Bars in the Caribbean

The British Virgin Islands (BVI)


The Caribbean hospitality is as you would expect in these parts with people who are gracious and fun as long as you realize that island time is what you should be on. Foxy will sing to you or talk to you and he’ll make sure the food comes out as it should. You’ll see many people who come here over and over as it is an institution in Great Harbour. Stop in on a weekend night for BBQ and a party under the stars.

Soggy Dollar Bar

The drink you are having is called the painkiller and it is said to have originated here but realistically the beach, the vibe, and the music will kill any pain. Your money will be wet after you swim over from your boat anchored just off shore. A few hours here and you’ll never want to leave Jost Van Dyke, however, with so many great places to have a drink and work on your tan this is where you anchor for a few days just to take it all in. The lobster roll is savory and the crispy fish is salty so naturally, you’ll need a sweet cocktail to round out the experience for your taste buds.

Cow Wreck

It’s hard to imagine a spot that looks so beautiful actually exists in real life. This off the beaten path location is not as easy to get to as the other beach bars that are flocked to by boat charters and tourists but a trip to Anegada is not complete without an afternoon at the Cow Wreck. The waist deep, crystal clear warm water is the calling card of the Caribbean but once you couple that with the hospitality at the bar and the sense that you’ll be “wrecked” for life, you will find it hard to leave.

The Willy T

It’s not just a boat with cocktails, music and a great deck to jump into the ocean from, the Willy T is an icon. The Willy T is one of those spots on the planet that you must see, like Mt. Everest and the Grand Canyon. Well, maybe this is a bit of an over exaggeration but you’ll have a good time, you’ll drink plenty of rum and the conch fritters are worthy of a second order. Technically the Willy T is a floating bar but it is a beach bar in spirit.


Sunshine Shack Anguilla

Like many spots in the Caribbean, Hurricane Irma did a number on this beach bar but a quick rebuild brought it back to life. There will be a lot of friendly people at the bar and your feet will be in the sand while looking across the water to neighboring St. Martin. You’ll probably want to dance when the music gets going and the drinks start flowing but be sure to pause and look out at the water and across to St.Martin. This is what paradise looks like.

Prickly Pear, Anguilla

You’ll drop anchor in a neighboring cove and dinghy around the rocks to a pristine beach with calm, clear water and powdery white sand. It will feel like paradise. It will feel like every dream you have ever had of getting stranded on an island. Then you’ll see the tiny beach shack and your dreams will come true. The bar is primitive but there is a blender and the beers are cold. The conversations will center around the sun, the wind and nearby bars. This is a destination for sailors making the trip over from St. Martin or the occasional tourist boat coming over from Anguilla. Either way, you won’t see many people but those that you do see will be happy about this tiny outpost.

Charter Resources

  • Your First Charter Sailing Vacation Today bareboat chartering is the culmination of your sailing education. When you walk across the deck and get your sailing diploma you step on to the metaphorical boat of your future and you can sail it anywhere you want!
  • Charter Sailboat Resources Whether you have just begun to sail and have recently earned your ASA 101 certification or if you have already mastered ASA 114 and are a veteran of bareboat charters this resource should help you.
  • Bareboat Charter in the BVI Getting aboard your bareboat charter is the goal when you get your ASA sailing certifications. Where do you begin? For many, it is a sailing vacation in the British Virgin Islands.
  • Choosing a Charter Boat Company It’s time for you to set off on your own and explore endless shorelines and secluded coves. You have mapped out your plan and you have reserved your vacation time now all you need is a boat. How do you choose a charter company to rent a boat for a week?
  • Choosing The Right Boat for Your Sailing Charter When you decide to take a sailing vacation aboard a sailing vessel that you will call home for a week or two you’ll be surprised by just how much you think you need.
  • Sailing in Europe? Chartering overseas is on the bucket list of many a sailor, but making it happen comes with a stipulation or two. A sizable number of countries require an International Proficiency Certificate that lets them know the charterer is trained, qualified and prepared to take one of their boats out to sea.