Journey Through Time in Historic St. Augustine

Explore St. Augustine’s rich history with us, discovering tales in every cobblestone and around every corner. Tour the Old Jail Museum, visit the oldest wooden schoolhouse, and marvel at Castillo de San Marcos, then stroll St. George Street for culinary delights and cultural experiences on Florida’s Historic Coast.

Enjoy Round Trip Shuttle Service to St. Augustine 

1 Night  | St. Augustine, Florida | September 28 – 29


(save $50, includes round trip shuttle service only)

Early Bird Pricing Ends July 1, 2024

From Lake County to Florida’s Historic Coast

For comfort and convenience, we’ll pick you up from your doorstep in Lake County, Florida for a round-trip 1-night getaway to St. Augustine. 

Hurry! Seats are Limited

What’s Included:


Round Trip Shuttle Service to St. Augustine


Lake County Pick-Up & Drop-Off


Transportation to Attractions

Additional Cost:

Hotel Accommodation

Food & Beverage

Ticket Prices for Attractions

Discover St. Augustine’s Historic Coast: Your Exclusive Round-Trip Shuttle from Lake County, Florida


Discover St. Augustine’s rich history at the Old Jail, a National Historic Landmark since 1891. Explore its cells with guided tours led by period-dressed “inmates.” Then, visit the Castillo de San Marcos, the oldest masonry fort in the continental US, a testament to Spanish colonial ambitions over 327 years ago.


Explore the Old Jail, a National Historic Landmark dating back to 1891.


Discover Castillo de San Marcos, the oldest masonry fort in the United States.


In the afternoon, walk St. George Street, transporting to Spanish Colonial times through the City Gate. Explore architecture, museums, and landmarks like the Oldest Wooden School House. Admire the Cathedral Basilica, the nation’s oldest Catholic Church. Sample local cuisines and browse unique shops for the perfect souvenir.


Explore the Oldest Wooden School House from the 18th century.


Enjoy lunch on St. George Street, then explore 20+ shops and boutiques.

After Dark

Immerse yourself in St. Augustine’s nightlife with dinner on St. George Street by the coast, followed by a bar crawl for cocktails, mocktails, and live entertainment.


Experience St. Augustine's vibrant nightlife on St. George Street by the coast.


Enjoy a bar crawl with cocktails, mocktails, and live entertainment.


Book accommodations at Southern Oaks Inn, the exclusive drop-off and pick-up point for our private round-trip shuttle. Nestled amid St. Augustine’s captivating landscape of beaches, historical sites, and old-world charm, Southern Oaks offers spacious rooms and exceptional hospitality. 

Learn More

Embark on your St. Augustine Historic Getaway with visits to 3 top attractions. Secure your spot by purchasing advance tickets for the Old Jail.


Old Jail

  • Cost: $16.99
  • Date: Saturday, September 28

 Learn More

Castillo de San Marcos

  • Cost: Free (save $15)
  • Date: Saturday, September 28

Learn More

The Colonial Experience

  • Cost: $15.99 
  • Date: Saturday, September 28

Learn More

Complete the form below to reserve your seat(s)


Traveler Information:

Travelers must be 21 and over to board the shuttle.
Please be advised: The 1-Night Historic St. Augustine Getaway is an exclusive offer reserved for Elite and Business Members of The Bond Maker (also known as the BOND Community) and their guests. Non-member travelers interested in this exclusive getaway must register within 7 days of booking at to qualify. Or if you're interested in a Business Members visit Failure to register as an Elite or Business Member will result in the cancellation of the booking, with a refund issued minus a 3% service charge.

OPTIONAL: Guest Information

Each member is welcome to bring along one guest, regardless of gender, provided they are over the age of 21. Guests must board the shuttle at the same location of the Elite or Business member. Guests must have a Boarding Pass to board the shuttle.

Frequently Asked Questions

When will the shuttle service pick up and drop off travelers for the St. Augustine Historic Getaway?

The shuttle service will pick up travelers between 5 a.m. and 7 a.m. on Saturday, September 28, and drop them off by 1 p.m. on Sunday, September 29, in Lake County, Florida.

What are the carry-on restrictions for the getaway?

Travelers can bring one carry-on bag, not exceeding 22 x 14 x 9 inches, to be stored under their seat. Pack essentials and wear comfortable clothing for walking.

What does the Boarding Pass cover?

The Boarding Pass includes round trip transportation from Lake County, Florida, to St. Augustine, as well as transportation to the Southern Inn Hotel, The Old Jail, and St. George Street parking. Most attractions, shopping, and dining are within walking distance.

What is the refund policy for Boarding Passes?

Boarding Passes are refundable until August 23, 2024.

Are there limited spaces available for the getaway?

Yes, seats are extremely limited, and a waitlist will open after full booking.

Who is eligible to participate in the St. Augustine Historic Getaway?

Participation requires Elite membership in the BOND community. Travelers have 7 days to sign up, or seats will be cancelled with a 3% service charge.

Can guests accompany Elite members on the getaway?

Yes, Elite members may bring one guest. However, guests must have a Boarding Pass to board the shuttle.

What attractions are included in the getaway?

The getaway includes visits to The Old Jail, Castillo de San Marcos, and The Colonial Experience. Advance tickets for The Old Jail are recommended.

Where should travelers book accommodations?

Travelers must book at Southern Oaks Inn, which offers free shuttle service to St. George Street and continental breakfast. Shuttle services exclusively to Southern Oaks.

What activities are planned for the evening?

After check-in, rest and recharging, travelers will enjoy dinner on St. George Street and visit up to 3 bars for cocktails, mocktails, and live entertainment.