Sailing


Aerial view of sailboats navigating the calm waters of Lake Michigan on a clear summer day.

8 great new sailboats worth watching in 2026

Boatsetter Team · Jul 22, 2026

Boat shows keep pushing sailboat design forward, and the 2026 lineup blends fast monohulls, spacious cruising cats, and one clever trimaran. Here's what's landing on US shores, what each one costs, and how owners are offsetting the price by chartering.

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Sailboat on the Hudson River with the New York City skyline as a backdrop.

Sailing NYC: your guide to charters and harbor tours

Boatsetter Team · Jul 22, 2026

New York looks different from the water. Under sail, the skyline slides past the Statue of Liberty and the Brooklyn Bridge at a pace that lets you actually take it in. Here's how to book a sailing charter, what it costs, and what you'll see along the way.

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Annapolis sailing charter guide: everything to know before you go

Boatsetter Team · Jul 21, 2026

Annapolis earned its nickname as America's Sailing Capital for good reason, and chartering is the easiest way to get out on the Chesapeake without owning a boat. This guide walks you through why the Bay sails so well, what a charter costs, and how to book one that fits your skill level.

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sailing lake michigan with captain Jim

How to Sail: A 20-Year Expert Shares How to Begin

Captain Jim · Feb 24, 2025 · Updated Mar 7, 2025

For veteran sailor and Captain Jim, sailing isn’t just a skill—it’s a lifelong passion that began with a childhood experiment involving an inflatable raft, two oars, and a beach towel. [...]

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Sailing in San Francisco Bay Guide

Zuzana Prochazka · Jan 28, 2025

It doesn’t get much better for diehard sailors than San Francisco Bay where the winds are almost always steady, and the water is (mostly) protected. Whether your next sailing expedition [...]

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best sailboat brands

15 Best Sailboat Brands

Zuzana Prochazka · Sep 24, 2024

When choosing a sailboat, the brand can make a big difference in quality, performance, and resale value. But picking the “best sailboat brand” means swimming through a lot of different [...]

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Small catamaran vs. Pontoon Boats

Ding, Ding, Ding: Small Catamarans vs. Pontoon Boats

Zuzana Prochazka · Oct 25, 2023

Both small power catamarans and pontoon boats are often called multihulls, but, depending on the day on the water you have planned for yourself, one will ultimately be better than [...]

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What to Pack for a Sailing Trip

Zuzana Prochazka · Sep 30, 2023 · Updated Feb 18, 2026

Packing the right gear and clothing for a sailing trip can make the difference between a great and miserable outing. Believe it or not, not all sailing is created equal. [...]

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How to Sail Against the Wind.

Sailing Explained: How to Sail Against the Wind

Zuzana Prochazka · Sep 18, 2023

Sailing is a beautiful and majestic sport. It’s pretty clear how a boat sails downwind with the breeze pushing against the sails, but have you ever wondered: how do you [...]

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Beaufort Scale Explained.

Beaufort Scale Explained: Understanding the Wind for Sailing

Zuzana Prochazka · Aug 28, 2023 · Updated May 24, 2024

The Beaufort Wind Scale is a measure of wind speed and accompanying sea state. It is an internationally recognized standardized model created by Irishman Francis Beaufort in 1806, who went [...]

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Budget to Buy a Sailboat.

How to Build a Budget to Buy a Sailboat

Zuzana Prochazka · Aug 28, 2023

Budgeting is key to financial soundness. It should come as no surprise when buying a new or used sailboat that setting a budget for yourself is the way to go! [...]

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Retiring on a Sailboat.

Retiring on a Sailboat: 5 Tips & Best Boat Types

Zuzana Prochazka · Aug 28, 2023

So you’ve reached the golden age of retirement— congrats! And you’re considering retiring on a sailboat? Smart move. It can be a rewarding experience, but before you pack up your [...]

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