Top 10 Sailing Destinations to Explore in 2023

Last Updated on November 3, 2023 by Boatsetter Team

Making a top 10 list of sailing destinations is tricky because how do you limit yourself to just 10? Whether you’re looking for a self-drive bareboat, a fully crewed luxury catamaran, or even a funky old-school gullet, you can find lots of ways to raise sail in the following fabulous destinations:

1. Chicago
2. Newport (Rhode Island)
3. Annapolis
4. Tampa Bay
5. San Francisco Bay
6. Southern California
7. Bahamas
8. Croatia
9. Greece
10. British Virgin Islands

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1. Chicago

Prevailing westerly winds make for some fantastic sailing on Lake Michigan, where you can practice tacking all day, cruise along on a beam reach, take in the fabulous Chicago skyline at sunset, or watch a moonrise reflected off the length of the lake. Twice a week in summer, between Memorial Day and Labor Day, Navy Pier sets off fireworks which you can enjoy from your front-row seats on deck.

If you’ll be the captain of your vessel, don’t forget Illinois boater safety course requirements.

2. Newport (Rhode Island)

Arguably the world’s sailing capital for centuries, there’s a lot for sailors to love about Newport, Rhode Island. The breezes are steady on Narragansett Bay, dockage is plentiful at numerous marinas and on mooring balls, and the sailing is mostly protected, so you never need to head out to the open waters of the ocean.

Newport is steeped in nautical history, and the city has been a magnet for international regattas, including:

• America’s Cup
• The Volvo Ocean Race
• The biannual Newport to Bermuda Race

If you rent a boat and plan to hoist sails on your own without a captain, make sure you’re certified via the state’s boating safety course.

3. Annapolis

The Chesapeake Bay is the largest estuary in the nation, with over 4,000 square miles of water and 11,000 miles of shoreline. A fair chunk of this sailing playground centers around the nautical town of Annapolis, also home to the Naval Academy.

Summer sailing offers calm waters and warm breezes, and many coves and rivers to duck into that you could sail Annapolis all summer long and not get to see it all. However, two things to watch for are shoals and the ever-present crab pots. Keep a good lookout for those and you may even spot the Navy cadets sailing by.

4. Tampa Bay

The largest port in the southeast, Tampa Bay, is made for sailors. The waters are protected, so the sailing is easy even for those who get seasick, and the Bay is fairly shallow, so it’s easy to drop a lunch hook just about anywhere. Most importantly, there are many places to explore, including Egmont Key, Caladesi Island State Park, Beer Can, and Honeymoon Islands.

If you want to check out the warm waters of the Gulf, sail under the Sunshine Skyway Bridge past Fort De Soto Park and out along the coast from Clearwater to Sarasota. You’ll be rewarded with a beam reach and clear blue water.

5. San Francisco Bay

San Francisco Bay is vast, and the weather is perfect for serious sailors. It doesn’t matter whether you’re city cruising from one marina to the next or dropping anchor behind Angle Island – there’s always something to do.

From the deck of a sailboat, you’ll enjoy views you simply can’t get from land, including:

• The city skyline
• The Golden Gate Bridge
• Alcatraz Island
• Fourth of July fireworks (near Pier 39)

Pro Tip: Fourth of July is a popular holiday for people to get out on the water. Boats get picked up fast. Plan ahead and book your Fourth of July boat trip now.

6. Southern California

You can sail year-round off the coast of sunny Southern California. The 200-mile stretch from Ventura to San Diego offers plenty of harbors to explore, including Long Beach, Newport Beach, and Dana Point, all of which offer plenty of rental boats.

You can even opt to go offshore to Catalina Island, which is a wildly popular weekend destination with the remote Two Harbors destination near the western end and the quaint town of Avalon to the east. Dolphin and whale sightings are common, and you can even sail right under the Pacific Air Show near Huntington Beach in October.

7. Bahamas

Set your eyes on the bluest of blue; you’ll want to set sail in the Exumas chain of the Bahamas. Head southeast on your charter to the beautiful Norman, Allan, and Shroud Cays for so much to see and do like:

• Hiking to Boo Boo Beach at Warderick Wells
• Swimming with pigs at Big Major
• Exploring the Thunderball Grotto (used for a James Bond movie set)

Don’t forget to snorkel on the semi-submerged plane on Norman Cay that once belonged to a Medellin drug kingpin. Two things to keep in mind in the Central Exumas – 1) the water is shallow and full of coral heads, so chartering with a captain may be a better choice, and 2) you’ll never see so many shades of blue as you will around these beautiful islands.

8. Croatia

Sail the lovely Dalmatian Coast in Croatia, where the breezes funnel through the islands, and the water begs for you to dive in. The cruising grounds between Split and Dubrovnik serve up island after island, each one different from the one before and most designated as UNESCO Heritage sites.

The towns have medieval roots, and some served as shooting locations for the Game of Thrones, so there’s plenty to explore. The Island of Vis is popular due to the nearby Modra Spilja (Blue Cave) and Tito’s submarine tunnel, both of which you can enter. Try booking in June and September to avoid the worst of the summer crowds.

9. Greece

Set sail through history when you cruise the islands of Greece, whether in the Saronic, Cyclades, or Corfu. You’ll positively marinate in antiquities when you visit islands like Delos, Spetses, and Hydra. You can also party in Mykonos, snorkel in the caves of Milos, or hike the hills of Kya. Each island is a world in itself.

The Cyclades serve up strong winds and long distances, so the sailing can be challenging, and you’ll need to be proficient with Med mooring at city wall docks. If that doesn’t sound fun, charter with a captain and crew on some fun boats, including the iconic gullets.

10. British Virgin Islands

There is not a more popular cruising destination in the world than the British Virgin Islands in the Leeward Islands of the Caribbean. The trade winds are predictable, the navigation is line-of-sight, and there are restaurants and bars on every island, so you’ll never be bored. Snorkel at the Indians, dive on the wreck of RMS Rhone, check out the caves at the Baths on Virgin Gorda, and enjoy a lovely beam reach to the remote island of Anegada.

There are more boats available for charter here than anywhere, and the sailing is so easy you can opt to be your own captain. Most of the time is good to sail the BVI but stay clear from August to October, which is the height of hurricane season.

Explore destinations without ever having to leave the water! Find your next trip at Destination Guides and other boating resources here.

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