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26 results | All Puerto Rico Tours

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Authentic Sail by the Bay of San Juan

Authentic Sail by the Bay of San Juan

star-4.5
26
Navigate the seas aboard an authentic sailboat during this excursion in the Bay of San Juan. While most boats these days have noisy motors, this sailboat experience exclusively uses the power of the wind. Enjoy views of Old San Juan from a different perspective and sip on beer or sangria as you sail; you may even encounter local wildlife like dolphins.
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  • 2 hours
  • Free Cancellation
From
$76.93
From
$76.93

Deserted Island Catamaran Day Sail from Fajardo

Deserted Island Catamaran Day Sail from Fajardo

star-4.5
458
Live out your island castaway fantasies aboard a luxury catamaran as you visit the deserted tropical island of Cayo Icacos from San Juan on this half-day sailing cruise. Sail into the aquamarine waters of the Caribbean, admiring views of the El Yunque mountains in the distance, before arriving at the nature preserve of Icacos for a leisurely day of swimming, snorkeling, and a lunch buffet with drinks.
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  • 5 hours 30 minutes
  • Free Cancellation
From
$117.00
From
$117.00

Private Sailing Excursion from San Juan

Private Sailing Excursion from San Juan

star-4.5
28
This private sailboat charter from San Juan allows you (maximum 6 passengers) 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. Bring whatever you prefer to sip on, as you watch the scenery. 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. Our prices already include all taxes and fees.
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  • 3 hours
  • Free Cancellation
From
$652.76
per group
From
$652.76
per group

Sunset Sail by San Juan Historical Bay

Sunset Sail by San Juan Historical Bay

star-4.5
228
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.
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  • 2 hours
  • Free Cancellation
From
$93.00
From
$93.00

Old San Juan Harbor Sailing Tour

Old San Juan Harbor Sailing Tour

star-4.5
114
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$110.00
From
$110.00

Old San Juan Sunset Sail

Old San Juan Sunset Sail

star-4.5
129
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.
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  • 2 hours
  • Free Cancellation
From
$139.00
From
$139.00

San Juan Catamaran Sunset Sail
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San Juan Catamaran Sunset Sail

star-5
252
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.
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  • 2 hours
  • Free Cancellation
From
$119.00
From
$119.00

Old San Juan Walking Tour

Old San Juan Walking Tour

star-5
735
Explore the colorful buildings and charming streets of Old San Juan in a small group with the help of writer David Rodriguez, author of ‘The Rise and Fall of the Great Barbate.’ During the course of your day, the knowledgeable author helps you discover the area’s key historic sites and gain new insight into Puerto Rican culture. It’s a great opportunity to learn about the many stories of the people who helped to define this unique neighborhood. Your walking trip’s length is flexible based on your needs, and also includes bottled water.
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  • 2 hours
  • Free Cancellation
From
$41.03
From
$41.03

San Juan Bay Day Sail
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San Juan Bay Day Sail

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133
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.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$99.00
From
$99.00

Sunset Walking Tour in the Historic Old San Juan

Sunset Walking Tour in the Historic Old San Juan

star-5
127
Explore Old San Juan at the most magical time of day during a sunset walking tour around the historic centre of Old San Juan. Exploring on foot means you’ll notice architectural details that you might otherwise miss if you were traveling in a traditional tour vehicle, while guide commentary brings the town to life with stories you’re unlikely to find in the guidebook.
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  • 2 hours
  • Free Cancellation
From
$35.00
From
$35.00

Sunset Harbor Boat Ride in San Juan

Sunset Harbor Boat Ride in San Juan

star-4.5
203
Enjoy a new perspective on Old San Juan—and soak up Caribbean breezes and sunset views—aboard this evening boat tour. Following pickup at select local hotels, hop aboard the boat and find a comfortable seat on the deck. Then, spy highlights like Paseo De La Princesa, La Fortaleza, the San Juan City Walls, and more, all while the sun goes down. Light refreshments and alcoholic drinks are available on board.
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  • 1 hour 30 minutes
  • Free Cancellation
From
$89.00
From
$89.00

Janise Sailing and Snorkeling Day Charter

Janise Sailing and Snorkeling Day Charter

star-5
25
Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea. Great for birthdays and any special private event. Come experience first class service by our professional and friendly crew. Our great reviews have positioned us as the #5 Tripadvisor company in Fajardo.
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  • 5 hours
  • Free Cancellation
From
$299.00
From
$299.00

No crowd sail & snorkel, classic 50 sailboat in Puerto Rico with transportation.

No crowd sail & snorkel, classic 50 sailboat in Puerto Rico with transportation.

star-5
39
On the sail boat, passengers will have the opportunity to set sail on a classic 50-foot vessel that will take them away from the hustle and bustle of the city and it will give you the opportunity to enjoy the wonders of the sea while practicing some snorkeling, enjoying the warm tropical climate of la Isla del encanto.
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  • 5 to 6 hours
  • Free Cancellation
From
$185.00
From
$185.00

Private Snorkel & Island Hopping on the East Coast of Puerto Rico - Open Bar

Private Snorkel & Island Hopping on the East Coast of Puerto Rico - Open Bar

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15
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.
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  • 6 hours
  • Free Cancellation
From
$1,290.00
per group
From
$1,290.00
per group

DAY SAIL aboard PRIVATE SAIL YACHT in Fajardo
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DAY SAIL aboard PRIVATE SAIL YACHT in Fajardo

star-5
9
Venture away from the main island and explore the smaller, eastern islands of Puerto Rico aboard your own charter boat. Sail from Fajardo and spend the day swimming, sunbathing, paddleboarding, and snorkeling in and around Palominos Island. While you sail, enjoy light refreshments and snacks, or bring your own meal aboard.
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  • 6 hours
  • Free Cancellation
From
$1,250.00
per group
From
$1,250.00
per group

Private Snorkeling & Sailing on the East Coast of Puerto Rico - Open Bar

Private Snorkeling & Sailing on the East Coast of Puerto Rico - Open Bar

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3
Discover the eastern islands off the coast of Puerto Rico during this private day trip. Board your boat and sail off into the Caribbean and stop at Palominos, Lobos, and/or Icacos islands, depending on the weather conditions. Enjoy plenty of time to paddleboard, snorkel, swim, and soak up the sun over the course of the day, and indulge in a selection of appetizers and an open bar aboard the vessel.
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  • 6 hours
  • Free Cancellation
From
$1,290.00
per group
From
$1,290.00
per group

Janise Sailing Sunset Charter in Fajardo, Puerto Rico

Janise Sailing Sunset Charter in Fajardo, Puerto Rico

star-5
2
Experience a stunning Puerto Rican sunset aboard a charter boat during this excursion. Sail along Fajardo’s coastline and to nearby islands before dropping anchor for sunset. Enjoy the catamaran’s trampoline, sip on some wine or beer, and enjoy local appetizers and snacks while you wait for the sun to dip below the horizon. Then head back to the marina to continue the rest of your evening as you wish.
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  • 2 hours
  • Free Cancellation
From
$199.00
From
$199.00

Private Sailing, Island Hopping Tour with Appetizers and Open Bar

Private Sailing, Island Hopping Tour with Appetizers and Open Bar

star-5
17
Sandy Bottoms offers personalized & boutique snorkel tours, island hopping, & sailing lessons to the offshore islands on the East Coast 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. Snorkeling equipment, paddle boards, and fun floats are included in this trip. We also provide a brief snorkel and paddle board lesson upon request. 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. All of our trips also include a large selection of appetizers including a gourmet cheese and fruit tray, guacamole, hummus, assorted snacks and cookies. Our Ship Bar is also open for your enjoyment. We offer rum, vodka, tequila, and white wine, along with a selection of organic juices, sodas, and drink mixers. Our local beer is also onboard.
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  • 6 hours
  • Free Cancellation
From
$1,290.00
per group
From
$1,290.00
per group

DAY SAIL aboard PRIVATE SAIL YACHT in Fajardo w/ Lunch & Deluxe Service
Likely to Sell OutLikely to Sell Out

DAY SAIL aboard PRIVATE SAIL YACHT in Fajardo w/ Lunch & Deluxe Service

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5
Experience Puerto Rico’s eastern shore aboard your own charter boat during this full-day excursion. Sail from Fajardo and enjoy stops at Palominos Island, several beautiful beaches, and popular snorkeling spots where you can discover the local marine life. Enjoy plenty of amenities including paddleboards, floaties, a barbecue lunch, assorted beverages, and beach snacks for a hassle-free experience.
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  • 6 hours
  • Free Cancellation
From
$1,670.00
per group
From
$1,670.00
per group

Private Day Sail - South Coast of Puerto Rico

Private Day Sail - South Coast of Puerto Rico

star-5
1
Experience the stunning southern coast of Puerto Rico on this full-day, private boat tour. Climb aboard your sailboat with your group and venture out to explore the Jobos Bay Reserve, Cayo Caribe, and other wetland locations. Use the provided snorkel equipment and listen to informative commentary from your captain about local marine life.
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  • 6 hours
  • Free Cancellation
From
$680.00
per group
From
$680.00
per group

PRIVATE SAILING LESSONS - Experience-Based, Hands-on in Fajardo
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PRIVATE SAILING LESSONS - Experience-Based, Hands-on in Fajardo

star-5
1
Take advantage of Puerto Rico’s east coast striking vistas and superb sailing conditions to practice and improve yours skills or learn the principles of sailing, weather interpretation and GPS navigation. Practice how to steer the helm and trim the sails under professional sail instruction. Sail off to a charming location and celebrate the day’s lessons in style. Jump for a swim, go snorkeling or paddle boarding as we treat you to a BBQ meal, beach snacks and drinks. Lesson includes: • Sailing off the coast of Fajardo to the offshore islands, destination determined by you and the captain • Hands-on lessons with a qualified captain on the basics of sailing, sail trimming, helm steering, water safety, weather interpretation and GPS navigation • On-board amenities (snorkeling equipment, paddle board and floaties) • Food: Beach Snacks and BBQ Lunch • Beverages: Choice of two (2) hard liquors (rum, vodka, whiskey or tequila), sparkling wine, mixers, water, assorted soft drinks & juices
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  • 6 hours
  • Free Cancellation
From
$1,670.00
per group
From
$1,670.00
per group

Sailing and Snorkeling Experience with Lunch from San Juan

Sailing and Snorkeling Experience with Lunch from San Juan

star-1
1
Admire unparalleled views and feel a cool breeze as you sail to your island paradise on a spacious, 54-foot (16-m) catamaran. Hop off the boat into the inviting waters of the Atlantic ocean. After spending time in the water, a scrumptious prepackaged lunch and tropical drinks are served. With a piña colada, relax before hopping back on the boat and finding a spot in the shaded cabin area or on the deck in the open air for the cruise back to San Juan.
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  • 5 hours
  • Free Cancellation
From
$169.00
From
$169.00

Private Sunset Sail - South Coast of Puerto Rico

Private Sunset Sail - South Coast of Puerto Rico

Cath the most amazing sunsets from a secluded spot on the Jobos Bay National Estuarine Research Reserve (JBNERR) with our experienced USCG Captain and crew, in the comfort and privacy of our 36-foot sailboat fit for six (6) passengers. Your departure time is schedule and confirmed according to the sunset hours. Sábila Sailing Charters depart from the gorgeous town of Guayama at the docks of the Guayama Fishing Club, famous for its stunning sunset views. The departure dock in the town of Guayama is about an hour drive away from San Juan, through the amazing landscapes of the Cordillera Central, the main mountain range in Puerto Rico.
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  • 2 hours
  • Free Cancellation
From
$449.00
per group
From
$449.00
per group

SUNSET SAIL aboard PRIVATE SAIL YACHT in Fajardo
Likely to Sell OutLikely to Sell Out

SUNSET SAIL aboard PRIVATE SAIL YACHT in Fajardo

Catch the sunset from the best seat in the house… the water! Wind down while cruising around the east coast islands of Puerto Rico. Follow the winds and soak up the day’s last rays of sunshine as we pamper you. Tour includes: • Sail around the coast of Fajardo and the local offshore islands. Departure times will be adjusted to best capture the sunset. • Briefing on sailing basics and safety. • Planning assistance—to create a unique experience. • Food: Choice of Fresh Fruits Platter or Cold-Cuts & Cheeses Platter. You may request a combination of the two. • Beverages: Choice of two (2) hard liquors (rum, vodka, whiskey or tequila), sparkling wine, mixers, water, assorted soft drinks & juices. Mojito or sangria pitchers available at additional cost. Tour Upgrades: Extra hours, photos or short video edit, special occasion planning like birthdays, proposals or family reunions.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$900.00
per group
From
$900.00
per group

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Day Trips from Puerto Rico