SAILING

The 15 Best Sailing Trips Worldwide

29 trips  ·  from $65 a head

This is the shortlist you would send a friend: 15 sailing trips worth the money, each with its price, its traveller verdict and the one thing to know before you paddle out.

Private Catamaran Swim sail snorkel cliff jumping SUP - Sailing through West Bermuda
Cruises & Boat Tours, Private, Private Surf Lessons, Sailing, Stand-Up Paddleboarding, Surf & Snorkel Trips, Surf Trips, Tour Reviews

Private Catamaran Swim sail snorkel cliff jumping SUP

1.Private Catamaran Swim sail snorkel cliff jumping SUP

★★★★★★★★★★5.0 · 232 reviews Our pick

Spend three flexible hours on a private Bermuda catamaran with Captain Mark, Alex, Georgia, or Matt and crew. Sail around West Bermuda, stop for snorkeling and swimming, try cliff jumping, use the SUP and crystal kayak, and play your own music. The boat has a restroom and space for 15.

“We had a fantastic afternoon with Captain Alex and his first mate, Georgia. They were so accommodating, and made us all feel at home on the catamaran. They gave us suggestions on how to best spend the afternoon, even though the harbRead more”

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Lérins Islands Sailing Discovery, snorkeling and paddle SUP - Île Sainte-Marguerite and the story of Fort Royal
Cruises & Boat Tours, France Surf Trips, Island & Bay Paddle Tours, Sailing, Snorkeling, Stand-Up Paddleboarding, Stand-Up Paddleboarding in France, Surf & Snorkel Trips, Surf Trips, Tour Reviews

Lérins Islands Sailing Discovery, snorkeling and paddle SUP

2.Lérins Islands Sailing Discovery, snorkeling and paddle SUP

★★★★★★★★★★4.7 · 110 reviews · 3h 30m · from $100

Sail from Antibes with a French or English-speaking skipper, often Valentin, toward Île Sainte-Marguerite and Fort Royal. You’ll learn basic sailing, stop for snorkeling and paddleboarding, admire Riviera yachts, and enjoy a comfortable 9-person boat. Swimming stops run May 15 to September 15.

“This activity was INCREDIBLE! The water was so blue and a perfect temperature for exploring and relaxing. However, there were some unhappy people on board, which was a bummer! Part of the group couldn’t swim and thought that they’d be able to explore the island while others snorkel/swim. (Obviously not!) And then others weren’t strong swimmers and were upset that the boat didn’t dock in shallow water (Obviously, it can’t!). If you’re looking for an island-hopping on-land activities, this isn’t for you! All this to say — this activity is amazing! You’re on a sailboat in the Mediterranean and sailing along the coast — and then jumping off the boat…”

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Airlie Beach: Whitsunday Islands Sailing, SUP & Snorkel Tour - Boarding at Coral Sea Marina
Australia Surf Trips, Cruises & Boat Tours, Island & Bay Paddle Tours, Island Paddle Tours in Australia, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Australia, Surf & Snorkel Trips, Surf Trips, Tour Reviews, Tours

Airlie Beach: Whitsunday Islands Sailing, SUP & Snorkel Tour

3.Airlie Beach: Whitsunday Islands Sailing, SUP & Snorkel Tour

★★★★★★★★★★4.8 · 90 reviews · 6 hours · from $162

Spend six hours aboard the air-conditioned Wings III, a 60-foot sailing catamaran with a jacuzzi, shaded decks, and space for 29 people. Sail near Hook Island and Hayman Island, snorkel fringing reefs, paddle at Langford Island, and enjoy fresh morning tea and lunch. Bring your own drinks.

“what a relaxing day! the team really looked after us, and the sailing was amazing. thanks so much 🙏🏼😊”

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Private Yacht Cruise 4 Hour- Snorkeling & Paddle Boarding - Seeing Cabo’s Arch from the water
Cabo San Lucas Surf Trips, Cruises & Boat Tours, Mexico Surf Trips, Private, Private Surf Lessons, Private Surf Lessons in Mexico, Sailing, Snorkeling, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Mexico, Surf & Snorkel Trips, Surf Trips, Tour Reviews

Private Yacht Cruise 4 Hour- Snorkeling & Paddle Boarding

4.Private Yacht Cruise 4 Hour- Snorkeling & Paddle Boarding

★★★★★★★★★★5.0 · 74 reviews · 4 hours (approx.)

Spend four hours on a private yacht with crew members such as Lewis, Leo, or Sergio, depending on availability. Cruise past Cabo’s Arch, watch sea lions, then swim, snorkel, fish, and paddle board at Santa Maria or Chileno Bay. Drinks, snacks, gear, towels, and water are included.

“Absolutely amazing! We had a private yacht and felt like royalty! Our captain and crew was phenomenal and met needs we didn’t even knew we had. They were always ready with drinks and snack (beautiful cheese/meat/fruit trays, nuts/snack mix, and fresh caught fish). They also had rigorous cleaning and sanitizing policies that made us feel much safer during the pandemic. They even had a warm rinse following our snorkeling adventure! Weather was perfect and we even saw the rays flying out of the water (mating season). One hundred thumbs up!”

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Milos: Full-Day Catamaran Cruise with Paddle Board - Meeting the crew in Adamas
Cruises & Boat Tours, Full-Day, Greece Surf Trips, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Greece, Surf Trips, Tour Reviews

Milos: Full-Day Catamaran Cruise with Paddle Board

5.Milos: Full-Day Catamaran Cruise with Paddle Board

★★★★★★★★★★5.0 · 62 reviews · 8 hours · from $235

Join a small-group, all-inclusive catamaran cruise from Adamas with an English-speaking crew. Swim at remote coves, ride a dinghy into Sykia and Kleftiko caves, paddleboard, enjoy Greek food and drinks, and receive GoPro photos after your day at sea.

“Our boat day in Milos was incredible—by far our favorite day on the island! The crew was absolutely amazing—so warm, welcoming, and knowledgeable. They made us feel completely at home from the moment we stepped on board, and they truly went above and beyond to maximize our experience. Exploring the caves, swimming in the crystal-clear water, and soaking up the beauty of the coastline was unforgettable. We can’t recommend this experience highly enough—an absolute must if you’re visiting Milos!”

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Barcelona: 2-Hour Sailboat Tour with Paddle Boarding - Leaving Port Olimpic and finding the right meeting point
2-Hour Experiences, Barcelona Surf Trips, Cruises & Boat Tours, Sailing, Spain Surf Trips, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Spain, Surf Trips, Tour Reviews, Tours

Barcelona: 2-Hour Sailboat Tour with Paddle Boarding

6.2-Hour Sailboat Tour with Paddle Boarding

★★★★★★★★★★4.9 · 44 reviews · 2 hours · from $65Best value

Sail from Port Olimpic for two hours, with views of Sagrada Familia, Torre Agbar, Tibidabo, and Montjuic. Your guide handles the boat, explains sailing basics, and may let you steer. Stop for a swim, paddle boarding, floating toys, snacks, soft drinks, and one glass of cava.

“A great experience for an excellent price! You can play music on the boat, enjoy sailing, explore all parts of the ship, and drinks are free. There is also food and snacks. At one point, they provide water gear, so you can swim and jump off the boat as many times as you like. The guide even lets you steer the boat on the way back. Highly recommended for everyone!”

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Afternoon yacht charter in lagos with drinks, tapas, paddle boards and kayak - Cruising toward Ponta da Piedade
Cruises & Boat Tours, Kayak & Canoe Trips, Kayak Trips in Portugal, Lagos Surf Trips, Portugal Surf Trips, Sailing, Surf Trips, Tour Reviews

Afternoon yacht charter in lagos with drinks, tapas, paddle boards and kayak

7.Afternoon yacht charter in lagos with drinks, tapas, paddle boards and kayak

★★★★★★★★★★5.0 · 30 reviews · 3 hours 30 minutes (approx.)

Cruise Lagos aboard Karma with a private group of up to eight. The crew handles the route while you enjoy Ponta da Piedade, local wine, tapas, snorkeling, two paddleboards, and a two-person kayak.

“Wonderful afternoon out on the water with Ze and Lucas. Fun stories and information about the history of Lagos and the rock formations. We were fortunate to have calm weather which allowed for mooring at a deserted beach for paddle boarding and kayaking. Very nice charcuterie and wine service as well! The boat is beautiful and well maintained. Highly recommend!”

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Private tour on a sailboat Swim and stand up paddle Antibes cape - Sailing past the villas and superyachts
Cruises & Boat Tours, France Surf Trips, Private, Private Surf Lessons, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in France, Surf Trips, Tour Reviews, Tours

Private tour on a sailboat Swim and stand up paddle Antibes cape

8.Private tour on a sailboat Swim and stand up paddle Antibes cape

★★★★★★★★★★5.0 · 24 reviews

Join Nicolas for a private sailboat outing from Port Vauban in Antibes. Cruise around Cap d’Antibes, stop near Billionaires Bay or La Garoupe, then swim, snorkel, and use the paddleboard. Drinks, water, soda, masks, and snorkels are included. The boat carries groups of up to eight.

“This was a fantastic experience with a friendly and competent crew. We enjoyed a swim and paddleboarding in a beautiful bay following a short trip along the coast. The access, instructions and ease of boarding made this very hassle free with two small children.”

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From Ornos: Mykonos Delos Catamaran Cruise with Meal & SUP - Passing Delos without going ashore
Cruises & Boat Tours, Greece Surf Trips, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Greece, Surf Trips, Tour Reviews

From Ornos: Mykonos Delos Catamaran Cruise with Meal & SUP

9.From Ornos: Mykonos Delos Catamaran Cruise with Meal & SUP

★★★★★★★★★★4.6 · 23 reviews · 5 hours · from $165

Sail from Ornos with a group of up to 10, passing Delos before anchoring near Rhenia for swimming, snorkeling, SUP, and lunch. The crew serves Greek food, fruit, water, soft drinks, and Mykonos wine. Demitris captains the boat and Emil handles the onboard cooking.

“Die Katamaran-Fahrt war einfach fantastisch! Sehr entspannt, freundliche Crew, Top-Service, leckeres Essen und Getränke – alles inklusive. Schwimmen im Meer war ein Highlight und der Sonnenuntergang war der schönste, den wir je gesehen haben. Absolut empfehlenswert! - The catamaran trip was absolutely fantastic! Very relaxing, super friendly crew, excellent service, delicious food and drinks – all included. Swimming in the sea was a highlight, and the sunset was the most beautiful we’ve ever seen. Highly recommended!”

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Full day private yacht from lagos with drinks, tapas, paddle boards and kayak - The blue lagoon and Ria de Alvor
Cruises & Boat Tours, Full-Day, Kayak & Canoe Trips, Kayak Trips in Portugal, Lagos Surf Trips, Portugal Surf Trips, Private, Private Surf Lessons, Private Surf Lessons in Portugal, Sailing, Surf Trips, Tour Reviews

Full day private yacht from lagos with drinks, tapas, paddle boards and kayak

10.Full day private yacht from lagos with drinks, tapas, paddle boards and kayak

★★★★★★★★★★5.0 · 17 reviews · 7 hours (approx.)

You’ll charter a private yacht from Lagos for about seven hours, choosing a route toward Portimão and Benagil or Sagres. The crew provides wine, beer, soft drinks, snacks, paddle boards, and a kayak, with lunch on board or at a local restaurant. Crew members may include Zee, Lucas, Ricardo, or Rodrigo.

“This was a day on the ocean that we will never forget. The captain and skipper were super informative and it was amazing to see the beaches and Benagil Caves from a different point of view. I also highly recommend the restaurant that was suggested. Freshest seafood and great people watching!”

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Mykonos Catamaran Cruise with Meal Drinks and Sup - Leaving Mykonos New Port by minivan and catamaran
Cruises & Boat Tours, Greece Surf Trips, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Greece, Surf Trips, Tour Reviews

Mykonos Catamaran Cruise with Meal Drinks and Sup

11.Mykonos Catamaran Cruise with Meal Drinks and Sup

★★★★★★★★★★5.0 · 14 reviews · 5 hours (approx.)

You’ll sail from Mykonos toward Delos and Rhenia on a private catamaran for up to 10 people. Tasos and Margarita may handle the onboard service, with Greek food, wine, swimming, snorkeling, and optional sunset sailing. Delos is viewed from the water, not visited ashore.

“(5 friends from London/mid July/ Friday)The day started off with us being picked up from our hotel, with a lovely driver. On board they explained the layout of the day, our first stop was an hour away to another island where we stayed to swim, eat, swim again and just relax. Special shout out to Margarita and Tasos, who made sure we had a great time. Not only did they prepare the food a bit eariler as we were all starving but also dealt great, with the one person who did have a dietary requirement. The food was amazing, Greek style, fresh and enough for seconds. We were also able…”

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Pula: Half-Day Sailing with Drinks, SUP & GoPro (Max 6 Guests) - Kozada Island for swimming and snorkeling
Croatia Surf Trips, Cruises & Boat Tours, Half-Day, Pula Surf Trips, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Croatia, Surf Trips, Tour Reviews

Pula: Half-Day Sailing with Drinks, SUP & GoPro (Max 6 Guests)

12.Pula: Half-Day Sailing with Drinks, SUP & GoPro (Max 6 Guests)

★★★★★★★★★★5.0 · 13 reviews · 4 hours (approx.) · from $84

Set sail from Marina Polesana with an English-speaking skipper, possibly David, for four hours along Pula’s coast. You’ll view Brijuni, stop at Kozada Island and another cove, and use the SUP, snorkeling gear, shared GoPro, WiFi, music, and included drinks.

“Great afternoon on the yacht. Very friendly skipper with wine and soft drinks available plus snorkelling kit and paddle board . Nice relaxed vibe”

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Cabo Private Catamaran: Chill Experience with Sup and Float Mat - Cruising Past Medano Beach
Cabo San Lucas Surf Trips, Cruises & Boat Tours, Mexico Surf Trips, Private, Private Surf Lessons, Private Surf Lessons in Mexico, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Mexico, Surf Trips, Tour Reviews

Cabo Private Catamaran: Chill Experience with Sup and Float Mat

13.Cabo Private Catamaran: Chill Experience with Sup and Float Mat

★★★★★★★★★★4.5 · 12 reviews · 4 hours (approx.)

Take a private catamaran from Cabo San Lucas around the Arch, Medano Beach, and nearby sights, then anchor at a semi-private beach. Swim, snorkel, paddle board, use the floating mat, or relax aboard. Snacks, soft drinks, water, restroom, and Bluetooth speakers are included.

“This tour operator canceled on us. We were there at 8:30 AM. Our reservation is at 9:00 AM. We waited until 9:45am and somebody came only to tell us that their boat is not in or being repaired. We were on a cruise ship with limited time, they offered to still take us but for 2.5 hrs vs the 4 hrs. This is just horrible, I booked this trip more than 6 mos in advance and there are 12 of us in the group. Worst service ever. He then said he has another boat that we can take but at 10:30 AM and he said he’s gonna push the other…”

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Lérins Islands Sailing Discovery, snorkeling and paddle SUP - Île Sainte-Marguerite and the story of Fort Royal
Cruises & Boat Tours, France Surf Trips, Island & Bay Paddle Tours, Sailing, Snorkeling, Stand-Up Paddleboarding, Stand-Up Paddleboarding in France, Surf & Snorkel Trips, Surf Trips, Tour Reviews

Lérins Islands sailing discovery, snorkeling and paddle SUP

14.Lérins Islands sailing discovery, snorkeling and paddle SUP

★★★★★★★★★★4.5 · 10 reviews · 3 hours 30 minutes (approx.) · from $102

Join skipper Valentin for a 3.5-hour sailing trip from Golfe-Juan to the Lérins Islands. Swim beneath Fort Royal, use the onboard snorkel gear and paddleboard, or explore Sainte-Marguerite Island when the sea is cold. Small groups are limited to nine people.

“It was a great boat ride! Our guide was fantastic. It was a wonderful tour with the whole family. My kids loved it.”

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SUP Safari - Catamaran Cruise Dia Island & Gourmet Delights! - Sailing from Heraklion Port to Dia Island
Cruises & Boat Tours, Greece Surf Trips, Island & Bay Paddle Tours, Safari, Sailing, Stand-Up Paddleboarding, Stand-Up Paddleboarding in Greece, Surf Trips, Tour Reviews

SUP Safari – Catamaran Cruise Dia Island & Gourmet Delights!

15.SUP Safari – Catamaran Cruise Dia Island & Gourmet Delights!

★★★★★★★★★★5.0 · 9 reviews · from $169

Sail from Heraklion to Dia Island aboard an EOS Yachts catamaran. With certified instructor Thanasis, you’ll paddle, snorkel, swim, and relax over Cretan treats, gourmet cold cuts, fruit, dessert, and unlimited drinks. Intermediate SUP skills are required.

“We travel a lot and are always looking for activities to keep us active. We're casual paddlers, not experts, and found it an awesome idea to combine a catamaran trip to Zeus Island (which we hadn't visited before) with a SUP tour. Our guide, Thanasis, was very experienced, we felt safe and relaxed throughout the activity. The island’s waters are crystal clear. Overall, a magical trip. Thank you all!”

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New in Sailing

★ 5.04-Hours Private Luxurious Yacht Snorkelling and Paddle Surf2 reviews
★ 5.0Benagil private yacht from lagos with drinks, tapas, paddle boards and kayak2 reviews
★ 5.0Kinloch: Lake Taupo Catamaran Cruise with PaddleboardingFrom $1704 reviews
★ 5.0Marseille: Sunset Catamaran Tour with Stand-up Paddle & WineFrom $934 reviews
★ 5.0Private Sailing Trip from Heraklion to Dia with meal & SUP2 reviews
★ 4.7Berlengas Island Catamaran Tour + Stand Up PaddleFrom $1163 reviews
★ 3.0Miami Yacht Rental with Jetski, paddleboards, Inflatables3 reviews
★ 5.0Majorca: Dinner aboard a private catamaran with snorkeling and paddle surfing2 reviews

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