The Best Places for Sailing in the US: 8 Amazing Holiday Destinations

Best Places for Sailing in the US

With international leisure travel largely (if momentarily) off the table, many Americans are wondering what do and where to go for vacation. Here’s an idea: why not explore the beautiful and inimitable USA on an amazing boat holiday? A safe, domestic travel vacation on a private boat in one of the best places for sailing in the US might just be the perfect remedy for the travel bug in the current situation. (Boat holidays are certainly the safest travel option at the moment.)

If you’re not sure where to start, here are eight of our favorite US sailing vacation destinations:

  • Sand Diego, California
  • Newport, Rhode Island
  • Key West, Florida
  • St. Thomas, US Virgin Islands
  • Annapolis, Maryland
  • Fort Lauderdale, Florida
  • Los Angeles, California
  • Chicago, Illinois

Discover the best places for sailing in the US — 8 amazing boat holiday destinations

San Diego, California

Good vibes and awesomeness shine day and night” promises the city’s tourism board — and boy, does San Diego deliver with its diverse and virtually endless offerings of exciting attractions, engaging activities, and of course, exquisite sailing conditions.

Charter a yacht in San Diego

san diego sailing usa

Newport, Rhode Island

newport sailing boat

Brimming with quaint New England charm and boasting dramatic craggy shorelines, the “Classic Coast” is perfect for both lovers of a good old-fashioned Colonial American atmosphere and modern sailing enthusiasts alike.

Boat rental in Newport

Key West, Florida

An offbeat subtropical island paradise that has lured in the likes of Ernest Hemingway, Key West has an undeniable appeal: from its striking pastel-hued houses to its electric nightlife, palmy beaches, and friendly dolphins that’ll keep your boat company, the city makes for a fantastic US sailing trip.

Yacht charter in Key West

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St. Thomas, US Virgin Islands

st thomas sailing yacht charter

Yes, you absolutely can have an ultra-relaxing Caribbean vacation while remaining in the US. The most cosmopolitan of the US Virgin Islands, St. Thomas is still the perfect place to unwind with its emerald-green golf courses and sunsets so pretty, you’ll think you’re in a painting.

Boat rental in St. Thomas

Annapolis, Maryland

In the heart of the Chesapeake Bay, Annapolis not only has a rich and world-renowned sailing tradition, it’s also a popular haven for leisure travelers who come to spend time on the water, take in the history, and feast on the sweet and tender delicacy that is the famous Maryland blue crab.

Book a boat in Annapolis

annapolis usa sailing

Fort Lauderdale, Florida

sailing in the usa fort laudardale

Beyond the gold-sand beaches and nearly year-round sunshine, Fort Lauderdale has lots going for it to make it a top US sailing destination — not least of all, the city’s totally unique travel experiences, including a live mermaid show and nighttime tours of the Everglades.

Yacht charter in Fort Lauderdale

Los Angeles, California

LA needs no introduction, but here’s one anyway: glorious weather, star-studded beaches, iconic landmarks, and one of the most diverse culinary scenes in the world — plus a million other reasons to visit — make the City of Angels a US cultural hot spot and brilliant sailing holiday destination.

Rent a boat in Los Angeles

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Chicago, Illinois

chicago sailing yacht

You just know that the “Windy City” is going to be great for sailing — and you can be sure that a town as historic, eclectic, and proud as Chicago is well worth a visit. Whether you’re in it for the comedy clubs, the deep-dish pizza, or simply the unique energy that the whole city buzzes with, Chicago does not disappoint.  

Charter a yacht in Chicago

Never sailed before? That’s no reason to not explore one of the best places for sailing in the US

If you’ve never considered a sailing holiday before, it might seem a bit intimidating — but it doesn’t have to be! Making it easy to book a great boat holiday deal is what Zizoo is all about. Plus, you’ll find plenty of helpful sailing guides right here in the magazine, including tips on how to choose the right boat and a comprehensive sailing checklist.

So you’ve got nothing to worry about and plenty to get excited about as you plan your amazing sailing holiday in the US.