For many of our Lykkers, the allure of sailing comes with the promise of adventure, the challenge of competition, and the serenity of the sea.

Yet, whether you're trimming the sails towards the sunset or racing against the wind, a sailor's journey is paved with critical tactical decisions.

Let's hoist the sails and delve into the sailing destinations that can make your sailing both joyous and triumphant.

The world's best sailing destinations

Dear Lykkers! Ready to set sail on the open seas? It's high time for an epic adventure, don't you think? But let's talk destinations—where's the ultimate sailing spot? Well, let us share some top-notch destinations that'll have you itching to hoist those sails and explore!

1.Chicago, Illinois

You can bet your bottom dollar that the "Windy City" is a prime spot for sailing, and let us tell you, a place as rich in history, diversity, and pride as Chicago is an absolute must-visit. Whether you're drawn in by the comedy clubs, the legendary deep-dish pizza, or simply soaking up the vibrant energy that pulses through every corner, Chicago pulls out all the stops to leave you in awe.

Sailing Destination:

Chicago Sailboat Charters

Chicago Sailboat Charters

Address: 2 W Belmont Harbor Dr, Chicago, IL 60657, United States

Open Hours: 8 AM- 11:30 PM

Official Site:

Contact Number: +1 773-236-7245

Booking: $249 (73% Off)


Experience the ultimate luxury sailboat adventure with Chicago Sailboat Charters' stylish 39′ cruisers where you are sure to create unforgettable memories on Lake Michigan.

What's Included:

-Up to 8 people

-Onboard Bathroom

-Beverage packages or BYOB

-Spacious interior

-Upgraded audio system


Not Included:

-Captain fees not included in the voucher price; Additional $150 fee.

-Gratuity of 15-20% of the retail cost, but of course at your discretion.

2. Key West, Florida

A hidden gem of a subtropical island paradise, Key West has attracted luminaries like Ernest Hemingway, and it's easy to see why. With its charming pastel-colored houses, lively nightlife, palm-fringed beaches, and playful dolphins frolicking alongside your boat, this city promises an unforgettable sailing experience in the US.

Sailing Destination:

Sunset Sail Key West

Sunset Sail Key West

Address: 202 William St, Key West, FL 33040, United States

Open Hours: 8 AM–10 PM

Official Site:

Contact Number: +1 305-587-4488

Booking: $109 Adults; Ages 13+ $45; Children Ages 3 - 12 • Must be accompanied by an adult

Duration: 2 Hours

Please Bring:

-Any necessary sun protection

-Appropriate weatherwear for the day - it can be cool on the water after sunset

Ahoy, Lykkers! As we chart our course through the vast expanse of the sea, it's clear that sailing offers not just adventure, but a fusion of excitement, competition, and tranquility. Whether we're navigating towards the sunset or racing against the wind, each decision shapes our journey.

From the historic charm of Chicago to the tropical allure of Key West, these destinations beckon with promises of unforgettable experiences on the waves. So let's unfurl our sails, embrace the thrill of the unknown, and embark on a voyage filled with joyous moments and triumphant adventures. Fair winds and following seas!