Sailing holidays in the USA

Sailing holidays in the USA

The Ultimate Guide to sailing Annapolis, Newport, Lake Champlain

A sailing guide that has everything you need to know about your next sailboat charters in Newport, Annapolis, Lake Champlain.

An iconic yachting destination, America has a longstanding sailing tradition starting in 1851 with the first America’s Cup. Our three unique yacht charter destinations offer the best of United States sailing. 

Want to know more? Keep reading…

If you are familiar with USA and want to look at boat options for your next yacht charter, then:  Request a Tailor-made Quote for FREE!

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Sailing US Bases: Annapolis, Newport, Lake Champlain

Explore America’s “Sailing Capital”, Annapolis, where you can discover the many rivers, inlets, bays, and quaint coastal towns of the Mid-Atlantic egion.

Meaning “Great Shellfish Bay,” the Chesapeake Bay is ripe with crabs, oysters, and more!

Take advantage of the amazing seafood on your charter.

If you visit Newport you can immerse yourself in preppy, nautical New England culture.

Island hop between Aquidneck Island, Block Island, Nantucket, and Martha’s Vineyard for a classic New England sailing experience. Learn all about the history of yachting at the many sailing museums, or get transported back in time to the opulent Gilded Age on a Newport Mansions tour.  

Or, if you’d like something a little different head to upstate New York for an unforgettable boat rental in the USA, on Lake Champlain!

Surrounded by rural, forested mountains, you can enjoy long summer days spent hiking and swimming. Become one with nature, secluded from busy modern life. Slow down and enjoy the tiny towns and local restaurants and watering holes.

Best time to rent a boat in Annapolis, Newport or Lake Champlain & sailing conditions

Annapolis, Newport and Lake Champlain share fairly similar climates as they are all in the Northeast Region of the United States. 

This means that the best time to visit is over the summer months, between May and October.

July and August offer the warmest temperatures - ranging between 80-90°F (27-32°C), but will be the busiest. 

If you’re looking to escape the crowds, wait until school is back in session and catch the remaining summer weather in September and October, which often stay nice and warm.

Anytime after that won’t be much fun as winters in the Northeast tend to be very cold and blustery. 

Sailing conditions will differ a bit more than the weather from destination to destination. In Annapolis, you will find southerly or westerly winds of about 5-10 knots on average.

In Newport during sailing season, you will find the best wind in July, with winds reaching around 5 knots or so. Lake Champlain will have westerly winds that can reach up to 8 knots between August and December

Where to start sailing in the North America from & how to get there


As Maryland's capital, Annapolis is well-situated and very accessible. Being in such close proximity to Washington, DC also  helps. To get to Annapolis, we recommend flying into BWI Airport in Baltimore, or into Dulles International Airport in Virginia. These are both very large international airports that offer direct flights from both the UK and the EU.

You can also get to Annapolis from Washington, DC by train (3 hrs) or driving (3.5 hrs).

Time from BWI to Base - 40 mins by car

Time from Dulles to Base - 1 hr 20 mins by car



To start your boat rental in the usa in Newport, you should fly into either T.F. Green International Airport (PVD) or Logan International Airport (BOS). T.F. is the closer option, but a smaller airport with fewer international routes. Boston is a larger regional hub and might have more options for European and UK travellers. 

If you choose to fly into Boston, it is easy to get to Newport via car (1.5 hrs), or bus (3.25 hrs).

Time from PVD to Base - 30 mins by car

Time from BOS to Base - 2 hrs by car/shuttle  


Lake Champlain, NY

For your America sailing on Lake Champlain, you’ll want to fly into Burlington International Airport (BVT). Burlington has a fairly small international airport, with limited international routes, so you may want to consider flying into a larger regional hub like Montreal, Ottawa, or New York City. 

Time from BVT to Base - 10 mins by car

USA Boating Holiday Tips

In all three locations, Annapolis, Newport and Lake Champlain - night sailing is not permitted. 


If you are interested in fishing on an Annapolis yacht charter, a fishing or crabbing license is required. For provisioning, Yacht4Less recommends Giant Food, located about 1.4 miles from the base. You might also wonder about mooring on your charter, and in the Chesapeake you will rarely find mooring balls. You will likely need to book a slip at a marina or drop your anchor at an anchorage somewhere.


For mooring in Newport, there is an abundance of yacht clubs and marinas where you can “park” for the evening. For provisioning, try the Stop and Shop on Bellevue Avenue where you can find all the essentials you’ll need for your trip.     

Lake Champlain, NY 

It is important to note that while you do not have to account for the tides, you should be aware of any season changes in water level. Using a depth finder will help ensure you do not run aground! Finding an anchorage on Lake Champlain is a breeze. With few crowds, and a nice muddy clay bottom, you'll find good holding and secure, stress-free anchoring. Most mooring are private moorings that are not open to the public, however, if you’re looking for a more secure option than free-swinging, Burlington Harbor offers some public mooring pendants.

Recommended 7-day Sailing Itinerary from Annapolis

⚓ Day 1. Port Annapolis Marina to Herrington Harbour

⚓ Day 2. Herrington Harbour to Oxford

⚓ Day 3. Oxford to Cambridge

⚓ Day 4. Cambridge to St. Leonard Creek

⚓ Day 5. St. Leonard Creek to Solomon’s Island

⚓ Day 6. Solomon’s Island to St. Michael’s

⚓ Day 7. St. Michael’s to Port Annapolis Marina


Recommended 7-day Sailing Itinerary from Newport

⚓ Day 1. Newport to Cuttyhunk 28NM

⚓ Day 2. Cuttyhunk to Oak Bluffs, Martha’s Vineyard 28NM

⚓ Day 3. Explore Martha's Vineyard

⚓ Day 4. Oak Bluffs to Nantucket 30NM

⚓ Day 5. Nantucket to Menemsha Basin 49NM

⚓ Day 6. Menemsha Basin to Jamestown Island 39NM

⚓ Day 7. Jamestown Island to Newport (check out)


Recommended 7-day Sailing Itinerary from Lake Champlain

⚓ Day 1. Burlington to Valcour Island, New York

⚓ Day 2. Valcour Island to Willsboro Bay

⚓ Day 3. Willsboro Bay to Shelburne Bay

⚓ Day 4. Shelburne Bay to Burlington, Vermont

⚓ Day 5. Burlington to Mallets Bay

⚓ Day 6. Mallets Bay to Burton Island

⚓ Day 7. Roche State Park, New York to Burlington


Prices: How much does it cost to charter a yacht in the US?

It depends. For example, the most important ones are the type of boat you will choose and whether you require a professional crew on board (e.g. skipper, hostess or cook). So, as you can see, there are many factors that can shape a price for a boat rental.

Check our full guide about yacht charter cost and how you can save much money in your next sailing holidays.


Alternative sailing destinations nearby

Sailing holidays in Mexico

Sailing holidays in Brazil

Sailing holidays in Belize



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