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St. Augustine for Valentine’s Day | February 14-16, 2027
Tour Highlights:
Enjoy a premium romantic two-night getaway to Florida’s Oldest City! Stay at the beautiful Hilton St. Augustine Historic Bayfront, located in the heart of the historic district and within walking distance of charming shops, restaurants, historic sites, and the waterfront.
Experience some of St. Augustine’s most delightful offerings, including a Chocolate Tour & Tasting at Whetstone Chocolate, a wine tasting at San Sebastian Winery, and a sunset boat cruise aboard a private Great Blue Heron charter. Celebrate Valentine’s Day with an included dinner at the iconic Columbia Restaurant, while still enjoying plenty of time to explore and experience St. Augustine at your own pace.
Accommodation Details:
Hilton St. Augustine Historic Bayfront
Tour Includes:
Two Nights Lodging
3 Meals: 2 Breakfasts & 1 Dinner
Sightseeing & Admissions
Tips and taxes on included meals
Trip Details:
Activity Level: Relaxed
ITINERARY:
Day 1: Valentine’s Day in St. Augustine
Depart The Villages (844 Duck Lake Road) at 8:00 a.m. aboard a comfortable deluxe motorcoach and travel to beautiful St. Augustine.
Upon arrival, enjoy a light lunch on your own a recommended local favorite or start your sightseeing or shopping before experiencing a Chocolate Tour & Tasting at Whetstone Chocolate and a wine tasting at San Sebastian Winery.
Later, get settled at the beautiful Hilton St. Augustine Historic Bayfront, ideally located in the heart of the historic district and within walking distance of shops, restaurants, historic sites, and the waterfront.
This evening, celebrate Valentine’s Day with an included dinner at the iconic Columbia Restaurant. After dinner, the rest of the evening is yours to enjoy together in historic St. Augustine.
Day 2: St. Augustine & Sunset Boat Cruise
Enjoy a leisurely day to explore St. Augustine on your own.
Book the Hop-On-Hop-Off Trolley, visit Castillo de San Marcos, explore Historic Downtown and St. George Street, visit the Lightner Museum, enjoy a leisurely lunch, or simply relax and enjoy the city at your own pace. Your tour host will provide recommendations to help you make the most of your day.
Dinner is on your own before or after this evening’s special experience: a private sunset boat cruise aboard the Great Blue Heron. Sit back, relax, and enjoy beautiful views of St. Augustine as the sun sets while you are on the water.
Day 3: Leisurely Morning & Return to The Villages
Enjoy breakfast at the hotel before departing for home at 10:00 a.m.
Arrive in The Villages around 12:00 p.m., after a memorable Valentine’s Day getaway in beautiful St. Augustine.
PRICING:
$1,029.00 per person, Double Occupancy
$1,479.00 per person, Single Occupancy
A $600 deposit (per person) is required upon booking. Deposit is refundable until December 30, 2026, less a $150.00 per person cancellation fee.
Final payment is due December 30, 2026. Entire cost is non-refundable after this date.
Travel Insurance is strongly recommended and can be purchased through Travel Insured (outside company-separate from Workman). To purchase, click here: TRAVEL INSURED / WORKMAN TRAVEL INSURANCE | or call, 1-855-752-8303. Our agency # is 53258. Mention our Name & Number to receive the best rate.
No meet & greet. You will receive all information needed for this trip 7-10 days prior to trip departure.
_____________________________________________________________
Workman Transportation uses their own deluxe motor coaches. They are driven by drivers certified and licensed for motor coach transportation. Our motor coaches are air conditioned, equipped with Wi-Fi, video monitors, on-board restroom, and reclining seats.
Our hosts are experienced and will help make your trip enjoyable. They will give you lots of information along the way to make the traveling time fun and interesting. We will strive to keep you comfortable by having rest stops every two to two and 1/2 hours in the schedule.
All tours require some walking and the ability to embark/disembark a motor-coach without assistance. Advance notice is required for special dietary requests and handicap seating.
Prices are per person. Rates and space are subject to availability. A minimum number of people is required for the trip to commence. Specified inclusions i.e. hotels, restaurants, shows, etc. are subject to change. Cancellation penalties will apply. Bus driver and Host gratuities are not included. Itinerary subject to modification based on host discretion and unforeseeable circumstances such as inclement weather.
Workman Transportation / Workman Travel is not responsible for errors and omissions in our print ads.
Tour Highlights:
Enjoy a premium romantic two-night getaway to Florida’s Oldest City! Stay at the beautiful Hilton St. Augustine Historic Bayfront, located in the heart of the historic district and within walking distance of charming shops, restaurants, historic sites, and the waterfront.
Experience some of St. Augustine’s most delightful offerings, including a Chocolate Tour & Tasting at Whetstone Chocolate, a wine tasting at San Sebastian Winery, and a sunset boat cruise aboard a private Great Blue Heron charter. Celebrate Valentine’s Day with an included dinner at the iconic Columbia Restaurant, while still enjoying plenty of time to explore and experience St. Augustine at your own pace.
Accommodation Details:
Hilton St. Augustine Historic Bayfront
Tour Includes:
Two Nights Lodging
3 Meals: 2 Breakfasts & 1 Dinner
Sightseeing & Admissions
Tips and taxes on included meals
Trip Details:
Activity Level: Relaxed
ITINERARY:
Day 1: Valentine’s Day in St. Augustine
Depart The Villages (844 Duck Lake Road) at 8:00 a.m. aboard a comfortable deluxe motorcoach and travel to beautiful St. Augustine.
Upon arrival, enjoy a light lunch on your own a recommended local favorite or start your sightseeing or shopping before experiencing a Chocolate Tour & Tasting at Whetstone Chocolate and a wine tasting at San Sebastian Winery.
Later, get settled at the beautiful Hilton St. Augustine Historic Bayfront, ideally located in the heart of the historic district and within walking distance of shops, restaurants, historic sites, and the waterfront.
This evening, celebrate Valentine’s Day with an included dinner at the iconic Columbia Restaurant. After dinner, the rest of the evening is yours to enjoy together in historic St. Augustine.
Day 2: St. Augustine & Sunset Boat Cruise
Enjoy a leisurely day to explore St. Augustine on your own.
Book the Hop-On-Hop-Off Trolley, visit Castillo de San Marcos, explore Historic Downtown and St. George Street, visit the Lightner Museum, enjoy a leisurely lunch, or simply relax and enjoy the city at your own pace. Your tour host will provide recommendations to help you make the most of your day.
Dinner is on your own before or after this evening’s special experience: a private sunset boat cruise aboard the Great Blue Heron. Sit back, relax, and enjoy beautiful views of St. Augustine as the sun sets while you are on the water.
Day 3: Leisurely Morning & Return to The Villages
Enjoy breakfast at the hotel before departing for home at 10:00 a.m.
Arrive in The Villages around 12:00 p.m., after a memorable Valentine’s Day getaway in beautiful St. Augustine.
PRICING:
$1,029.00 per person, Double Occupancy
$1,479.00 per person, Single Occupancy
A $600 deposit (per person) is required upon booking. Deposit is refundable until December 30, 2026, less a $150.00 per person cancellation fee.
Final payment is due December 30, 2026. Entire cost is non-refundable after this date.
Travel Insurance is strongly recommended and can be purchased through Travel Insured (outside company-separate from Workman). To purchase, click here: TRAVEL INSURED / WORKMAN TRAVEL INSURANCE | or call, 1-855-752-8303. Our agency # is 53258. Mention our Name & Number to receive the best rate.
No meet & greet. You will receive all information needed for this trip 7-10 days prior to trip departure.
_____________________________________________________________
Workman Transportation uses their own deluxe motor coaches. They are driven by drivers certified and licensed for motor coach transportation. Our motor coaches are air conditioned, equipped with Wi-Fi, video monitors, on-board restroom, and reclining seats.
Our hosts are experienced and will help make your trip enjoyable. They will give you lots of information along the way to make the traveling time fun and interesting. We will strive to keep you comfortable by having rest stops every two to two and 1/2 hours in the schedule.
All tours require some walking and the ability to embark/disembark a motor-coach without assistance. Advance notice is required for special dietary requests and handicap seating.
Prices are per person. Rates and space are subject to availability. A minimum number of people is required for the trip to commence. Specified inclusions i.e. hotels, restaurants, shows, etc. are subject to change. Cancellation penalties will apply. Bus driver and Host gratuities are not included. Itinerary subject to modification based on host discretion and unforeseeable circumstances such as inclement weather.
Workman Transportation / Workman Travel is not responsible for errors and omissions in our print ads.