Aboard · SAILING
Some of these put the sails up properly and some motor out and hoist them for the photographs. The 15 below are honest about which is which, plus crew size, whether you can take the helm, and what the wind usually does at that hour.
You sail from Malaga for 1 to 1.5 hours aboard a spacious catamaran, with English- and Spanish-speaking crew, coastline views, chillout music, and an optional glass of cava. Choose a simple sunset cruise or add a romantic light show. Live music runs on select dates until mid-September.
“It's always an excellent option, during the day as during sunset!”
Set out from Oslo City Hall Pier on a traditional sailing ship with a heated main deck, blankets, bar, and English commentary. You’ll pass Hovedøya, Dyna Lighthouse, the Opera House, Munch Museum, and Bygdøy, where you can hop off to visit a museum before returning later.
“The information was timely as we passed interesting parts of the fjord”
Sail along Valencia’s coast for 60 to 90 minutes with a Spanish- or English-speaking crew. Choose a daytime or sunset departure, enjoy views of the City of Arts and Miquelet, and select the seasonal Wednesday DJ option with cava at sunset.
“I did really like it. The music could be a little bit quiter (so the talking would be easier) but overall really nice”
Sail from Lloret de Mar along the Costa Brava, then anchor for swimming, snorkeling, and a BBQ of burgers, chicken, pasta, salad, and fruit. Choose a family-friendly morning, adults-only afternoon, or Saturday celebration cruise with music, drinks, and a lively return trip.
“Couldn’t have asked for a better experience! 100% worth the price!!”
Board Sebago’s spacious catamaran at 205 Elizabeth Street for a two-hour Key West sunset sail. Expect live local music, peel-and-eat shrimp, wine, sangria, beer, cocktails, and soft drinks as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Bring a sweater and arrive 30 minutes early.
“Very well done. Great attitude from the crew which made for a great rise in morale for all the guests.”
Sail from San Jose del Cabo toward Santa Maria or Chileno Bay, with snacks, an open bar, snorkeling, paddleboards, and lunch aboard a boat limited to 16 people. You may also see El Arco and seasonal whales. Confirm pickup details, fees, and safety limits before departure.
“The crew and sailing were fabulous as was the food. Pictures and whale spottings were great. Snorkeling was disappointing and we could not get on the beach where we anchored!! Ugg!”
Sail from Cancun to Isla Mujeres on a catamaran with hotel pickup, an open bar, light lunch, snorkeling when conditions allow, and island free time. The crew may include guides such as Enrique, Christina, Judy, or Abraham. Choose a family-friendly or adults-only departure, but confirm the option carefully.
“We didn't know what to expect and probably brought too many things. A specific itinerary would have been nice.”
Spend two hours on a small sailboat with guides such as Benny, Miguel, Telma, or Luiz, hearing Lisbon stories as you pass Belém Tower, MAAT, Alfama, and Christ the King. Choose daytime, sunset, or night sailing. A drink, water, blankets, and a toilet are provided.
“We did the sunset cruise and couldn’t recommend it more! I flew in from the far south with my 79- and 84-year-old family members, and it was the perfect way to start our trip — low activity, high impact, and absolutely stunning. The vessel was comfortable and easy to move around, and the crew were warm, attentive, and genuinely engaging. One guide was a nautical scientist and the other a former banker — both were delightful, sharing interesting insights and keeping our glasses topped up. The music was perfectly curated — relaxed remixes of classic jazz, never too loud — and it truly elevated the atmosphere. We loved every minute…”
Join a skipper-led evening sail from Alcântara, with Portuguese wine and views of Belém Tower, Jerónimos Monastery, the 25 de Abril Bridge, and Christ the King. Crew members such as Joe, Henry, JP, and Marta are praised for friendly commentary. Bring a warm layer, since the river air can turn cool.
“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.”
Set sail from Belém’s Doca do Bom Sucesso for a relaxed Tagus cruise with a small crew. Pass the Discoveries monument, 25 de Abril Bridge, Belém Tower, and Christ the King. You can help steer, enjoy a drink, or choose a sunset departure. Captain Luis has been praised for his sailing knowledge and lively narration.
“It was a lovely one hour sailing trip across the Tagus to the bridge and back It was slightly windy so on a hot day I’m sure it would be even better. Free beer water and the young skipper and his mate were very good Worth the money and definitely recommend”
Sail from Heraklion’s Venetian Harbour to Dia Island aboard a yacht limited to 14 people. Captain Petros and crew members such as Sofia and Giannis provide swimming, snorkeling, paddleboarding, a Mediterranean meal, and unlimited drinks during this 5.5-hour cruise.
“Perfect friendly Crew. Nice Katamaran. Good drinks and delicious food. It was my third time with this company. Sofia, Giannis and our Captain Petros are a super Crew. I will make the Dia Tour again. I love it sooooo much. Thank you Guys. Nicole”
Join the 65-foot Arusun from Palm Beach for a 2.5-hour sail with snorkeling at the Antilla Shipwreck and Catalina Bay. Captain Amanda, Ronnie, Gabriel, and other crew members have earned praise for friendly service. Expect an open bar, light wraps, shade, lounging nets, and a maximum of 35 people.
“This boat was a lot of fun - the crew of two was very friendly and fun- interacting with the passengers. It was nice no one tried to sell you on photo packages or upgrades. The drinks weren’t watered down and the snacks were really good wraps. They took us to two snorkeling spots and the second one had a bunch of sea turtles- we were impressed.”
Spend three hours aboard The Dolphin catamaran from Noord, with snorkel stops at the Antilla shipwreck and Boca Catalina Bay. Guides share local stories, while you enjoy a rope swing, spinning slide, wraps, fruit, and drinks. Crew members including Frederick, Oscar, Rio, Jay, and Brandon have earned warm praise.
“Get ready for JUST RELAX, WE ALL HAD SUCH A GREAT TIME, People were friendly especially papi. lol music was great, swimming. going down the slide , snorkling. well i did not snorkle, just sat and watched , enjoyed everything, i would highly recommmend”
Sail Cabo San Lucas Bay for about 2.5 hours on a 50-foot boat, passing Lover’s Beach and El Arco as the sun sets. Expect a small group of up to 16, an open bar, shared appetizers, music, and attentive crew members such as Tito, Chino, Aldo, and Ronnie, depending on the departure.
“Wonderful The crew were amazing The snacks, the open bar was amazing and very friendly the three persons in charge”
Spend 75 minutes aboard a classic Turkish Gulet, sailing from Barcelona’s port along the coast with an Aperol Spritz included. Choose the rooftop, interior lounge, or aft chill-out area. The crew speaks English and Spanish, and children ages 4 to 12 sail free.
“It was a great experience. It is value for money. I enjoyed this activity. The description was perfect.”
Pick a river, a coast or a harbour.
