Sailing & Sunset Cruises

Experience Puerto Rico's beauty from the sea

Discover Puerto Rico by Sail

There's no better way to experience Puerto Rico's tropical splendor than from the deck of a sailboat. Our sailing and sunset cruise adventures combine the romance of sailing with the thrill of exploration. Whether you're a seasoned sailor or a first-time voyager, Puerto Rico's pristine waters and coastlines provide the perfect backdrop for a memorable trip.

Our catamaran and sailing tours offer a range of experiences from leisurely afternoon sails to romantic sunset cruises and full-day island-hopping adventures. Professional crews handle the sailing while you relax, swim, snorkel, and enjoy Puerto Rico's natural beauty. Popular routes include exploring nearby islands, visiting secluded beaches accessible only by boat, and witnessing spectacular sunsets over the Caribbean Sea with refreshing drinks in hand.

Each sailing tour includes professional crew, safety equipment, and often complimentary snorkeling at pristine reef locations. Many cruises feature light snacks and beveragesβ€”some include full meals. Tours accommodate all experience levels and are perfect for couples celebrating special occasions, families seeking adventure, and groups looking for a unique Puerto Rico experience. All our sailing vessels are Coast Guard certified and operated by experienced captains.

Available Sailing & Sunset Cruises

Public Icacos Double Dip Power Catamaran Snorkeling and Beach Tour

Public Icacos Double Dip Power Catamaran Snorkeling and Beach Tour

Sail Getaways

πŸ“ Fajardo

CatamaranSnorkel
Sunset + Swim the Bioluminescent Bay Tour

Sunset + Swim the Bioluminescent Bay Tour

Hook'd on Adventure Parguera

πŸ“ Lajas

Boat TourFood TourSnorkel
Fajardo Morning Snorkeling Tour - Check in by 7:15 AM

Fajardo Morning Snorkeling Tour - Check in by 7:15 AM

Sea Ventures Pro Dive Center

πŸ“ Fajardo

Boat TourFood TourSnorkel
La Parguera Adventure Tour Chiliboats Water Bike

La Parguera Adventure Tour Chiliboats Water Bike

Caribbean Chiliboats

πŸ“ Lajas

CatamaranSailing
Fajardo Afternoon  snorkeling boat tour check  in by 1:00pm

Fajardo Afternoon snorkeling boat tour check in by 1:00pm

Sea Ventures Pro Dive Center

πŸ“ Fajardo

Boat TourFood TourScuba
Public Icacos Luxury Sailing Catamaran Twilight Beach and Sunset Sail

Public Icacos Luxury Sailing Catamaran Twilight Beach and Sunset Sail

Sail Getaways

πŸ“ Fajardo

CatamaranSailing
Snorkel & Slide Boat Tours

Snorkel & Slide Boat Tours

Snorkeling Puerto Rico

πŸ“ Fajardo

Boat TourSnorkel
All Inclusive Culebra Snorkeling Excursion

All Inclusive Culebra Snorkeling Excursion

Sea Ventures Pro Dive Center

πŸ“ Fajardo

Boat TourMarinaSnorkel
Public Culebra Power Boat Snorkeling &  Beach Tour

Public Culebra Power Boat Snorkeling & Beach Tour

Sail Getaways

πŸ“ Fajardo

Boat TourSnorkel
Public Icacos Luxury Sailing Catamaran Beach Day

Public Icacos Luxury Sailing Catamaran Beach Day

Sail Getaways

πŸ“ Fajardo

CatamaranSailingSnorkel
Icacos sailing & snorkeling tour

Icacos sailing & snorkeling tour

East Island Excursions

πŸ“ Fajardo

Boat TourCatamaranSailing
Culebra Blue Paradise Experience

Culebra Blue Paradise Experience

East Island Excursions

πŸ“ Fajardo

Boat TourCatamaranKayak

Frequently Asked Questions

Do I get seasick easily, should I be concerned?

Most sailing tours operate in calm, protected waters where seasickness is rarely an issue. If you're prone to motion sensitivity, sit in the middle of the boat and focus on the horizon. Bring over-the-counter motion sickness medication as a precaution. Our crew can provide additional tips to enhance your comfort.

What should I bring on a sailing tour?

Wear a light swimsuit or clothing you don't mind getting wet. Bring sunscreen, sunglasses, and a hat. A light sweater is useful for cooler ocean breezes. Most tours provide life jackets and snorkel gear if needed. Avoid heavy perfume or cologneβ€”sun and sea water may cause discomfort.

Are sunset cruises romantic for proposals or special occasions?

Absolutely! Our sunset cruises are incredibly romantic and perfect for proposals, anniversaries, and special celebrations. We can arrange champagne, special decorations, and personalized experiences. Contact tour operators in advance to arrange surprise elements or special menus for your occasion.

What if the weather is bad on my sailing tour day?

Safety is our priority. Tours may be rescheduled or cancelled if weather is unsafe. Most operators offer flexible rescheduling or refunds if tours are cancelled due to weather. We monitor conditions closely and will communicate with you about any adjustments to your tour.

Ready to Book?

Set sail on a Puerto Rico adventure with our sailing and sunset cruise tours

Explore Tours Now

2026 Awards · editorial spotlights

Nominees we wrote up ourselves. They did not pay for these pages and had no say in them.

Best Icacos Catamaran DaySail GetawaysFajardo, Puerto Rico · from $100 Best Culebra Day TripEast Island ExcursionsMarina Puerto del Rey, Fajardo, Puerto Rico · Culebra trip $160 Best Private Boat CharterEncanto Boat ToursFajardo, Puerto Rico · from $349

Planning Guides

All Puerto Rico tour guides β†’