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Top Naples Holidays in 2026

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Sailing Up!

Set sail on this beautifully appointed Catamaran, "Cool Beans", and start making lasting memories! Cool Beans Cruises is the perfect way to see SW Florida, By Water! Choose from a 2.5 hr. Day-Sail or a 2 hr. Champagne Sunset Cruise. With quick access to the Gulf of Mexico, you will experience true sailing with limited motoring. A stop for a swim to a secluded pristine beach for shelling can be part of the Day Sail Only(weather permitting). Keep your cameras ready to capture a photo of the local wildlife to see along the way! Cool Beans Catamaran will accommodate up to 20 passengers. PRICE INCLUDES SODA, WATER, BEER, & WHITE WINE . A CHAMPAGNE TOAST AT SUNSET IS INCLUDED FOR THE SUNSET CRUISE. Please note that parties of 7 or more, an 18% gratuity is added to our base price and is due and payable to the Captain. Also available is our 25 Ft .Pontoon, Lil' Beans! Perfect for up close eco/nature /shelling and island hopping. Book a Private tour for a group for up to 6 guests

Sightseeing and Sunset Catamaran Sailing Excursion

2 hours 30 minutesFree Cancellation

Member Pricing

Naples Sunset & Dolphin Cruise with Charcuterie and Wine

Naples Sunset & Dolphin Cruise with Charcuterie and Wine

2 hoursFree Cancellation

Member Pricing

Marco Island and Naples Pedal or Paddle Kayak Tour

Get an up-close view of Florida’s spectacular, coastal mangrove forests—and enjoy an active way to explore—on this kayaking or paddleboarding tour. Pick from multiple tour times, head to the departure point, and meet your guide: after an introduction to your kayak or paddleboard, you’ll hit the water. Paddle through mangrove tunnels, have the chance to spot wildlife like dolphins and manatees, and learn more about the forests from your guide.

Marco Island and Naples Pedal or Paddle Kayak Tour

2 hoursFree Cancellation

Member Pricing

Backwater Adventure's CraigCat Tours of the 10,000 Islands

Exploring the Ten Thousand Islands National Wildlife Refuge on your own can be intimidating if you don’t know your way around on the water. Book this Thousand Islands 2-person Catamaran Tour to follow a knowledgeable guide who will keep you from getting lost and ensure you enjoy this pristine preserve to the fullest, with great opportunity to view the wildlife and sea life that inhabit the refuge.

Backwater Adventure's CraigCat Tours of the 10,000 Islands

1 hour 30 minutes to 2 hours 30 minutesFree Cancellation

Special Offer

Private Naples Dolphin & Sunset Cruise with Charcuterie and Wine

Private Naples Dolphin & Sunset Cruise with Charcuterie and Wine

2 hoursFree Cancellation

Member Pricing

Dolphin Spotting!

Ten Thousand Island Jet Ski Eco Tour - Marco Island

2 hoursFree Cancellation

Member Pricing

Evening Experience at a Carioca Samba School

You’ll immerse yourself in the vibrant world of a Rio de Janeiro samba school, accompanied by a tour guide accredited by the Brazilian Ministry of Tourism. Transportation is included from Downtown Rio and the South Zone. On Saturdays, the experience takes place at Salgueiro Samba School, in Andaraí. Salgueiro is renowned for celebrating African heritage and has roots in a community historically associated with a quilombo. The school is also home to one of the most popular samba songs in Brazil, “Peguei um Ita no Norte / Explode Coração,” a true samba anthem. Come experience the energy, history, and cultural legacy of one of Rio de Janeiro’s most iconic samba schools! Duration: 4 hours.

Evening Experience at a Carioca Samba School

5 hoursFree Cancellation

Price varies by group size

Member Pricing

2 Hour Dolphin, Birding and Shelling Tour

2 Hour Dolphin, Birding and Shelling Tour

2 hoursFree Cancellation

Member Pricing

Private Marco Island Boat Bar Hopping Experience

Cruise the waterways of Southwest Florida on a customizable private Marco and Goodland bar hopping trip that combines sightseeing with food and drink experiences along the water. Skip the car and travel by boat between waterfront bars and restaurants while your captain handles the navigation. This flexible outing allows your group to spend more time at favorite stops, enjoy a leisurely cruise through mangroves and island waterways, and take in opportunities to spot local wildlife. Whether celebrating a birthday, gathering with friends, or simply looking for a different way to explore the area, this private boat experience makes the journey as memorable as the destinations, with options to enjoy beer, spirits, and other refreshments available for purchase at each stop.

Private Marco Island Boat Bar Hopping Experience

4 hoursFree Cancellation

Member Pricing

Half-Day Super Shelling Tour

Shelling is practically the state sport in Florida, and you’ll go home with a veritable haul on this small-group shelling tour. The adventure starts on the water, where you’ll take a boat ride to Marco Island, spotting dolphins along the way. Once on land, your guide will clue you into all the remote hotspots to find shells and sand dollars, ensuring you don’t leave without one-of-a-kind souvenirs.

Half-Day Super Shelling Tour

4 hoursFree Cancellation

Member Pricing

Epic Naples Bar Crawl: By Let’s Roam

Epic Naples Bar Crawl: By Let’s Roam

Member Pricing

Bachelorette Party Boat Dolphins Sandbar and Shelling Adventure

Gather your crew for an unforgettable bachelorette party on the Island Hopper, a spacious boat designed for fun in the heart of the Ten Thousand Islands. Encounter wild dolphins as they dance alongside the boat, revel in the tranquility of a private sandbar perfect for swimming and photo ops, and search for unique shells on pristine shores. Led by knowledgeable USCG-licensed captains from Sand Dollar Shelling & Boat Tours, this experience accommodates up to 12 guests, ensuring you celebrate without the tourist hustle. Bring your own drinks and playlist to truly make this day yours. (can add additional guests up to 19 for a fee)

Bachelorette Party Boat Dolphins Sandbar and Shelling Adventure

2 to 4 hoursFree Cancellation

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