Cooler temperatures, fewer crowds, and stunning foliage make Autumn a breathtaking season to set sail. It doesn't matter whether you're cruising the lakes of the northern U.S. and Canada or enjoying the Caribbean's warmer waters; these fall sailing destinations offer something for every sailor.
Top 10 Best Fall Sailing Destinations
Wondering where to go sailing in the fall? We recommend starting here:
1. Newport, Rhode Island
Known as the "Sailing Capital of the World," Newport, Rhode Island, should be on every sailor's bucket list. This historic town is renowned for its rich maritime history and seaside charm. Fall is a wonderful time to visit, as the coastline is full of gold, orange, and crimson hues.
The cooler temperatures and lesser traffic make Autumn an ideal time to explore the coastal lighthouses, scenic cliffs, and famous Newport mansions.
2. San Juan Islands, Washington
The San Juan Islands are a group of over 170 islands nestled in the Pacific Northwest. More specifically, you'll find them between Washington state and Canada in the Salish Sea. They are beloved for their calm waters, scenic harbors, and impressive wildlife – visitors often spot orcas, sea lions, bald eagles, and more.
The calm, predictable winds and peaceful anchorages make Autumn sailing in the San Juan Islands particularly enjoyable. After a day on the water, we recommend docking in one of the charming seaside towns to enjoy some fresh, local seafood.
3. Thousand Islands, Ontario
Located on the St. Lawrence River, Ontario's Thousand Islands region offers some of the best fall sailing in North America. Essentially, it's a maze of over 1,800 islands — some privately owned, but others accessible to sailors — and fall is the perfect time to navigate them.
Sailors can explore secluded coves, historic lighthouses, and castles while taking in the beautiful fall foliage.
4. U.S. Virgin Islands, Caribbean
Do you prefer tropical waters and warmer temperatures? The U.S. Virgin Islands is the fall sailing destination for you. Although the weather is enjoyable year-round, peak tourist season ends with summer. If you're looking for crystal clear waters, beautiful beaches, and vibrant coral reefs, we recommend sailing between St. Thomas, St. John, and St. Criox.
5. Block Island, Rhode Island
Nestled just 13 miles off the coast of Rhode Island, Block Island is a sailor's paradise. While it's a popular summer vacation destination, the island quiets down in the cooler months – offering a peaceful escape for sailors. And the many rolling hills and bluffs are even more breathtaking with their fall foliage.
Additionally, Block Island has tons of charming inns, quaint restaurants, and historic lighthouses to explore.
6. Chesapeake Bay, Maryland/Virginia
Not only is the Chesapeake Bay one of the largest estuaries in the U.S. but it's known for its rich maritime history. Plus, Autumn in the Chesapeake Bay offers cooler temperatures and stunning landscapes.
Need help figuring out where to stay? We recommend Annapolis, St. Michaels, or Oxford. (Note that the Annapolis Boat Show happens every October – if that's something you're interested in.)
7. Georgian Bay, Ontario
Georgian Bay — also known as the "Sixth Great Lake"— is one of Canada's premier sailing destinations. It has over 3,000 islands for sailors to explore – many belonging to the UNESCO Georgian Bay Reservoir. And like so many other fall sailing destinations, it truly comes to life in Autumn. Fall sailors can expect peaceful waters, abundant wildlife, and minimal company.
8. The Florida Keys, Florida
This string of tropical islands offers beautiful sailing conditions year-round. They're situated about 120 miles off the coast of Florida, connected by the scenic Overseas Highway. And with crystal clear waters and abundant coral reefs, the Keys boast some of the most idyllic sailing conditions in the U.S.
The journey from Key Largo to Key West offers a blend of vibrant nightlife, historic sites, and natural wonders. The protected anchorages and well-marked channels make it accessible to sailors of all skill levels.
Check out our Florida Keys Boating Guide for more info.
9. Lake Champlain, Vermont
On the border of New York and Vermont, Lake Champlain is one of the most picturesque fall sailing destinations. Sailors flock to it for its sparkling waters, rolling hills, and colorful fall foliage. Additionally, Autumn is an ideal time to explore, as the summer crowds have left and the lake becomes a tranquil oasis. With a backdrop of the Adirondack and Green Mountains, this serene sailing sanctuary should be on every sailor's bucket list.
10. Outer Banks, North Carolina
The semi-protected waters of the Outer Banks make for an ideal fall sailing excursion. There are hundreds of bays and coves to explore, and the charming coastal towns are full of quaint restaurants and shops. Personally? We recommend exploring Pamlico Sound for fall fishing and leaf-peeping.
Where to Sail in the Fall
Whether you're looking for fall foliage, serene lakes, or tropical paradises, these fall boating destinations have you covered. From the breathtaking landscapes of the Northeastern U.S. and Canada to the sparkling waters of the Caribbean, Autumn is the perfect time to set sail and explore these beautiful waterways.
