Boat Rentals, Charter Boat Rentals, and Yacht Rentals on Sailo (2024)

Embark on a unique aquatic adventure in the heart of the Windy City with Chicago captained boat rentals. Sailo is here to provide you with an unforgettable boating experience, offering a range of captained boat rentals in Chicago that cater to both enthusiastic sailors and those new to the joys of boating. Our approach is friendly and direct, ensuring your journey along Lake Michigan and the Chicago River is not just about renting a boat, but about enjoying a memorable day on the water.

Chicago's stunning skyline and historical waterways make it a prime destination for yacht charters. With our Chicago yacht rentals, you have the opportunity to see famous landmarks like Navy Pier, the Magnificent Mile, and the Chicago skyline from a unique perspective. Whether you're looking to rent a yacht in Chicago for a leisurely cruise, a special celebration, or an exciting day out, our fleet will provide you with the perfect vessel for your needs.

When you hire a captained boat in Chicago, you're choosing a stress-free way to enjoy the city's waterways. Our experienced captains are knowledgeable about the best routes and spots, ensuring your trip is safe, enjoyable, and tailored to your preferences. Whether you’re seeking a peaceful afternoon sail or an adventure-filled day, our captains are ready to guide you through an amazing boating experience.

Our premium selection of private captained boat rentals in Chicago

At Sailo, we offer a premium selection of private captained boat rentals in Chicago. Our fleet includes a variety of boats, from luxurious yachts to cozy sailboats, all equipped with the amenities needed for a comfortable and enjoyable voyage. Whether planning an intimate outing or a large gathering, we have the perfect boat to match your occasion.

For those seeking a more personalized and exclusive experience, our captained boat charters in Chicago are the ideal solution. These charters provide the luxury of a private vessel with the added convenience of a professional crew, allowing you to relax and enjoy your time on the water. Chicago captained boat charters are perfect for special events, offering a unique and elegant way to celebrate on Lake Michigan or the Chicago River.

How to find a captained boat rental in Chicago

Finding the perfect captained boat rental in Chicago is easy and convenient with Sailo. Our user-friendly platform allows you to browse through our diverse fleet and select the boat that best fits your needs. You can filter your search by boat type, size, and additional features, making it simple to find your ideal match for a fantastic day at sea.

How much does it cost to charter a captained boat in Chicago for a full day?

The cost of chartering a captained boat in Chicago for a full day varies based on several factors, including the type of boat, its size, and the duration of the rental. Prices can range from a few hundred dollars for smaller vessels to several thousand dollars for larger, more luxurious yachts. It’s important to consider additional expenses like fuel, docking fees, and optional services like catering or special equipment.

When budgeting for Chicago captained boat charters, remember to consider the entire experience. This includes any extra amenities or activities you wish to include, ensuring that your day at sea is as enjoyable and seamless as possible. Our team at Sailo is committed to providing transparent pricing and will help you understand all the costs involved in your boat rental.

Can I rent a captained boat charter in Chicago with a captain?

Yes, you can! Renting a captained boat charter in Chicago with a captain is the best way to enjoy a stress-free and delightful day on the water. Our captains are experienced navigators and knowledgeable guides who can enhance your boating experience. They know the best spots for sightseeing, exploring the city's architectural marvels, or simply relaxing. With a captain on board, you can fully immerse yourself in the experience without any concerns about operating the boat.

Discover the beauty of Chicago with:

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Rent a boat near Chicago

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Boat Rentals, Charter Boat Rentals, and Yacht Rentals on Sailo (2024)

FAQs

How much is it to stay on a sailing yacht? ›

(If the yacht has a celebrity owner, well that too, can add to the cost.) Therefore, yacht charters have a wide range of base prices. That's why charters can cost from $10,000 per week on smaller sailing yachts and catamarans, up to $150,000+ per week on the most luxurious motor superyachts.

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Are yacht charters worth it? ›

Instead of having to hire your own crew and pay their salaries – whether you set foot on your boat or not – a boat charter lets you simply enjoy the use of your preferred boat, captain and crew included. In fact, you can customize your entire experience based off of your crew expectations.

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What is the difference between charter and rental boat? ›

Rentals are typically priced by the hour or day, and the price varies based on the size and type of boat. Additionally, you will need to consider fuel costs, security deposits, and insurance fees. Charters, on the other hand, are usually priced per trip and include the services of the crew.

How much does it cost to rent a yacht for a few hours in Miami? ›

The average cost of a charter in Miami is $2,200. Renting a yacht can cost as little as $500 for a half-day and as much as $15,000 - $20,000 for a full day.

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How much does it cost to rent the boat on below deck sailing? ›

Below Deck Yacht Rental Costs

Hiring a yacht from Below Deck isn't cheap. The majority cost in the neighborhood of $150,000 per week. Yet, that charter rate doesn't include expenses, including fuel, dockage fees, and taxes. Yet, for that price, you'll get a truly world-class experience.

What is the most expensive yacht to charter? ›

1 – LADY JORGIA (EX AHPO) yacht for charter – from 2.6 million Euros per week. The 115-metre LADY JORGIA is considered the world's most exclusive charter yacht, priced at a cool 2.6 million Euros per week.

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Where is it cheapest to charter a yacht? ›

Croatia is still considered among most affordable sailing destination on Mediterranean sea, where you can find best deals on bareboat yacht charters.

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Is yacht charter all inclusive? ›

The short answer is yes! All-inclusive yacht charters are available, but the majority operate in just a few charter destinations in the world.

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Are yacht charter rates negotiable? ›

The charter fee may also fluctuate depending on the period of your yacht rental. Some yachts have high and low season rates. Obviously, the charter fee tends to be higher and less negotiable in the summer peak season as there is much more demand.

How much is it to charter a yacht for a week in the Caribbean? ›

For motor yacht rentals in the Caribbean, prices can range from $39,167 to $1.4m per week, plus expenses. For luxury sailing yacht rentals in the Caribbean, prices can go from $29,855 to $276,495 weekly, plus expenses.

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How much is it to rent a yacht for a week in the Bahamas? ›

The average cost for a weekly catamaran rental in Nassau is $14800 (mandatory extras and service fees not included). Your total budget when you rent a yacht for a week from Nassau can start at as low as $4500 for an exciting adventure for your family or friends in the friendly waters of The Bahamas.

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How much does it cost to charter a boat from Miami to the Bahamas? ›

Motor yacht from Miami to the Bahamas

On average we can say that the average weekly cost of a 100-foot sailing yacht is between $ 50,000-100,000 while for a motor yacht of the same size it is between $ 50,000 and 80,000.

How much does it cost to live full time on a sailboat? ›

I estimate that our monthly spending (including marina fees, entertainment, boat work, food, wifi, phone, laundry, etc.) is around $1800 – $2000. But you CAN do it on a lot less, and I know people who spend a lot more.

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How much is a live aboard sailboat? ›

On average, you can expect annual costs to fall within the $10,000 to $50,000 range, but let's break it down: Purchase Price: The initial cost of the boat itself can vary significantly. Smaller, used sailboats might start around $10,000, while larger yachts can soar into the millions.

Is it cheap to live on a yacht? ›

Living on a boat can be cheaper than living on land. This is because you save money on certain items like rent and car payments.

Can you permanently live on a yacht? ›

It's easy to romanticize the idea of living on a boat full-time; however, it's an alternative lifestyle like that takes preparation, organization and an ability to roll with changes. When you commit to moving aboard, make checklists of necessities and talk to your partner about deal-breakers.

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