Top Puerto Rico Cruises, Sailing & Water Tours

Q: Which Puerto Rico Cruises, Sailing & Water Tours have Instant Confirmation?

Puerto Rico Cruises, Sailing & Water Tours with Instant Confirmation include: San Juan Sunset Harbor Boat Ride Small-Group El Yunque Waterfall & Waterslides with Pickup Icacos Island Catamaran Day Sail from Fajardo Culebra Full Day Beach and Fun Experience by Catamaran Clear Kayak Tour in Condado Lagoon View all Tours with Instant Confirmation →

Q: Got any more Puerto Rico trip ideas?

We sure do. Check out our curated lists of hand-picked Puerto Rico Tours. Top 10 Puerto Rico 2026 Senior-friendly tours Puerto Rico The best tours and activities for culture lovers in Puerto Rico Top Day Trips from Puerto Rico Things to do in Puerto Rico this summer View all Puerto Rico Trip Ideas →

Q: What are the most popular styles of Tours and Activities in Puerto Rico?

Based on our sales data over the past year, the most popular styles of tours and activities in Puerto Rico are: Puerto Rico Luxury & Special Occasions Puerto Rico Luxury Tours Puerto Rico Tours & Sightseeing Puerto Rico Outdoor Activities Puerto Rico Half-day Tours View all tour styles in Puerto Rico →

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting. …More

Fajardo, Puerto Rico

4.9 (21)

Janise Sailing Afternoon Charter in Fajardo, Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable voyage in the beautiful waters of the Caribbean Sea ending in an amazing sunset setting....

3 hours Free Cancellation

4.9 (21)

from
$229

Cueva del Indio and Charco Azul Cave and Waterfall Adventure

This is the best adventure tour in all Puerto Rico as it completely avoids the tourist traps of the island & focuses exclusively on amazing …More

Arecibo, Puerto Rico

4.9 (43)

Cueva del Indio and Charco Azul Cave and Waterfall Adventure

This is the best adventure tour in all Puerto Rico as it completely avoids the tourist traps of the island & focuses exclusively on amazing...

8 hours Free Cancellation

4.9 (43)

from
$175

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by …More

Fajardo, Puerto Rico

5.0 (16)

Private Janise Sailing Full Day Charter in Fajardo, Puerto Rico

Come aboard the comfortable Janise Lagoon 380 for a memorable 8-hourfull day charter in the beautiful Spanish Virgin Islands. Come experience first class service by...

8 hours Free Cancellation

5.0 (16)

from
$2,395

"San Juan: La Parguera Bio Bay Swim & Rum Tasting"

Embark on a magical journey from San Juan to La Parguera and discover one of Puerto Rico's breathtaking bioluminescent bays! This 10-hour all-inclusive adventure begins …More

Isla Verde, Puerto Rico

4.8 (144)

"San Juan: La Parguera Bio Bay Swim & Rum Tasting"

Embark on a magical journey from San Juan to La Parguera and discover one of Puerto Rico's breathtaking bioluminescent bays! This 10-hour all-inclusive adventure begins...

9 hours Hotel pickup offered Free Cancellation

4.8 (144)

from
$250

Icacos or Palomino Private Sunset Boat Tour from Fajardo PR

You want to do something different? Enjoy a private boat sunset experience on a private island from the east coast of Puerto Rico. This is …More

Fajardo, Puerto Rico

4.8 (18)

Icacos or Palomino Private Sunset Boat Tour from Fajardo PR

You want to do something different? Enjoy a private boat sunset experience on a private island from the east coast of Puerto Rico. This is...

2 hours Free Cancellation

4.8 (18)

from
$399

El Yunque Rainforest, Waterslides & Beach Tour from San Juan

Experience the Best of Puerto Rico on This Unforgettable Full-Day Tour! Embark on an exciting adventure through the breathtaking El Yunque Rainforest, where you’ll explore …More

Isla Verde, Puerto Rico

5.0 (29)

El Yunque Rainforest, Waterslides & Beach Tour from San Juan

Experience the Best of Puerto Rico on This Unforgettable Full-Day Tour! Embark on an exciting adventure through the breathtaking El Yunque Rainforest, where you’ll explore...

6 to 8 hours Hotel pickup offered Free Cancellation

5.0 (29)

from
$95

Half-Day El Yunque Rainforest Wilderness Adventure

Take the time to escape to heaven on Earth. Adventure calls you and it's time to respond to that call of life to break the routine, …More

Fajardo, Puerto Rico

5.0 (140)

Half-Day El Yunque Rainforest Wilderness Adventure

Take the time to escape to heaven on Earth. Adventure calls you and it's time to respond to that call of life to break the routine,...

4 hours Free Cancellation

5.0 (140)

from
$179

Private Day Sail - South Coast of Puerto Rico

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve …More

4.9 (23)

Private Day Sail - South Coast of Puerto Rico

Our experienced USCG Captain and crew will make sure you experience the most beautiful and secluded spots of the Jobos Bay National Estuarine Research Reserve...

6 hours Free Cancellation

4.9 (23)

from
$680

Toro Negro River Hike & Cliff Jumping Adventure; San Juan Pick Up

This is hands down the best hike on the entire island. From breathtaking views, to cool natural tropical pools, to cliff jumps that can satisfy …More

5.0 (22)

Toro Negro River Hike & Cliff Jumping Adventure; San Juan Pick Up

This is hands down the best hike on the entire island. From breathtaking views, to cool natural tropical pools, to cliff jumps that can satisfy...

8 hours Free Cancellation

5.0 (22)

from
$165

Enjoy a luxurious all inclusive day in our 47 feet Power Catamaran. Our Captain will choose one of the beautiful locations the east cost of …More

Fajardo, Puerto Rico

5.0 (16)

Catamaran Charter Puerto Rico Jenica

Enjoy a luxurious all inclusive day in our 47 feet Power Catamaran. Our Captain will choose one of the beautiful locations the east cost of...

6 hours Free Cancellation

5.0 (16)

from
$2,600

Bioluminescent Bay Kayak Adventure Tour from San Juan

This is one adventure not to be missed while in Puerto Rico! Join this fully-guided nighttime BioBay kayak adventure into one of the most amazing …More

4.1 (182)

Bioluminescent Bay Kayak Adventure Tour from San Juan

This is one adventure not to be missed while in Puerto Rico! Join this fully-guided nighttime BioBay kayak adventure into one of the most amazing...

6 hours Hotel pickup offered Free Cancellation

4.1 (182)

from
$108

Bio Bay Night Kayak Tour with Transport from San Juan

Bring a little excitement to your vacation with our night kayaking tour in the Bio Bay of Laguna Grande Reserve in Fajardo. The Bio Bay …More

Luquillo, Puerto Rico

4.4 (134)

Bio Bay Night Kayak Tour with Transport from San Juan

Bring a little excitement to your vacation with our night kayaking tour in the Bio Bay of Laguna Grande Reserve in Fajardo. The Bio Bay...

4 hours Hotel pickup offered Free Cancellation

4.4 (134)

from
$125

Trio Tour: El Yunque, Luquillo Beach, and Bio Bay Night Kayaking

Blend a little excitement to your vacation with our Rainforest River – Luquillo Beach & Bio Bay Night Kayaking Trio! This adventure is a full-day …More

Luquillo, Puerto Rico

4.5 (37)

Trio Tour: El Yunque, Luquillo Beach, and Bio Bay Night Kayaking

Blend a little excitement to your vacation with our Rainforest River – Luquillo Beach & Bio Bay Night Kayaking Trio! This adventure is a full-day...

12 hours Hotel pickup offered Free Cancellation

4.5 (37)

from
$189

Discover the beauty of Cayo Icacos, Puerto Rico, on a private boat excursion departing from Marina Puerto del Rey in Fajardo. Enjoy crystal-clear turquoise waters, …More

Fajardo, Puerto Rico

5.0 (18)

Fajardo Puerto Rico Private Boat Tour to Cayo Icacos

Discover the beauty of Cayo Icacos, Puerto Rico, on a private boat excursion departing from Marina Puerto del Rey in Fajardo. Enjoy crystal-clear turquoise waters,...

4 hours Free Cancellation

5.0 (18)

from
$850

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a …More

5.0 (51)

San Juan Bay Private Tour with Drinks and Tapas: 4+ people

Get more time, See more do more!, More Space! Welcome aboard your private water tour aboard a choice between a 37 foot sailboat ot a...

3 hours Free Cancellation

5.0 (51)

from
$166

The sail with us for the ultimate Puerto Rican boat experience! Whether you’re looking to make new friends at our lively Mix & Mingle boat …More

Fajardo, Puerto Rico

5.0 (21)

Private Boat Trip to Icacos & Palomino

The sail with us for the ultimate Puerto Rican boat experience! Whether you’re looking to make new friends at our lively Mix & Mingle boat...

4 hours Free Cancellation

5.0 (21)

from
$1,300

Private Meet your Guide El Yunque and Waterslides Adventure

Connect with nature and breathe in the fresh air on this exhilarating tour to Las Tinajas in Ceiba, Puerto Rico. The clear trails make this …More

Fajardo, Puerto Rico

5.0 (10)

Private Meet your Guide El Yunque and Waterslides Adventure

Connect with nature and breathe in the fresh air on this exhilarating tour to Las Tinajas in Ceiba, Puerto Rico. The clear trails make this...

5 hours 30 minutes Free Cancellation

5.0 (10)

from
$600

Bioluminescent Night Kayaking with Transport from San Juan 4pm

Feel the anticipation of exploring a new place, will escort you on a memorable journey to the mangrove forest of Laguna Grande where you will …More

Isla Verde, Puerto Rico

4.4 (31)

Bioluminescent Night Kayaking with Transport from San Juan 4pm

Feel the anticipation of exploring a new place, will escort you on a memorable journey to the mangrove forest of Laguna Grande where you will...

2 hours Hotel pickup offered Free Cancellation

4.4 (31)

from
$115

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

Outtaheretours is led by a team of Sailors,Divers, Instructors and Seaman with many years working in Aquatic Tourism. We are positive that nothing short of …More

Fajardo, Puerto Rico

5.0 (11)

Island Hopping and Snorkeling Sailing and Boat Tours Fajardo

Outtaheretours is led by a team of Sailors,Divers, Instructors and Seaman with many years working in Aquatic Tourism. We are positive that nothing short of...

3 to 5 hours Free Cancellation

5.0 (11)

from
$850

Fajardo: Full-Day Private Fishing Charter with Snorkeling, Beach

This Inshore Fishing Trip is designed by Pure Adventure’s Marine Biologist and fishing experts to ensure a sure catch in a short period, so everybody …More

Fajardo, Puerto Rico

5.0 (3)

Fajardo: Full-Day Private Fishing Charter with Snorkeling, Beach

This Inshore Fishing Trip is designed by Pure Adventure’s Marine Biologist and fishing experts to ensure a sure catch in a short period, so everybody...

7 hours Free Cancellation

5.0 (3)

from
$1,400

Frequently Asked Questions

These answers are based on answers previously given to Cool Shore Excursions customers' questions.

What are the best options for Puerto Rico Cruises, Sailing & Water Tours?

According to verified reviews on Cool Shore Excursions and TripAdvisor, the best Puerto Rico Cruises, Sailing & Water Tours are:

What are the best kid-friendly options for Puerto Rico Cruises, Sailing & Water Tours Tours?

Which Puerto Rico Cruises, Sailing & Water Tours have Instant Confirmation?

Which Puerto Rico Cruises, Sailing & Water Tours have Free Cancellation?

Puerto Rico Cruises, Sailing & Water Tours with Free Cancellation (in most cases up to 24 hours in advance of your tour date, check the specific tour page) include:

View all Tours with Free Cancellation →

I need a ride! Which Puerto Rico Cruises, Sailing & Water Tours have Hotel Pickup?

No problem. These Puerto Rico Cruises, Sailing & Water Tours include Hotel Pickup:

View all Tours with Hotel Pickup →

Got any more Puerto Rico trip ideas?

What are the most popular styles of Tours and Activities in Puerto Rico?