Escape Winter & Grab Some Summer Fun Sailing In Antigua

Whether you like sailing or the Caribbean beach life as a “landlubber”, you will love Antigua!

INSTAGRAM @@catwalk_yeti

Note that this is a sailing vacation mainly and although we bareboat sail (captain ourself), you can always hire a captain if you are so inclined. Not that much more expensive actually, we just like to sail!

Flash back to 3 weeks before the trip. I get the idea (thanks Camille!) to go sailing over Thanksgiving. Who on earth would be available on that notice to go? I email Matt and Thierry that night, who I have sailed with internationally a few times, but 10 years ago. A day later, the boat is booked, another day later flights are booked. Wow, that escalated quickly…

Fast forward…I land in Antigua, the land of 365 beaches (one for every day of the year they say!) and make my way to the Dream Yacht Charter base in English Harbor. I find a nearly brand new deluxe 40’ Lagoon catamaran. Everything is electric and push button including air conditioning with individual climate control per cabin. This is a find! I am first to arrive, so head across the bay to get provisions at Crab Hole. Not great for perishables but they have everything else and it is close. Matt, Thierry, and Jen arrive (Names not changed to protect the innocent). We unload and take our dinghy over to other side for dinner. Someone walking down the street recommends Le Cap Horn and they were not lying! Thin crust artisan pizza and sizzling hot stone plates dinners. The French owners run a hidden gem.

INSTAGRAM @jcanter71

We hit the rack (air conditioning heaven!) and wake up to set sail for Nonsuch Bay and anchor off Green Island for lunch. This is a private island leased by Mill Reef Yacht Club so you are technically not allowed on it. But it is deserted, so if a tree falls in the forest… Swimming and charcuterie and cheese and Rosé and sunset and an early peaceful night. The next morning we pull anchor to Pick up 4th mate Michael across the bay.   Dinner with the hottest bbq’d jerk chicken, my (now) famous broccoli, onion, garlic, green peppers and spicy tunisian harissa stir fry is a hit.

The next morning, back to English harbor to fix our propane situation and to restock the Rosé and Rum. We discover the best provisioning spot in English Harbor, Covent Garden. It is pretty much like a mini Whole Foods, quite the find. Off to Cad reef to snorkel during our lunch break. The reef is not in good shape, not a lot of fish a broken coral bone yard, hopefully this is a temporary situation based on the last Hurricane, but this will be a pattern we see the rest of the trip. Then we anchor off a beautiful beach with several good spots including Rum Bus Beach bar and then OJ’s at Crabb Hill for dinner. We grab a table and sit with our toes in the sand. Red snapper offered three ways as long as you want it the way they make it. Luckily the way they make it is awesome, somewhere between grilled and fried I would say. Mango daiquiris were to die for. Iced glasses for all cold drinks are a nice touch you don’t always find in the Caribbean.

INSTAGRAM @catwalk_yeti

The next morning we pull anchor and go exploring. We head into Jolly Harbor to check it out but realize it is more of a resort area, so vini vici arrivaderci! I spy a sandy island in the distance so we beeline it out there. Turns out it is called Sandy Island. Sounds perfect. Not so much. There is a major shallow reef around it with a big surf break on top. We try to swim in, but decide to turn back for safety. Maybe that is there is a wreck 100’ off the beach… So back to mainland and heaven, now known as Deep Water Bay! There is one small, well marked wreck near surface in middle of a beautiful bay rimmed perfectly with white sand. Nice lunch break and swim, repeatedly jumping off the Catamaran from various levels keeps us occupied. We then pull anchor and sail up to Dickenson Bay and drop anchor right off the cutest little floating bar, Kon Tiki. Emma and Johnny run it, she is English, he is Danish, and they opened it 3 weeks ago. She pours and he rows (to pick up people from shore), but both find time to drink and smoke with the patrons. Michael got to drink straight from bottle after the topper went in to the best rum punch we have ever hard. About 5 later…we go ashore to Coconut Grove (beach bar front to a cute boutique hotel named Siboney Beach Club) to party with the bartender known as Big Sexy to the ladies, Jermaine Andre to the rest of us… Went up the beach to Ana’s on the Beach for dinner, but not the same great memories from my past Caribbean cruise post. So back to Coconut Grove for dinner and such an epic night partying, that the next day we all forgot we even had dinner the night before…

INSTAGRAM @jcanter71

Wed was a slow day for all, very hung over from the um, island hospitality, but we manage to pull anchor and sail to Prickly Pear Island, a deserted island with a makeshift beach bar that is closed since it is shoulder season. Since uninhabited, Thierry and Jen “marked their territory” and now apparently by maritime law (of some kind? French?) own the island. We continue on to Great bird island, which was cool to explore via dinghy. We saw lots of turtles from the boat coming in, but unfortunately none snorkeling. Another epic dinner with filet mignon, champignon risotto, and my (now again) famous stir fry.

Thursday we pull anchor and try to go to the D-Boat bar (floating ex-oil tanker turned into a party palace and water park) for greasy burgers to revive the crew from 2 nights ago… but they don’t open until 2pm. #islandtime! So we head off to Falmouth Harbour and in so doing have completed our circumnavigation of Antigua along the way! Apparently it takes 6 hours when racing but we took 5 days. #antiguaraceweek. Anchored near the big boat area and went to a very fancy dinner at Cambusa. Some boat literally reserved all lobsters so we had fish. Sad. Got invited to the crew thanksgiving dinner at end of dock with crew from all the 100’ custom yachts there. Fun times!

In the morning we headed to Carlisle bay for swim and that (onboard) greasy burger bbq we wanted the day before. Found out top 3 ingredients in bad hamburger patties are beef, water, and beef hearts, in that order. Interesting… Back to Crabb Hill and OJ’s for more snapper and mango daiquiris. Yes, it was that good!

Fun facts – We bought 4 bags of ice on day 1 and still have almost 2 left. Dinghy started every time on 1 pull and was inflated enough to hold 5 easily. These are things none of us have ever seen on charter. Dream Yacht Charter rocks!

We motor back to English Harbor to drop boat off in the morning. Others are flying out, but I head to Jolly Beach Resort for some pampering for a few days. At $75 a night all-inclusive, the beach and pool scene make up for the lackluster food and initially multi-colored water from the tap. Worth the price, but not everybody will like it.

So whether you like to sail yourself, like sailing, like the Caribbean beach life as a landlubber (look it up), you will love Antigua!

Jason Canter


Jason loves beaches, sailing, diving & trying new foods. His travel style is about staying central & close to the action. His favorite country is Mexico & he never travels without his Tumi roller.

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