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Our Favorite Things to do While Sailing

Sail Rocks North anchorage

Long, lazy days on the water. Sails up with a fresh breeze. Rocking out to some sailing tunes. A snorkel stop for lunch. Freshly caught fish for dinner. A secluded anchorage with a gorgeous sunset across the horizon.

That is all I need for a perfect day during a sailing trip in the caribbean. There are many other things to do though!

Besides sailing, of course, these are our top activities.

muskmelon bay at guana island in the bvis
You'll find snorkeling opportunities everywhere

Snorkel secret reefs

Access secret snorkel spots other vacationers can’t! There will be plenty of lunch snorkel stops and many anchorages that offer great underwater sea life.

You might want to consider bringing your own snorkel and mask – many charter companies have stopped providing these due to Covid. You can check out the model we have listed on our sailing trip packing list page.

HMS Rhone snorkeling
Diving the HMS Rhone in the BVIs

Scuba dive a famous wreck

We usually rent dive equipment and tanks (if you are certified, of course). All you have to do is jump off the back of the boat! Ask your charter company and they can arrange a dive equipment provider to meet you at check-in.

This picture above is from the HMS Rhone, one of the most popular dive sites in the area.

If are new to diving or want a local guide, you can also arrange with local dive operators to pick you up right from your anchorage or mooring.

Northern Exumas Wahoo
Recent wahoo caught while trolling

Catch some pelagic fish

Some of the best fishing destinations also happen to be popular for yacht charters. We fish almost whenever we are sailing, and we usually land a few fish to make tacos or ceviche. It doesn’t get any better than that!

We mostly troll surface and diving lures and target the drops where you can catch wahoo, mahi, and tuna. Bottom dropping at anchor is another easy way to add some excitement to the trip.

Step up your fishing game – our guide will provide you with some tips to land more fish.

Sail Rocks North anchorage sunset
Secluded sunset in the northern Exuma Cays

Enjoy a sunset at anchor

The golden hour is my favorite time of day. Some of the best sunsets I’ve ever seen have been on a sailboat. It gets even better when you have the anchorage all to yourself.

Hiking on Compass Cay Exumas
Hiking to Crescent Beach at Compass Cay

Hike to secluded beaches

You can find trails at every sailing destination. Some of my favorites include the hike to the lighthouse at Culebrita, the baths at Virgin Gorda (BVI), and exploring the Exuma Cays Land and Sea Park on Warderick Wells in the Bahamas.

Get a birds eye view of your yacht lying at anchor down below and check out beaches that can’t be accessed any other way.

Painkiller at the famous Soggy Dollar Bar in Jost Van Dyke

Sip tropical drinks at a beach bar

We love taking it easy with a tropical beverage at one the many beach bars and restaurants accessible from your dinghy.

Some of our favorites include the Soggy Dollar Bar in the British Virgin Islands, Cow Wreck Beach Bar in Anegada, and the Staniel Cay Yacht Club in the Exumas, Bahamas.

Stand up paddleboarding in the Exumas
Paddleboarding in calm conditions in the Exumas

Paddleboard around the anchorage

In addition to snorkeling and diving, you can kayak or go stand up paddle boarding. Most charter companies will give you the option to rent the equipment. Stow it right on the sailboat’s deck. We’d recommend the SUP since it’s lighter and easier to deploy.

Sailboat regatta

Join a regatta

If you enjoy sailboat racing, enjoy the camaraderie and competition of a regatta. The BVI Spring Regatta is one of the more popular ones that you can join. Sign up early!

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