Sailing in Saint Petersburg, FL


$395 for Private 2-Hour Sunset or Day Cruise for Up to 12 guests from Dolphin Landings Charter Boat Center ($786 Value)

Dolphin Landings Charter Boat Center

Multiple Locations

Private cruise of Boga Ciega Bay on a 41-foot sailboat stocked with soft drinks and water; passengers can also bring their own beverages

$786 $395

2.5-Hour Discover Sailing Class for One or Two from Seaduced Watercraft Adventures (Up to 50% Off)

Seaduced Watercraft Adventures

Bradenton

Seasoned sailors on a 30-foot boat demonstrate basic sail handling, boat safety, and boat parts during 2.5-hour classes

$199 $99

One Two- or Three-Hour Electric-Boat Rental from Simple Sailing Charters, LLC (Up to 57% Off)

Simple Sailing Charters, LLC

St. Petersburg

Groups of up to 8 pile onto an electric boat for a two- or three-hour jaunt around Tampa Bay while enjoying snacks brought from home

$210 $99

$25 for a 90-Minute Waterfront Segway Tour from All About Fun Tours ($50 value)

All About Fun Tours

St. Petersburg

Scenic tour of St. Petersburg’s waterfront; basic training, tour guide, and personal headgear provided

$50 $25

Two- or Four-Hour Kayak Rental for Two People at Kayak Valet (Up to 51% Off)

Kayak Valet

Multiple Locations

Kayaks designed for safety and stability engage first-timers in water sports.

$80 $39

Paddleboard, Kayak, or Bike Rental for Two from Shoreline Surf & Skate Shop (50% Off)

Shoreline Surf & Skate Shop

Redington Shores

Customers enjoy the great outdoors by land or by sea with paddleboard, kayak, and bike rentals

$50 $25

$75 for 90-Minute Pokémon Go Safari for Up to Two from Sprides ($135 Value)

Sprides

Downtown St. Petersburg

Experienced Pokémon hunters lead explorations around Tampa Bay in search of adorable critters for the wildly popular mobile game

$135 $75

One- or Two-Hour Kayak or Paddleboard Rentals for One or Two at Watersports at Little Harbor (Up to 56% Off)

Watersports at Little Harbor

Little Harbor Resort

One- and two-seater kayaks; easy-to-navigate paddleboards; region teeming with dolphins, stingrays, and manatees

$25 $13

Half-Day Kayak Rental for One or Two or Two-Hour Paddleboard Rental at Cove Cay Marina (Up to 45% Off)

Cove Cay Marina

Largo

Climb aboard a paddleboard, or a one-person or tandem kayak and drift past mangrove trees, red fish, and manatees

$30 $17

Bike and Boat Rentals from Wheel Fun Rentals (57% Off). Three Options Available.

Wheel Fun Rentals

Multiple Locations

Enjoy a ride on a beach cruiser, multiple-rider surrey, or quad-sport bikes; or take a ride on the water with a pedal boat or kayak

$30 $15

Fruit-Farm Outing with Grove Tour and Ice Cream for Two or Four at Mixon Fruit Farms (Up to 47% Off)

Mixon Fruit Farms

Mixon Fruit Farms

Tram tours wind through citrus trees and stop at a wildlife refuge before dropping visitors off at the café for ice cream

$54.60 $29

One or Two Half-Day Kayak Rentals at Belle Harbour Marina (Up to 56% Off)

Belle Harbour Marina

Tarpon Springs

Kayaker gets four hours to explore Anclote River

$40 $20

Four-Hour Rental of One Tandem Kayak or Two Single Kayaks from Palma Sola Kayaks (51% Off)

Palma Sola Kayaks

Palma Sola Kayaks

In a single or two-person kayak, explore the picturesque waters of Palma Sola Bay while keeping your eyes peeled for dolphins and manatees

$80 $39

Up to 51% Off Kayak, Hobie Cat & SUP Rental at Sand Key Power Sports

Sand Key Power Sports, Paddle Boards and Kayaks

Clearwater

From the merchant: Kayak, Paddle Board or sail on the beautiful Gulf of Mexico at the Sheraton Sand Key Resort.

$85 $42

Manatee River Boat Tour for One, Two, or Four from Riverside Tours (Up to 36% Off)

Riverside Tours

Riverside Tours Inc

Guests bring food and drinks to the cruise focusing on history and ecology or while watching the sunset and night lights.

$35 $23

Wine-Tasting Package for Two or Four with Tour and Take-Home Bottles at Aspirations Winery (Up to 54% Off)

Aspirations Winery

Clearwater

Enjoy wine samples and food pairings before taking a behind-the-scenes tour, leaving with souvenir glasses and a 750ml bottle of wine

$70 $35

One-Hour or Half-Day Paddleboard or Kayak Rentals for Two or Four at Sand Key Paddle Sports (Up to 57% Off)

Sand Key Paddle Sports

Sand Key

Explore the crystal-clear waters of Clearwater Harbor atop a paddleboard or kayak during one-hour or half-day rentals

$60 $29

Wildlife Tour for One Adult or One Adult and One Child at Odessa Wildlife Rescue and Sanctuary (Up to 51% Off)

Odessa Wildlife Rescue and Sanctuary

Odessa Wildlife Rescue and Sanctuary

Guests can pet and feed over 50 different animals, from alpacas and miniature zebu cattle to gray foxes and bouncy wallabies

$80 $39

Wine Tasting for Two at Land O Lakes Winery (Up to 38% Off)

Land O Lakes Winery

Land O' Lakes

Sample carefully selected wines from around the world paired with cheese

$32.50 $20

Four- or Eight-Hour Single Kayak, Tandem Kayak, or Stand Up Paddleboard Rental at Gill Dawg (Up to 56% Off)

Gill Dawg

Port Richey

Take in the natural beauty of mangrove forests, salt marshes, and manatees from a kayak or stand up paddleboard

$45 $22

Semi-Private or Private Manatee Tour at Nature Coast Manatee Tours (Up to 50% Off). Three Options Available.

Nature Coast Manatee Tours

Homosassa

The houseboat boasts satellite TV and a hearty breakfast spread, although swimming alongside manatees trumps those amenities

$130 $69

$169 for a Helicopter-Flying Lesson with a Simulator Session and Flight at Tampa Bay Aviation ($312 Value)

Tampa Bay Aviation

Clearwater

Learn basic flight maneuvers in an FAA-approved simulator before piloting an R22 helicopter over the scenic coast

$312 $169

Wine, Chocolate, & Cheese Package with Bottle of Wine at Tarpon Springs Castle Winery (Up to 60% Off)

Tarpon Springs Castle Winery

Tarpon Springs

Enjoy wine with chocolate, cheese, and nuts; couples take home one bottle of wine and two keepsake glasses

$94 $39

Four-Hour or Eight-Hour Rental of a Single or Tandem Kayak from Windsong Charters (Up to 57% Off)

Windsong Charters

Flor-a-mar

Captains outfit clients for paddle amid the wildlife, hidden channels, and sunken boats of Florida’s coastline

$45 $21

$39 for Wine Tasting at The Wine Room on Park Avenue ($63 Value)

The Wine Room on Park Avenue

Winter Park

156 wines from temperature-controlled Enomatic wine-dispensing machines; receive $10 off a $50 purchase of retail wines on return visit

$63 $39

Orlando Explorer Pass includes admission to 3 or 5 attractions from 15 options. Pay Nothing at The Gate.

Go City Card

Online Deal

Choose 3 or 5 attractions from 15 popular options and save up to 35% off combined admission. Pay nothing at the gate

$49 $49.40

Wacky Walk Game for Two or Four at Wacky Walks (Up to 50% Off)

Wacky Walks

Downtown

Small groups utilize their wits and teamwork while trying to solve clues that lead to a big puzzle

$39.95 $20

Urban Scavenger Race for Two or Four from 3Quest Challenge (50% Off)

3Quest Challenge - Tampa

Downtown

Racing against the clock, players progress through three quests where they find checkpoints, seize clues, and solve the final puzzle

$39.95 $20

Wine and Chocolate Tasting with Keepsake Glasses for Two or Four at Tarpon Springs Castle Winery (Up to 61% Off)

Tarpon Springs Castle Winery

Tarpon Springs

Sip five wines with chocolates before choosing a full glass to enjoy; couples take home one bottle of wine and two keepsake glasses

$95 $39

South Florida Explorer Pass includes admission to 3, 4, or 5 attractions from 25+ options. Pay Nothing at The Gate.

Go City Card

Online Deal

Choose 3, 4, or 5 attractions from 25+ popular options and save up to 40% off combined admission. Pay nothing at the gate

$85 $76.50

Select Local Merchants

  • Tampa Speed Boat Adventures
    Turning the traditional boating tour on its head, Tampa Speed Boat Adventures encourages visitors to don the captain’s hat as they pilot their own sightseeing experiences. From a base in St. Petersburg, seasoned instructors teach tour takers the essentials of operating one of the company’s eco-friendly, 13-foot mini speedboats as they cover topics such as boating basics, rules of the water, and at what speed time begins to flow in reverse. Once participants are confident in their training and have donned their life jackets, they snuggle into their vessel and take off on a 15-mile tour of the waterways of Tampa Bay and St. Petersburg. One of the company’s quick-witted, knowledgeable guides joins boaters in an adjacent watercraft on the two-hour sojourn, broadcasting commentary about the area’s history through the boat’s radio-communication system. As speedboats wend past jaw-dropping sites such as national wildlife refuges and Fort De Soto Park, passengers can keep their eyes peeled for passing seabirds and the mansions that famous dolphins call home.
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    200 Madonna Blvd
    St. Petersburg, FL US
  • Simple Sailing Charters and Sales
    Charter one of Simple Sailing Charters, LLC's sailboats, and take a relaxing trip to Tampa Bay, Sarasota, or Egmont Key. You can gauge just how relaxing the trip will be by the boats' names—_The Simplicity_, The Miracle, and The Dream, to name a few—and their amenities. The Simplicity, for example, boasts three cozy cabins for downtime, and their fleet of wind-powered catamarans means there's not a noisy motor in sight. Even the company's three electric powerboats are unobtrusive, gliding through the water silently unless passengers choose to use the onboard iPod docks to play their favorite tunes or whale songs. The fleet isn't just good for vacations, though. The company doubles as an ASA-certified sailing school, where sailors can hit the decks for lessons that introduce beginners to the sailing world. Other sessions cover specialized topics such as coastal cruising or navigating by the stars instead of just following the most confident-looking bird.
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    165 5th Avenue Northeast
    Saint Petersburg, FL US
  • Dolphin Landings Charter Boat Center
    The veteran captains at Dolphin Landings Charter Boat Center promise tour-takers a 99% chance of spotting bottlenose dolphins during excursions in Boca Ciega Bay. That’s because the bay is home to more than 700 resident Atlantic bottlenose dolphins, along with manatees, and tropical sea birds. During voyages, guests cruise in comfort on a US Coast Guard–inspected vessel. The boats serve complimentary soft drinks and water, and BYOB is welcome.
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    375 2nd Ave. NE
    Saint Petersburg, FL US
  • Broad Reach Charters, Inc.
    Originally from central New York, Captain Brian spent years navigating the region's lakes, rivers, and canals. Long, brutal winters inevitably cut his sailing seasons short though. So Brian jumped at the opportunity to retire to Florida and commit to spending even more time on the water. Today, he shares his passion by welcoming passengers aboard his 38-foot sailboat—aptly named Nowhere to Be—and leading casual, laid-back charters. During outings, guests can dive into the surrounding waters, savor sunset views, or even steer the boat with Captain Brian's supervision.
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    1260 80th Street South
    Saint Petersburg, FL US
  • Tampa Bay Boat Rental
    Tampa Bay Boat Rental helps patrons access some of the top beaches on Florida’s west coast, including Treasure Island, St. Petersburg, and Indian Rocks Beach. Its fleet of 24-foot pontoon boats can accommodate up to 9 passengers for a fishing trip if guests so choose. Ice and bait are available for purchase in the shop. The company also offers a number of private boat charters and guided excursions such as two-hour dolphin tours that allow guests to witness dolphins in their natural habitats and luxurious TV lounges.
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    13205 Gulf Blvd
    Saint Petersburg, FL US
  • Tierre Verde Boat Rentals
    Take some time off to unwind on the water. Your ship awaits at Tierra Verde Marina in Saint Petersburg. What's a fine center without fine dining to accompany it? Be sure to pick up a tasty meal when you visit their great restaurant. Tots are more than welcome to hang with their parents at this center. Parking is plentiful, so guests can feel free to bring their vehicles. Make your next outing a splash! Check out the exciting boats at Tierra Verde Marina in Saint Petersburg today.
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    100 Pinellas Bayway South
    Saint Petersburg, FL US

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