From breezy U.S. ports to dreamy Mediterranean coastlines, these sailing spots are ready to sweep solo and social travelers off their feet and out to sea….in a good way!
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Why It’s Great: One of the most iconic U.S. sailing towns. Tons of public sailing charters, regattas, and harbor cruises.
Solo Tip: Join a small group sunset sail or a day cruise on a schooner.
Best Time to Go: June–September
Solo Selfie It! On deck at sunset with the Newport Bridge behind you.
Why It’s Great: Calm waters, whale sightings, and a relaxed sailing vibe.
Solo Tip: Join a women-only sailing retreat or book a spot on a small catamaran tour.
Best Time to Go: July–September
Solo Selfie It! With orcas in the distance and evergreen islands all around.
Why It’s Great: Caribbean vibes without leaving the U.S., plus lively sunset sails and reef snorkel trips.
Solo Tip: Join a day sail with Fury or Danger Charters for a casual social vibe.
Best Time to Go: November–May
Solo Selfie It! On a sailboat with a mojito and that famous Key West sunset.
Why It’s Great: Laid-back Pacific vibes, dolphin sightings, and wine-and-sail experiences.
Solo Tip: Great spot to try a sailing lesson or book a coastal cruise.
Best Time to Go: May–October
Solo Selfie It! Sailing by the coastline with the Santa Ynez Mountains behind you.
Why It’s Great: Island-hopping heaven with tons of women-only and solo-friendly group sailing trips.
Solo Tip: Companies like Girls Love Travel, Flash Pack, or Sail Week offer solo-friendly trips.
Best Time to Go: May–October
Solo Selfie It! Posing on deck with the white-and-blue backdrop of Santorini or Paros.
Why It’s Great: Affordable, beautiful, and full of group sailing options geared toward solo travelers.
Solo Tip: Join a cabin charter (like MedSailors or Yacht Week’s more chill spinoffs).
Best Time to Go: June–September
Solo Selfie It! On a sailboat anchored in a quiet cove near Hvar.
Why It’s Great: Unreal turquoise waters and dreamy, calm sailing conditions.
Solo Tip: Try a sailing catamaran tour with a few other travelers or book a learn-to-sail experience.
Best Time to Go: May–October
Solo Selfie It! Floating above a reef with your sailboat in the background.
Why It’s Great: Limestone cliffs, warm water, and island-hopping galore.
Solo Tip: Join a solo-friendly sailing tour like G Adventures or Intrepid Travel.
Best Time to Go: November–April
Solo Selfie It! On deck with the towering cliffs of Phang Nga Bay behind you.
Why It’s Great: Gorgeous coastline, charming ports, and fresh seafood after every sail.
Solo Tip: Opt for a small group charter or sailing + cooking tour (hello pasta at sea!).
Best Time to Go: May–September
Solo Selfie It! With the cliffs of Positano rising behind your sailboat.
