Day 1 - Freedom Trail and Beacon Hill
The Freedom Trail is a walkable path that marks a unique collection of museums, churches, meeting houses, burying grounds, a ship, and historic markers that tell the story of the American revolution. You can book a tour or download the map online for a self-guided tour. A short drive from the Freedom Trail is Beacon Hill, a beautiful historic neighborhood lined with cobblestone roads. Take a stroll through the neighborhood, and be sure to take a picture on famous Acorn Street!
Day 2 - Cambridge and Harvard University
Cambridge is about a 20-minute drive from Boston. It is worthwhile to walk around the Harvard University campus to observe student life at this famous university. The town of Cambridge is great to visit because of its excellent restaurants and prestigious universities.
Top 3 Boston Restaurants
1) Row 34 – With locations in Boston’s historic Fort Point neighborhood and Cambridge, you can’t go wrong with this stylish brick and wood eatery that serves an extensive oyster menu plus fish entrees and craft beers.
2) Fuji at Ink Block – this sleek Japanese spot offers elegant and reasonably priced sushi, tasting menus, stir fry dishes and more.
3) Mamma Maria – This restaurant has a refined Italian menu with a focus on local ingredients, served in a romantic townhouse.
Read more about Boston’s food scene here.
Boston Best Hotel Recommendations
While location is a matter of preference, you can find affordable hotels on booking.com and priceline.com, and budget friendly accommodation on Airbnb.
2 Days in Cape May: Vacation Itinerary
Day 1 - Washington Square Mall and Tisha's for Dinner
Cape May is a city and seaside resort at the tip of southern New Jersey’s Cape May Peninsula. Although Congress Hall is a beautiful hotel option, there are other budget friendly travel options on Airbnb. When you arrive, explore the beach area and walk through Washington Square Mall. In the mall, you will find excellent fine dining at Tisha’s. The steak and fish dishes are all amazing!
Day 2 - Harriet Tubman Museum, Lighthouse and Cape May Winery
Start your day with a tour of the Harriet Tubman Museum, and learn about the history of the Underground Railroad in Cape May. Then, take a quick drive to the Cape May Lighthouse to climb the stairs of the lighthouse or explore the grounds. Afterwards, try a wine flight and grab a snack at Cape May Winery. If you like white wine, I recommend the Vintage Sauvignon Blanc from 2021. After the winery, go back to your hotel to rest. End your evening at the Lucky Bones Backwater Grille and enjoy a delicious plate of pasta with mussels.
If you live in northern New Jersey or New York, you may stay a second night in Cape May to hear some live music at the Boiler Room in Congress Hall. Before you head home, be sure to have a satisfying brunch at the Blue Pig Tavern.
Read more about Cape May’s local spots here.
7 Days in San Francisco: Vacation Itinerary
Day 1 - Golden Gate Park
Golden Gate Park is a beautiful, expansive park with many family-friendly activities to choose from. My childhood favorite spot has always been The Japanese Tea Garden. You can walk through the gorgeous gardens or enjoy tea and treats at the tea house. The Academy of Sciences is a fun and educational museum that features an aquarium, planetarium, and numerous science related exhibits. On a nice day, go boating at Stow Lake. It’s easy to spend an entire day at Golden Gate Park!
Day 2 - Golden Gate Bridge and Sausalito
One of the best ways to view Golden Gate Bridge is to drive over it to Marin County. During the summer months, the bridge is covered in fog and only viewable from up close. Stop in Sausalito for views of San Francisco, and have lunch at Sweet Ginger or Saylor’s Restaurant and Bar. If you want to venture more into Marin County, hike through the redwood forest at Muir Woods.
Day 3 - Pier 39 and Fisherman's Wharf
Pier 39 has numerous attractions and restaurants. If you appreciate sea life, visit the aquarium or view the seals sunbathing on the pier. Enjoy clam chowder in a sourdough bread bowl at Boudin Bakery. Next, walk to Fisherman’s Wharf for some souvenir shopping and fresh seafood. Ghiradelli Square is a short walk from Fisherman’s Wharf, and worth a stop for hot chocolate and other chocolate treats.
Day 4 - Lombard Street and Trolley Ride
Known as the “most crooked street in the world,” drive down Lombard Street. From there, take a ride on an iconic trolley. The closest trolley to Lombard Street is the Powell/Hyde cable car, and pre-sale trolley tickets and maps are available online.
Day 5 - Twin Peaks and the Painted Ladies
For beautiful views of San Francisco, drive through the windy roads of Twin Peaks. Then, head to Alamo Square to see the famous painted ladies that were featured in “Full House.” Walk to the Tanner home, and take a picture in front of the home that was featured in “Full House.” For dinner, check out the amazing Chinese food and dumplings at Dumpling Home.
Find San Francisco’s most Instagram worthy spots here.
Day 6 - Day Trip to Napa County
Napa is over an hour drive from San Francisco. If you plan to drink wine, be responsible and hire a designated driver or book a tour. There are numerous wineries to choose from: Domaine Carneros is known for its champagne selection and Truchard Vineyards features vineyard tours and wine tastings. There are also several underrated wineries in Sonoma County that are great to visit.
To sample local cuisine prepared by training chefs, visit the Culinary Institute of America. The food is incredible, and the pricing can fit any travel budget!
Day 7 - Mount Shasta
Although Mount Shasta is a four-hour drive from San Francisco, it’s worthwhile to extend your vacation to visit. Set in the mountains in northern California, it’s a beautiful place to visit at any time of year. The spring and summer months are the best time to enjoy hiking and swimming in the local lakes and rivers. Since it’s a distance from San Francisco, you should stay in Mount Shasta for at least one night. An excellent and unique option for accommodation is Guru Shasta. Since space is limited at Guru Shasta, another budget friendly option is Airbnb.
3 Days in Portland: Vacation Itinerary
Day 1 - Portland Head Light, Dinner and Brewery
Before you drive into downtown Portland, Maine, make a stop at the Portland Head Light. It’s Maine’s oldest lighthouse, with a beautiful view of Portland Harbor. Portland can be cold for much of the year, so dress for the weather. The area surrounding the lighthouse, Fort Williams, is perfect for a stroll. Afterwards, drive to your hotel in Portland, Maine, and check in. A great hotel option is Courtyard Portland Downtown/Waterfront, because of its central location and proximity to many restaurants. For dinner, check out Street and Co. for excellent local fish and seafood. Then, walk to Liquid Riot Bottling Company to sample some locally brewed beers.
Day 2 - Brunch, Victoria Museum, and Spring Point Ledge Lighthouse
For brunch, head to Artemisia Cafe for a delicious locally sourced meal. Then, walk to Victoria Mansion to explore an impressive 19th century Italian villa style home. Victoria Mansion is closed in the winter months, and opens in May. It is strongly encouraged to purchase tickets online. After your mansion tour, drive to the Spring Point Ledge Lighthouse. If it’s not too cold or wet outside, walk along the rock path all the way to the lighthouse. Make sure to explore the Southern Maine Community College campus grounds next door before you leave! For dinner, try Scales for a fabulous upscale seafood meal.
Day 3 - Breakfast, Deering Oaks Park, and Dumpling Lunch
Portland is known as a foodie destination with beautiful outdoor spaces, so enjoy local cuisine and a scenic park on your last day! Start the day with Chicken and Waffles at Hot Suppa, an excellent Southern restaurant. If the weather permits, take a long stroll through Deering Oaks Park. Then, try an assortment of dumplings at Bao Bao Dumpling House.
If you have time to linger in Portland a bit longer, check out more things to do in this great city!
3 Days in Washington, DC: Vacation Itinerary
Day 1- National Mall and Mexican Dinner
Spend your day walking through the national mall, and view all of the historic monuments. Don’t miss the Washington Monument, Lincoln Memorial, and the numerous war memorials along the way. If you have time and energy, walk to the Supreme Court and Capitol buildings. Take a picture in front of the White House as well. In spring, definitely check out the beautiful cherry blossoms along the Tidal Basin!
For a more detailed walking tour itinerary, click here.
After your long walk, head back to your hotel and freshen up. Finish your day with a Mexican dinner at Oyamel. Be sure to try the ceviche and tacos!
Day 2 - Mount Vernon and the Yards
Take a 30 minute drive south from Washington DC to Mount Vernon, the historic home of George Washington. Tour tickets for the home and gardens are sold online. After spending a couple of hours at Mount Vernon, drive back to Washington DC and check out The Yards. This neighborhood is located on the Anacostia River, between Nationals Park and the Washington Navy Yard. The Yards offers great restaurants, breweries, and shops with riverfront views. If you enjoy Caribbean cuisine, definitely have dinner at Bammy’s. The food is delicious, the music is great, and you can’t beat the view!
Day 3 - Museums and Tapas Dinner
One of the wonderful things about Washington DC is that most museums are free. So, visit the National Gallery of Art and The Holocaust Memorial Museum in one day at no cost. Before you leave Washington DC, be sure to sample some sangria and Spanish tapas at Jaleo, by Jose Andres.