Don’t just tour Anna Maria Island, Experience Anna Maria Island
Every Beatrice Bradley trip is crafted to maximize the experiences had during the trip.
The itineraries are specially made to allow time for engaging in conversation and having belly laughs with a new friend. We hope that the activities and experiences may allow you to come out of your comfort zone and to try new or unique things.
These trips are made to replicate a ‘friends get-away trip’.
Overall Trip Highlights
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Private Beachfront House: Stay in a stunning 10-bedroom beachfront home with private beach access on Anna Maria Island. This serene location offers the perfect setting to create lifelong memories with friends, as you enjoy the pristine sands and tranquil Gulf waters right at your doorstep.
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Champagne Welcome: Begin your adventure with a champagne toast upon arrival. As you raise your glass with new and old friends, celebrate the start of a week filled with shared experiences on this beautiful island known for its welcoming atmosphere.
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Egmont Key Private Boat Tour: Embark on a private boat tour to Egmont Key State Park, an island accessible only by boat. Discover the rich history of this secluded spot, from its lighthouse built in 1858 to the remnants of Fort Dade. Exploring this hidden gem with friends adds a special bond to your island adventure.
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Kayak ECO-Tour: Experience the natural beauty of Anna Maria Island on a guided kayak eco-tour. Paddle through serene waters with opportunities to spot dolphins and manatees. Sharing these moments of awe with friends makes the experience even more magical.
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Golf Cart Island Exploration: Hop on a golf cart and explore the island at your own pace. Discover charming local spots and hidden treasures together, creating a fun and carefree way to bond as you navigate the island’s scenic routes.
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Sunset Beach Walks: Take evening walks on the beach and watch the sun set over the Gulf of Mexico. These quiet moments, shared with friends, provide the perfect opportunity to reflect on the day’s adventures and the beauty of Anna Maria Island.
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Painting Sand Dollars: Visit Shiny Fish Emporium for a sand dollar painting activity. This creative experience offers a unique way to bond with friends while crafting a personalized keepsake to remember your time on the island.
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Tiki Bar Hop Cruise: Join a Tiki Bar Hop Cruise for dinner and socializing. As you visit different tiki bars around the island, enjoy the lively atmosphere and the joy of sharing laughter and good times with your travel companions.
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Docent-Led History Tour: Learn about the island’s rich history with a guided docent-led tour. Discover stories of the past and gain a deeper appreciation for Anna Maria Island, all while strengthening the friendships that make this trip special.
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Live Music at Ugly Grouper: Enjoy a lively dinner with live music and dancing at the Ugly Grouper. This local favorite is the perfect place to let loose and celebrate the bonds formed during your island getaway.
Multiple Departures Available
February 27 – March 3, 2027
March 3 – March 7, 2027
5 Days / 4 Nights
OR CHOOSE BOTH FOR A 9 DAY / 8 NIGHT EXPERIENCE
BACK-TO-BACK February 27– March 7 – $250 off for back-to-back
Group Size: 11 Guests per date set
Your BB Hostesses: 2 Fabulous Hosts
Note: This itinerary serves as a general guide to what we will be doing, seeing, and eating, with the final version provided approximately two weeks prior. The published itinerary is an example and may be adjusted to include accommodations, tours, or restaurants of comparable quality to ensure the best experience.
View Rooming Options, Details, and Availability at the Bottom of the Trip Page
| Single Occupancy | Double Occupancy |
| $4,767 to $5,397 | $1,990 to $3,990 |
| *Pricing details are found below | *Pricing details are found below |
| Deposit Due at Time of Booking: $250 for Domestic/$500 for International |
Deposit Due at Time of Booking: $250 for Domestic/$500 for International |
| Click to Book Single Occupancy | Click to book Double Occupany |
Beatrice Bradley Experiences are All Inclusive. What does that mean?
- Airport Group Transfers: Seamless airport pickups and drop-offs by our friendly hostesses, ensuring a smooth start and end to your adventure.
- Dedicated BB Hostess: Travel with peace of mind knowing a dedicated Beatrice Bradley hostess will be with you throughout the trip, ensuring every aspect of your journey is unforgettable.
- Full Dining: Enjoy 2-3 daily meals carefully selected to reflect the local cuisine, inclusive of all tips. Whether it’s a quick breakfast or a sumptuous dinner, we’ve got it all covered.
- Unique Accommodations: Stay in boutique hotels or unique properties that are handpicked for their charm and comfort, providing an authentic and intimate experience.
- Curated Activities: We find the BEST of the best tours. Making the absolute most out of our time.
- Included Gratuities: Tips for tour guides, meals, and transportation are all taken care of. We ensure that those who make your trip special are rewarded, without you needing to worry about the details.
- Transportation: All transportation is included throughout the experience, from airport pickup to your final drop-off.
- You won’t see “Free Days” on our itineraries: Our trips are made for a balanced experience. We carve out time to bond, laugh, shop and explore but we will never just send you out on your own and say “good luck” we do everything together or smaller group breakouts.
With Beatrice Bradley, every detail is meticulously planned to ensure you have a memorable and carefree travel experience. Join us and discover the joy of true hassle-free travel!
We Offer Flex-Pay! What is that?
Flexible Payments at Your Fingertips: You can use your invoice to pay any amount you choose, as frequently as you wish, until the full payment deadline.
Want to make a payment? Click “Review and Pay” on your invoice whenever you’re ready.
Pay Your Way: You can adjust the payment amount by selecting “Edit Amount,” allowing you to manage your budget flexibly.
Final Countdown: Ensure everything is paid up 60 days prior to your trip for domestic and 90 days prior for international. Don’t worry, we’ll send you reminders! If there’s any remaining balance, we’ll automatically process it, allowing you to focus on the excitement of your upcoming adventure!
| Arrival Information | Departing Information |
| Sarasota International Airport (SRQ) | Sarasota International Airport (SRQ) |
| Pick up’s starting at 3PM | Earliest departure after 11AM |
This trip offers a balanced mix of leisurely and moderate activities suitable for most fitness levels. Expect relaxed beach walks, casual golf cart explorations, and serene beachfront relaxation. Moderate activities include the Kayak ECO Coastal Island Tour and the Tiki Bar Hop Cruise. Guests can also choose optional activities like beach massages or exploring historical sites on foot. Overall, the trip provides both opportunities for relaxation and light adventure, making it ideal for those looking to unwind and socialize in a beautiful coastal setting.
As your hostesses, we understand that traveling solo can be intimidating, but rest assured, making you feel welcomed and comfortable is our top priority. Our experiences are designed for building new and lasting friendships in a warm and welcoming environment.
From the moment you arrive until we bid you farewell, we’ll be right by your side. We meticulously handle all the details and manage the logistics seamlessly behind the scenes, ensuring your journey is truly unique and worry-free. While we aren’t local experts or tour guides, we work with a network of local professionals carefully selected for each location to enrich your experience.
Read more about our Hostesses Here
Thinking about joining us?
If you’re on the fence or have any questions, we’re here to help. Simply fill out this form to get in touch. We can’t wait to assist you in planning an unforgettable adventure!
If you have any immediate questions, please feel free to get in touch: 763-864-8291 | Lindsay@bbgage.com
Ready to book? We’re happy to have you!
Check Out Our Beachfront Mansion
Day One: Welcome to paradise!
Your island escape begins the moment you land in sunny Florida. Fly into Sarasota–Bradenton International Airport where your Beatrice Bradley hostesses will be waiting to greet you with a warm welcome and big smiles.
From the airport, we’ll head to our beautiful beachfront home on Anna Maria Island, where swaying palms, warm ocean breezes, and the sound of the waves set the tone for the days ahead. This stunning coastal retreat will be our home for the next four nights — the perfect place to relax, laugh, and soak in island life together.
After everyone has settled in, we’ll gather for our welcome dinner right at the house. With the Gulf of America just steps away, it’s the perfect setting to share a delicious meal, get to know your fellow travelers, and kick off what promises to be an unforgettable week in paradise.
Highlights:
- Arrival at Sarasota–Bradenton International Airport (SRQ)
- Warm Beatrice Bradley hostess welcome
- Transportation to our beachfront Anna Maria Island home
- Time to settle in and explore the property
- Welcome dinner together to kick off our island adventure
Day Two: Sandy Toes and Egmont Key Boat Tour
The morning sun kissed the beach as early risers enjoyed a coffee beach shell walk, savoring the tranquility and natural beauty of the Gulf of Mexico. After a delightful breakfast at the house, the group hopped on golf carts and headed to Pine Street. At the charming Shiny Fish Emporium, everyone painted sand dollars, creating unique keepsakes. A delicious lunch at Pizza Social followed before embarking on a private boat tour to Egmont Key State Park, a secluded paradise with rich history. The day concluded with dinner at The Chateau and a relaxing evening at the house.
Highlights:
- Early Risers Coffee Beach Shell Walk: Stroll along the white sand beach, collecting seashells and spotting shorebirds.
- Breakfast at the House: Enjoy a hearty breakfast and coffee with fellow travelers.
- Golf Cart Ride to Pine Street: Explore the island on golf carts.
- Painting Sand Dollars at Shiny Fish Emporium: Create personalized sand dollar art at this adorable island shop.
- Lunch at Pizza Social: Relish delicious pizzas in a cozy setting.
- Egmont Key Private Boat Tour: Discover the natural beauty and history of Egmont Key State Park, accessible only by private boat.
- Dinner at The Chateau: Savor a meal at one of Anna Maria Island’s favorite restaurants.
- Evening at the House: Relax, socialize, or enjoy the hot tub with new friends
Day Three: Kayak ECO-Tour and Grouper at Ugly Grouper
The day began with a serene coffee beach shell walk for the early risers, followed by a refreshing al fresco breakfast at the house. Guests then embarked on an unforgettable Kayak ECO Coastal Island Tour, where expert guides pointed out dolphins, manatees, and other marine life. The afternoon offered a choice between a relaxing beach massage, free time at the beach or pool, or exploring Pine Street on golf carts. The evening wrapped up with a lively sunset dinner at Ugly Grouper, complete with live music, dancing, and a nightcap or ice cream by the poolside.
Highlights:
- Early Risers Coffee Beach Shell Walk: Enjoy a peaceful morning stroll, collecting shells along the shore.
- Al Fresco Breakfast at the House: Savor a delicious breakfast outdoors with fellow travelers.
- Kayak ECO Coastal Island Tour: Experience an adventure spotting dolphins, manatees, and diverse marine life with expert guides.
- Beach Massage or Free Time: Opt for a soothing beach massage, relax at the beach or pool, or explore Pine Street’s shops via golf carts.
- Sunset Dinner at Ugly Grouper: Delight in a meal with live music, dancing, and fabulous food.
- Nightcap or Ice Cream Poolside: End the day with a drink or ice cream by the pool, enjoying the company of new friends.
Day Four: History of Anna Maria & Tiki Bar Hop Cruise
The morning started with an invigorating coffee beach walk for early risers. Guests enjoyed breakfast either at the house or the charming North Shore Café on Pine Street. The day continued with a docent-led history tour, visiting the Anna Maria Island Historical Society Museum, the Old City Jail, Belle Haven Cottage, and the Mangrove Walk. After some free time for shopping on Pine Street or relaxing at the house, the evening featured a lively Tiki Bar Hop Cruise dinner. The day ended with a peaceful late-night beach walk or a relaxing poolside nightcap.
Highlights:
- Early Risers Coffee Beach Walk: Start the day with a rejuvenating stroll along the beach.
- Breakfast Choices: Enjoy breakfast at the house or at the North Shore Café on Pine Street.
- Docent-Led History Tour: Explore the island’s history at the Anna Maria Island Historical Society Museum, Old City Jail, Belle Haven Cottage, and the Mangrove Walk.
- Free Time: Shop and explore Pine Street or relax on the beach at the house.
- Tiki Bar Hop Cruise Dinner: Experience a fun-filled dinner cruise, hopping between tiki bars.
- Late-Night Beach Walk or Poolside Nightcap: End the day with a serene beach walk or a relaxing nightcap by the pool.
Day Five: Departure day
Highlights:
- Last Early Risers Coffee Beach Walk
- Goodbye Breakfast at the house
Beachfront luxury 10-bedroom home! Rooftop deck, pool, hot tub, private beach access and 2 elevators.
King Suite with Private Balcony – $5,397
Bring a BFF or Sister and Split the King Bed for an additional $1,975
Double Bedroom with 2 Queen Beds – $3,990
No Roommate – No problem, we’ll pair you!
King Suite – $4,767
Bring a BFF or Sister and Split the King Bed for an additional $1,725
Triple Occupancy with Private Balcony – $1,990
Tri-Level bunks triple occupancy grab this Best Value!
*EACH GUEST WILL HAVE A TRI LEVEL BUNK LOW CLEARANCE!
You Might Be Wondering…
Read through our frequently asked questions.
I've never traveled solo; Is this travel group for me?
Yes! In fact, many of our guests are first-time solo travelers. Beatrice Bradley is designed exactly for women like you. Those ready to explore but not alone. From the moment you arrive, you'll be welcomed into a fun, supportive group of like-minded women. We take care of the details so you can relax, make fast friends, and enjoy the adventure. You may come solo, but you’ll never feel alone.
Beatrice Bradley Experiences are All Inclusive. What does that mean?
Included:
- Accommodations: Stay in boutique hotels or unique properties that are handpicked for their charm and comfort, providing an authentic and intimate experience.
- Tours / Activities: We curate only the best of the best experiences to make the most of our time together. Please note that tours and activities listed on the website are subject to change based on availability, group size, and weather. If adjustments are needed, we’ll always replace them with something equally special
- Food / Beverages: Meals eaten with the group are fully covered by Beatrice Bradley. Typically this includes 2 meals a day.
- Transportation: All transportation is included throughout the experience, from airport pickup to your final drop-off.
- Airport Group Transfers: Seamless airport pickups and drop-offs by our friendly hostesses, ensuring a smooth start and end to your adventure.
- Dedicated BB Hostess: Travel with peace of mind knowing a dedicated Beatrice Bradley hostess will be with you throughout the trip, ensuring every aspect of your journey is unforgettable. Please remember Your BB Host is not your tour guide.
- Included Gratuities: Tips for local tour guides, meals, and transportation are all taken care of.
not included:
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Airfare to and from the destination – You’ll arrange your own flights based on our suggested arrival and departure times.
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Hotel incidentals and personal expenses – Things like room service, minibar items, or personal shopping aren’t included.
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Meals eaten outside the group – If you choose to skip a group meal or explore on your own, those meals are at your own expense.
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Activities done outside the group itinerary – Any optional excursions, spa treatments, or activities not part of the planned group experience will be at your discretion and cost.
- Tips for your Beatrice Bradley Host
We keep things simple and transparent—so you can focus on enjoying every moment.
Are the deposits refundable / What is the cancellation policy.
What if i want to skip an activity? - How important is it to be on time?
You are never required to do all activities! Sometimes you need a little downtime, and you’re welcome to skip an activity if you'd prefer to rest or recharge. Just keep our hosts in the loop.
Being on time is also very important. We run a thoughtful schedule to make sure everyone gets the most out of each day. Out of respect for your fellow travelers and our guides, we ask that you arrive on time and ready to roll so we can keep the adventure smooth and stress-free for all!
What can I expect from a Beatrice Bradley Host?
Our Beatrice Bradley hosts are the glue that holds each trip together. They understand how intimidating solo travel can feel, and they’re dedicated to making your experience warm, welcoming, and full of laughter. From the moment you arrive, they’ll be there with a smile—helping you settle in, making introductions, and setting the tone for a fun and connected adventure.
Our hosts aren’t just handling logistics—they’re the heart of the journey. They create a sense of community, offer support, and help every woman feel seen, included, and valued.
Please note: our hosts are not local tour guides—we hire local experts for that. In some cases, it may even be their first time in the destination, just like you! While they’re often going above and beyond to ensure everything runs smoothly, we kindly ask that you treat them with respect. They are not personal assistants or luggage porters—they are your fellow travelers, dedicated to making this trip unforgettable for everyone.
How does tipping work?
We take care of all standard tips for included meals, local guides, and drivers—so you don’t need to worry about those details.
If you’d like to show appreciation to your Beatrice Bradley host, gratuities are always welcome but never expected. A general guideline is $5–$10 per day, per host, depending on your experience. Most guests find it a meaningful way to say thank you for the care, energy, and fun our hosts bring to each trip!
