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St Augustine Luxury & Special Occasions

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St Augustine Tours

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Freeedom Photo Adventure Experience In St. Augustine

This is a one-of-a-kind tour in which you get to stroll around historic St Augustine getting your picture taken while learning tidbits of interesting facts …More

Likely to Sell Out
Likely to Sell Out
5.0 (6)

Freeedom Photo Adventure Experience In St. Augustine

This is a one-of-a-kind tour in which you get to stroll around historic St Augustine getting your picture taken while learning tidbits of interesting facts...

1 hour 30 minutes • Free Cancellation
5.0 (6)
from
$150
Wine & Dine Pairing Tour (St. Augustine, Rolling)

A 'Progressive Style' Foodie Adventure (ROLLING): This unique food tour invites you to explore the vibrant neighborhoods BEYOND the historic core. Satisfy your appetite with …More

4.9 (263)

Wine & Dine Pairing Tour (St. Augustine, Rolling)

A 'Progressive Style' Foodie Adventure (ROLLING): This unique food tour invites you to explore the vibrant neighborhoods BEYOND the historic core. Satisfy your appetite with...

3 hours • Free Cancellation
4.9 (263)
from
$155
St. Augustine's Wine, Cocktail and Food Experience

Ranked #8 in the U.S.A. on Cool St. Augustine, our award-winning Wine, Cocktail & Food Experience is the ultimate way to discover why St. Augustine …More

5.0 (1,422)

St. Augustine's Wine, Cocktail and Food Experience

Ranked #8 in the U.S.A. on Cool St. Augustine, our award-winning Wine, Cocktail & Food Experience is the ultimate way to discover why St. Augustine...

3 hours 30 minutes • Free Cancellation
5.0 (1,422)
from
$159
The Last Stop Private Paranormal Investigation up to 7 people!

A ghoulish golf cart ride with an experienced paranormal investigator. Will stop at paranormal hot spots in scenic St Augustine. Tour includes a paranormal tech …More

4.9 (19)

The Last Stop Private Paranormal Investigation up to 7 people!

A ghoulish golf cart ride with an experienced paranormal investigator. Will stop at paranormal hot spots in scenic St Augustine. Tour includes a paranormal tech...

1 hour 45 minutes • Free Cancellation
4.9 (19)
from
$160
Tarot Tour

Embark on a mystical journey through the enchanting streets of downtown St. Augustine with our Tarot Tour. Glide effortlessly on our electric golf cart for …More

4.3 (3)

Tarot Tour

Embark on a mystical journey through the enchanting streets of downtown St. Augustine with our Tarot Tour. Glide effortlessly on our electric golf cart for...

1 hour 30 minutes • Free Cancellation
4.3 (3)
from
$175
St Augustine Private Horse-Drawn Carriage Ghost Tour

Experience a different side of St. Augustine on a horse-drawn carriage ghost tour through the city's historic streets. As you travel through the oldest city …More

5.0 (1)

St Augustine Private Horse-Drawn Carriage Ghost Tour

Experience a different side of St. Augustine on a horse-drawn carriage ghost tour through the city's historic streets. As you travel through the oldest city...

45 minutes • Free Cancellation
5.0 (1)
from
$175
Private St Augustine Inshore Fishing Charters

Experience America's oldest city from a completely different perspective on a private inshore fishing charter through the historic waterways of St. Augustine. Explore scenic backwaters, …More

Likely to Sell Out
Likely to Sell Out
4.9 (9)

Private St Augustine Inshore Fishing Charters

Experience America's oldest city from a completely different perspective on a private inshore fishing charter through the historic waterways of St. Augustine. Explore scenic backwaters,...

4 to 6 hours • Free Cancellation
4.9 (9)
from
$188
St. Augustine Private Tour on Premium Electric Cart with Pick Up

Bring your sense of adventure, and up to 6 of your closest friends for a private tour that is second to none. Explore themes like …More

Likely to Sell Out
Likely to Sell Out
4.7 (12)

St. Augustine Private Tour on Premium Electric Cart with Pick Up

Bring your sense of adventure, and up to 6 of your closest friends for a private tour that is second to none. Explore themes like...

1 hour 30 minutes • Hotel pickup offered • Free Cancellation
4.7 (12)
from
$199
2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to …More

4.8 (8)

2 hours - Shared Sunset Sail along Historic St Augustine Bayfront

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to...

2 hours • Free Cancellation
4.8 (8)
from
$199
Private Guided Historic Electric Cart Tour of St. Augustine

Join local guides on a tour of St. Augustine's walled city featuring the city's 450-plus-year history. This 90-minute, personally narrated tour occurs on the comfort …More

5.0 (1,235)

Private Guided Historic Electric Cart Tour of St. Augustine

Join local guides on a tour of St. Augustine's walled city featuring the city's 450-plus-year history. This 90-minute, personally narrated tour occurs on the comfort...

1 hour 30 minutes • Free Cancellation
5.0 (1,235)
from
$200
Nights of Lights Private Electric Joy Ride up to 5 people!

Join us for the jolliest Nights of Lights Joy ride in St. Augustine, a fun-filled holiday tradition! Experience the magic of our stunning holiday lights …More

4.5 (136)

Nights of Lights Private Electric Joy Ride up to 5 people!

Join us for the jolliest Nights of Lights Joy ride in St. Augustine, a fun-filled holiday tradition! Experience the magic of our stunning holiday lights...

45 minutes • Free Cancellation
4.5 (136)
from
$200
Private Golf Cart Tour in St. Augustine

Experience the historic charm of St. Augustine, Florida, in style with our luxury, 8-passenger including the guide, and golf cart tours. Discover the nation's oldest …More

5.0 (54)

Private Golf Cart Tour in St. Augustine

Experience the historic charm of St. Augustine, Florida, in style with our luxury, 8-passenger including the guide, and golf cart tours. Discover the nation's oldest...

1 hour • Free Cancellation
5.0 (54)
from
$200
Bourbon and Whiskey History Tour in St Augustine

Experience the best bourbon tour in St. Augustine, starting with a behind-the-scenes visit to the city’s celebrated distillery. Enjoy a guided bourbon tasting created just …More

5.0 (21)

Bourbon and Whiskey History Tour in St Augustine

Experience the best bourbon tour in St. Augustine, starting with a behind-the-scenes visit to the city’s celebrated distillery. Enjoy a guided bourbon tasting created just...

3 hours 30 minutes • Free Cancellation
5.0 (21)
from
$209
Haunted Echoes: St. Augustine’s Ghostly Adventure Private Tour

Enjoy a private, exclusive tour with your own local guide. Embark on a journey through the shadowy streets of America’s oldest city with our “Haunted …More

5.0 (1)

Haunted Echoes: St. Augustine’s Ghostly Adventure Private Tour

Enjoy a private, exclusive tour with your own local guide. Embark on a journey through the shadowy streets of America’s oldest city with our “Haunted...

2 hours • Free Cancellation
5.0 (1)
from
$211
Private Historical Tour of St. Augustine

Best first way to see St. Augustine. See the highlights of St. Augustine the easy way on a small group golf cart tour. The best …More

Likely to Sell Out
Likely to Sell Out
4.9 (206)

Private Historical Tour of St. Augustine

Best first way to see St. Augustine. See the highlights of St. Augustine the easy way on a small group golf cart tour. The best...

1 hour • Free Cancellation
4.9 (206)
from
$225
Nights of Lights Private Electric Joy Ride up to 7 People!

Join us for the jolliest Nights of Lights Joy Ride in St. Augustine, a fun-filled holiday tradition! Experience the magic of our stunning holiday lights …More

4.7 (15)

Nights of Lights Private Electric Joy Ride up to 7 People!

Join us for the jolliest Nights of Lights Joy Ride in St. Augustine, a fun-filled holiday tradition! Experience the magic of our stunning holiday lights...

45 minutes • Free Cancellation
4.7 (15)
from
$250
Haunted in Pink Ghost Tour

Experience the paranormal like never before with Haunted in Pink, the most stylish ghost tour in St. Augustine! Ride through America’s oldest city in our …More

5.0 (2)

Haunted in Pink Ghost Tour

Experience the paranormal like never before with Haunted in Pink, the most stylish ghost tour in St. Augustine! Ride through America’s oldest city in our...

1 hour • Free Cancellation
5.0 (2)
from
$270
1 Hour Private Historical Tour of Saint Augustine, Florida

***Nights Of Lights tours are available directly on our website ONLY*** See Saint Augustine like you never have before on one of Pineapple Ride and …More

4.7 (40)

1 Hour Private Historical Tour of Saint Augustine, Florida

***Nights Of Lights tours are available directly on our website ONLY*** See Saint Augustine like you never have before on one of Pineapple Ride and...

1 hour 10 minutes • Hotel pickup offered • Free Cancellation
4.7 (40)
from
$325
St. Augustine Private Day or Sunset Boat Tour, 6 passengers max

Experience St. Augustine's historic waterfront from the comfort of a private, captain-led boat tour. Unlike crowded cruises, our sunset tours are personalized for your group, …More

5.0 (24)

St. Augustine Private Day or Sunset Boat Tour, 6 passengers max

Experience St. Augustine's historic waterfront from the comfort of a private, captain-led boat tour. Unlike crowded cruises, our sunset tours are personalized for your group,...

2 to 3 hours • Free Cancellation
5.0 (24)
from
$345
St. Augustine Island Tour, up to 6 passengers

Private day 4-hour day trip for a group of up to 6 passengers. Approximately 4-hour day trip out of the Saint Augustine area to include: …More

5.0 (2)

St. Augustine Island Tour, up to 6 passengers

Private day 4-hour day trip for a group of up to 6 passengers. Approximately 4-hour day trip out of the Saint Augustine area to include:...

3 to 4 hours • Free Cancellation
5.0 (2)
from
$395

Frequently Asked Questions

These answers are based on answers previously given to Cool St. Augustine customers' questions.

Recent tour reviews
Best focused tour!
New York City
Private Guided Historic Electric Cart Tour of St. Augustine
Carole_K, Sep 2026
Best focused tour!
The host is very knowledgeable. His tour has a smaller range but goes into depth pulling the architecture and history of the central historic area. We had 6 on our group and each of us agreed that the tour was we'll worth the time and money. You can't go wrong.
Read more
The Real St. Augustine.
New York City
St. Augustine’s Wine, Cocktail and Food Experience
patrickwD9139TF, Sep 2026
The Real St. Augustine.
If you want to experience the “real” St. Augustine, book your tour with Garry. You will not be disappointed. His insights into the history, the people, and the food and beverage scene in SA are on point, and we’ve been coming to SA for over 30 years. We would highly recommend this.
Read more
Awesome must see
New York City
St. Augustine’s Wine, Cocktail and Food Experience
18mariles, Sep 2026
Awesome must see
Garry was so amazing! Quirky guy, incredibly knowledgeable on all the city’s history and will not give you a watered down version. The drinks and food pairings were special and delicious, and the walk was wonderfully entertained by Garry’s natural storytelling. I would come back just for the places he showed us, and I’d book another trip just to see what else he has in store! Thank you!
Read more
Super cool
New York City
St Augustine Private Horse-Drawn Carriage Ghost Tour
kayla_a, Sep 2026
Super cool
Went with my partner and had an amazing time! Cool stories and a beautiful “happy” did an amazing job getting us around. :)
Read more
A lovely experience
New York City
Private Guided Historic Electric Cart Tour of St. Augustine
Y2307LPsuzanner, Sep 2026
A lovely experience
We had a wonderful time! Dale was friendly and knowledgeable. He seems passionate about the history of St. Augustine and his enthusiasm is contagious.
Read more
St Augusrine wine and dine
New York City
Wine & Dine Pairing Tour (St. Augustine, Rolling)
45billied, Aug 2026
St Augusrine wine and dine
If you are ever in St Augustine this is definitely something to book. Katie made our experience the highlight of our trip! Well worth the money. Kudos Katie for a wonderful time
Read more
Wonderful!
New York City
Private Historical Tour of St. Augustine
Helen_A, Jul 2026
Wonderful!
Super experience! Learned so much! Ask for Karen, she’s AMAZING! And I’m going to buy her book on Amazon to refresh my memory of all the great information.
Read more
Sunset proposal
New York City
St. Augustine Private Day or Sunset Boat Tour, 6 passengers max
dylancP5990PH, Jul 2026
Sunset proposal
Captain Dan was the best tour guide we could have asked for, we will definitely be booking with him again. He helped my proposal go amazingly!
Read more
Anniversary trip
New York City
Wine & Dine Pairing Tour (St. Augustine, Rolling)
Steven_O, Jul 2026
Anniversary trip
Amazing from Start to finish, Ira was fantastic. Every place we visited was awesome. This is a must when visiting St Augustine
Read more
Book the Private Tour!
New York City
The Last Stop Private Paranormal Investigation up to 7 people!
Erica_T, Jul 2026
Book the Private Tour!
What a gem! I Highly recommend the private tour. Karl was amazing at tailoring everything for our family. He knew so much history. He gave spooky fun without nightmare inducing for the kids, but he definitely knew more. We enjoyed the history combined with the ghost hunting tools. It was an overall fantastic experience and the private tour allows tailoring to your group's level of scary tolerance and your interest areas.
Read more
Awesome Tour & Guide!
New York City
1 Hour Private Historical Tour of Saint Augustine, Florida
S1548WVcheryls, Jul 2026
Awesome Tour & Guide!
I booked the private 2 hour tour for my family to celebrate the 250th on Saturday July 4th! Ryan our guide provided a fantastic experience and was quite knowledgeable about the history of St. Augustine. We got to see so much of the area in 2 hours- highly recommend the private tour. I would definitely book this again when returning to St. Augustine!
Read more
A golf cart tour is the...
New York City
St. Augustine Private Tour on Premium Electric Cart with Pick Up
Sheila_H, Jun 2026
A golf cart tour is the...
A golf cart tour is the most comfortable and best way to take it all in. You will need to drive back to the Fountain of Youth and purchase a ticket to see the fountain. Highly recommend.
Read more
Great Day With Friends!
New York City
Bourbon and Whiskey History Tour in St Augustine
609sylviaz, May 2026
Great Day With Friends!
What a fun and educational experience! My husband and I enjoyed our walking history tour in February so much with Russ as our guide, we couldn't wait to return with friends for the Bourbon and Whiskey Tour. Everyone especially enjoyed the St Augustine Distillery private tour. Thanks for a great day Russ!
Read more
Explore Tours for a Private Golf Cart Tour of St. Augustine
New York City
Private Historical Tour of St. Augustine
TwoputtandMore, May 2026
Explore Tours for a Private Golf Cart Tour of St. Augustine
We were recently scheduled to have a private tour with another tour company and the tour was cancelled due to a medical emergency, but the owner recommended Explore Tours, and it was a great recommendation. We purchased the private tour; the instructions were clear and Karen our tour guide texted me about 20 minutes before that she was on her way and where to meet her. She was great! Friendly, fun and lots of information about the history of St. Augustine and the area. Would highly recommend Explore Tours. We definitely would come back for a Night of Lights private tour in December.
Read more
Great Bourbon & Whiskey tour and tasting experience with Russ!
New York City
Bourbon and Whiskey History Tour in St Augustine
kathysC3827YV, May 2026
Great Bourbon & Whiskey tour and tasting experience with Russ!
Had a fabulous time on this tour with Russ as our guide. I would recommend this tour to anyone who wants to get a deeper appreciation about bourbon and the opportunity to taste some outstanding ones, an interesting walking tour around St. Augustine, as well as some great food at local restaurants. If you're hesitant about booking - please don't be. It exceeded our expectations in every way, and we felt like it was well worth the money spent. Looking forward to repeating the tour again.
Read more
Awesome tour
New York City
1 Hour Private Historical Tour of Saint Augustine, Florida
dgeansjay, May 2026
Awesome tour
Awesome tour, expert knowledge, learned about several places in St Augustine that I've never heard of.
Read more
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