Philadelphia and Annapolis 2025 Trip - Beatrice Bradley

Experience the historic, PATRIOTIC cities of Philadelphia and annapolis
April 28 – May 3, 2025 

philly and annapolis


Single Occupancy -$4,250

Double Occupancy- $3,550

Dates:  April 28 – May 3, 2025

Location: 3 nights in Philadelphia, PA and 2 nights in Annapolis, MD

Airport: FLYING IN AND OUT OF DIFFERENT AIRPORTS Philadelphia International Airport (PHL), and Baltimore  International Airport (BWI)

Accommodations: The Kimpton Monaco Hotel and The Graduate Hotel Annapolis

 Meet your hosts

2 of our fabulous BB Hosts

Sharon & Connie

I'm thinking about it

Let our team know that you are interested in joining us on this tour. Our team will reach out via email and will be available to chat about this trip.

Make a Reservation

Secure your reservation here. We only take 10-12 women on each trip. Making a reservation is the only way to secure your name to the trip list.

Don’t just tour Philly and Annapolis, Experience Philly and Annapolis

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’. 

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Overall Trip Highlights

  • Luxurious lodging experiences at The Kimpton Monaco Hotel and The Graduate Hotel
  • Guided tours of Liberty Bell, Constitutional Center and Independence Hall
  • Private Food Tour including Philly Cheesesteak!
  • Eat and shop around The Reading Railroad Market Terminal 
  • Private tour of the famous Shofuso Japanese Garden 
  • Private guided tour of historic downtown Annapolis on Golf Carts
  • Group dinner on the Chesapeake Bay views
  • Sunset Schooner Cruise through the Chesapeake Bay
  • Tour of the Naval Academy
  • Explore the famous Spruce Street Harbor Park and Boardwalk 

Day One: Monday, April 28, 2025 – Arrival Day

Welcome to Philadelphia! Please fly into the Philadelphia International Airport before 3 pm. You we will greeted and picked up from the airport by our hosts and head out to our luxurious downtown hotel… The Kimpton Monaco Hotel. Once we check into our rooms and have a short time to freshen up after the day of travel, we will head downstairs for a Welcome Happy Hour for a chance to meet and greet your fellow travelers,.  Then, we will head out to our first dinner as a group for a local dining experience.


  • Airport pickup and drive to downtown Philly
  • Check in to the historic, and luxurious Kimpton Palomar Hotel
  • Welcome Happy Hour
  • Meet all your wonderful Beatrice Bradley trip mates and review the itinerary
  • Welcome Dinner together at fabulous Philly restaurant to get to know each other


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Day Two: Tuesday, April 28, 2025 – A day of HISTORY and Cheesesteaks!

After a good nights rest, and a quick local breakfast/coffee stop, we will head out on foot to our first historic landmarks. Our first stops will include the Liberty Bell experience and photo opp as well as a tour through Independence Hall and the National Constitutional Center! After working up an appetite from visiting these patriotic and historic landmarks we will take a food tour!  Then, we will check out the Philly Flower Show!!!

A Food Tour including Philly Cheesesteak tastings!

Start off walking through Old City, learning about the historical center of Philadelphia and hearing stories about revolutionary times, as well as an introduction to one of Philly’s most famous inventions: The Cheesesteak. Take a quick pass by Jefferson Hospital – one of the first hospitals in the United States before heading south. Next, head north through the historic Italian Market and back onto South Street. Stopping again for another bite and hearing about how this area became the “alternative” section of the original city. One of the oldest neighborhoods in Philadelphia, Society Hill boasts beautiful, classic homes. 


  • Revolution and the Founder’s Guided History Tour
  • Spending time at the Liberty Bell, Constitutional Center and Independence Hall
  • Private Walking Food Tour – including Philly Cheesesteak tastings!
  • Touring the 18th Century Garden
  • Charcuterie & Appetizer dinner with cocktails at the hotel


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Day Three: Wednesday, April 30, 2025 – The Reading Market Terminal and an E-Bike tour of Fairmont Park and a tour of the famous Shofuso Japanese Garden 

We will begin our day by strolling through the beautiful Spruce Street Harbor Park with a stop at a local cafe for breakfast and coffee. Explore the boardwalk along the Delaware River, stopping for photo opportunities and taking in the bustling streets and sights of the stunning boardwalk. From there we will head to the Fairmont Park and will see the Rocky monument!  Then, we will take a private tour of the famous Shofuso Japanese Garden with waterfalls, koi ponds and cherry blossoms this ancient architecture inspired garden is truly beautiful!.  Then, off to the The Reading Terminal Market to explore and do some shopping!  Finally we will head to The Crown and Harp for a delicious chef crafted dinner with an old world luxury atmosphere!


  • Explore the Spruce Street Harbor Park and Boardwalk
  • Seeing the famous Rocky monument
  • Private tour of the famous Shofuso Japanese Garden
  • Free time to shop around The Reading Market Terminal
  • Group Dinner at the famous Harp and Crown Restaurant


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Day Four: Thursday, May 1, 2025 – Let’s go to Annapolis!

After our amazing time in Philadelphia we will now head to the historic waterfront city of Annapolis, after a quick stop for breakfast and the final stroll through Rittenhouse Square. Enjoy the scenic drive from Philadelphia to downtown Annapolis .Once we arrive in Annapolis we will pull into a local sandwich shop for fresh caught lobster rolls. After fueling up on yummy lobster, we will meet our tour guide for a private tour of downtown Annapolis while riding around the bustling streets on all-electric golf carts!

Now it is time to check into our amazing downtown boutique hotel The Graduate. Freshen up and take a quick break at the hotel before heading out for our first dinner in Annapolis, with wonderful views of the Chesapeake Bay, ending the night with a local creamery for an ice cream nightcap.


  • Final stroll through and coffee in Philly
  • Taking a shuttle ride to Annapolis
  • Fresh caught lobster roll lunch
  • Private tour of historic downtown Annapolis on electric golf-carts
  • Group dinner at The Choptank, a new fish & crab house located in one of the best waterfront locations in the entire state of Maryland
  • Ice cream nightcap and walk before bed

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Day Five: Friday, May 2, 2025 – The Naval Academy and a Schooner Sunset Cruise 

Upon waking we will take a stroll down the beautiful Annapolis streets to a cute and quaint cafe for breakfast and coffee. After we are fueled up with yummy breakfast we will head out to the Naval Academy which is located directly on the beautiful Chesapeake Bay, for a private and in depth tour filled with history! Plenty of time to explore the Navy gift shop following the tour for any souvenirs before heading back out onto the downtown streets on Annapolis for a delicious lunch filled with fresh lobster and fish!

From there, you will have the option to explore, shop, and walk around the beautifully historic Downtown Annapolis. Filled with local stores featuring clothes, shoes, antiques and many other goodies. After you have fully experienced the downtown we will make a quick stop at the hotel to freshen up before heading out to the final dinner at waterfront.

Finally, After dinner we will head to the Chesapeake Bay port, to board our Sunset Cruise on a Schooner! This boat ride gives us beautiful views, and a whole new experience of Annapolis and the bay!


  • Private tour of the Naval Academy
  • Explore Downtown Annapolis
  • Waterfront Farewell Dinner on the bay
  • Sunset cruise on Chesapeake Bay


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Day Six: Saturday, May 3, 2025 – Departure Day

Please depart from Baltimore International Airport. Departure should be after 12:00 PM, with group drop off at 10:00 AM.


  • Farewell breakfast at local Annapolis cafe
  • Last minute shopping or exploring in downtown Annapolis
  • Head to airport to catch your flight home



Experience All-Inclusive Travel with Beatrice Bradley

At Beatrice Bradley, we pride ourselves on delivering exceptional, all-inclusive travel experiences with absolutely no hidden fees. From the moment you step off the plane to the moment we bid you farewell, every detail is taken care of. Our goal is to provide a completely hassle-free experience, allowing you to focus solely on enjoying your journey and creating lasting friendships.

Here’s What Our All-Inclusive Experience Includes:
  • Airport Group Transfers: Seamless airport pickups and drop-offs by our friendly hosts, 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 all 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 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 during the experience.
  • 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!

Flexible pay-as-you-go payment plan

How it Works:

Step 1 Choose Payment Plan (available with credit card and ACH payment options)
Step 2 Your $250 Deposit will be processed within 2 business days
Step 3 When you are ready to make a payment, click the “Review and Pay” button on your invoice
Step 4 Once clicked, in the top left of the invoice, next to the amount, you will see “Edit Amount.” Here you will be able to enter the amount you would like to pay
Step 5 Full amount needs to be paid by 60 days prior to the trip. *If there is a remaining balance at 60 days prior to the trip then an automatic payment for the remaining amount will be charged.

Activity Level – Moderate

2 moderate

There will be walking and standing during the tour.  You will need to be able to get in and out of a van.

It is your responsibly to fully read and understand the physical abilities that correlate to this Beatrice Bradley Experience. Difficulty level of activity is subject to individual interpretation so it is extremely important that you read the itinerary and reach out if you have concerns or questions.

If you have questions about the specifics of the physical activity during this trip, please give us a call at 763-784-8291

Role of a Beatrice bradley hostess

Beatrice Bradley is an Experience Company not a Tour Company.  The role of a Beatrice Bradley Host is to be warm and welcoming. To relate and connect. To have attention to details. And to manage the behind-the-scenes magic so your experience is one-of-a-kind. They are not local experts nor are they tour guides. We hire local experts, guides, and historians as each location warrants. They are expert hosts and manage the camaraderie and logistics of the experience. Our goal is that your hostess will make you feel welcomed, comfortable, and that you will walk away with new & lasting friendships made during an unforgettable experience.

Flight Details

Airport Pick Up is included when arriving at the designated airport within the specified pick up window.

Arrival Airport: Philadelphia International Airport (PHL)
Arrival Date:  April 28, 2025
Pick Up Times: Please Arrive by 3:00 PM

Departure Airport: Baltimore International Airport (BWI)
Departure Date:  May 3, 2025
Drop off Times: Drop off at 10:00 am – Flights 12:00 pm or later

Important information

As a solo-traveler, we need you to provide self-awareness and an understanding that you are fully responsible for yourself. This includes: your possessions, your physical abilities or fitness, your attitude, and all other aspects that relate to traveling solo in a group. 

  • Connect with our Members on our Private Facebook Group – Beatrice Bradley Member’s Only
  • You must be able to manage your own luggage and all of your personal belongings on this trip
  • This is not a handicap accessible able trip – you must be able to get in and out of a Large Passenger Transit Vehicle
  • All Ground transportation is included on this trip
  • Group Airport transfers are included in this trip
  • This trip will have have a maximum of 13 women
  • This trip will have 2 Beatrice Bradley Hostesses
  • If you need a roommate, we will happily pair you with another Beatrice Bradley traveler
  • Travel insurance is not included. Beatrice Bradley is not a licensed travel insurance operator nor is our staff trained to in travel insurance. You can choose to purchase travel insurance through any licensed provider you choose. We will ask you upon booking if you would like us to send you some suggested licensed insurance companies.