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

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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 when the travel bug catches you. (Boat holidays are certainly the safest travel option at the moment.)

If you are unsure where to start, here are eight of our favorite US sailing vacation destinations:

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

Discover the Best Places for Sailing in the US — 8 Amazing Boat Holiday Destinations

8. Sail in 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

You can see the skyline of San Diego, California, and a lot of boats anchoring in front of the city

7. Rent a boat in Newport, Rhode Island

This is a pretty picture of Newport, Rhode Island with the great skyline in the background and the lovely sandy, but rocky beach in the front

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

6. Sail along the Coast of 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

Key West in Florida is often considered one of the best places for sailing in the US and this picture shows you why. A lovely canal framed by palm trees and plenty of boats line the canal

5. Explore St. Thomas, US Virgin Islands, by Boat

The picture shows St Thomas, which is part of the US Virgin Islands and many mega yachts mooring at the marina. Framed by lush green mountainous landscapes and pretty pink flowers, it is a great destination for sailing in the US

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

4. Charter a Boat in 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.

This picture shows Annapolis in Maryland and has a strong resemblance to Amsterdam

3. A Yacht Charter in Fort Lauderdale, Florida, Awaits You

This picture shows the big marina of Fort Lauderdale with boats mooring side by side and showing the skyline and the blue water as well

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

2. Explore Los Angeles, California, by Boat

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

This picture shows one of the marinas in Los Angeles and you can see a lot of boats lining up here. With the skyscrapers and mountains in the background, it is a pretty sight during sunset as you can see

1. Rent a Boat in Chicago, Illinois

You can see the skyline of Chicago and many sailboats anchoring in front of it, clearly making it one of the best places for sailing in the US

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 Borrow A Boat 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.