Historic and Patriotic Annapolis and Philadelphia

American history, timeless charm, and blooming beauty come together.

From the historic streets of Philadelphia to the waterfront elegance of Annapolis

This March Experience VIP Access to the Nation’s Largest Flower Show!

Overall Trip Highlights 

Liberty Bell
See America’s iconic symbol of independence with its famous crack and inspiring inscription.

Independence Hall
Stand in the very room where the Declaration of Independence and Constitution were signed.

VIP Philadelphia Flower Show
Enjoy exclusive early access to the nation’s largest and longest-running flower show.

Flavors of Philly Food Tour
Taste Philly classics—pretzels, tomato pie, cheesesteaks—on a guided culinary walk.

Reading Terminal Market
Wander one of America’s oldest indoor markets, filled with Amish treats and local favorites.

Historic Old City Walk
Stroll cobblestone streets and landmarks where American democracy was born.

Rittenhouse Square
Relax among tree-lined paths, historic homes, and lively city vibes.

Annapolis Schooner Sunset Cruise
Sail the Chesapeake at sunset aboard a classic schooner.

U.S. Naval Academy Tour
Explore the historic grounds where generations of naval leaders trained.

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.
• Happy Hour: Unwind with city views and good cocktails 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!

Day Two: Flowers, Philly Flavor & Open-Air Views

Today is a vibrant mix of blooming beauty, beloved local food, and sweeping city views — all Philadelphia style!

We’ll begin with breakfast at the hotel before heading out for one of the city’s most iconic annual events: the Philadelphia Flower Show at the Pennsylvania Convention Center. As the largest and longest-running indoor flower show in the United States, this spectacular showcase transforms the space into a colorful wonderland of botanical art, garden design, and floral creativity.

After our group experience, you’ll have time to continue exploring the show at your own pace — whether you’re browsing jaw-dropping installations, snapping photos, or picking up a few garden-inspired ideas of your own.

When you’re ready for lunch, we’ll walk just next door to the historic Reading Terminal Market, one of the oldest and most famous public markets in America. This is your chance to eat like a local — whether it’s a classic roast pork sandwich, fresh-baked Amish pretzels, or a sweet treat from a local bakery.

In the afternoon, we’ll shift gears and board the Hop-On Hop-Off Bus Tour, giving you an open-air view of Philadelphia’s most famous landmarks. Snap photos at Independence Hall, cruise past the Liberty Bell, and take in the sights and stories that shaped our nation’s beginnings.

We’ll return to the hotel to relax and freshen up before heading out for a delicious group dinner at LaScala’s Fire, where the menu blends rustic Italian comfort food with a modern twist — perfect for great conversation and a cozy end to a packed day.

Highlights

• Philadelphia Flower Show Admission – Experience the country’s premier indoor flower show, filled with immersive garden displays and floral artistry.

• Explore the Show at Your Own Pace – Enjoy time to wander and take in the beauty after our group visit.

• Lunch at Reading Terminal Market – Savor Philly’s favorite eats from one of America’s most historic public markets.

• Hop-On Hop-Off Bus Tour – Discover Philadelphia’s historic core with an open-air sightseeing adventure.

• Dinner at LaScala’s Fire – End the day with a flavorful Italian-American meal in a lively, welcoming setting.

Day Three: Colonial Legends, Philly Flavors & Smooth Jazz

Today brings together a rich dose of American heritage, iconic local eats, and live jazz in one unforgettable Philadelphia day.

We’ll start with breakfast at the hotel, giving you time to fuel up and connect with fellow travelers before heading out to explore the stories behind one of America’s most famous historical figures.

Our first stop is the Betsy Ross House Museum, where we’ll step into the life and legacy of the woman credited with sewing the first American flag. This immersive museum offers a fascinating look into 18th-century life and the quiet revolutionaries who shaped a nation.

From there, we’ll head over to the starting point of the Flavors of Philly Food Tour. This beloved culinary experience will take us on a guided tasting adventure through some of Philly’s most legendary dishes — from cheesesteaks to soft pretzels and local sweet treats, you’ll get a true flavor of the city’s food culture (and a few surprises too).

After the food tour, we’ll return to the hotel for a little downtime before the night comes alive.

In the evening, we’ll head to Chris’s Jazz Café, Philadelphia’s most iconic live jazz venue. With its intimate setting and rich musical legacy, this soulful space is the perfect backdrop for smooth tunes, cozy vibes, and unforgettable moments shared with new friends.

Highlights

• Betsy Ross House Museum Tour – Dive into Revolutionary War history at the home of one of America’s most iconic women.

• Flavors of Philly Food Tour – Taste your way through the city’s culinary musts on a fun, flavorful walking tour.

• Relax at the Hotel – Take a well-deserved break after a full afternoon of history and food.

• Live Music at Chris’s Jazz Café – Wind down the day with world-class jazz in a warm, intimate venue.

Day Four: From Founding Fathers to Naval Traditions — Welcome to Annapolis

Today we shift gears from the cobblestone charm of Philly to the harbor-front elegance of historic Annapolis — a city steeped in nautical tradition and small-town charm.

We’ll start the day with breakfast and coffee at the hotel before checking out of the Kimpton Hotel Monaco Philadelphia. Your hosts will be waiting in the lobby to assist with luggage and help you board our private shuttle, making for a comfortable and scenic drive to Maryland’s capital city.

By midday, we’ll check in at the Graduate by Hilton Annapolis, a stylish boutique hotel that blends playful design with historic character — located just steps from the harbor and downtown shops.

Next up, we’ll enjoy a casual lunch at Mason’s Famous Lobster Rolls, a local favorite where buttery rolls and fresh seafood come together in true East Coast fashion.

After lunch, we’ll take a relaxing stroll through downtown Annapolis, known for its charming brick sidewalks, colonial architecture, and waterfront views.

The highlight of the afternoon is a privately guided tour of the United States Naval Academy. Led by expert guides, we’ll explore this iconic campus, from its grand halls and chapels to the stories of midshipmen past and present. It’s a moving experience that connects tradition, service, and the spirit of leadership.

Afterward, we’ll return to the hotel with time to rest and refresh before our final event of the day: dinner at the Chart House Prime, a stunning harborside restaurant known for upscale seafood, elegant ambiance, and views of the water that will take your breath away.

Highlights

• Private Shuttle from Philadelphia to Annapolis – Travel in comfort with your group as we journey to Maryland’s capital.

• Check-in at Graduate Annapolis – Unwind at a vibrant, boutique hotel that celebrates local charm and Naval pride.

• Lunch at Mason’s Famous Lobster Rolls – Indulge in a classic East Coast favorite just steps from the harbor.

• Downtown Annapolis Stroll – Explore this picturesque town filled with history, charm, and waterfront views.

• Guided Tour of the U.S. Naval Academy – Walk the grounds of one of the most prestigious institutions in the country, guided by local experts.

• Dinner at Chart House Prime – Dine harborside with fresh seafood and stunning sunset views in a truly memorable setting.

Day Five: Colonial Paths & Coastal Farewells

Our final full day in Annapolis blends the rich colonial heritage of Maryland’s capital with a serene sendoff on the water — the perfect close to an unforgettable journey.

We’ll begin the morning with breakfast and coffee at the hotel, enjoying one last relaxing start with the group before heading out for a deep dive into local history.

A short walk will bring us to the Annapolis Visitor Center, where we’ll meet our guide for a Colonial History Walking Tour through the heart of the historic district. As we stroll past 18th-century buildings and charming brick sidewalks, you’ll hear captivating stories about the city’s role in shaping America’s past — including visits from founding fathers and the signing of the Treaty of Paris.

After the tour, we’ll return to the hotel for a leisurely afternoon and time to rest or pack before our celebratory evening.

Later, we’ll gather for a farewell dinner at Ram’s Head Tavern, one of Annapolis’s most beloved historic pubs. With cozy Colonial ambiance, hearty fare, and good conversation, it’s the ideal spot to share memories, laughter, and maybe a toast or two.

To close out the evening — and the trip — we’ll take to the water for a sunset schooner cruise. As the sky glows gold over the Chesapeake Bay, you’ll feel the peaceful rhythm of the wind and waves while reflecting on the new friendships and unforgettable experiences of the week.

Highlights

• Colonial History Walking Tour – Explore the streets of historic Annapolis and hear stories that shaped the early days of the republic.

• Annapolis Visitor Center – Begin your journey with insights from local experts and a stroll through Maryland’s charming capital.

• Farewell Dinner at Ram’s Head Tavern – Enjoy a cozy final meal in one of the city’s most iconic historic taverns.

• Sunset Schooner Cruise – Sail into the evening aboard a classic schooner, with stunning views and serene farewell vibes.

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