San Juan, Puerto Rico is one of the hottest vacation destinations for people around the world. Not only is it conveniently-located for those who live in North America, it’s full of rich culture, delicious food, colorful architecture, and beautiful naturaleza.
If you’re going to see all of the beauty San Juan has to offer, we have the perfect tours for you: the best sunset sailing tours! These take place out on the water, where the rich oranges and reds reflect perfectly – offering an unmatchable view that is best enjoyed on a sailboat.
We’ve done the “hard” part for you, making sure you are getting the best bang for your buck, and a sailing experience that you’ll want to take over and over again.
Be sure to see our reviews of Puerto Rico Kayaking Tours, El Yunque Rainforest Tours and Puerto Rico ATV Tours.
Best Sunset Sailing Cruises From San Juan
| San Juan Catamaran Sunset Sail | SUNSET SAIL aboard PRIVATE SAIL YACHT in Fajardo | Janise Sailing Afternoon Charter in Fajardo, Puerto Rico | |
|---|---|---|---|
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| Departure: | Avenida Campo Rico ("Roberto Sanchez Vila Avenue"), Este Final, Carolina | Pickup available | San Juan, (point will be determined upon booking) |
| Start: | 5:00 PM | Contact tour operator | 2:30 PM |
| Duration: | 2 hours | 1 hour | 7 hours |
| Includes: | 2-hour ATV adventure, basic ATV instructions | Transport from San Juan, 1-hour ATV adventure | Air-conditioned vehicle, snacks, 3.5 hour ATV adventure |
Quick Answer: The 6 Best Sunset Sailing Cruises in Puerto Rico
- San Juan Catamaran Sunset Sail
- SUNSET SAIL aboard PRIVATE SAIL YACHT in Fajardo
- Janise Sailing Afternoon Charter in Fajardo, Puerto Rico
- Sunset Sail by San Juan Historical Bay
- Sunset Harbor Boat Ride in San Juan
- Private Sunset Sail on the East Coast of Puerto Rico
San Juan Sunset Sailing Reviews
1. San Juan Catamaran Sunset Sail
- Duration: 2 hours
- Departure: 482 Av. Manuel Fernández Juncos, San Juan, 00901
- Departure Time: 5:00 PM
- Includes: Professional captain and guide, beverages
Let’s start things off with the beautiful San Juan Catamaran Sunset Sail. This 2-hour sail is the perfect way to lead you from the warm day into a refreshing evening.
While sailing on just about any bay will make for a picturesque moment, the San Juan Bay and port have a rich history and various landmarks that make this tour particularly special. You’ll meet up with the rest of your group/guides at Slip A72 on the main dock at San Juan Bay Marina.
The crew makes this process seamless, so everyone can get acquainted, go through safety information, and focus on the incredible view and having fun! The captain and crew are so warm and friendly, and really make the entire experience pleasant from the beginning.
Start off at La Puerta de San Juan, or “San Juan Port”. This landmark is very important in the history of the country. Founded all the way back in the early 1500’s by Ponce de Leon, it has become a major seaport for the country in culture, manufacturing, tourism, and more.
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While a lot has changed in so many hundreds of years, a lot has stayed the same, which makes it such a tourist hot spot.
You’ll then spend the rest of the tour sailing around the bay, catching up-close views of the castle “Castillo San Felipe del Morro”, and the fort, “La Fortaleza – Palacio de Santa Catalina” from the water.
The captain and crew are very experienced and will tell you all about these crucial pieces of history that will only make the adventure that much more interesting!
Tour Information & Booking
100% refund for cancellations within 24 hours of tour experience
Other Puerto Rico Experiences You May Enjoy:
2. SUNSET SAIL aboard PRIVATE SAIL YACHT in Fajardo
- Duration: 2.5 hours
- Departure: 4900 State Road 3 Km. 51.4, Fajardo, 00738, Slip 1089
- Departure Time: Contact tour operator
- Includes: Coffee and/or tea, bottled water, soda, alcoholic beverages, snacks
Are you looking for a captivating cruise in Puerto Rico, but one that offers style and luxury? If so, then look no further than the Sunset Sail Aboard Private Sail Yacht in Fajardo! This 2.5-hour cruise simply offers the best seat in the house for appreciating all that this beautiful country and city has to naturally offer.
Start off by meeting with the captain and crew, and board the private yacht. Before you get to sailing around the sparkly azure seas, they’ll brief you on sailing basics and safety precautions to take so that all the fun is to be had.
Sit down on the ample seating aboard, and get ready to just relax and take it all in. According to the weather, the captain will take the best route possible so that you’ll comfortably get to see all around the islands and cays on the eastern coast of the country.
Meanwhile, enjoy some delicious fresh fruit platters and/or platters of cold cuts and cheeses! Wash it all down with up to 2 hard liquor drinks, sparkling wine, mojitos, or sangria!
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Something else that really makes this tour stand out is the way that the staff makes an effort in ensuring you have the best experience possible. This isn’t a cookie-cutter tour. Nope, they will offer you planning assistance in your tour to make sure you (realistically) can see everything you want to on board.
While the tour is by default around 2.5 hours, you can add extra hours, photos, video edits, or even make special accommodations for occasions like birthdays, proposals, and more.
Tour Information & Booking
100% refund for cancellations within 24 hours of tour experience
Search For San Juan Experiences You May Enjoy:
3. Janise Sailing Afternoon Charter in Fajardo, Puerto Rico
- Duration: 3 hours
- Departure: Puerto Del Rey Marina, 00735
- Departure Time: 2:30 PM
- Includes: Romantic sailing with a beautiful sunset backdrop, alcoholic beverages, soft drinks
Are you looking for a tour that lasts a bit longer? Then check out the Janise Sailing Afternoon Charter in Fajardo, Puerto Rico. There are various start times to choose from, from the afternoon until the evening so you can choose what works best for you and the rest of your group!
Your tour will take place aboard the Janise Lagoon 380, which is a stunning charter that offers comfortable seating with excellent views of the island and surrounding seas.
No matter if you’re looking for a fun time with friends or a romantic evening with your significant other, this is sure to be one of the best ways to spend 3 hours in Fajardo.
Your voyage will go all around the shores and secluded islands of the eastern coastline, which feel almost like you have them all to yourself. This is definitely one of the top activities to take if you want something away from the hustle-and-bustle of crowds and touristy spots.
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After sailing for a nice amount of time, the captain and crew will drop anchor on the coastline, where you’ll be able to select your next activity. You can either take a refreshing dip in the ocean, kick your feet up in the catamaran, or enjoy some mouth-watering snacks and beverages; all while watching the electric sunset.
There are all kinds of snack options on board, along with water, sodas, beer, wine, sangria, and more. If this sounds like a good time to you, then hurry and make your reservation for one of the top-rated San Juan sunset cruises around!
Tour Information & Booking
100% refund for cancellations within 24 hours of tour experience
4. Sunset Sail by San Juan Historical Bay
- Duration: 2 hours
- Departure: 480 Av. Manuel Fernández Juncos, San Juan, 00907
- Departure Time: 5:00 PM
- Includes: Refreshments, beverages, bottled water, snacks, unlimited beer, wine and soft drinks, alcoholic beverages
Are you on the hunt for a tour that combines sportsmanship, history, and exploration all into one adventure-packed activity? Then get yourself ready for the Sunset Sail by San Juan Historical Bay tour!
On this tour, you’ll not only get to see the natural beauty of San Juan, but also learn all about it and its iconic landmarks!
Meet up with the captain and crew to board the awesome 30-foot racing boat! This boat seats 6, which means it’s great for intimate groups, personalized attention, learning, and of course high speeds!
If you have a need for speed, then this is one of the best tours to take, but rest assured the captain will always make sure you’re okay with going that fast beforehand. With his clear competence, you can feel confident that you’re in good hands.
Of course, not everything is about getting the adrenaline pumping. You’ll sail very close to important landmarks such as the Castillo San Felipe del Morro, La Fortaleza – Palacio de Santa Catalina, and San Juan Bay.
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El Castillo San Felipe del Morro has been around for hundreds of years, and currently is the governor’s mansion. “El Morro” is very impressive to look at, and was built on the orders of King Charles V of Spain. “La Fortaleza” has been around since 1846 and is the oldest executive mansion in continuous use in the New World.
San Juan Bay also has an interesting commercial history, with notoriously flat waters. While you learn, try to keep an eye out for dolphins playing around the boat while watching the sun set over the pristine Caribbean.
Tour Information & Booking
100% refund for cancellations within 24 hours of tour experience
5. Sunset Harbor Boat Ride in San Juan
- Duration: 1.5 hours
- Departure: 482 Cll Guamani, San Juan, 00901
- Departure Time: 5:00 PM
- Includes: Bottled water, local beers, sodas, appetizers
Say you’re tight on time or simply want to pack in as many activities as possible into your day, but still want to partake in a sunset tour. If so, then the Sunset Harbor Boat Ride in San Juan is just for you! This 1.5-hour tour may be a bit compact but it sure is full of fun!
With a pickup from select hotels, the entire experience is streamlined so you can make the most of your time and don’t have to worry about finding a meetup point or transportation
. As with the other tours, the captain and crew are very friendly and knowledgeable about the area, ensuring everyone has a great time.
Take a seat on the relaxing boat ride while enjoying some snacks, soft drinks, and alcoholic beverages. This makes for an excellent precursor to a full dinner on shore while also learning new things and enjoying some fresh air and breathtaking nature.
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Partake in some grapes, cheese, chips, and other snacks and beverages. This tour will take you by all kinds of island highlights, such as the Paseo de La Princesa, La Fortaleza, the San Juan City Walls, El Morro, and more!
The excursion involves commentary by the onboard tour guide who knows all about the history of these landmarks, giving you a perspective into colonial times to present-day.
If that weren’t enough, with the sun setting it makes for an even more magical time, illuminating the centuries-old buildings and seas. It makes you feel almost like you’re transported back to “the olden days”.
Tour Information & Booking
100% refund for cancellations within 24 hours of tour experience
6. Private Sunset Sail on the East Coast of Puerto Rico
- Duration: 2.5 hrs
- Departure: Puerto Del Rey Marina, 00735
- Departure Time: 4:30 PM
- Includes: Snacks, alcoholic beverages, water, soft drinks
Are you looking for a perfectly romantic way to spend an evening with your special someone? Maybe you’re just looking for a relaxing tour to enjoy San Juan’s naturaleza? If that sounds like something up your alley, take a good look at the Private Sunset Sail on The East Coast of Puerto Rico.
Lasting 2.5 hours, this tour is an excellent way to break up the common stress of scheduling in as much as possible or navigating crowds. Here, you’re going to relax and let any tension melt away while you sip on delicious cocktails, munch on some appetizers, and enjoy the picturesque Costa Rican sunset on the water.
You can choose to sit inside or outside on the deck – whatever you prefer. Seating up to just 6 people, the private sail is meant to be personal. This is also a great way to ask your onboard guide and crew any questions that you may have about the area, the sea, or anything else relating to San Juan.
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They’re all very knowledgeable and will provide you with an educational commentary on the area on the landmarks.
Start out by sailing from the marina to the private islands on the eastern coast of Puerto Rico. Once the captain finds the perfect spot, they’ll drop anchor so you can just enjoy all kinds of cocktails and eats while watching the sun set.
This is also the ideal time to take some videos or photos, should you like. You may even see some dolphins or other sea critters, if you’re lucky!
Tour Information & Booking
100% refund for cancellations within 24 hours of tour experience
Comfort
Tour Guides
Value
The San Juan Catamaran Sunset Sail is our Editor's Choice so the top sailing cruise in Puerto Rico
