It is widely believed that Mark Twain said “Twenty years from now, you will be
more disappointed by the things you didn’t do than those you did. So, throw off
the bowlines. Sail away from the safe harbor. Catch the wind in your sails.
Explore. Dream. Discover.”
There’s just something special about sailing. The open
water, sunshine on your face, the wind in your hair and a total sense of
freedom, relaxation and centering, a perfect antidote to the stresses of living
in today’s modern world.
Whether you decide to be part of a crew manning the sails or
just along for the ride, we are so fortunate to have so many incredible
destinations here in the US to sail, whether it be a tranquil lake or riding the
ocean waves.
Newport, RI
Often referred to as the ‘sailing capital of the world,’
Newport offers a deep maritime history, ideal sailing conditions and an
important role in international competitive sailing. The coastal town hosted
the America’s Cup from 1930 to 1983 and continues to attract sailors from
around the globe to its annual sailing events.
Newport has been a longtime training hub for Olympic and
professional sailors, and there’s nothing like moving under the impressive
Newport Bridge, the longest suspension span in New
England.
Sailing on the Chesapeake Bay in Annapolis (Photo Credit: Noreen Kompanik)
Chesapeake Bay, Annapolis, MD
Sailing in Annapolis is a major part of the city’s identity,
other than being the location of the United States Naval Academy (USNA), where
future naval officers are trained in the art. Located where the
Severn River meets the Chesapeake Bay, the area offers easy access to both open
water and protected coves making it a sailor’s haven.
The bay’s deep navigable waters make it ideal for
recreational and competitive sailing and the destination hosts numerous sailing and regatta events and boat shows throughout the year.
Charleston, SC
This southern belle consistently ranks as one of the top
places in the US for sailing, offering incredibly picturesque views. With its
historic charm, great sailing conditions and a vibrant maritime culture, it’s
only natural that sailors want to be out on the water.
Charleston has some top-notch marinas and yacht clubs,
sailing schools and charters and the College of Charleston sailing team is
nationally ranked. My favorite time to sail is at day’s end with an impressive
combination of historic skyline, calm harbor waters and glowing sunsets over
the Charleston peninsula creating an unforgettable experience.
(Courtesy of Air Canada)
Florida Keys
The Florida Keys are home to the only barrier coral reef in
North America and the third largest in the world and sailing here is a
tropical dream. The Keys multi-hued waters, warm trade winds and laid-back
island culture make for a paradise without having to venture further into the
Caribbean with a passport.
Stretching over 129 miles from Key Largo to Key West, the
island chain with more than 800 keys offers so many places to sail, anchor,
dock and explore. Constant trade winds, shallow warm waters (especially on the
Gulf side) and easy access to snorkeling, diving and fishing right off the boat
make the Florida Keys a popular sailing destination.
Smathers beach at sunrise in Key West, Florida. (Photo Credit: aiisha / Adobe Stock)
Santa Barbara, CA
Known for its mild weather, rich maritime history,
picturesque coastline and vibrant sailing community, Santa Barbara is a haven
for sailors of all levels. Affectionately known as ‘The American Riviera,” this
jewel of the California coast’s mild winds, calm seas and near-constant
sunshine makes for picture-perfect sailing conditions.
Those into competitive sailing can join in the adventure on
Wet Wednesday races at the Santa Barbara Yacht Club, a beloved tradition in the
sailing community. The region also hosts several regattas and sailing festivals
throughout the year.
SunSwept Kelpie Harbor Fest Santa Barbara (Photo Credit: SunSwept Sailing and Visit Santa Barbara.)
Finger Lakes, NY
This region consists of 11 glacial lakes and one Great Lake
(Ontario) making it a superb destination for the sailing fan. Visitors can choose
from a number of sailing companies or use private charters such as Sail True
Love out of Watkins Glen and Sail Seneca from Geneva.
The lakes are long and narrow creating consistent and
moderate wind channels that funnel down the length of the lake, making for
reliable sailing conditions. Many of the Finger Lakes are deep and clear, good
for keelboats, helping to avoid hazards like submerged rocks or sudden shoals.
And it’s hard to beat the views with waters surrounded by hills, vineyards and
charming small towns.
True Love Sailboat, Watkins Glen, Finger Lakes (Photo Credit: True Love)
San Diego, CA
America’s finest city as it’s often called is home to almost
year-round picture-perfect weather, reliable winds and a stunningly picturesque
and protected sheltered bay with easy access to the open Pacific.
San Diego has a long naval and maritime history which means
sailors will not only get great views of the city, Embarcadero and Coronado Island
from the water, but also a myriad of US Navy ships. It’s also a great chance to
view gray whales, blue whales, dolphins and a slew of various seabirds.
With its vibrant racing and cruising community and notable
yacht clubs, this Southern California gem is a true sailor’s city.
San Juan Islands Washington (Photo via Noreen Kompanik)
San Juan Islands
Located in the Pacific Northwest, the San Juan Islands with
over 170 islands and reefs are a hidden gem for sailors seeking peaceful tranquility
while surrounded by stunning landscapes and quiet coves. Yet they are still considered
one of the top sailing destinations in the region.
Situated in the rain shadow of the Olympic Mountains, the
islands offer calmer seas, less wind and rain than the outer coast, ensuring smoother, safer sailing. Sailors regularly spot seals, sea lions, porpoises, bald
eagles and orcas, especially around San Juan Island.
San Francisco, CA
An individual sail might be a challenge here unless you’re a
skilled sailor or racer due to the bay’s strong winds and currents. However, there
are plenty of opportunities to get out on the water by a guided catamaran.
Seeing the City by the Bay skyline via water is a rewarding
experience, sailing beneath one of the world’s most recognizable bridges and
past the haunting site of the abandoned Alcatraz Island. You’ll encounter calm
waters turning gusty, choppy and tide-driven, but it’s all part of the fun. The
city hosts world-class regattas including the America’s Cup and SailGP events.
Sailing in St. Thomas, USVI (Photo Credit: Noreen Kompanik)
US Virgin Islands
Sailing the cerulean waters of the US Virgin Islands
provides an exhilarating, authentic Caribbean experience without needing a passport.
It’s best to hire a boat captain for the day or take a catamaran sail as you
would need a passport to enter British Virgin Island waters.
The three islands making up the US Virgin Island chain are
only a few miles apart making for easy navigation and line-of-sight sailing. Warm
water temperatures and steady trade winds make for nearly perfect sail conditions
and the crystalline waters with their colorful, stunning coral reefs and
tropical fish make for amazing snorkeling or diving conditions.
For the latest travel news, updates and deals, subscribe to the daily TravelPulse newsletter.
