The 10 Best Places for Sailing in the USA

Last Updated on January 22, 2024 by Nikki Jain

Whether you’re recreational or a racer, it’s no secret that sailing is a spectacular sport. There’s nothing like the feeling of gliding across the water while the wind whips around you. The right conditions are just as important as the right boat for a successful day on the water, and a nice view doesn’t hurt, either.

There are endless opportunities for sailing around the United States, from private and public charters to the joy of owning a boat and taking it out on the water as you please. Regardless, the best sailing conditions and locations are important to enjoying a day at sea.

Let's take a look at the top sailing destinations in the US.

Best Places to Sail in the US

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1: Newport, Rhode Island

Newport, Rhode Island
Flickr/U.S. Naval War College

As a sailing capital of the world, Newport is one of the United States’ favorite spots to sail. With all its offerings, Newport has something for everyone when it comes to sailing. Not only it is home to Sail Newport, New England’s largest public sailing center, but it also houses the country’s largest fleet of America’s Cup 12-meter yachts, which you can schedule to charter.

Every summer as the warmth rolls in, visitors to Newport will see hundreds of beautiful sailboats sailing through the harbor. Nestled on the southern edge of Aquidneck Island with ocean access through Narragansett Bay, Newport’s location provides the perfect breezy spot for sailors.

If you don’t have your own boat or a newbie to the world of sailing, locals offer a variety of sailing adventures, from cruises to private charters. There are also a few sailing schools in the town where you can learn the basics.

Address: Newport, RI

2: Maui, Hawaii

Maui, Hawaii
Flickr/Giles Douglas

Imagine sailing through the ocean with a palm tree-lined island behind you, lei necklaces around your neck, and a colorful sunset lining the horizon. You can’t beat a day on the water in the Hawaiian Islands, and Maui provides year-round sailing and water excursions for visitors and locals. Sitting between two mountains, this island is known as “The Gathering Place.”

This Pacific island is a tourist hot spot, so numerous sailing companies offer private and public charters, sailing excursions, and lessons for sailors of all abilities. Some sailing teams even offer packages that include snorkeling and whale watching to create an unforgettable Hawaiian vacation.

The waters are calmer in the evening if you want a more relaxing sail while you watch the sun set over the horizon. The weather is always warm and sunny in Hawaii, so year-round sailing is popular here.

Address: Maui, HI

3: San Juan Islands, Washington

San Juan Islands, Washington
Flickr/Sean O'Neill

This scenic destination in northwest Washington state is a favorite for sailors to explore and enjoy. The climate stays temperate year-round, with 70-degree averages in the summer and 40s in the winter, making it one of the top US spots to sail for the spring, summer, and fall. Located off the state’s coast past Bellingham Bay, it offers an unforgettable getaway.

The San Juan Islands is a sailing mecca for the Pacific Northwest, and because of that anyone can charter boats or take courses in sailing. From weekend and week-long instruction to women’s classes and private instruction, sailing organizations here have everything you need for a successful trip.

If you’re a beginner at sailing, it’s recommended to visit in the spring, when the winds are ideal for learning. In the summer, the islands offer beautiful hiking and explorations that sailors like to stop and enjoy.

Address: San Juan Islands, WA

4: Key West, Florida

Key West, Florida
Flickr/Joshua Duggan

If you’re looking for a year-round sailing destination in the US, Key West is the place to go. The Florida Keys provide a getaway from the mainland United States. This island city is a favorite for tourists, so local companies offer everything from charters and tours to lessons and private sails.

The nearby reefs are a sailors’ favorite destination, especially during the summer when it’s most visible, and the gorgeous year-round Florida weather can’t be beaten. The best time for sailing is from January through April, when the wind is strong. Hurricane season begins in June and ends in November, so plan accordingly and watch the Atlantic weather patterns!

Address: Key West, FL

5: Apostle Islands, Wisconsin

Apostle Islands, Wisconsin

Comprised of 22 islands scattered in Lake Superior, the Apostle Islands is a beautiful, scenic spot if you are far from the ocean but still want to enjoy great sailing conditions. The protected bays and natural beauty provide some of the best sailing opportunities. Visitors can book multi-trip sailing adventures around the islands or take a private yacht out onto the water.

Locals can join the Apostle Islands Yacht Club and join a community of avid sailors and pay to store and launch their boats. One of the lakeshore’s most popular attractions is its sea caves that you can sail right into and stop for a swim. The sunsets at Apostle Islands are also unforgettable, especially as you’re sailing through the calm evening waters.

Weather in the Apostle Islands can change drastically, and wind shifts, fog, and sudden storms are frequent. If you adventure here, continually monitor the marine and weather forecasts during your trip.

Address: Apostle Islands, WI

6: Grand Haven, Michigan

Grand Haven, Michigan
Flickr/Rachel Kramer

This moderately sized city sits on the shores of Lake Michigan. It’s a tourist destination popular for its scenic Great Lake beaches and historic lighthouses. It’s known as a boater’s paradise, and lake lovers of all types hop aboard schooners, yachts, and powerboats to enjoy the great conditions Lake Michigan has to offer.

The area features several bayous, where locals sail and tie up their boats to swim and enjoy each other’s company. The sunsets on the lake are also a must-see as you sail across the endless waters.

The weather conditions in the area allow boaters to enjoy a five-month season, but the water gets frigidly cold at night, especially as fall approaches. You’ll see many sailors dressed warm clothes to protect themselves from cold winds and low temperatures.

Address: Grand Haven, MI

7: Bellingham Bay, Washington

Bellingham Bay, Washington
Flickr/Jerry McFarland

If you’re visiting the San Juan Islands, you’ve most likely accessed them through Bellingham Bay, but this Pacific Northwest bay is more than just a place to pass through for greater adventures. Bellingham Bay itself is a beautiful recreational area.

The bay’s strong winds provide great sailing conditions and Mount Baker in the background creates breathtaking views as you whip across the salty water. The Community Boating Center offers rentals and classes for those looking to brush up on boating and sailing. You can also book day-long and multi-day sailing trips for the ultimate adventure.

The month of June is one of the best times to sail in the area, as the winds are around 7 knots, which is near-perfect sailing conditions. Like the San Juan Islands, the spring brings the best weather for beginners.

Address: Bellingham Bay, WA

8: Santa Catalina Island, California

Santa Catalina Island, California
Flickr/Alfonso Andrada

Sail southwest of Los Angeles to find Santa Catalina, a quaint channel island that has become of the United States’ best places to sail. With beautiful white sand beaches and the bluest waters, you’ll quickly forget that smoggy, busy Los Angeles is just a boat ride away.

The island’s city of Avalon houses a lot of the island’s mooring rentals. There are also small bays available to anchor at. The island is also home to several yacht clubs, and visitors can book public and private charters for their enjoyment.

Santa Catalina Island is best visited in the spring and fall when the weather and marine conditions are most temperate. Southern California summers are often overcast until late afternoon, and winter storms can create choppy waters.

9: Oriental, North Carolina

Oriental, North Carolina

On the east coast, this small North Carolina town nestled on the Neuse River has been home to one of the best spots to sail for years and has become known as “The Sailing Capital of North Carolina.” The year-round warm weather brings boaters of all kinds throughout the year.

As a sailing destination in the US, regattas are held nearly every month of the year. Many Oriental residents are avid sailors of all levels. There are also classes and charters available if you need a refresher or a boat.

Address: Oriental, NC

10: Hudson River Valley, New York

Hudson River Valley, New York
Flickr/Bill Benzon

The Hudson River Valley stretches from Westchester County to Albany. Famous for vineyards and orchards and quaint New York living, it’s also a sailing hot spot with miles and miles of a wide river with the perfect winds for boating. If you don’t have your own boat, you can book day-long or sunset charters to sail the river and sightsee from the water.

The region is known for its breathtaking views and fresh air away from bustling New York City. There are also sailing classes available. With the quiet waters away from oceans and Great Lakes, the Hudson Valley is the perfect place to learn to sail.

The river stretches up the state, but you can make your way to New York City to take in the city’s skyline from the harbor. The best time to visit the region is between late April and late October when the sailing season invites hundreds of sailors and boaters.

Address: Hudson River Valley, NY

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