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How to Spend 3 Days in St. Augustine

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409 Reviews
How to Spend 3 Days in St. Augustine
Settled by Spanish explorers in 1565, led by Pedro Menendez de Aviles, St Augustine is the oldest continuously-occupied European settlement in the USA. Landing on the feast day of Augustine of Hippo, they named the town San Agustin and quickly dug in fortifications to protect themselves. And so a town was born and continues to thrive over 400 years later with many of the original buildings still standing.

These days visitors flock to Saint Augustine for its history and beauty. Horses clip-clop through the 144-block National Historic Landmark District as the townspeople drift by in period costume. There are regular historical re-enactments and music festivals. And when you get tired of venturing into the past, there’s that long sandy beach to head for, or even Florida’s oldest alligator farm.
 
Day 1: Step Back in Time

If you’re in Saint Augustine you’re obviously ready to step into the past. Take the trolley tour and find out about the history, sights and attractions from a well-informed trolley conductor. Check out Saint Augustine’s oldest house; the old jail – definitely haunted; the Fountain of Youth; Lightner Museum; and the magnificent 17th century fortificiation, Castillo de San Marcos. Wander through the old colonial Spanish neighborhoods, and sit in an old-time café and imagine it’s 200 years ago.

Day 2: Take to the Skies
To get a wider perspective, take a helicopter tour. Check out Saint Augustine, Porpoise Point  and Old Downtown from a bird’s point of view. Or fly high over Saint Augustine Beach, perhaps even include neighbouring Viliano Beach, Conch Island, Bird Island, San Jose Forest and Fort Matanzas and Saint Augustine Lighthouse on a long ride through the skies. If you’re a bit of a romantic, take an evening flight and let the sunset add that extra bit of beauty.

Day 3: Beach and Island

It’s time to get back into this century with a bit of beach fun. Head out to Anastasia Island for long, sandy beaches: Saint Augustine Beach, Crescent Beach and Matanzas Inlet. Then in the evening, just when you’ve forgotten all about history, meet some of Saint Augustine’s oldest residents on the ghost trolley ride.
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29 Tours and Activities | All St Augustine Tours

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Take a Scenic Boat Ride in St. Augustine

Take a Scenic Boat Ride in St. Augustine

star-4.5
A unique view of St Augustine available only from the water. Since the 1900’s St. Augustine Scenic Cruise has been giving visitors to St. Augustine a unique view of the city and a way to enjoy St. Augustine’s historic land marks and natural beauty. Our 75 minute cruises, narrated by the captain, provide an incomparable way to enjoy St Augustine's historic landmarks and natural sites of interests.
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  • 1 hour 15 minutes
  • Taking safety measures
From
$19.00
From
$19.00
Taking safety measures

St. Augustine Hop-On Hop-Off Trolley Tour

St. Augustine Hop-On Hop-Off Trolley Tour

star-4.5
Explore the best of St Augustine on this narrated Old Town trolley tour. See more than 100 points of interest such as the Old Jail, Flagler College, and Spanish Colonial neighborhoods. Discover more about America’s oldest city, founded in 1565 by Pedro Menendez de Aviles, from your friendly and informative conductor who shares interesting narration about St. Augustine's history.
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  • 2 to 8 hours
  • Free Cancellation
  • Taking safety measures
From
$30.15
From
$30.15
Taking safety measures

Haunted Trolley Tour of St Augustine

Haunted Trolley Tour of St Augustine

star-3.5
St. Augustine’s original “frightseeing” tour is an evening of fear and fun. Board Ghosts and Gravestones' Trolley of the Doomed for a spooky ride through St. Augustine's sinister past. Listen to stories of the ghosts and ghouls believed to still wander the streets of the town as you pass haunted hot spots. Expect a tour so scary, it should come with a warning.
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  • 1 hour
  • Free Cancellation
  • Taking safety measures
From
$22.87
From
$22.87
Taking safety measures

Sunset Cruise of St. Augustine with a Local Guide

Sunset Cruise of St. Augustine with a Local Guide

star-5
See St. Augustine from a new perspective with this leisurely sunset cruise. Climb aboard a boat for a scenic cruise including views of Castillo de San Marcos National Monument, the Bridge of Lions, and the St. Augustine Lighthouse. Sip beer or wine from the on-board bar during this tour reserved for guests 21 and older.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$29.00
From
$29.00
Taking safety measures

Saint Augustine Day Trip from Orlando

Saint Augustine Day Trip from Orlando

star-4.5
Step back in time with a visit to enchanting St Augustine — one of America’s oldest towns — on this full-day tour from Orlando. This 10-hour excursion arrives in St Augustine by mid-morning, giving you hours to spend on your favorite activities. Stroll along cobbled pathways, admire Spanish Colonial architecture, indulge in delicious seafood at a waterside restaurant, see historic landmarks, and add on an optional sightseeing cruise or trolley tour.
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  • 10 hours
  • Free Cancellation
  • Taking safety measures
From
$74.99
From
$74.99
Taking safety measures

Dolphin Odyssey and Sightseeing Tour

Dolphin Odyssey and Sightseeing Tour

star-5
Cruise out over the waters of St. Augustine in search of pods of bottlenose dolphins on this 90-minute boat tour. Greet the crew and find your spot on the padded bench seats, then set out in search of the local cetaceans. Learn about the animals' biology and behavior through the commentary of the crew, who know just where to find these animals. Other marine life sightings include turtles, manatee, osprey, and pelicans.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$24.00
From
$24.00
Taking safety measures

Sea Dragon Airboat Safari in Saint Augustine with a Guide

Sea Dragon Airboat Safari in Saint Augustine with a Guide

star-5
Explore the freshwater tributaries along the scenic St. Johns River on a thrilling airboat ride that skims through a maze of shallow waterways. Watch for alligators, manatees, birds, and snakes as you speed through the watery Florida landscape, and learn the story of an infamous pirate ship that sank in the St. Johns River. This St. Johns River airboat tour includes personal headsets, so you won't miss a word of the captain's fun and informative commentary.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$74.95
From
$74.95
Taking safety measures

St Augustine Boat and Walking Tour

St Augustine Boat and Walking Tour

star-5
Unique opportunity to see the Old City from water and land. Our guide will meet you at the Plaza de la Constitucion, accompany you on board during the boat tour and then guide you around downtown St. Augustine for a one hour walking tour of the most important landmarks and monument.
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  • 2 hours 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$49.00
From
$49.00
Taking safety measures

Wine Tasting Cruise in St. Augustine

Wine Tasting Cruise in St. Augustine

star-5
Start your evening out by winding down on the water! Let us take you on an adventure to the bay-front, where our experienced guides will give you a tour on nature, wildlife, and famous historic landmarks. You will receive a presentation and sampling of 6 fabulous wines (including local favorites). Our bar on board has an excellent variety of beer, wine, bubbly and soft drinks for purchase at very reasonable prices. This tour includes the sampling plus a discounted beverage of what ever you'd like, and an assortment of cheese and crackers. (As of right now we are not serving cheese and crackers due to Covid-19, you are allowed to bring your own!) There are no other tours like this in St. Augustine! **No outside alcohol allowed.**
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$29.00
From
$29.00
Taking safety measures

St. Augustine's Not Just A Chocolate Tour

St. Augustine's Not Just A Chocolate Tour

star-5
Chocolate. Pralines. Do we need to say more?! Have a sweet time winding your way through historic downtown on our Not Just a St Augustine Chocolate Tour. Discover some of St. Augustine’s best unique sweets and chocolates while learning about what makes these treats so addicting! Each of our tours is as much about local history as it is about chocolate. Our local guides have gone to great lengths to understand the areas we take you to so we can share some of its fascinating stories. With personable guides and small groups, it should always feel like having a friend in St. Augustine. A variety of samplings will be provided along with extra to take home and enjoy later. To keep your sweet buzz going, we provide a thermal bag and extra take home goodies we sampled on tour to enjoy later.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$75.00
From
$75.00
Taking safety measures

Sunset Cruise on St. Augustine’s Intracoastal Waterway

Sunset Cruise on St. Augustine’s Intracoastal Waterway

star-5
Prebook for a bring-your-own-beverages sunset cruise on St. Augustine’s intracoastal waterway and save the hassle of booking on vacation. Board the comfortable boat and admire sights including the Bridge of Lions from the water at the most scenic time of day—sundown. Watch for dolphins and other marine life in the wild, hear tales about the city you may otherwise miss, and enjoy your drinks as you sail and sightsee.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$24.00
From
$24.00
Taking safety measures

St Augustine Inshore Fishing Charters

St Augustine Inshore Fishing Charters

star-5
A St Augustine Inshore Fishing Charter is truly unique because it allows you to experience the Oldest City of the Nation from an on-the-water adventure. You have the ability to cruise out to your fishing location with a local expert and professional fishing captain and enjoy the day in the sun. Your licensed professional guide will take care of all your fishing needs while discovering what the backwaters of St Augustine are all about. Also, a St Augustine Inshore Fishing Charter is only 45 minutes away from Jacksonville, FL. While inshore fishing for Seatrout, Black Drum, Redfish, Snook, Tarpon, Sheepshead and much more you can get a true feel of what this beautiful destination is all about. As well, travelers also enjoyed a St Johns River Airboat Safari, St. Augustine Disterilly, or St. Augustine Beach.
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  • 4 to 8 hours
  • Free Cancellation
  • Taking safety measures
From
$435.89
per group
From
$435.89
per group
Taking safety measures

Discover St Augustine: Attractions Pass with Hop-On Hop-Off

Discover St Augustine: Attractions Pass with Hop-On Hop-Off

star-4.5
Explore the best that St Augustine has to offer with admission to three historic attractions plus a hop-on hop-off trolley tour of the city. Visit the Old Jail, the St Augustine History Museum and the Oldest Store Museum Experience, plus more than 100 other points of interest among the city’s top attractions. Board the trolley at any of the 22 stops. It's a great way to see everything St Augustine has to offer.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$51.42
From
$51.42
Taking safety measures

Nights of Lights: St. Augustine Night Boat Cruise

Nights of Lights: St. Augustine Night Boat Cruise

star-3.5
Our one hour tour allows you to Enjoy St Augustine's famous "Nights of Lights" as only seen from the water.
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  • 1 hour
From
$21.30
From
$21.30

St. Augustine Dolphin and Wildlife Adventure Cruise

St. Augustine Dolphin and Wildlife Adventure Cruise

star-5
This relaxing cruise is great for nature lovers, families, or those who simply enjoy being out on the water. Cruise the Intracoastal Waterway—an inland waterway that runs parallel to the coastline—for a calm ride exploring St. Augustine’s estuaries. Keep your eyes peeled for marine life such as dolphins, manatees, sea turtles, pelicans, osprey, and spoonbill. Along the way, you’ll spot landmarks including the Bridge of Lions, Castillo de San Marcos, St. Augustine Lighthouse, and more.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$26.00
From
$26.00
Taking safety measures

World Famous - St Augustine Nights of Lights - Water Tour

World Famous - St Augustine Nights of Lights - Water Tour

star-5
National Geographic has selected The Ancient City, one of the top-10 places in the world to see Christmas lights, for over a decade! Each year, more lights are added and the Nights of Lights Festival becomes more and more popular. Why struggle, maybe for hours, to find a place to park and then walk to see just a few blocks of lights? Step aboard the White Pelican and let us take you downtown, like you've never been downtown! The reflections on the water appear to double the number of lights in the city, while the fresh night air in the bay makes some of the best restaurants on the east coast, smell even better!
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  • 1 hour 15 minutes
  • Free Cancellation
From
$40.00
From
$40.00

 Nights of Lights Boat Tour (Adults Only)

Nights of Lights Boat Tour (Adults Only)

star-4
Join us for a one hour cruise from Vilano Beach to the downtown Bayfront and the City of Lights from 11/23/19 - 02/02/20. We run 2-3 trips per night 7 nights per week (weather permitting) Come enjoy the reflections of millions of white lights by the Bayfront in downtown St. Augustine
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  • 1 hour
  • Free Cancellation
From
$39.00
From
$39.00

Ale Trail Craft Beer Tour

Ale Trail Craft Beer Tour

star-5
Beer. History. Do we need to say more?! Take a fun and fascinating step back into Florida history with our Ale Trail Craft Beer walking tour! On this uniquely curated experience, you and your licensed, knowledgeable guide will stroll around the charming streets of St. Augustine, the oldest city in the nation, discovering the best in Florida craft beers. Learn about the early days of St. Augustine and how the business of beer has evolved in the Sunshine State. See for yourself why we are one of the fastest growing and most highly regarded beer producing regions in the country. As part of this journey, we will visit notable landmarks, unique brewpubs, and state-of-the-art tap rooms, all while learning about the legacy that beer has left on St. Augustine. Hear tales of coastal Florida’s brewing past and visions of its promising future while sampling an abundance of delicious beer along the way.
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  • 2 hours 30 minutes
  • Free Cancellation
From
$95.00
From
$95.00

The Original Pour Tour- Craft Beer in St. Augustine

The Original Pour Tour- Craft Beer in St. Augustine

star-5
Hop on the party bus and visit 4 breweries while sampling the award winning beers that make St. Augustine a craft beer destination City! Your brew guide will tell you everything you want to know about the breweries, the brewmasters, the local beer scene, home brewing, beer history, and the history of St. Augustine!
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$55.00
From
$55.00
Taking safety measures

Rhythm of the Night Tour - Old Town Cycle Cruise

Rhythm of the Night Tour - Old Town Cycle Cruise

Old Town Cycle Cruise is the ultimate party on the water in St. Augustine. The city's first-ever cycleboat to hit the water! We provide 90-min Public & Private BYOB Tours in the Historic St. Augustine waters. We have space for 20 passengers and the tours include Master Captain, First Mate, 12-Cycle Stations, Music, Party Lights, Party Props, Ice and Beautiful Views of the Best Sightseeing. Come pedal or kick back & party with us! Perfect for Bachlorette Parties, Birthdays, Ladies Night and Team Building!
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$57.70
From
$57.70
Taking safety measures

Sunset Cruise - Old Town Cycle Cruise

Sunset Cruise - Old Town Cycle Cruise

star-5
Old Town Cycle Cruise is the ultimate party on the water in St. Augustine. The city's first-ever cycleboat to hit the water! We provide 90-min Public & Private BYOB Tours in the Historic St. Augustine waters. We have space for 20 passengers and the tours include Master Captain, First Mate, 12-Cycle Stations, Music, Party Lights, Party Props, Ice and Beautiful Views of the Best Sightseeing. Come pedal or kick back & party with us! Perfect for Bachlorette Parties, Birthdays, Ladies Night and Team Building!
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$57.70
From
$57.70
Taking safety measures

Day Cruisin' Tour - Old Town Cycle Cruise

Day Cruisin' Tour - Old Town Cycle Cruise

star-3.5
Old Town Cycle Cruise is the ultimate party on the water in St. Augustine. The city's first-ever cycleboat to hit the water! We provide 90-min Public & Private BYOB Tours in the Historic St. Augustine waters. We have space for 20 passengers and the tours include Master Captain, First Mate, 12-Cycle Stations, Music, Party Lights, Party Props, Ice and Beautiful Views of the Best Sightseeing. Come pedal or kick back & party with us! Perfect for Bachlorette Parties, Birthdays, Ladies Night and Team Building!
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$57.70
From
$57.70
Taking safety measures

St Augustine Inshore Fishing Charter

St Augustine Inshore Fishing Charter

star-5
Fish St. Augustine and experience the inshore backwaters of Matanzes River, Tolomato River and Salt run which have an abundance of Redfish, Tarpon, Spotted Sea Trout, Flounder and Cobia. Just minutes from famed sandy white beaches and overlooking the waterfront resorts. St. Augustine has all types of fishing in an eye’s view. View the beautiful scenery, while experiencing the thrill of a chance to catch the local inshore favorite, “the Redfish” as well as other species. A fishing enthusiast may choose to chase the resident fish, but there is a lot of variety for every angler. All charters are guided by a licensed Captain in a modern inshore flats or bay boat. Captain provides the fishing rods and reels, right and left handed and all the tackle you can use, as well as all other necessities including safety equipment.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$543.79
per group
From
$543.79
per group
Taking safety measures