Philadelphia and Annapolis 2025 Trip - Beatrice Bradley

Historic and Patriotic Annapolis and Philadelphia

Visit the Liberty Bell, Chesapeake Bay, Independence Hall, and Iconic Philly Cheesesteaks

Experience the historic, PATRIOTIC cities of Philadelphia and annapolis

April 28 – May 3, 2025
6 days / 5 nights / ALL INCLUSIVE THAT MEANS EVERYTHING IS INCLUDED!!

Philadelphia and Annapolis 2025 Trip

Overall Trip Highlights

  • Liberty Bell & Independence Hall: Walk in the footsteps of America’s founders, exploring these iconic landmarks where history was made.
  • Private Cheesesteak Tour: Indulge in Philly’s famous cheesesteaks while discovering Old City and the lively Italian Market.
  • Shofuso Japanese Garden: Stroll through this peaceful oasis, featuring koi ponds and cherry blossoms—perfect for reflection and relaxation.
  • Naval Academy Tour: Explore this historic academy along the scenic Chesapeake Bay and learn about naval traditions.
  • Schooner Sunset Cruise: Sail into the sunset on a schooner, soaking in the Chesapeake Bay’s stunning views.
  • Rittenhouse Square Stroll: Enjoy a leisurely walk through this elegant park, surrounded by cozy cafés and lush greenery.
  • Spruce Street Harbor Park: Savor breakfast by the Delaware River, taking in the vibrant boardwalk and peaceful waterfront.
  • Downtown Annapolis Exploration: Shop and explore the charming, historic streets, filled with local boutiques and treasures.

April 28 – May 3, 2025

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

Group Size: 10-13 Guests

Hostesses:  2 Fabulous BB 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.

Single Occupancy Double Occupancy
$4,250 $3,550
Private Room with Private Bath Shared Room, Separate Beds, Shared Bath
Deposit Due at Time of Booking:
$250 for Domestic/$500 for International
Deposit Due at Time of Booking:
$250 for Domestic/$500 for International
Single Occupancy – Sold Out
Click for Waitlist
Double Occupancy – Sold Out
Click for Waitlist


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
Philadelphia International Airport (PHL) *NOTE flying in and out of different airports  Baltimore International Airport (BWI) *NOTE flying into PHL and out of BWI
April 28, 2025 May 3, 2025
Must arrive before 3:00 PM First drop off at 10:00 am – Flights 12:00 pm or later

This 6-day trip is designed with a relaxed pace, ideal for women who enjoy light activities and plenty of downtime. It includes leisurely strolls through historic sites, visits to the Philly Flower Show, and scenic experiences like a sunset cruise on Chesapeake Bay. There’s a walking tour of Fairmont Park, perfect for those who want to explore at their own speed, and free time to relax and savor the charm of both cities, offering a balance of sightseeing and relaxation.

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!

Book Here

philly and annapolis

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’. 

Day One: Arrival Day

Welcome to the historic city of Philadelphia! After arriving at Philadelphia International Airport, you’ll be whisked to the elegant hotel, located in the heart of the city. Take some time to relax before joining your fellow travelers for a Welcome Happy Hour at the hotel’s rooftop lounge, offering stunning views of Independence Hall. End the evening with a delightful group dinner at a renowned local restaurant, perfect for starting your adventure on a high note.

Highlights

  • Airport Transfer: Effortless transfer to the centrally located hotel.
  • Elegant Hotel: A stylish, historic hotel offering both comfort and luxury, steps from top attractions.
  • Rooftop Happy Hour: Unwind with panoramic city views while getting to know your travel companions.
  • Group Dinner: Enjoy a delicious meal at a highly-rated Philadelphia restaurant, perfect for mingling and sharing excitement.

Fun Fact: The Kimpton Monaco Hotel sits directly across from Independence Hall, where the Declaration of Independence was signed!

skagit valley tulip
Philadelphia and Annapolis 2025 Trip
skagit valley tulip

Day Two: Revolutionary Streets, Philly Eats & Jazz Beats

Today is the perfect blend of American history, iconic food, and unforgettable music—Philly style!

We’ll start the morning at your leisure with coffee and breakfast at Red Owl Tavern, fueling up for a day full of discovery.

Next, we’ll head out for a private guided walking tour through Philadelphia’s most historic sites. From the grounds of America’s first White House and Supreme Court, to the meeting places of the First and Second Continental Congress, we’ll explore the footsteps of the Founding Fathers and Mothers, uncovering some of 1776’s best-kept secrets along the way.

After soaking in the sights, it’s time to eat like a local! We’ll join a Philly-themed City Food Tour, sampling the city’s most beloved bites while learning how food and culture go hand in hand in this vibrant city.

Later, we’ll return to the hotel to relax and freshen up before heading out for a memorable evening of live music at Chris’s Jazz Café—Philadelphia’s most legendary jazz club. With a rich musical history and a cozy, soulful atmosphere, it’s the perfect way to wind down and celebrate another unforgettable day.

Highlights:

  • Red Owl Tavern Breakfast – Enjoy a relaxed start to the day in a charming, historic setting.
  • Private History Walking Tour – Walk the same streets as America’s founders and uncover the hidden stories of 1776.
  • City Food Tour – Taste your way through Philly’s favorite bites and neighborhood gems.
  • Free Time to Refresh – Relax and recharge before an exciting night out.
  • Chris’s Jazz Café – Experience live music in Philly’s most iconic jazz venue.

Fun Fact:

Chris’s Jazz Café is the longest continuously operating jazz club in Philadelphia’s history and has hosted legends from around the world—right in the heart of the city!

Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip

Day Two: Tranquility, History & Local Flavor in Philly

Today, we dive deeper into the heart of Philadelphia—where peaceful gardens, rich history, and iconic local eats come together for an unforgettable day.

We begin the morning at a relaxed pace with coffee and a light breakfast downstairs at the hotel, before meeting up with fellow travelers and hosts to head out on a refreshing stroll through Fairmount Park, one of the largest and most scenic urban parks in the country.

From there, we step into serenity with a private guided tour of the Shofuso Japanese Garden, a hidden gem tucked away in the city. With its koi ponds, traditional architecture, and peaceful beauty, this garden offers a moment of reflection and calm in the middle of bustling Philly.

Next, it’s time to turn up the energy and head over to the iconic Reading Terminal Market—a food lover’s paradise! Here, we’ll have time to shop, explore, and grab lunch from one of the countless vendors serving up everything from Philly favorites to global cuisine.

After lunch, we enjoy a scenic walk through the city to our next historic stop: the Betsy Ross House Museum. We’ll tour the home of the legendary woman who is said to have sewn the first American flag and learn more about her story and the world she lived in.

The afternoon wraps up with time to relax and freshen up at the hotel before we head out for the evening. Dinner tonight is at LaScala’s Fire, a warm and lively spot known for its delicious Italian-American fare and inviting atmosphere—the perfect way to end a full day of Philly exploration.

Highlights:

  • Morning Walk in Fairmount Park – Enjoy fresh air and beautiful views in one of the country’s most historic urban parks.
  • Shofuso Japanese Garden Private Tour – Experience the peaceful beauty and cultural elegance of this authentic Japanese garden.
  • Reading Terminal Market – Shop and sample local flavors at this iconic Philly institution.
  • Betsy Ross House Museum Tour – Step into the past and learn about the life of the woman behind the stars and stripes.
  • Dinner at LaScala’s Fire – Unwind with a cozy and delicious meal in the heart of the city.

Fun Fact:

The Shofuso Japanese House and Garden was originally built in Japan and reassembled in Philadelphia in 1958 as a symbol of friendship between Japan and the U.S.—a hidden cultural gem in the City of Brotherly Love.

Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip

Day Four: Let’s Go to Annapolis!

After an exciting stay in Philadelphia, we’ll begin our scenic journey to the charming waterfront city of Annapolis. Before leaving, enjoy a final stroll and coffee at Rittenhouse Square. Upon arrival in Annapolis, savor a delicious fresh lobster roll lunch at a local sandwich shop. Then, hop onto electric golf carts for a private tour of historic downtown Annapolis. After checking into our elegant hotel, relax before heading to The Choptank for a seafood dinner with stunning views of the Chesapeake Bay. End the day with a sweet treat from a local creamery.

Highlights

  • Morning in Philly: A relaxing final stroll and coffee in Rittenhouse Square before heading out.
  • Scenic Shuttle to Annapolis: Enjoy a picturesque drive from Philadelphia to the historic heart of Annapolis.
  • Lobster Roll Lunch: Savor fresh, local lobster rolls at a popular sandwich shop in downtown Annapolis.
  • Golf Cart Tour of Downtown Annapolis: Explore the city’s history while riding in style through the charming streets.
  • Dinner at ChartHouse Prime: Enjoy a delicous harbor side dinner
  • Ice Cream Nightcap: Stroll through the scenic streets and enjoy a sweet ice cream treat from a local creamery.

Fun Fact: Annapolis is known as the “Sailing Capital of the U.S.” and its vibrant waterfront has been a hub for maritime history for centuries!

Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip

Day Five: The Naval Academy and a Schooner Sunset Cruise

Kick off the day with a peaceful stroll through the charming streets of Annapolis, stopping at a cozy café for a delightful breakfast. Then, dive into history with a private tour of the prestigious Naval Academy, located along the scenic Chesapeake Bay. Afterward, shop for souvenirs at the Navy gift shop and enjoy a fresh seafood lunch. Spend the afternoon exploring Downtown Annapolis, filled with local boutiques and antiques. In the evening, enjoy a farewell waterfront dinner, followed by a stunning Schooner Sunset Cruise on the bay.

Highlights

  • Naval Academy Tour: Delve into U.S. history with an insider’s view of the academy, set against the backdrop of the beautiful Chesapeake Bay.
  • Downtown Annapolis Exploration: Wander through the cobblestone streets of Historic Downtown Annapolis, browsing charming boutiques, local art, and unique antiques.
  • Waterfront Farewell Dinner: Savor a gourmet seafood dinner at a top-rated restaurant with breathtaking views of the bay.
  • Schooner Sunset Cruise: End the day with a peaceful sail on a classic schooner, watching the sun set over the Chesapeake Bay, creating lasting memories.

Fun Fact: Annapolis is home to the oldest state capitol still in continuous legislative use in the United States!

Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip
Philadelphia and Annapolis 2025 Trip

Day Six: Departure Day

As your incredible journey winds down, start the day with a delightful farewell breakfast at a cozy Annapolis café, surrounded by new friends and fond memories. Enjoy some time for one last stroll through Downtown Annapolis, where you can pick up final keepsakes from local boutiques or simply soak in the charm of this historic town. The group will head to Baltimore International Airport, ensuring a smooth and relaxed departure.

Highlights

  • Farewell Breakfast: A heartfelt gathering to reminisce about your adventure.
  • Downtown Annapolis Exploration: Time to wander the charming streets and do some last-minute shopping.
  • Airport Transfer: Group transportation to Baltimore International Airport for an easy departure.

Fun Fact: Annapolis is known as “America’s Sailing Capital,” so don’t forget to grab a nautical-themed souvenir!

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.

***Itinerary is subject to change

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