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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:

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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:

• boat rentals in San Juan, Puerto Rico
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• sailing in Puerto Rico
• private catamaran rentals in Puerto Rico
• San Juan sailboat charters

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English / Español (678) 640-4530

We provide Puerto Rico yacht charters as well as Puerto Rico fishing charters. We can arrange fishing trips out of San Juan harbor, day or night cruises of San Juan harbor or luxury yacht charters to the Puerto Rico islands of Culebra, Vieques, Palomino and Icacos.

Private Yacht Charters in Puerto Rico

Live an unmatched vacation experience in some of the most beautiful waters in the world. charters puerto rico is the private charter to go to for the perfect balance of relaxation, safety and unforgettably-luxurious onboard trip. travel to the best destinations in the area and discover a unique tropical paradise., choose a yacht, our most popular vessels, this spacious, comfortable, deluxe yacht will elevate your vacation experience to a whole new level. modern and intimate, you will have an unforgettable vacation tailored to your needs. our puerto rico yacht rental is a unique and stress-free experience that will provide you with safety, relaxation, and comfort out on the water, select a destination.

Discover Puerto Rico & the Virgin Islands

Puerto rico is a location you can’t miss. filled with pristine beaches and breathtaking scenery, it’s no wonder people know it as the island of enchantment. puerto rico is an ideal destination whether you plan on staying there or also visiting the british virgin islands. with a pleasant tropical climate, you’ll be able to enjoy nice weather while you explore new places., · san juan bay, · virgin islands: culebra & vieques, · palomino island, · cayo icacos, · and much more.

The British Virgin Islands seem to just have pleasant weather all year. It’s one of the best sailing destinations in the Caribbean Sea. Filled with culture, history, and beautiful views, this destination is unforgettable. With secluded coves, bays, and beaches, you’ll understand why this place is paradise. Known for its pristine sandy beaches and crystal clear water, this is the perfect place for your next vacation.

· virgin gorda, ·  jost van dyke, · white bay, have a memorable vacation, we offer an array of activities meant to fit all personalities..

•         Golfing
•         Snorkeling
•         Water Sports
•        Exploring
•         Dominican Republic transfers
•         Horseback Trails
•        And more!

We Create Exceptional Onboard Experiences for You

With charters puerto rico you will enjoy a completely relaxed and safe trip from the moment you step on one of our vessels. our crew is licensed and trained to offer you an unforgettable getaway through high-class service and dedication. experience the caribbean like never before. book a yacht charter today., contact info.

• Puerto del Rey Marina, km. 51.4, Fajardo, 00738, Puerto Rico
• (678) 640-4530
• [email protected]

Privacy Overview

Are you ready to choose your destination!

San juan destinations:, puerto rico islands (culebra, vieques, etc), or u.s. virgin islands:.

Call Us: +1 (305) 515 4735

Puerto Rico Yacht Charter | Puerto Rico Luxury Boat Rentals | San Juan Yacht Charters

Puerto Rico Yacht Charters

Day Yacht Charters Puerto Rico

Luxuxry Yacht Charters in Puerto Rico

Wondering what we do at Day Yacht Charters Puerto Rico? We make your Puerto Rico Yacht Charter dreams come true. Specializing in exclusive luxury yacht charter packages, we are regarded by countless clients as the top resource for yacht charter packages in Puerto Rico. The possibilities are endless, from swimming with sea turtles and dolphins in the bay to whale watching on the Hispaniola Trench and relaxing onboard of a sophisticated yacht – you will create memories that will last a lifetime. With Day Yacht Charters Puerto Rico, any island you want to visit is within your reach. We offer crewed, all-Inclusive weekend vacation charter packages. We will take care of every detail, ranging from transportation to a food and beverage menu. Day Yacht Charters Puerto Rico is the first and most trusted private yacht charter company in Puerto Rico. We are proud to offer one of the area's largest fleets of gorgeous, well maintained, newer-model yachts. Whether you are looking to rent a yacht for a day trip or a relaxing weekend getaway we are here to serve you. Originated in South Florida, Day Yacht Charters has now expanded to Puerto Rico due to popular demand – all our crew is licensed and specially trained to ensure a safe, luxurious experience for all our guests. Our crew specializes in creating the perfect balance of relaxation, safety, and unforgettably luxurious experiences. The Caribbean is our home and we are happy to share our insider knowledge, taking you places most tourists never get to see. With a motto that proudly states “We never say no!” we deliver world-class service that exceeds your expectations. If you have a special request, let us know and we will make it happen. Reserve your luxury charter yacht with Day Yacht Charter Puerto Rico in San Juan, Puerto Rico and live a memorable experience that you will love to share with your friends and family. Get in touch with one of our charter specialists today!

Suitable and Adequate Marinas Incorporating the competitive port fee and berthing costs, Puerto Rico is definitely one region in the Caribbean wherein super yachts can dock alongside and as a result of its unique jurisdiction, there is virtually no passport requirements or even custom inspections for folks visiting from the mainland United States, which makes it the perfect destination for luxury yacht rental vacations. Puerto Del Rey Puerto Del Rey is located on the east coast of Puerto Rico, between San José and St. Thomas. It features the largest marina in the Caribbean and has a capacity for charter boats from 30 feet all through to huge yachts of over 200 feet. Additionally, it is an excellent base from where you can venture to see some of Puerto Rico's most renowned attractions.

Map of the best beaches in Pueto Rico - ClICK HERE TO VIEW MAP!

The Yacht Club Nestled on the beautiful southeastern coast of the island, TYC is equipped with modern facilities for mega yachts, in conjunction with having access to an elite resort community and the legendary Palmas del Mar.

Yacht Maintenance and Repair Services Marinas in Puerto Rico are likewise well equipped to address any specified repair, maintenance and also inspection for yachts of all shapes and sizes. Luxury Attraction for Yacht Charters in Puerto Rico Exotic luxury spas, magnificent restaurants and deluxe hotels and most notably the new Ritz Reserve, present guests on luxury yachts with avenues for ease and comfort. Vieques is a must-visit destination on any Puerto Rico luxury yacht charter, widely known for the brightest bioluminescent bay in the world. Culebra is yet another amazing destination to see, with its Flamenco Beach recognized as the second best beach in the world by The Discovery Channel. Amid the natural pleasures, Puerto Rico comes with delightful thermal hot springs and 14 state forests, which include El Yunque, the only tropical rainforest in the United States. Puerto Rico is also a haven for San Juan, the most retained colonial city in the Americas.

Puerto Rico Super yacht Charter Vacations The Yacht Club is an exclusive, state-of-the-art marina offering exceptional service in peaceful, family-oriented surroundings. It happens to be the only marina in Puerto Rico connected with a major resort community, the well-known Palmas del Mar. Because of this incomparable set up and distinguished features to accommodate yachts of up to 175 feet, The Yacht Club is redefining the marina experience. When making a reservation for your dream holiday in Puerto Rico, ensure that you contact a company that provides access to all the boats… And also go with an impartial one that works for you particularly with your best interests at heart – such as Day Yacht Charters.

Please Email us for a Full List of Boats we offer.

32' Sea Ray Boat for Charter

Port: Fajardo Marina

45' Fishing Boat

50' Yacht Great for Snorkeling and Swimming

43' Balize Catamaran

55' Azimut Yacht

66' Sunseeker Predator Yacht

70' Princess Yacht

60' Rio Granturismo Yacht

100' Azimut Luxury Yacht

Yacht charter puerto rico.

When making a reservation for your dream holiday in Puerto Rico, ensure that you contact a company that provides access to all the boats… And also go with an impartial one that works for you particularly with your best interests at heart – such as Day Yacht Charters.

Puerto Rico Yacht Charter | Puerto Rico Boat Rentals | San Juan Yacht Charters

Palmas del mar.

Palmas del Mar is a destination resort community within Puerto Rico's southeastern coastal area, precisely 45 minutes from San Juan; and merely 15 minutes from the private airport at the former Roosevelt Roads Navy Base. The Palmas del mar extends over 2, 700 acres and is marked by breathtaking beaches, fancy homes, extensive gardens, two championship golf courses, the largest tennis facility in the Caribbean, Hotel with Casino and The Yacht Club Marina. It is also home to exceptional academic facilities for children from kindergarten to high school, an array of restaurants, an equestrian facility, as well as beaches and country clubs.

THE GOLF CLUB

Experience spectacular views of the Caribbean Sea while you satisfy your passion for the sport of golf in one of our two championship 18-hole golf courses.

Explore the Flamboyán course, an 18-hole championship standard course, and appreciate the game through the eyes of well known course architect Reese Jones. The Flamboyán course provides you with image views of the ocean designed to keep you returning for more. The Palm course, an 18-hole championship caliber course created by champion golfer Gary Player, features a tournament-grade challenge for the passionate golfer. The Palm is a resort model course with incredible landscapes and amazing views of the Caribbean Sea, water hazards, strategic bunkers and undulating greens.

THE BEACH CLUB

Here, you could possibly enjoy the natural splendor of the tropics at the member exclusive Beach Club facility. It is an exotic bungalow-style pavilion with spectacular views of the Caribbean which serves as the reception of this exclusive service facility. The wonder of the crystal blue waters of the Caribbean unfolds right before you and time stops while relaxing in this tropical resort ambiance. Savor an awesome tropical drink poolside on the chaise lounge or you could go for a stroll on the beach and reflect on the appeal of the island of Vieques. The Beach Club is ideal for both the idle sunbather and the active member.

THE TENNIS CENTER

This is the largest and most complete tennis facility in the Caribbean. Palmas is a tennis lover's fantasy with 20 courts; 2 artificial grass Omni Courts, 4 Har-Tru clay courts and 14 hard courts, most of them being lighted for night play. It is acknowledged as one of the most prominent and active private tennis clubs in Puerto Rico and ranked among the first 50 tennis resorts by tennisresortsonline dot com

EQUESTRIAN CENTER

Have a great time on a horseback ride and connect with all of nature's wonders in the Equestrian Center. Feel the tempo while your Paso Fino or Paso horse struts in our Equestrian Center. With 64 stables, the Rancho Buena Vista Equestrian Facility in Palmas del Mar, it is regarded as the most complete in the Caribbean. It consists of round pen training, extensive routes, together with a structure devised for international competition which is why it is regarded as the best training center in the Caribbean.

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Luxury Yacht Rental in Puerto Rico

We’re a private Yacht Charters Company in Puerto Rico with more than 20 years of experience. If you’re looking for a romantic getaway, an adventure with friends and family, or even a day just for yourself then you have come to the right place.

Visit paradise and reconnect with yourself

Puerto Rico is the ultimate place for people looking for fun, adventure, and relaxation in the Caribbean.

What we offer

Wether it's a romantic getaway, adventure, pleasure or a family trip, Water Time Charters is your answer for memories that last a lifetime.

Top of the Line

Our unique yachts accommodate all ages and interests. Browse our lineup and find your perfect match.

Leopard 75'

Azimut 68'

Princess 58'

Hydra Sport 30'

World class chef wide variety of water sports & activities we've got you covered.

Joyful experiences for you and your family

From snorkeling to paddle boarding, sea bobs & floating pads.

Swim in pristine waters and discover an underwater oasis.

Paddleboarding

Unique exercise activity that connects you with nature like never before.

For the adventurers - we have a really cool toy for you.

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• Boat Rentals

Puerto Rico

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Private San Juan Bay Cruise 37' Sailboat

Private Bay/Sunset/Beach Time Quality 25' Power Boat with Free Drinks/Food

NOW OPEN! Explore the majestic views of San Juan Bay, Puerto Rico by boat!

Private Luxury Sailing Experience out of Old San Juan

Private Sail Classic 1969 Sloop in San Juan, Puerto Rico

3 Islands Tour @Pursuit 2670 Twin '2022 Center Console with Yamaha F250 Engines

Sunset Cruise in San Juan Puerto Rico

Inboard Propulsion Rental in Carolina

San juan reviews.

Miguel was absolutely phenomenal! His communication was great, he was flexible and worked with us! His boat was clean and he provided a large cooler with ice for us, even offer a grill for lunch! He knows all the spots to go and was extremely helpful! Thank you for a lovely day Miguel!

As advertised, super fun. Beautiful views. Super relaxing and free drinks. Would definitely book again.

We had a great sailing experience with Captain Luis! The trip around Old San Juan was beautiful. He was very knowledgeable of the area and wildlife around us. The snacks and sangria were great! Don’t hesitate, book now with Captain Luis!

Don’t second guess it. Just book it. Luis and Andrea were great! They were helpful before and during the trip. We had gone for a relaxing trip for my cousin’s bachelorette. They offered a charcuterie tray and some Sangria. I would definitely book again, on another trip to PR (:

This was the highlight of our trip to Puerto Rico. Captain Luis was so communicative and friendly from booking to the end of the trip. I booked this experience for a friends bachelorette and it was her favorite part. He provided sangria and a small charcuterie board which was delicious. We asked to swim and he anchored for about an hour for us to enjoy the beautiful waters. Safety was a priority which we appreciated. He and his first mate Andrea were amazing. Andrea is incredible. Captain Luis even danced salsa for us hahaha.

This was a total highlight of our trip!!! The communication leading up to the charter was awesome and very prompt- all of my questions were answered. The captain (Krista!!) and crew were just amazing- truly had the most wonderful day. The boat is so comfortable, well stocked, and beautiful! They were super chill and worked with us on what we wanted to do and see. 10/10 would recommend and we will be back next time we come to PR!!!

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Make Your Vacations Special and Memorable With Yachts Puerto Rico Charters

Yachts Puerto Rico Charters

Explore Our Fleet

Our luxurious charters provide you with a 5-star experience, with delectable foods, plenty of water toy- add ons and a wide-ranging drink menu to keep your group satisfied.

Explore Puerto Rico Locations

Our captains specialize in staying up to date with all the best chartering locations that will give you a glimpse of this paradise. Explore the beauty of Puerto Rico with us!

Charter Occasions We Host

Whether you planning a relaxing charter or romantic outing, we specialize in making your special occasion that much more memorable.

Enjoy a Luxurious Yacht Vacation in Puerto Rico

When you imagine a beach vacation, you think of crystal clear waters, bright blue skies and picturesque white sands. Right? Do you know Puerto Rico is an ideal beach location for millions of travelers? With tropical rainforests, magnificent bays, nature reserves and pristine beaches, Puerto Rico is one of the most stunning destination in the Caribbean Island. Do not miss your chance to explore the beauty that Puerto Rico offers.

At Yachts Puerto Rico Charters, we are here to help you have an amazing vacation, full of beach strolls, fishing, snorkeling, diving, sailing or whatever your heart desires. We are a premier luxury charter company. We provide luxury yachts for varied destinations in Puerto Rico. From San Juan yacht charter/yacht rental/boat charter/boat rental , Culebra yacht charter/boat charter/yacht rental/boat rental to the British Virgin Islands yacht charters , we fine tune your charter to match all of your wants and needs.

Our Yacht Charter/Yacht Rental/Boat Charter/Boat Rental Services in Puerto Rico

Our services let you experience everything Puerto Rico has to offer. We have an extensive range of vessel options varying in different sizes, comforts and amenities to offer you a charter catered to your specification. We have highly experienced and talented crew members to help you enjoy Puerto Rico in your own way.

Our services will give you an opportunity to enjoy an array of Puerto Rican delights. For the beach lovers, we can explore all the top beaches and islands around Puerto Rico during your yacht charter vacation. Whether you require a luxury yacht, classic or mega yacht, catamaran or sailing boat, we have numerous options to cater to you.

Events We Host

Our yachts are readily available for your events and special occasions. You can contact us to charter for weddings, honeymoons, corporate events yacht , wedding proposals, reunions, birthday parties yachts , anniversaries, bachelor or bachelorette parties, etc. We have an attentive crew, 5-star catering, outstanding event facilities, amazing music, delicious cuisine, a wide-rangeof drink options, luxurious rooms and a lot more to make your event memorable. Contact us and book your yacht today!

Here at Yachts Puerto Rico Charters we pride ourselves as an international company and specialize in providing consistent luxury charters, worldwide. Since our establishment, we have represented ourselvesto appeal to a clientele who are looking for a stress free, luxury vessel booking service. Our stunning yachts give you the privacy of staying in a luxury villa, with 5-star customer service, water sport equipment and delicious food to enhance the richness of your vacation. Read More

What Our Clients Say

“Hi Yachts Puerto Rico Charters, I booked my bachelorette party with you guys last summer and I just wanted to leave a review. I was astonished with the charter from start to finish. The girls had a blast! Thank you for going out of your way to take pictures for us and make the day, truly one to remember.”

- Alyssa R.

Sunset Cruises

Whether you like shopping, water sports, beautiful beaches, or you’re just seeking a relaxing vacation, Puerto Rico has it all. From the charm of Old San Juan, the upmarket scene of Calle Fortaleza, the nightlife of Condado or the rustic beauty of Culebra, Puerto Rico has everything tied together in one place.

Romantic Outing

Puerto Rico is a paradise filled with romantic beaches, beautiful coastline, pristine waters and consists of numerous activities you and your loved one can enjoy together. Whether you are coming to Puerto Rico on your anniversary, wedding, proposal or Valentine's Day, we can ensure you two will...

Fun Charter

Imagine cruising the Caribbean Sea, eating great cuisine, tanning and enjoying water sports! At Yachts Puerto Rico Charters, every vessel in our luxury fleet is packed with luxurious accommodations, appetizing dining options, amazing entertainment and incredible activities for all ages.

Marriage Proposals

Are you planning to propose to your significant other? If yes, then Yachts Puerto Rico Charters is here to help plan the best marriage proposal for you aboard one of our luxury vessels. We have some of the best luxury fleets in Puerto Rico and trained professionals to organize everything for you...

Extended Stay Charters

Pristine beaches, majestic mountains, sun-kissed Caribbean waters, exotic wildlife and numerous cays and islets – that's what Puerto Rico is. It is called the heart and soul of the Caribbean where old world charm meets modern luxurious. You cannot explore all the treasures of Puerto Rico in...

Are you looking for a wonderful way to celebrate your 25th birthday, 50th birthday, or daughter's sweet sixteen? Nothing can match the natural beauty, amazing coastline and sparkling waters of Puerto Rico when it comes to celebrating your special day with your loved ones aboard a luxury yacht.

Our Favorite Charter Locations

82 Ft Sunseeker Mega Yacht

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16  Crewed Luxury Yachts for Charter in Puerto Rico

Puerto Rico Yacht Charters

Nestled in the Greater Antilles island chain of the Caribbean , Puerto Rico boasts a series of blemishless beaches and a range of historic attractions on the mainland. From basking in the sun kissed harbour of San Juan to diving in the azure waters, those arriving on board superyachts are sure to discover exactly why it has earned the reputation for being the ‘island of enchantment’.

Luxury yacht charters in Puerto Rico Belonging to the Spanish Virgin Islands, Puerto Rico is an ideal yacht charter destination to visit either in isolation, or as part of a larger itinerary which includes Isla de Culebra and the Isla de Vieques. Boasting a year-round climate which is technically defined as ‘tropical marine’, visitors are able to sun themselves on the glistening beaches of Condado and Balneario as well as sampling the local cuisine in suitably inviting surroundings. For adventurous charter guests, a trek through the El Yunque Forest is sure to please, whilst the more peacefully inclined will find their own paradise around the restaurants and bars of Old San Juan.

Puerto Rico yacht charter guide Bursting with possibilities, Puerto Rico is best visited from November through to April. During this time, visitors are able to visit attractions like the 16th century Fort San Felipe del Morro and the nearby city of Fajardo in the best possible climate. Ideal for motor yachts as well as sailing yachts , Puerto Rico is surrounded by fantastic anchorages and vast cruising grounds which make being underway a complete pleasure. There’s also plenty of opportunities to explore beneath the water thanks to snorkelling spots of Vieques and Culebra which belong to the nearby Spanish Virgin Islands.

Yacht charter itineraries in Puerto Rico As one of the largest harbors in the Caribbean, and situated close to the nearby Fernando Ribas airport, San Juan is the place where yacht charters in Puerto Rico typically begin. From here, there are a variety of different ways for you to being discovering this enchanting island and its neighbors. You might, for example, wish to cruise over to the Spanish Virgin Islands which are a mere 15 nautical miles from the coast to indulge in the hot springs produced by an unusual volcanic formation at the Isla De Culebrita. Alternatively, you may wish to set out for Ensenada Honda to unwind against a scenic bay lined by mangrove trees.

Planning a yacht charter in Puerto Rico In order to get started with the planning of your yacht charter in Puerto Rico you should take a look at all of the of the crewed yachts found below before getting in touch with a charter broker who will be able to advise you on their current availability and the best times to visit.

Crewed Charter Yachts in Puerto Rico

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27m   Leopard

from $45,000 p/week

Queen South III

Black Pearl 14

105m Oceanco

105m   2018

90m Oceanco

90m   2018/2024

from $1,334,000 p/w eek ♦︎

from $300,000 p/w eek

48m Dunya Yachts

from $334,000 p/w eek ♦︎

46m   1984/2016

from $230,000 p/w eek

Big Aron 10

46m Royal Denship

46m   2004/2020

from $165,000 p/w eek

Queen South III 8

36m Tuzla Shipyard

36m   1999/2013

from $43,900 p/w eek

Sensation 8

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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

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

Maritana added to fleet, sea of memories added to fleet.

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.

Weekly Featured Boat

33′ beneteau oceanis 331.

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Featured Boat Weekly Special

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

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Class & Charter Bundle Save $1,900

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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UCSG licensed 100 Ton Expert powerboater, fisherman, and local guide.  Spanish and English.

“I want everyone to have fun and see my beautiful island.”

Capt Sebastian

USCG licensed 100 Ton inland. Sailor, English.

“The waters of Puerto Rico are beautiful. The boating opportunities here are world class. When in the Caribbean get on a boat and enjoy one of life’s best experiences.”

Capt Caitlyn

USCG licensed 100 Ton. Sailor, Powerboater.

“Puerto Rico is a wonderful place to visit and sail.  The waters are beautiful and the people are friendly as can be.”

San Juan  Private Yacht Cruises Experience a Private Yacht Sail in San Juan Bay

Premier Yacht  Cruises Experiences

Choose your package, private chef   |   equipped bar   |   corporate events private ground transportation, uscg certified captain uscg certified boat.

Brunch Cruise 3 Hours | 11:00 am - 1:00 pm Sail in the San Juan Bay over looking  the Morro, Paseo La Princesa, and Old San Juan sightings. Capacity: 12 passengers Experi ence Includes:

​ Captain & Mate

Water, Soft Drinks, Ice

Welcome Mimosas

Brunch Menu

Sunset  Cruise 3 Hours | *4 :00 p m - 7:00 pm Sail in the San Juan Bay over looking  the Morro, Paseo La Princesa, and Old San Juan sightings. Capacity: 12 passengers Experi ence Includes:

White Wine & Sparkling Wine

Charcuterie Board

Premier Dinner  Cruise 3 Hours | 8:0 0 p m - 11:00 pm Sail in the San Juan Bay over looking  the Morro, Paseo La Princesa, and Old San Juan sightings.  Private Chef Dinner. Capacity: 12 passengers Experi ence Includes:

Chef Dinner Menu

Corporate Events Potential Clients, Staff Incentives, Team Building, and more...  

Bachelorette partys food & drinks packages available  , the ultimate party yacht vip party at the dock in san juan bay  , the yacht: princess 65'.

Luxurious Yach t: Your private yacht is equipped with state-of-the-art amenities, including spacious decks, comfortable lounging areas, and premium entertainment systems.

Professional Crew: A highly skilled and attentive crew ensures that your every need is met, guaranteeing a seamless and enjoyable experience.

Customization: Tailor the cruise to your preferences, whether it's a champagne toast, m usic, or a surprise celebration.

Sail into Paradise: San Juan Yacht Cruise Experience

With a modern and luxurious style, we will deliver a one-on-a-lifetime experience cruising around San Juan Bay.

Your journey begins at the historic Old San Juan Harbor, where the blend of colonial architecture and modern luxury sets the stage for an enchanting voyage. Cruise past iconic landmarks such as El Morro and San Cristobal forts, providing a unique perspective of these historic structures from the shimmering waters. ​

​ Escape the ordinary and elevate your experience with a San Juan yacht cruise, where the union of luxury and natural beauty creates memories that will last a lifetime. Immerse yourself in the Caribbean charm as you sail along the shores of this historic city, experiencing the magic that only a private yacht cruise can provide.

Travel with confidence!

Charter a private boat in puerto rico.

A UNIQUE EXPERIENCE AWAITS

I VENTURES provides the largest variety of private boat charters in Puerto Rico along with five-star local customer service. Explore all-inclusive packages, including our own private ground transportation options from

San Juan, Rio Grande, and Fajardo.

Whether you are hosting a Caribbean getaway, family trip, birthday, bachelorette, corporate gathering, wedding, or anniversary, we will deliver a once-in-a-lifetime experience. 

Your needs are important to us to personalize your escape, don’t hesitate to ask for add-ons for a fantastic experience. Our private boat charters in Puerto Rico will allow you to experience this beautiful island in an elegant, fun manner.

Departures from San Juan and Fajardo:

San Juan Bay Marina

Safe Harbor Puerto del Rey Marina

Villa Marina Yacht Harbor

Puerto Chico M arina

Sunbay Marina

*All Boat Charter departures are from Fajardo. Marina locations are

a 1-hour drive from San Juan,

ask for our ground transportation services and we will provide a quote.

    Destinations:

San Juan Bay, Icacos, Palomino, Culebra, Vieques

Your needs are important to us to personalize your perfect getaway, don’t hesitate to

ask for add-ons for a fantastic experience.

Chef & Food Service

Ground Transportation

Professional Video & Pictures

Book Online Today!

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