san juan sailboat rental

Welcome to San Juan Sailing

Rated #1 in the world by the readers of Cruising World in customer service and in charter value. We don't try to be the biggest...but we passionately want to be the best.

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One of the most experienced, well-respected sailing schools in the Northwest and accredited by the internationally recognized American Sailing Association.

With over 40 years of experience and 55 well-maintained sailboats and powerboats, our passion is to provide the very best bareboat charter vacation possible.

Our brokers have logged a lot of sea time. They understand boats, value, and the individual client needs. Most of all, whether you are a seller or a buyer, they deliver.

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T. 360-671-4300 (charter) | T. 360-671-8339 (school) | T. 360-671-0829 (brokerage)

2615 South Harbor Loop, Suite 1, Bellingham, Washington 98225

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Sail the San Juans

Make a Reservation (800) 729-3207

Relaxing 6 and 12 day sailing adventures aboard Northwind!

Humpback whale encounter...

Afternoon nap...

Northwind's elegant salon.

Sailing with a pod of resident orcas.

Gourmet cuisine by Chef Jette.

San Juan Islands Sailing Charters and Cruises

We provide yacht and crew. you relax and enjoy., the art of slow travel.

Something special happens when we cast off the dock lines and head out into the San Juan Islands on a sailing charter. We become aware of the rhythm of the tides, the wind filling the sails, the salty sea air, and the porpoise following in our wake. The hidden coves and diverse marine life of the San Juans beckon us to make discoveries and submerge ourselves in its delightfully relaxed pace.

So much of the world passes by without our being able to see, touch, or feel it. A sailing charter through the San Juan islands allows us to take a moment to slow down and experience it for ourselves.

We have been perfecting the art of “slow travel” for over 25 years. Our new 55′ sailboat Northwind , offers a luxury yacht charter experience for up to six guests in private staterooms with ensuite baths. Each one of our San Juan Sailing Charters and Inside Passage cruises are one of a kind, designed for your group from the ground up. From your preferences on food and drink , to where we go and what we see and do, the result is a perfect blending of islands, yacht, crew, and cuisine. It’s your perfect vacation, Sailing the San Juan Islands in style.

 This is what a carefree sailing vacation is all about

Sailing the san juan islands.

Captains Jette & Jon Baker, with TailR

A fully crewed sailing charter with Sail the San Juans is a world away from any vacation experience you probably have ever had. A sailboat charter aboard Northwind  will open a door to see and experience the more remote islands and coves that are not easily accessible to most people.

At the same time, sailing yachts are in a unique position to be less intrusive to marine mammals which helps encourage encounters with Orca, seals and porpoise.

A sailboat charter with Sail the San Juans is a first class experience, from our impeccable yacht and crew to your private chef’s menu built around your preferences.

Join us to explore over 200 forested islands, help trim the sails on Northwind, or just relax while you savor gourmet fare , and great hiking and kayaking through protected bays and inlets.

This is the art of slow travel.

Request our 16 Page Full-Color Brochure

Two booking options

Private Charters: Groups of up to six people receive exclusive use of the sailboat for their group.

Join A Cruise: Reserve a stateroom for two, and let us take care of filling the other cabins.

Learn more about Booking Options and Rates

Two unique island cruises

San Juan Islands:  These six day sailing trips cruise through the San Juan Islands, an enchanting archipelago of hidden coves, abundant wildlife, and forested islands located in the sheltered inland waters of Washington State.

Learn more about San Juan Islands Sailing Charters

The Inside Passage: These twelve day wilderness sailing trips cruise through the southern portion of the Inside Passage, an area rich with native culture, mountain vistas, fjords and waterfalls located in British Columbia.

Learn more about Inside Passage Sailing Charters

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Trip duration, multiple days (less than 1 week), weekly trip show boats that have weekly prices. most weekly boats outside of the us are available only saturday to saturday., boat length: 5ft -, manufacturer, boat build year: -, weekly trip, price: $ - $, 40 boat rentals in san juan, puerto rico: yacht charters.

In addition to the best offers we have for boat and yacht charters in San Juan, Puerto Rico, see also options available for rent in these nearby locations:

• 39 boat rentals in San Juan, Puerto Rico
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Rent a Private Boat Charter in San Juan with Sailo

Looking for a boat rental in San Juan, Puerto Rico? With Sailo, you’ll find a great choice of private boat charters in San Juan, Puerto Rico for everything from a day trip through to a longer sailing vacation. If you’re visiting old San Juan boat tours with friends or family, you’ll find ample choice to try San Juan water tours with Sailo. Step aboard your own private boat charter in San Juan Islands and discover this amazing sailing location!

Our prime selection of private yacht charters in San Juan, Puerto Rico

Want to rent a boat in San Juan, Puerto Rico? You’ll find 3 boats waiting for you to take them on an adventure here on Sailo. Choose from our line up of TOP San Juan sailboat charters . Prefer catamarans? No problem…. Sailo currently has catamaran rentals in San Juan . Want to see Puerto Rico in style? One of our motor yachts in San Juan will fit the bill. If you’re planning a big party or event with over 12 people, you can also choose from our party boats in San Juan for an incredible day on the water.

How to find the right boat cruise among San Juan yacht charters

Renting a boat in San Juan, Puerto Rico has never been easier! When searching for a boat rental in San Juan, make sure to include your dates, trip duration and number of guests to get a first accurate selection of available charters. Daily experiences last for 2, 4 hours or a full day. You may further personalize your results by choosing the type of boat you’d like to rent, your price range and whether you want to hire a captain or you’re interested in a bareboat. Click on the boat rides in San Juan you like to get to the next page where you can view more photos, read the boat description and the reviews to see if it's the right fit for your old San Juan boat tours. You can always message the owner if you have any questions about their boat or you want to make special arrangements.

How much does it cost to rent a boat in San Juan, Puerto Rico for a day?

The best Sailo deal for daily boat rentals in San Juan, Puerto Rico starts at $250. The average price for a daily San Juan boat cruise is $1100, making it the best choice for a private sunset cruise, a sightseeing tour or an action-packed day on the water with family or friends! For those of you who are looking to splurge, check out our luxury yacht charters in San Juan with prices up to $6500 (service fee and mandatory extras not included).

San Juan Island boat rentals: Do I need a licence to rent a yacht on Sailo?

No, you do not need a license to charter a yacht in San Juan Island on Sailo as long as you are renting a boat with a captain included. There are two types of boat tours in San Juan, Puerto Rico available on our website: bareboat and captained charters. If you rent a bareboat yacht, then your charter comes without any crew, and you or someone in your group will need a license. The boat owner will require you to upload the boating resume or license of the person who will drive the boat. Most of our boat owners might also like to test your boating skills before you take your bareboat charter out on the water. When you charter a yacht in San Juan with a captain included or add the captain and/or crew as an extra to your sailing adventure, then a certified skipper will be provided.

Responsible boating guidelines

However long you’re on a boat, it’s always a thrilling and fun experience. Here at Sailo, we like to make sure that the stunning beauty of the seas, lakes and rivers of our planet stay as pristine as possible. If you’re going to charter a yacht, from a few hours to week, try to follow these sustainable boating tips:

• Take your rubbish home
• Use eco-friendly sunblock
• Avoid single use plastic

Much of the world’s plastic ends up in the sea, so reduce, reuse and recycle. Read more about responsible boating.

Popular luxury yacht rentals in Puerto Rico among renters:

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Escape the ordinary with a San Juan Islands yacht charter vacation.

Adventure awaits

The San Juan Islands and Gulf Islands are some of the most popular cruising areas in the world.

What is it that draws people to these islands? A big reason is because the islands are remote but accessible at the same time. A short drive from Seattle or Vancouver puts you in Anacortes, Washington, the “Gateway to the San Juan Islands.” From there, the San Juan Islands start a mere 15 miles away.

Your Cruise. Your Choice.

Once in the islands, you’ll find quaint both communities and hidden hideaway, all surrounded by a calm inland sea. Seemingly endless miles of coastline and over 100 islands give you plenty of options for exploring and relaxing. Drop anchor in a quiet cove, or tie up at one of the island marinas – it’s your choice when you charter!

Anacortes Yacht Charters has provided San Juan Islands yacht charters for 45 years. We have the largest selection of motor yachts and sailboats in the Northwest. Our experience and fleet mean we can match you with the perfect boat for a trip of lifetime.

To book a bareboat or skippered San Juan Islands yacht charter contact us at:

800-233-3004 or [email protected]

Big Boat Charter Sale

We are offering our biggest savings on the biggest boats in the fleet.

Class/Charter Bundle

Save $1,900 and launch or build your bareboat charter resume.

Our Guarantee

Should you have a breakdown during your charter, we will complete repairs within four hours of notification for any vessel within 20 miles of our charter base. View Guarantee

Yacht Charter

A private yacht charter is your ticket to a Pacific Northwest vacation of a lifetime. Choose to bareboat charter a powerboat or sailboat for a hands-on adventure. Or, hire a skipper for a more guided experience. A few of our larger boats require a crew and are shown on the crewed yacht page.

Yacht Ownership

If you own a boat, or are pondering a purchase, consider placing your boat into charter service. This a great option to help offset the cost of ownership and earn real tax advantages, Use our in-house service department for year-round care of your boat. Arrange time on your boat for yourself as desired.

News and Announcements

Featured Boat Weekly Special

Book 6 nights and get the 7th night free in red and gold seasons..

Special available for new 2024 bookings made through 8/20/2024. Insurance & Daily Damage must be paid for the free night. Cannot be combined with any other offer or discount. Other restrictions may apply. Contact us for additional details on this special offer. 1-800-233-3004

Charter Bundle Save 1,900

See Details >

Big Boat Charter

Book 3 — get 1 free.

We are proud to be celebrating our 45th Anniversary in 2024. Over the years providing San Juan Islands yacht charters, our crew has pioneered mini-fleet management. Along the way we have provided over 15,000 charter trips – illustrating our commitment to quality and customer service.

All of our charter vessels are clean, well-maintained, and include a breakdown guarantee. We take the risk out of chartering to better ensure the quality of your charter experience.

Our yacht charter fleet includes a variety of power yachts , sailing yachts and crewed yachts from 27’ to 70’.  Make your choice to host nearly any group of friends and family for a magical San Juan Islands yacht charter.

Toll Free: (800) 233-3004 | (360) 293-4555 | [email protected]

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