15 Guided Sessions Worldwide Worth Booking

1.Guided Island EcoTour: CLEAR/Standard Kayak, SUP – Bonita Springs

★★★★★★★★★★5.0 · 793 reviews · 2 hours 30 minutes (approx.) · from $50Our pick

Paddle Naples takes you through mangrove passages, Estero Bay, and Gulf waters near Big Hickory Island. Choose a standard kayak, CLEAR kayak, or SUP, then look for dolphins, birds, fish, and warm-season manatees. Guides such as Hannah, Nick, Victoria, and Zach add local insight, shell lessons, and helpful paddling tips.

“Our group of six ranged in age from 12 to 81. Guide, Nick, was friendly, helpful, and very knowledgeable about the area and wildlife we saw. We had plenty of time to take in the beautiful sites and explore. No manatees in December (best in July this far south), but the time on the water was time well spent!”

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2.From Nerja: Guided Paddle Surf Cliffs and Maro Waterfall

★★★★★★★★★★4.5 · 400 reviews · 2.5 hours · from $41

Start at Burriana Beach with a short paddleboard lesson, then follow the Maro-Cerro Gordo cliffs to a waterfall and sea caves. Guides such as Yann, Juanma, and Miguel help beginners, lead snorkel stops, and take GoPro photos. Kayaking may replace SUP when wind or waves make boarding unsafe.

“My favourite activity of our trip! Was such a beautiful kayak and even though the water was choppy, it was a relax experience and we were well supported by our guide Juanca who was very informative, friendly and helpful. We had such a great time and would recommend the experience to anyone. It is a long amount of kayaking so you may get tired if not used to it but they do have the option of stopping and getting the boat back if you are struggling.”

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3.Lisbon Surf Guide – Surf class & Pick Up

★★★★★★★★★★5.0 · 210 reviews · 3 hours · from $58

Meet Inês or her surf team in central Lisbon, ride in a van to the best available beach near Cascais or Costa da Caparica, and spend about 90 minutes surfing after a safety briefing and warm-up. Boards, wetsuits, transport, and insurance are included.

“Thoroughly enjoyed my first surfing session with an amazing guide. I highly recommend!”

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4.Half Day Guided Surf Lesson in Byron Bay

★★★★★★★★★★5.0 · 160 reviews · from $60

Spend about four hours learning to surf with Soul Surf School. You’ll get a soft board, wetsuit, safety coaching, and close help from instructors such as Harry and Ben. The group may surf at Byron Bay, Lennox Head, or Ballina, depending on the waves and weather.

“We had a brilliant morning surfing in Byron. We even managed to stand up a few times which we were not expecting. The instructors managed the group well for everyone’s capabilities. Highly recommend whilst visiting Byron Bay!”

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5.Self-Guided Island Tour: CLEAR/Standard Kayak, SUP-Bonita Springs

★★★★★★★★★★5.0 · 159 reviews · 2 hours (approx.) · from $30

Choose a standard kayak, CLEAR kayak, or paddleboard and set your own course from Big Hickory Island. Paddle through mangroves, reach secluded beaches, and watch for dolphins, birds, stingrays, and manatees. Staff explain the map and equipment before you head out.

“Great option. Clear tandem kayaks are pretty nice. We had a beautiful day and found 2 dolphins in our way.”

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6.Guided paddleboarding (SUP) mangrove ECO tour for beginners

★★★★★★★★★★5.0 · 142 reviews · from $65

Learn stand-up paddleboarding with guides such as Dennis, Mat, Jeffrey, or Sophie, then follow calm mangrove channels and paddle downwind past Spanish Water villas. This two-hour Curacao outing includes equipment, instruction, photos, bottled water, a snack, and pickup from selected areas.

“Beautiful scenery and our guide was great! Was able to communicate with all participants in their own language”

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7.Chania: Boat Trip with Guided Snorkeling Tour & SUP

★★★★★★★★★★4.5 · 129 reviews · 3 hours (approx.) · from $119

Spend about three hours on Crete’s coast with Omega Divers guides such as Emma, Adriana, or Josh. Expect several snorkeling stops, optional SUP, safety gear, fruit, water, and complimentary underwater photos. Confirm pickup, boat size, and SUP plans before booking.

“We met many employees who were all polite and accommodating in finding suitable wetsuits masks and flippers. Also Orestis and Melina were lovely with patiently answering questions and taking photos. Thank you!”

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8.2-Hour Guided Private Surf Lesson in Kona

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.) · from $229

Meet your private instructor at Kahaluʻu Beach Park for two hours of hands-on surfing. You’ll use a foam board, reef shoes, and an SPF surf shirt while learning technique, etiquette, the pop-up, and water safety. Instructors including Thomas, Kai, Bradley, Kaleo, Alex, and Koa have taught beginners here.

“Did a two hour solo session and had a blast. It was my first time surfing and was actually able to ride some waves. Will definitely book again my next trip to Kona”

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9.Guided 2.5 Hours Kayaking & Paddle Boarding on Saguaro Lake

★★★★★★★★★★5.0 · 76 reviews · from $123

Spend about three hours on Saguaro Lake with a guide, using a sit-on-top kayak or paddleboard to reach desert cliffs, canyons, and possibly a quiet cove. Luis and Cooper have guided memorable outings here, but the guide assigned to your trip may differ. Basic instruction, life gear, snacks, and water are included.

“The landscape is incredible and we kayaked across the lake to a private cove which was peaceful and breathtaking. Our guide, Cooper was outstanding!!! Thank you Cooper for a wonderful tour!”

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10.Guided Paddleboard Tour Through Asheville’s River Arts District

★★★★★★★★★★5.0 · 64 reviews · from $85

Paddle four miles through Asheville’s River Arts District on a wide, stable board with a private guide such as Steve, Eric, Holly, or Danelle. You’ll learn basic strokes, hear local history, watch for herons and turtles, and finish near River Arts District restaurants and breweries.

“Peaceful gorgeous float with a fun and experienced guide. Def recommend if you come to Asheville nc. Steve was helpful and gave a great tour of the area”

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11.Nashville Guided Paddleboard Tour along Cumberland River

★★★★★★★★★★5.0 · 54 reviews · from $49

Meet at Shelby Bottoms Nature Center for a two-hour guided paddleboard trip on the Cumberland River. Josh, Dan, or another Big Willies guide provides gear, safety help, water, and sunscreen. Beginners are welcome, and windy conditions may mean switching to a kayak.

“Yes we could kayak at home but doing it in Nashville was an amazing experience!! Josh and Dan are the best… so funny!!!”

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12.Waikiki Beginner Private Surf Lesson- Female Guide

★★★★★★★★★★4.9 · 40 reviews · 1 hour · from $135

Meet Ali at Duke Kahanamoku’s statue for a private Waikiki surf lesson made for beginners. You’ll spend 20 to 30 minutes learning on the sand, then paddle out with your board to practice catching waves. A rashguard, sunscreen, water, and swimming ability are essential.

“My daughter (12) loved her surfing lessons! Ali was clear and accommodating with her instructions. She helped my daughter feel confident and ensured she was successful. Would definitely book again!”

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13.Malta: Guided SUP Tour

★★★★★★★★★★4.8 · 37 reviews · 1h 9m · from $29Best value

Meet your English or Spanish-speaking guide at Sensi Watersports in St Thomas Bay for a beginner-friendly SUP outing along Marsaskala’s coast. Learn basic technique, paddle toward caves and cliffs, and follow a flexible route. Guides Adrian and Alamin have helped guests find photo spots and sea arches.

“Great experience, very caring guide that took the time to teach basic techniques but also made sure to take us to the best swimming and pictures spots. The organizers ensure safety at all times. I would go back and try other water sports with them for sure”

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14.Flamingo Beach: Guided SUP and Snorkeling experience

★★★★★★★★★★4.7 · 36 reviews · 2 hours · from $69

Spend two hours at Playa Blanca learning stand-up paddleboarding and snorkeling in a small group of up to nine. Guides such as Laura, Lara, Mara, and Chiara teach patiently, point out fish, and take photos and videos. Pickup is included around Playa Blanca.

“i had great time with Chiara . Small group, excellent explanation of paddling and snorkeling. it was my first time doing this type of activity. loved it. highly recommend”

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15.Guided Dolphin Eco Tour by Kayak & SUP – Fort Myers Beach, FL

★★★★★★★★★★5.0 · 33 reviews · 2 hours 30 minutes (approx.) · from $50

Paddle with a small group through mangrove tunnels toward Big Hickory Island Preserve. Guides including Nick, Hannah, Seth, Josh, Victoria, and Glenn explain local wildlife, while dolphins, manatees, birds, crabs, and a shelling beach add interest. Kayak and SUP options are available.

“Our experience was outstanding! Hannah was knowledgeable and skillful and we had a wonderful time enjoying the beautiful scenery! Would recommend to anyone looking to have some fun and see a beautiful piece of Florida!”

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