Overnight Charters | Serendipity Sailing Trips Costa Rica

Costa Rica

Overnight Trips

Our Overnight trips take your vacation to a whole, other level. With Serendipity, we have the freedom to sail where no roads can take you. We will explore this lovely coastline in style and privacy. Together, with our Captain and our guests, we will chose the right anchorages, based on weather, tides and their needs. We can sail for 2 hours and find a secluded bay, with a pristine beach or we can sail for 4 hours up into the Santa Rosa National Park.

Sailing up to Santa Rosa National Park, is an incredible experience. You will enjoy a 4 to 5 hour sail in the comforts of our 50ft sailing yacht. Ten unique habitats span the 122,350 acre park, ranging from mangrove swamp to dry tropical forest, each of which provide sanctuary for copious animal species. A total of 250 species of bird inhabit the park as well as 115 species of mammals which include deer, monkeys (white faced, howler, and spider) and five species of big cats.

The Yacht:

3 Private cabins and bathrooms available to guests (Captain will use the 4th estate room)
Swim off and on Transom
Dingy to use to explore (crew will drive dingy)
Full Kitchen
Outdoor and indoor dining area

Yacht
20 guests
4 cabins

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Costa Rica

Overnight Trips

Flamingo Marina, Playa Flamingo, Costa Rica

Costa Rica

Overnight Trips

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Overall

Serendipity Charters

5.0

Based on 159 reviews

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Stephanie Hilpert

3 years ago

We had an amazing sunset sail. We actually sailed, which not all companies do despite having sails. The staff was extremely attentive and friendly. The food and hand mixed drinks were delicious. There was plenty of time to play in the water or snorkel as well; all gear was included and in good condition. We will definitely use Serendipity Charters again!

Toros Yeremyan

3 years ago

We booked a full day with Serendipity Charters. Bismark and Jefferey were excellent hosts, and we thoroughly enjoyed our time sailing. We had a party of eight (4 adults / 4 kids), and everyone enjoyed the sailing, snorkeling and swimming. We were treated with great drinks, snacks and a taco lunch. We finished the day enjoying the sunset on our way back to the harbor. I highly recommend this trip!

Delaney Grayson

3 years ago

We had a great time sailing with serendipity!! Nice people & great food and drinks!! It was the perfect day!! Would highly recommend to anyone and will definitely use them again when we’re back.

Matthew Raecker

3 years ago

Chris Perkins

3 years ago

Had a great experience with this crew. Hit the spot with a combination of small group, attentive and experienced crew, and a great plan. Saw lots of fish on the snorkel and had dolphins riding our wake during sunset.

Kirsten Protos

3 years ago

Our sailing experience with Jeffrey, Johnathan and Christopher was one of the best parts of our trip! Our extended family booked the sunset trip on New Year’s Eve and it was absolutely magical! Beautiful scenery, snorkeling, delicious drinks and food. The captain and crew were knowledgeable and friendly and we had the best time with them! We highly recommend sailing with Serendipity and we will absolutely book again with them, the next time we visit.

Tiana Hubbard

3 years ago

I booked a private sunset charter, and the experience was AMAZING!! Our sail was captained by Bismark and his secondhand Jonathan! They were very friendly and knowledgeable of the seas and boat. They were so welcoming and open to answering any questions we had! Jonathan was our snorkeling guide, and he was very calm and helpful with identifying sea creatures and the best areas to view them from. They provided delicious drinks from the open bar, great music, positive energy, and delicious cowboy caviar and chicken tacos. This was an awesome experience, we felt at home with this amazing crew, and were witness to a beautiful sunset to end the whole experience with. I couldn’t have asked for a better crew or company to live out this experience with!! If you’re looking for a private sunset charter, search no further, as Serendipity Charters is thee BEST option to choose!!

Eliska Broes

3 years ago

Such an amazing experience. The scenery was out of this world. Crew was great. Very attentive and guided us through snorkeling. We saw an octopus, sea cucumbers and amazing fish. Food and drinks on board were delicious. So much fun. Would highly recommend.

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      Excellent rating  
 Based on 771 reviews 
    
  
 
 
       Just do it.
We were originally interested in one of the catamaran tours but we were a bit turned off by the label of "booze cruise". If you just want to get drunk with other loud Americans and motor around on a catamaran there are lots of options. Then we discovered Serendipity charters. This is a true sailing experience with a wonderful crew that went way beyond our expectations. The boat itself is very comfortable with 14 passengers and 3 crew. We all staked out our real estate on deck and in the cockpit but eventually we all moved around freely and it never felt crowded or unsafe. The sailing itself was very comfortable and the captain was extremely communicative about what was happening at all times. We were able to snorkel around a nice rock formation where we saw plenty of fish and a few turtles. They also served us great cocktails and delicious food throughout our trip. The porpoises guided us for a little while and then we had another amazing sunset as we glided back to the marina. All in all it was worth every cent and we would eagerly do it again on our next visit.
     
   Andrew W 
 
 
 
 
 
     Amazing sail and sunset
Awesome experience! The boat was clean and high quality, the captain and staff were friendly, professional, and provided great service. It was a small group and very laid back and relaxing. Quality food and drinks were served, an hour plus spent in a beautiful calm bay/beach and a sail back during sunset. One of the best excursions I have taken on a vacation. If you are looking to relax and avoid the chaos of the booze cruise, this is a gem.
     
   Tina 
 
 
 
 
 
     Fantastic Sunset Cruise
Our group of eight had a great time with Captain Bismarck and Jonathon. They treated us so well with delicious cocktails, snacks and lunch. They were personable and worked so well together. The snorkel and swim spot was enjoyable. Then we had tacos for lunch that were so good! They cared for their passengers, and were very engaging and safety conscious. The beautiful sunset with great friends with perfect music selection made for a fantastic finale to the day! We highly recommend.
     
   D S 
 
 
 
 
 
     5 Star Trip! Excellent Experience
Our trip was fantastic!!!! Bismarck, Christopher and Daniel were amazing. The food and drinks were good. Snorkeling was a blast. Seeing the sun going down at the same time the moon was up was incredible. Truly breathtaking views on a beautiful sailboat. Highly Highly recommend Serendipity Charters.
     
   Linda 
 
 
 
 
 
     If you want to SAIL... take the sloop. Treated like royalty.
Wow. What a great experience. Bismark and his crew too such good care of us. We went out with our extended family. 7 adults and 7 children. The treated us like royalty. The sailing was wonderful, the cove we anchored in was quaint and had fun swimming and snorkeling. Lunch was fabulous and the drinks were...... copious. If you want to SAIL...... take the sloop, skip the catamarans. Highly recommended.
     
   Fearless819451 
 
 
 
 
 
     Pura Vida for Sure!
Amazing, carefree afternoon on the boat. Great snorkeling, tasty food and a fantastic crew made this trip special! Loved every minute of the cruise and will definitely do it again!
     
   Dan O 
 
 
 
 
 
     Amazing!
Amazing afternoon! 13 people was enough so it didn’t feel excess. Definitely not the booze cruise some of the catamarans can be! Crew were delightful and food fabulous I will certainly do this again if I return to beautiful Costa Rica
     
   alison m 
 
 
 
 
 
     A must do in Costa Rica
I cannot recommend Serendipity highly enough!! It was a fabulous day! Six of us booked the all day private charter. Jonathan was our captain and Gerald was his mate. We loved them. They anticipated our every need and were so gracious, fun, and friendly! The sailboat was a 50 ft well-appointed monohull. The food and drink were wonderful and the snorkeling was great as well. I will be back!
     
   Trish H 
 
 
 
 
 
     Another Fantastic Sail
We have gone out with Serendipity many times. AGAIN, they did not disappoint. The crew was fantastic. Excellent trip - food was great. Crew took us out snorkeling. Had a great time.
     
   Ailbe G 
 
 
 
 
 
     Happy Repeat Sailors.
We sail with Serendipity every year we come. We love the sunset cruise and have sailed both with Lucky 13 & private charter. The food and drinks are delicious & plentiful. They have even improved over the years. The service is top notch. We appreciate that they use the sails as much as possible. The marina location makes it so much easier to comfortably get in and out of the sailboat. The best thing is the passengers are limited which makes for a great experience.
     
   Lyn

Overnight Trips

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