Recent Searches
Clear

Top San Juan Sailing

Travel update: We’re doing our best to help keep you safe and your plans flexible. Learn more.

Read More
When are you traveling?
Select Dates
Popular
Search experiences that may have limited interaction with crowds.
Search experiences with increased health and safety practices.
Search tours and activities you can do from home.

You are viewing Virtual Experiences in San Juan. See more Virtual Experiences around the globe. 🌎

Price
$0
$500+
Duration
Time of Day
RatingClear
Specials

Travel update: We’re doing our best to help keep you safe and your plans flexible. Learn more.

Read More
Select Dates
Today
Tomorrow

11 San Juan Sailing | All San Juan Tours

Sort by:Featured

San Juan Catamaran Sunset Sail

San Juan Catamaran Sunset Sail

star-5
Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise. Enjoy a warm welcome aboard from your friendly captain and crew, then settle in for a scenic ride. Watch the island coastline glide by as the sun sinks toward the horizon. Sip a complimentary rum punch or sparkling wine with your family and friends and listen as your captain points out landmarks like El Morro Fort and San Juan Gate. Arrive back at the dock in time to continue your evening in San Juan.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$90.00
From
$90.00
Taking safety measures

Sunset Sail by San Juan Historical Bay

Sunset Sail by San Juan Historical Bay

star-4.5
Go sailing and watch the sunset on a cruise from San Juan. Get great photo ops of Puerto Rico’s coastline and enjoy a comfortable sail on the Caribbean Sea. Your captain shares commentary about the region and provides complimentary drinks for your group of no more than six people.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$81.03
From
$81.03
Taking safety measures

Old San Juan Sunset Sail

Old San Juan Sunset Sail

star-4.5
Float past hundreds of years of history and picturesque scenery during this 2-hour sunset sailing excursion in Old San Juan Harbor. Climb aboard the "Amazing Grace," a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you’ll enjoy up-close views of Old San Juan sights like El Morro fortress, La Fortaleza, Paseo la Princesa and more, all set aglow by the fading late afternoon light. A guide and complimentary beverages and snacks are all covered.
More
  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$95.00
From
$95.00
Taking safety measures

San Juan Bay Day Sail

San Juan Bay Day Sail

star-5
Set sail across the Caribbean on this 1.5-hour cruise from San Juan and enjoy unforgettable views of the Puerto Rican capital. Hop aboard a traditional sailboat and sip complimentary drinks as you cruise along the coast. Keep your camera to hand as you pass landmarks like San Juan Bay Marina and El Morro Fort, and spot dolphins and sea turtles swimming and playing around the boat.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$78.00
From
$78.00
Taking safety measures

Old San Juan Harbor Sailing Tour

Old San Juan Harbor Sailing Tour

star-4.5
Float past more than 500 years of history and picturesque scenery during this 1.5-hour sailing excursion in Old San Juan Harbor. Climb aboard the ‘Amazing Grace,’ a topsail schooner fashioned in the style of 19th-century American sailing vessels, for an unforgettable ride past the wonders of this historic area. As you sail you’ll enjoy up-close views of Old San Juan sights such as El Morro fortress, La Fortaleza, and Paseo la Princesa. A guide and complimentary beverages and snacks are all covered.
More
  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$59.00
From
$59.00
Taking safety measures

Sailing Excursion from San Juan

Sailing Excursion from San Juan

star-5
This private sailboat charter from San Juan allows you to choose your own adventure. Sail around the bay and harbor of Old San Juan with an experienced captain and crew at the helm; you can choose to help sail or just relax and enjoy the ride. Drinks are included to sip while you watch the shoreline scenery go by. Ask any questions you may have about boating or about owning a boat; your crew is there to educate you on potential future boat sailing and ownership.
More
  • 3 hours
  • Free Cancellation
From
$614.36
per group
From
$614.36
per group

Private, VIP, Island Hopping Trip on the East Coast of PR with Lunch & Bar!

Private, VIP, Island Hopping Trip on the East Coast of PR with Lunch & Bar!

star-5
This price is for a private tour, for up to 6 passengers. Sandy Bottoms offers personalized & boutique snorkel tours, island hopping, & sailing lessons to the off shore islands of Puerto Rico. Our tours are designed around you and your parties desires. Our boat holds a maximum of six passengers so that we may provide you with the best service and experience. We love to sail and love the ocean. Our captains have over 20 years of experience teaching sailing and racing in regattas around the world. Our crew are all experienced sailors and swimmers. Our captain & crew are all FOODIES with food allergies! Beyond your sailing, and snorkel adventures, we focus on your food preferences for lunch and prepare everything fresh considering all your dietary needs and allergies. Our philosophy is to share our love for sailing and the ocean with you. We adapt our daily schedules around you and your sailing, snorkeling goals. We are all about you and your FUN!
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$1,540.00
per group
From
$1,540.00
per group
Taking safety measures

Private, VIP Snorkel & Island Hopping Tour on the East Coast of PR !

Private, VIP Snorkel & Island Hopping Tour on the East Coast of PR !

star-5
For maximum flexibility, choose a schedule and activity to suit you during this boutique snorkeling, swimming, and sailing excursion. Skip the large tour groups and benefit from the personalized attention of your captain, something few travelers get to enjoy, while making the most of the provided paddle boards, floats, snorkels, as you sail to either Icacos or Palomino Island.
More
  • 6 hours
  • Free Cancellation
  • Taking safety measures
From
$1,020.00
per group
From
$1,020.00
per group
Taking safety measures

Private Sunset Sail on the East Coast of Puerto Rico

Private Sunset Sail on the East Coast of Puerto Rico

Bright pink sunsets set upon the gorgeous turquoise waters of the East Coast of Puerto Rico make this trip a perfect way to view the coast line of our special island! This trip holds a maximum of six passengers, giving you a private and boutique first class view of our special sunsets. Celebrate in style with appetizers and cocktails!
More
  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$653.85
per group
From
$653.85
per group
Taking safety measures

50ft Private Sailboat Experience!

50ft Private Sailboat Experience!

star-5
We are a local company dedicated to the Transport Service, for individuals . groups . companies through the Island. In addition to transport, we offer you aquatic and land experiences with which you can give that magical touch to your stay filling it with unforgettable memories. Just tell us what you wish for your stay or experience and we will make it happen. In Transport and Experiences Puerto Rico we want you to feel like part of our family, very welcomed and lovely treated. Our team will guide and advise in the best interest so you can fulfill all your desires for your stay in Puerto Rico. Transport . Experiences . Private Service
More
  • 7 hours
  • Free Cancellation
From
$250.00
From
$250.00

2-Days Package Experience!

2-Days Package Experience!

We are a local company dedicated to the Transport Service, for individuals . groups . companies through the Island. In addition to transport, we offer you aquatic and land experiences with which you can give that magical touch to your stay filling it with unforgettable memories. Just tell us what you wish for your stay or experience and we will make it happen. In Transport and Experiences Puerto Rico we want you to feel like part of our family, very welcomed and lovely treated. Our team will guide and advise in the best interest so you can fulfill all your desires for your stay in Puerto Rico. Transport . Experiences . Private Service
More
  • 2 days
  • Free Cancellation
From
$350.00
Price varies by group size
From
$350.00
Price varies by group size

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Sailing in San Juan?
Q:
What tours in San Juan are taking additional safety precautions?
Q:
What tours in San Juan are good for avoiding crowds?