Day 1 | Arrive and find your sea legs in Jolly Harbour

Once you arrive in Antigua your sailing yacht, Oryxx, awaits you at the Jolly Harbour so you can get settled in and find your sea legs. We’ll take a casual cruise to the outside of Jolly Harbour and anchor for the night. Jolly Harbour’s beach line is dotted with restaurants, bars, and shops for everyone to enjoy on the first night of your Caribbean sailing vacation.

Ffryes Beach and Coco Beach are two of the top favorite beaches while sailing in Antigua & Barbuda. We can even bring out the kayaks and paddleboards provided on board so you can start your sailing vacation off right – cruising at your own pace in the pristine waters of the Caribbean Sea.

Day 2 | Cruise over to the bustling hub of Dickenson Bay

On the morning of Day 2, we’ll set sail for Dickenson Bay located on the northwest of Antigua. This pure white sand beach is a bustling hub of activity with many fantastic beachside eateries where you can revel in Antigua’s authentic Caribbean culture. YA MON!

Dickenson Bay is a well-known tourist stop so if you prefer a more secluded destination Deep Bay is our suggested alternative. Here you have multiple options – relaxing on the beach, taking a hike up the 18th century Fort Barrington, kayaking, paddleboarding, and more.

Deep Bay also provides a great snorkeling site at the Wreck of the Andes. Since its sinking in 1905, this British Bark has provided a home to an abundance of coral, gorgonians, sponges, and tiny reef fish. A lively ecosystem of vibrant colors makes this snorkeling spot a personal favorite.

Day 3 | Set sail north to find Barbuda’s lobster strewn beaches

Today we’ll double check skies and weather permitting for your Antigua & Barbuda sailing charter, we’ll head north into the Atlantic where the island of Barbuda awaits. An early start is suggested as it’s a four-hour sail to Barbuda. Arriving around midday allows good visibility and the option to visit the island and it’s Frigate Bird Sanctuary.

This is the perfect spot to collect a few lobsters and prepare them onboard or enjoy the local take on this iconic dish ashore. We’ll anchor and spend the night in Low Bay where you can enjoy the stunning sunset of this remote gem.

Day 4 | Walk the “miles” of white sand beaches at the popular Eleven Mile Beach

Spend another day in Barbuda and you’ll have your pick along the stretch of paradise called Eleven Mile Beach. This long white strip of sand extends half the length of the west coast of Barbuda and offers some of the best beaches in the Caribbean.

Although Barbuda’s attraction is known for its isolation – Barbuda offers a plethora of activities both onshore and offshore. If you prefer to paddleboard, kayak or even kiteboard then the idyllic Gravenors Bay offers its tropical playground! This popular yacht anchorage provides the best snorkeling spot with its intense turquoise waters and the coral reefs surrounding it. If you’re lucky you might spot a dolphin or two!

Day 5 | Head back across the sea to underwater life of Green Island

On Day 5 of you Antigua & Barbuda sailing charter, we’ll once again check the weather forecast before setting sail into the blue. This time we’ll sail south for the east coast of Antigua. Another four-hour sail in the pristine waters of the Caribbean will bring you to Nonsuch Bay.

Before anchoring in Nonsuch Bay, we’ll stop at Green Island, which is situated to the east of Nonsuch Bay and a must see. Take a trip ashore to enjoy the lush foliage and meander around this uninhabited island with its velvety sandy beaches. You can’t miss out on the snorkeling off of Green island before heading further into the bay for sundowners and dinner.

Because of the clean easterly winds, this spot is a great kiteboarding site.

Devil’s Bridge is also a sight to see. This stunning wave-beaten limestone resembles a bridge-like structure. At high tide, you can watch the waves crash into the rocks spraying the foamy sea up into the air.

Day 6 | Explore the rich naval history at English Harbour

The 18th-century naval dockyard at English Harbour was home to Horatio Nelson’s fleet. Nelson was one of Britain’s best naval commanders. Through his master tactician skills, he was able to help defeat the French during the Napoleonic wars. Wander around Nelson’s Dockyard to the multiple forts which make up this national park. Some of the island’s best restaurants and bars are located within this dockyard for you to enjoy.

A scuba dive is also recommended here as this is the staging point to many of Antigua's best dives off the south coast. This includes the famous Pillars of Hercules which is also shallow enough to snorkel. These natural limestone pillars carved by wind, rain, and sea above shore provide just a lively ecosystem below the surface.

A short motor or walk over to Falmouth Harbour is probably the best place for a night out on the town enjoying local music and your favorite rum cocktail!

Day 7 | Hunt for seahorses and octopi in Carlisle Bay’s crystal clear waters.

On day 7 of your Caribbean sailing vacation, we’ll take a casual downwinder to Carlisle Bay. This picture perfect spot has some of the clearest water in the Caribbean and anything under or above the surface is a treat. This bay is home to 6 shipwrecks which house seahorses, octopus, turtles, eels, and an abundance of tropical fish. Carlisle Bay is swimming with sea life which is great for both scuba divers and snorkelers.

Day 8 | From stingrays to sun-rays, soak up your last day at Picarts Bay

Spend your last day stopping off at Cades Reef in search of rays and reef sharks before continuing down the coast to Picarts or Ffryers Bay. Here you can soak up the last of the Caribbean sun while collecting souvenirs and enjoying cocktails.

Slowly make your way back to Jolly Harbour and start planning your next trip back to your new tropical playground!


The sample itinerary for Antigua and Barbuda is only a glimpse of what these beachy islands have to offer. Remember that all sailing charters are fully personalized to your schedule, desired activities and destinations. Contact us today to talk about ideas of what your sailing charter could look like in the Caribbean.