San Juan Bay Attractions & Things to do

We will tour you through the waters of San Juan Bay and on a comfortable Yamaha Wave Runner.

On this tour, you will have the opportunity of observe multiple historic places like Castillo San Felipe from the water and have fun at the same time. You can take a relaxing swim in the water, feel the breeze, and clear your mind.
Duration: 1 hour 20 minutes.

Sailing is authentic to San Juan culture- having a conversation with a local, the power of the wind, the peace from no engine noise, no crowds, no fake pirates, no crowds, no need to scream. We sail aboard a real racer cruiser (J30), with a toilet and a cabin- just real life sailing. You'll get to see a different perspective of old San Juan, with complimentary drinks, feeling safe but free, in parties up to 6 people. This is great for a special moment, or turning this moment into an special one. While in contact with nature, you may spot a dolphin. This is not a luxury yacht or a catamaran, so it's possible to really connect with the nature around you.
Duration: 2 hours.

Private, AM. PM. or Sunset, sailing around the San Juan Bay and Harbor of Old San Juan, Puerto Rico. (Prices already include all taxes and fees) This sightseeing, sailing tour will pass historical, Old San Juan Forts and views of the Castle and city-scapes .  A truly exclusive, off the beaten path, Private Experience. If desired you can learn the skill of sailing with the optional request of a hands-on lesson always available to everyone. We differentiate ourselves as a stepping stone to the education of chartering. Also, discovering the facts of sailing to inform the client so that by the end of this trip you'll have the answers needed to make the decision of buying, chartering and planning for future ownership. For experienced Sailors we have a Bareboat imitation option where our Captain is simply there to answer questions and for safety.
Duration: 2 to 3 hours.

Authentic sailing is culture, having a conversation with a local, with the power of the wind, no engine noise, no crowds, no fake pirates, no stray cats, no crowds, no need to scream . . . we sail sideways, aboard a real racer-cruiser (J30), with a toilet and a cabin, just real life sailing. You'll get to see a different perspective of old San Juan, with complimentary drinks, feeling safe but free, in small groups (no crowds.) Good for any special moment, or turning this moment into an special one. While in contact with nature elements, sometimes you may get surprised by dolphins. There are 6 people maximum per sailboat. Sailboat model: Jboat J30 (racer-cruiser.) It's not luxury yacht or a catamaran. Let's sail with Sail San Juan Bay!
Duration: 2 hours.

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic moment with your loved one or a fun time with friends. Complimentary beer, rum & coke, rum punch, and sparkling wine will be available to celebrate that special occasion or just because you're on vacation. Your veteran captain will point out sights along the way as you enjoy the views and the company aboard.
Duration: 2 hours.

Discover San Juan, Puerto Rico aboard a 37-foot catamaran sailboat while enjoying complimentary mimosas, house rum punch, and other drinks in moderation. Take in the panoramic views on this pleasure sightseeing tour of San Juan Bay and adjacent waters. Relax on a romantic sail with your loved one or have a fun getaway with a group of friends. Take a break from the city and step out into the ocean with your professional captain on call.
Duration: 1 hour 30 minutes.

Glide through Old San Juan’s 500 years of history on this 2-hour Segway PT or scooter tour, exploring the scenic route on a Segway Kickscooter. Known as ‘The Walled City,’ Old San Juan was founded as a military stronghold and remains the oldest city under the American flag. This small-group tour is limited to 6 riders for Segway PT and 6 riders for Segway Kickscooter, allowing you to zoom around effortlessly and see more than 15 attractions. Learn from an informative guide about the city’s role during the Spanish empire, World War II, and as a US territory. Capture stunning views of San Juan Bay and Castillo San Felipe Morro along the way.

*Please note* tour schedules per vehicle type and weight restrictions are listed in the 'additional information section'.
Duration: 2 hours.

Our most complete tour for those explorers who would like a glimpse into San Juan's captivating history, have an adventure in the waters of the harbor at the helm of your own boat and stop to learn the highlights of the city’s history.

Duration: 1 hour 30 minutes.

★ Events and Celebrations: Consider the possibility of organizing unique events, from birthdays, bachelorets, weddings proposal to corporate gatherings, surrounded by a historic and romantic setting, ask for our Food Tasting Tour!
★ Amazing Sunset experience tour in the beautiful San Juan Bay look for the fullmoon days they are unique
★Admire the stunning views of the city’s iconic landmarks and enjoy a drink as you cruise
★ Photo stop, Guided tour, Boat cruise, Sightseeing, Sunset, Dolphin watching, Scenic views
★ 2 hour trip / Extra hours available for an extra fee
★ Great to take profesional pictures of Puerto Rico, Photo stop, Guided tour, Boat cruise, Sightseeing, Dolphin watching, Bird watching, Scenic views
★ Includes local beer & with snacks
★ 24/7 instant booking availability
★ Captain included in pricing
Duration: 2 hours.

Dare to experience an eco-friendly adventure aboard our Chiliboats Waterbike!
With easy pedaling, great stability, and maximum safety, you'll explore the Condado Lagoon estuary. Navigate under the Guillermo Esteves, El Ferrocarril, San Antonio, and Dos Hermanos bridges, and get close to Fort San Jerónimo. With luck, you might spot manatees, turtles, stingrays, and other marine species in their natural habitat. Enjoy unique marine landscapes right in the city!

All our tours are conducted on double Chiliboats.

What Makes Chiliboats Unique!
Chiliboats are catamaran-style waterbikes, designed for comfort, stability, and easy pedaling. Thanks to our human anatomy, pedaling becomes natural and easy, using your legs at all times. Additionally, they feature an ergonomic saddle with a rigid backrest, providing extra comfort throughout the ride. Enjoy a relaxing ride with the security and comfort that only Chiliboats can offer.
At Chiliboats, we cater to all adventurers.

Duration: 1 hour.

Experience some of the greatest sport fishing waters in the world when you take a full day or half day fishing charter from San Juan, aboard 'The Legend'! As you head out to the deep waters known as the Blue Marlin Alley, ready for luxurious cruising and the ultimate in sport fishing. Depending on Season you may catch dorado, wahoo, sailfish, tuna and blue or white marlin which offers an exciting challenge to all anglers! “The Legend” is a 48 ft. Hatteras fully equipped for luxurious cruising and the ultimate in sports fishing with top of the line fishing gear.
Duration: 4 hours.

Designed with kids in mind, the Old San Juan Sightseeing Educational tour offers a 2-in-1 experience in history and science, providing family fun designed to keep all ages engaged and learning! Kids will participate in a variety of exciting, handpicked on-the-go science experiments to learn about Puerto Rico's history, geology, geography, flora, and fauna.

After meeting at the entrance to the Compañía del Turismo at La Princesa promenade, kids and adults will enjoy a guided, narrated tour of the five centuries of history in Old San Juan and Puerto Rico led by a certified guide, Ed.D. - Professor Nat. Yummy frozen traditional Puerto Rican natural treats await the kids, and coffee for the adults, throughout the adventure!

We will walk along the monuments, fortifications, and rare sights, learning about Puerto Rican and Old San Juan history and planning. The kids' experience is the main focus, and we move at their pace. ❤️
Duration: 2 hours 30 minutes.

Professor Nat aims to provide a truly authentic experience in a one-of-a-kind destination of the Viejo San Juan. Old San Juan-the oldest city in the United States, has reached its 500th anniversary. This intense and rich with sites and experiences tour is designed for history savvy, a cultural buff, or a sightseeing enthusiast! Attendees will get to know Puerto Rican culture on a tour of most iconic historical sites in Old San Juan complemented with cultural experiences. Within the tour, there will be 32 narrated by professional guide landmarks for participants to see(not all are mentioned in the description ).For the Opulent experience I'll treat your taste buds to a one of a kind secret cocktail that you can only taste on this tour! Culminated with the tasting of 'Coffee of the Popes and the Kings' and crafting of a memorable souvenir with a certified artisan, for an ultimate cultural immersion!
Duration: 2 hours 30 minutes.

Personalized instruction tailored to your needs and skills.

We focus on safety and fun!

We use the best gear available on the market.

Unique location in San Juan Bay
Duration: 30 minutes.

★ Amazing Sunset Experience tour in the beautiful San Juan Bay
★ Admire the stunning views of the city’s iconic landmarks and enjoy a drink and snacks as you cruise
★ Photo stop, Guided tour, Boat cruise, Sightseeing, Dolphin watching, Scenic views
★ 1.5 hour trip / Extra hours available for an extra fee
★ Experience pricing are automated depends on guest amount and chosen dates
★ Includes local beer & soft drinks with snacks
★ 24/7 instant booking availability
★ Captain included in pricing:

The space

Guest acess
Yatch its located at San Juan Bay Marina
Captain & Host will be expecting you at the Marina

Guest interaction
Captain and host will be during your experience making it a safe and enjoyable one!

Other things to note
This activity has a Standard (24-hour) refund policy.
Duration: 1 hour 30 minutes.

★ 7 Tapa Courses from Farm to Table in a Sunset Cruise
★Admire the stunning views of the city's iconic landmarks
★ Photo stop, Guided tour, Boat cruise, Sightseeing, Sunset, Dolphin watching, Scenic views
★ 4 hour trip / Extra hours available for an extra fee
★ Experience pricing are automated depends on guest amount and chosen dates
★ Includes local beer & soft drinks with snacks
★ 24/7 instant booking availability
★ Captain included in pricing
Duration: 4 hours.

★ Amazing day tour in the beautiful San Juan Bay
★ Admire the stunning views of the city’s iconic landmarks and enjoy a drink and snacks as you cruise
★ Photo stop, Guided tour, Boat cruise, Sightseeing, Dolphin watching, Scenic views
★ 1 hour trip / Extra hours available for an extra fee
★ Experience pricing are automated depends on guest amount and chosen dates
★ Includes local beer & soft drinks with snacks
★ 24/7 instant booking availability
★ Captain included in pricing

Guest acess
Yatch its located at San Juan Bay Marina
Captain & Host will be expecting you at the Marina

Guest interaction
Captain and host will be during your experience making it a safe and enjoyable one!

Other things to note
This activity has a Standard (24-hour) refund policy.
Duration: 1 hour.

★ Amazing experience tour in the beautiful San Juan Bay
★ Admire the stunning views of the city’s iconic landmarks and enjoy a drink and snacks as you cruise
★ Photo stop, Guided tour, Boat cruise, Sightseeing, Dolphin watching, Scenic views
★ 1 hour trip / Extra hours available for an extra fee
★ Experience pricing are automated depends on guest amount and chosen dates
★ Includes local beer & soft drinks with snacks
★ 24/7 instant booking availability
★ Captain included in pricing:

The space

Guest acess
Yatch its located at San Juan Bay Marina
Captain & Host will be expecting you at the Marina

Guest interaction
Captain and host will be during your experience making it a safe and enjoyable one!

Other things to note
This activity has a Standard (24-hour) refund policy.
Duration: 1 hour.