Day Trip to Historic St. Augustine from Orlando with Hotel Pickup
Orlando, United States

Day Trip to Historic St. Augustine from Orlando with Hotel Pickup

Outty Ranking 76 4.5 · 259 traveler reviews10 hoursFrom $100
Instant mobile ticketSpots available today

Outty Ranking

76/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.5/5

Based on 259 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Day Trip to Historic St. Augustine from Orlando with Hotel Pickup worth booking?

Day Trip to Historic St. Augustine from Orlando with Hotel Pickup is a 10-hour experience in Orlando, United States, from $100 per person. It scores 76 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.5/5 rating across 259 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
76 / 100
Rating
4.5/5 (259)
Duration
10 hours
From
$100 per person

Enjoy a day in America's oldest town, St Augustine. On this day trip from Orlando, head northeast to the picturesque town, where you can wander the cobbled streets and enjoy a meal in one of the many promenade cafes. St Augustine is a unique city filled with colonial Spanish neighborhoods, magnificent buildings and a wonderful, old-time charm. As the oldest continuously occupied European-established settlement in the USA it has lots of history. From the Castillo de San Marco, to the Fountain of Youth there is something for everyone. Upgrade to add a scenic cruise, trolley tour or the Medieval Torture Museum to your visit. If you select the option including the Hop-On Hop-Off Trolley than you can have a guided tour throughout the historic old town, and jump on an off as you wish. The scenic boat tour option is a 1-hour boat ride with views from the waterways of the Bay of Matanzas! At the Medieval Torture Museum you see first hand the. grueling history of mad men and tyrants!

What you get

    About this experience

    Enjoy a day in America's oldest town, St Augustine. On this day trip from Orlando, head northeast to the picturesque town, where you can wander the cobbled streets and enjoy a meal in one of the many promenade cafes. St Augustine is a unique city filled with colonial Spanish neighborhoods, magnificent buildings and a wonderful, old-time charm. As the oldest continuously occupied European-established settlement in the USA it has lots of history. From the Castillo de San Marco, to the Fountain of Youth there is something for everyone. Upgrade to add a scenic cruise, trolley tour or the Medieval Torture Museum to your visit. If you select the option including the Hop-On Hop-Off Trolley than you can have a guided tour throughout the historic old town, and jump on an off as you wish. The scenic boat tour option is a 1-hour boat ride with views from the waterways of the Bay of Matanzas! At the Medieval Torture Museum you see first hand the. grueling history of mad men and tyrants!

    What's included

    Included

    • Trolley tour (if option selected at time of booking)
    • Pick up and drop off at a meeting point (Orlando, Kissimmee, Disney Lake Buena Vista & Universal)
    • Boat cruise (if option selected at time of booking)
    • Medieval Torture Museum (If option selected at time of booking)

    Not included

    • Gratuities
    • Food and drinks

    What you'll see and do

    1. Old St. Augustine Village

      The Historic District in St. Augustine is the heart of the city. This is where guests will find a majority of the city's restaurants, shopping, hotels, and attractions. The Historic District is the oldest part of the city with many buildings dating back to the 1700s. Even the streets are laid out as they would have been centuries ago, and are more walkable than a lot of cities visitors are used to seeing in America. Along with being a beautiful area for finding things to do like shopping, visiting museums, and dining, the Historic District is also home to the beautiful bayfront with lovely panoramic views of the Matanzasa Bay. The top rated attractions in the area are centered around the Historic District and reflect the importance of history in shaping St. Augustine into what it is today. For example, the Colonial Quarter is a living history museum with costumed reenactors and interactive experienes. The Castillo and the Fountain of Youth both have weapons demonstrations so guests can expect to hear the sound of canon and musket fire around the Historic District. Another defining feature of the Historic District is the architecture. The design on building facades represents the height of Spanish Colonial and Spanish Renaissance Revival architecture. The area of town showcases everything from early European design, Florida bungalow style houses, and Gilded Age extravegance. Being the nation's oldest city, the Historic District of St. Augustine represents all that history has built here since 1565.

      360 minutes here

    2. Oldest Wooden School House

      The Oldest Wooden School House is located at the entrance to St. George Street. During your free time be sure to stroll past it and down this cobble stoned street where there is great souvenir shopping and some great restaurents .

      Pass by without stopping

    3. Fort Matanzas National Monument

      Upgrade your tour and enjoy a one-hour-and-15-minute cruise aboard the Victory III through Matanzas Bay. Narrated by your captain, this boat tour provides an incomparable way to view St Augustine’s historical landmarks and natural sites of interest.

      75 minutes here · Admission not included

    4. Should you purchase the option to choose to take a 90-minute hop-on hop-off trolley tour for an easy way to get around the city and see the sights you want to see. You can get on and off as much as you’d like, or simply sit back and ride the entire loop. The local conductors make the tour even more entertaining by providing history and humor.

      90 minutes here · Admission not included

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers. Pickup begins about 45 minutes before departure.

    Options you can book

    • Plus Medieval Torture Museum

      Medieval Torture Museum : This includes transportation to St. Augustine and admission tickets to Medieval Torture Museum Pickup included

    • St Augustine & Scenic Cruise

      St Augustine with Cruise: Saint Augustine Day Trip from Orlando with Scenic Cruise Pickup included

    • Day Trip with Trolley

      Saint Augustine Day Trip from Orlando with Trolley Tour Pickup included

    • Added Pirate & Treasure Museum

      Added Pirate - Treasure Museum: This is the transportation to St. Augustine from Central Florida plus admission tickets to the Pirate and Treasure Museum. Pickup included

    • St Augustine Day Trip

      Saint Augustine Day Trip from Orlando Pickup included

    • Plus Historic Colonial Quarter

      This includes the transportation to St. Augustines and admission tickets to the Historical Colonial Quarter Living Museum Pickup included

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Mon, Fri
    Group size
    Up to 9 travelers per booking
    Operated by
    Gray Line of Orlando

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Infants are required to sit on an adult’s lap
    • Suitable for all physical fitness levels

    Photos

    This town has so much history and historic building, Day Trip to Historic St. Augustine from Orlando with Hotel PickupLightner Museum in St Augustine, Day Trip to Historic St. Augustine from Orlando with Hotel PickupThe tour guide will bring you to the trolley pick up if option is purchased, Day Trip to Historic St. Augustine from Orlando with Hotel PickupThe famous fort!, Day Trip to Historic St. Augustine from Orlando with Hotel PickupWalk around the old town, Day Trip to Historic St. Augustine from Orlando with Hotel PickupPurchase the trolley option to see the full city in a day, Day Trip to Historic St. Augustine from Orlando with Hotel Pickup

    What travelers are saying

    Outty’s summary of the themes that recur across 256 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    8 mentions

    Travelers single out the guide as the reason the experience works.

    Knowledge and storytelling

    6 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Organization

    2 mentions

    Pickup, timing, and logistics are described as running smoothly.

    Traveler reviews

    256 verified traveler reviews for Day Trip to Historic St. Augustine from Orlando with Hotel Pickup. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    189
    4 star
    40
    3 star
    12
    2 star
    5
    1 star
    10
    Sort
    O3438NAchristinem · September 2026

    Amazing thanks

    We had a great time with Ishmael his knowledge base is amazing We also went òn the Orlando tour which was great 👍

    via Tripadvisor

    Andrea_S · September 2026

    You have to pay extra if you want to see anything.

    Terrible experience overall, poor information given on Viator's website led to embarrassing situation with my 69 year-old mother. The "guide" was rude, asked for tips when in fact she wasn't even a guide, she was just a driver. When you get to the town you have to fend for yourself. You have to buy the trolley tour, otherwise you can't actually tour the town. None of this is explained in the description of the tour. Everything is extremely expensive in the town, you have to pay for simply everything - want to see the old school? Gotta pay. Want to see the fort? Gotta pay. And some folks are very rude as well, they don't seem to like tourists. Very bad experience!

    Response from the operator: We are sorry your visit to St. Augustine did not meet your expectations, particularly while traveling with your mother. Our driver-guides provide information during the journey, followed by free time to explore independently. The option booked includes roundtrip transportation, while the trolley and attraction admissions are included only with upgraded options. The historic district can be explored on foot, although individual attractions charge admission. We will review the Viator listing to ensure this is communicated clearly. We are also sorry that some local interactions felt unwelcoming, as St. Augustine is generally known for warmly welcoming visitors. Gratuities are always optional, and we regret that your overall experience was disappointing.

    via Viator

    108howardc · September 2026

    We enjoyed St. Augustine!

    We really enjoyed the St. Augustine tour. Although, the tour guide is just really a driver as the tour guide waits for you after you finish your tour, you are free to roam on your own and it includes the tram ticket where you can hop on and hop off all day. It’s about a two hour drive to St. Augustine. We recommend going to this historic town with many things to see and explore.

    Response from the operator: We appreciate your wonderful feedback! It’s great to hear that you had a good time exploring St. Augustine and made good use of the tram tickets. Thank you for recommending us, and we hope to welcome you back on another adventure in the future!

    via Tripadvisor

    Polly_K · July 2026

    Time flies fast

    It was a lovely experience. Our pick up was on-time our guide assistant/driver Kevin was very knowledgeable. The van was comfortable even during an excess heat warning. We loved exploring on our own based on Kevin’s excellent recommendations. The time just went by so fast.

    via Viator

    Ronald_A · May 2026

    Trolley Ride

    The van ride to St Austine was comfortable; the driver was a very entertaining, informative and talkative driver. The trolley driver we had was funny and informative.

    via Viator

    Good to know

    Duration
    10 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Mon, Fri
    Price range
    $100 to $135
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    91
    Verdict
    Strongly Recommended

    Who runs this experience

    Operated by Gray Line of Orlando, who run 24 experiences we rank across 3 cities, with an average Outty Ranking of 68.0 and 1 in the 90+ Club.

    See everything Gray Line of Orlando runs

    Why this scores 76

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)65
    Review evidence (18% weight)80
    Booking momentum (14% weight)77
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)36
    Booking flexibility (8% weight)100

    Day Trip to Historic St. Augustine from Orlando with Hotel Pickup: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Orlando.

    How much does Day Trip to Historic St. Augustine from Orlando with Hotel Pickup cost?

    +

    Prices start at $100 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Orlando usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Day Trip to Historic St. Augustine from Orlando with Hotel Pickup take?

    +

    Plan for about 10 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Orlando is not rushed.

    Is Day Trip to Historic St. Augustine from Orlando with Hotel Pickup worth it?

    +

    It holds an Outty Ranking of 76 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.5/5 across 259 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Orlando, and how flexible the cancellation terms are.

    Can I cancel or reschedule Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Day Trip to Historic St. Augustine from Orlando with Hotel Pickup suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 10-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

    +

    Around 91 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Orlando can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Orlando and add a light layer if any part of the 10-hour experience runs outdoors or after sunset.

    Where does Day Trip to Historic St. Augustine from Orlando with Hotel Pickup start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Orlando within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Orlando?

    +

    Orlando is a park town with a wetland wrapped around it. Multi-day theme park tickets and skip-ahead passes dominate, but the highest-satisfaction days are often the ones nobody plans: airboat runs on the St. Johns, manatee swims at Crystal River, and Kennedy Space Center on a launch day. We rank on wait-time value and how honestly an operator describes what is included. On Outty we rank every Orlando experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Escape Game Orlando: Epic 60-Minute Adventures on I-Drive, Kennedy Space Center with Transport from Orlando and Kissimmee, 2 HR Interactive Walking Ghost Tour in Downtown Orlando. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Orlando?

    +

    January to April, before the humidity and the afternoon thunderstorms settle in. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Orlando?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

    What is included in Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

    +

    Included: Trolley tour (if option selected at time of booking); Pick up and drop off at a meeting point (Orlando, Kissimmee, Disney Lake Buena Vista & Uni; Boat cruise (if option selected at time of booking); and Medieval Torture Museum (If option selected at time of booking). Not included: Gratuities; and Food and drinks. Always check the voucher for the final list before you travel.

    Does Day Trip to Historic St. Augustine from Orlando with Hotel Pickup include hotel pickup?

    +

    Yes, pickup is offered for every traveler from 305 listed pickup locations in and around Orlando. Be ready about 45 minutes before the start time.

    What languages is Day Trip to Historic St. Augustine from Orlando with Hotel Pickup offered in?

    +

    It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

    +

    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    Is Day Trip to Historic St. Augustine from Orlando with Hotel Pickup wheelchair or stroller accessible?

    +

    The operator notes: Infants and small children can ride in a pram or stroller; and Infants are required to sit on an adult’s lap. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Day Trip to Historic St. Augustine from Orlando with Hotel Pickup if the weather is bad?

    +

    This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.

    What do travelers say about Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

    +

    Across 259 reviews averaging 4.5 out of 5, recurring themes include the guide, knowledge and storytelling, organization. Travelers single out the guide as the reason the experience works.

    What booking options are available for Day Trip to Historic St. Augustine from Orlando with Hotel Pickup?

    +

    There are 6 options to choose from, including Plus Medieval Torture Museum, St Augustine & Scenic Cruise, Day Trip with Trolley, Added Pirate & Treasure Museum. Prices and start times differ by option, so compare them on the booking screen.

    Ready to lock in your spot?

    Pick a date, choose your group, and see the exact price for Day Trip to Historic St. Augustine from Orlando with Hotel Pickup.

    Pick your date