SAILING TOURS
Five continents, one question: which boat is worth the afternoon. These 15 are the sailings that earn the money anywhere they run, priced and timed, with the rest of the fleet underneath when you want to keep looking.
Board a spacious catamaran in Malaga for a 1 to 1.5-hour cruise along the coast. Watch the sun sink behind the mountains, enjoy chillout music and a glass of cava if selected, and choose an evening with a romantic light show. Live music is offered on Wednesdays, Fridays, and Sundays until mid-September.
“The boat trip was beautiful, good music, nice relaxed vibes and beautiful views.”
Cruise Oslo Fjord for two hours on a traditional heated sailing ship with blankets, a bar, and multilingual audio commentary. You’ll pass Hovedøya, Dyna Lighthouse, the Opera House, Munch Museum, and Bygdøy. Disembark at Bygdøy at 12:20 PM and return at 2:50 PM if you want time for the Fram or Maritime Museum. Guides such as Karen add lively local color.
“The weather was awful, it was raining all the time and it was just +13 and windy - but we managed to enjoy the trip (the boat is protected from rain + they gave us warm blankets)”
Join Mundo Marino at Valencia’s port for a 1 to 90-minute catamaran cruise along the Mediterranean coast. Choose a daytime ride or sunset sailing with cava. Seasonal Wednesday departures may include a live DJ. Expect skyline views, a bar, cushioned seating, and optional front net seats.
“I chose catamaran ride with net seat and it was absolutely worth it. So if you go with the catamaran I suggest to get the net seats, they watch your ticket for it. There was also music, that gave festive vibes, I wouldn't mind calm music or silence. There are 6 nets and it's allowed 6pers per net, so if you are big company note that. But nets are close to each other. I loved the ride very much. I took sunset ride and it was marvelous. I suppose if you take day ride, it's impossible to hide from the sun there, be aware.”
Sail from Lloret de Mar along the Costa Brava, then anchor for about two hours of swimming, snorkeling, floating, and a barbecue lunch. You get beer, sangria, soft drinks, and water, plus music and a DJ on selected departures. Choose a family-friendly morning trip, an adults-only afternoon or evening sailing, or a Saturday celebration cruise.
“The crew were very friendly, the food was good and so enjoyed swimming and snorkelling, I highly recommend books with them.”
Sail from Key West for about two hours aboard a spacious catamaran with an open liquor bar, champagne, sangria, wine, premium beer, soft drinks, and hors d’oeuvres. Local musicians provide live music as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Arrive 30 minutes early and bring a sweater for cool or windy evenings.
“The sunset was absolutely divine. We sat outside on the bow, drank wine, and took it all in. The crew were attentive and the company was a good time. 10/10 would do again.”
Sail from San Jose del Cabo toward Santa Maria or Chileno Bay, with Arch views, snorkeling, paddleboards, cocktails, and lunch aboard a small boat for up to 16 people. The crew may include guides such as Cesar, Israel, Michelle, Joe, or Poncho. Expect about four hours on the water, plus transfer time.
“Great experience. They had a professional photographer on board who took pictures of people while on board. The pictures are available for purchase at the end of the excursion. We got close to the arch for better pictures. You have 2 chances to see it, once on the way out and once on the way back into the marina. The snorkel spot was protected from strong currents and had rock formations that plenty of fish were hanging around.”
Sail from Cancun to Isla Mujeres on a five-and-a-half-hour catamaran trip with hotel pickup, snorkeling for ages 8 to 60, an open bar, light lunch, and free island time. Guides such as Enrique, Christina, Judy, Abraham, and Diego have led recent departures, though boat conditions and schedules can vary.
“Great experience and lots of fun. Staff was great and attentive! Christina and Judy were very friendly and entertaining as well as the rest of the crew!”
Join a small group of up to 10 for a two-hour sail from Belém. Your crew, sometimes including Benny, Miguel, Telma, Alex, or Vasco, shares Lisbon stories as you pass the Monument to the Discoveries, Belém Tower, MAAT, Commerce Square, and Cristo-Rei. Choose daytime, sunset, or night, and enjoy one beer, wine, or soft drink.
“Luis (apologies if I spelt that incorrectly!) was brilliant, he is so passionate about boats & what he does it's infectious. His appreciation for Lisbon & Portugal it's so respectful & proud he makes the history sound natural & interesting without being too much information you don't be able to retain when you leave! Thanks so much we had a brilliant time, it's a very romantic trip even though we went with friends!”
Sail from Alcântara for about two hours with up to 12 people, passing Belém Tower, Jerónimos Monastery, Ajuda National Palace, the 25 de Abril Bridge, and Cristo Rei. Skippers such as Joe, Henry, JP, and Marta offer informal Lisbon commentary while Portuguese wine is served. Bring warm layers, and allow extra time to find the marina office.
“The guide (JP) was very knowledgeable, and the tour was very relaxing. This was such a nice evening getting to know the other riders, and enjoying the atmosphere.”
Meet the crew at Doca do Bom Sucesso and cruise the Tagus for about 1 to 2 hours. You’ll pass under the 25 de Abril Bridge, see Belém Tower and Christ the King, and may help sail the boat. Choose a sunset departure for warm skyline views. The crew, including captains such as Luis when assigned, provides a relaxed, informal outing rather than a formal guided tour.
“Luis was an excellent captain and entertained us with narration of the sights. We had some avid sailers in our group and they enjoyed his answers to their questions about Tejo navigation, the boats rigging and more. We had a great time!”
Sail from Heraklion’s Old Venetian Harbour to Dia Island aboard a small yacht with up to 14 people. You’ll swim, snorkel, paddleboard, and eat shrimp linguini, Greek salad, and Cretan appetizers. English-speaking crew members such as Mariana, Manos, Sofia, Giannis, and Captain Petros have earned warm praise for friendly service, with afternoon trips offering sunset views.
“The perfect day! Our guided were all so kind and accommodating. The boat was beautiful, spacious, and had plenty of fun equipment. The lunch was delicious and abundant, as well and the drinks! Overall, a fantastic experience. Would absolutely do it again!”
Join the 65-foot Arusun from Palm Beach for a 2.5-hour sail with two snorkel stops, snacks, and an open bar. The crew may include Captain Amanda, Gabriel, or first mate Ronnie. Expect a spacious boat, shaded seating, lounging nets, and a short zodiac ride to board.
“Very fun excursion. Snorkeling was great, water felt wonderful. We saw lots of fish. The crew was knowledgeable and friendly. We were offered snacks and the open bar was a plus. The catamaran is big and beautiful with shade. We were on a cruise ship. Getting to the beach was easy by cab. It cost us 15 dollars. We got a cab back to the cruise ship by going to the taxi stand at the Hilton next door. Also very easy.”
Sail from the Hyatt Regency with Delphi Watersports aboard The Dolphin for three hours. Snorkel at the Antilla shipwreck and Boca Catalina Bay, then enjoy a rope swing, spinning slide, wraps, fruit, music, and drinks. The crew, including names such as Frederick, Oscar, Rio, Jay, and Brandon, keeps the outing friendly and active.
“Great trip! Just wish we could have had more time at the ship wreck. So much fun! The swing and slide were a great touch!”
Set sail from San Jose del Cabo on a 50-foot boat for 2.5 hours of sunset views, unlimited drinks, and light appetizers. You’ll cruise past Lover’s Beach and El Arco with up to 16 people, served by a captain and crew such as Tito, Chino, Chava, or Aldo. Pickup is available for $10 per person.
“Carlo’s and Sebastian were fantastic. My husband has a hard time walking and they were so kind and caring. Unlimited drinks met that. Food was shared between couples but more than enough and good.”
Sail Barcelona’s coast aboard a classic Turkish Gulet for 75 minutes, with rooftop views, an interior lounge, aft seating, chill-out music, and one Aperol Spritz included. Children ages 4 to 12 sail free. Meet at the City Sailing Barcelona ticket office. English and Spanish support is available.
“It was a lovely day to marvel at being out on the Mediterranean on a beautiful boat. It was clear this sailing boat was maintained and treated with the respect she deserved. It was a privilage to see her ( I did not see the boats name) handled so competently by her Captain and crew. It was a gorgeous, relaxing afternoon with the chance to see the city from the sea was really nice. Thank you for this gorgeous experience.”
Sunset, snorkel, or the whole boat.
