Romantic Long Weekend in Oakland

Experience love in the urban charm of Oakland.

22 April 2023

A romantic trip to Oakland promises an eclectic mix of activities that cater to different tastes. With its vibrant arts scene, waterfront parks, and trendy restaurants, Oakland has a lot to offer to couples looking to spend some quality time together. Whether you prefer strolling through street art murals, perusing farmers markets, or taking a sunset cruise on the bay, you will find plenty of options to create lasting memories with your loved one.

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Travel plan

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Day 1

Arrival and Exploration

  • Check into the gorgeous boutique hotel, The Claremont Club & Spa
  • Grab a coffee from the trendy Blue Bottle Coffee in the historic W.C. Morse Building
  • Stroll around the bohemian Temescal Alley and peek into the local artisan shops
  • Head to Lake Merritt and take a romantic gondola ride
  • Enjoy a farm-to-table dinner at the Michelin-starred Commis Restaurant
Day 2

Wine, Cheese and Views

  • Drive up to the stunning Napa Valley for a day trip
  • Visit the award-winning Domaine Carneros winery and marvel at the vineyard views
  • Indulge in a wine and cheese pairing at the picturesque V. Sattui Winery
  • Take a leisurely stroll around the quaint town of Yountville
  • End the day watching the sunset from the Golden Gate Bridge
Day 3

Culture and History

  • Head to the Oakland Museum of California and explore the state's art, history and culture
  • Take a tour of the famous Jack London Square and learn about the area's rich history
  • Have lunch at the bustling Bakesale Betty's, known for their delicious fried chicken sandwich
  • Visit the historic Paramount Theatre and catch a show or tour the ornate building
  • Enjoy dinner at the trendy and intimate Shakewell Restaurant
Day 4

Street Art and Tacos

  • Take a graffiti and mural tour of the vibrant and colorful Downtown Oakland
  • Have lunch at the famous Tacos Sinaloa food truck and enjoy authentic Mexican street tacos
  • Visit the quirky and hipster-filled area of Rockridge and browse through the many unique shops
  • Catch a movie at the restored and gorgeously renovated Grand Lake Theatre
  • End the day with a sunset cocktail at the scenic rooftop bar at The Rooftop Restaurant and Bar
Day 5

Beaches and Farewell

  • Take a day trip to the beautiful Half Moon Bay beach and walk along the picturesque coastline
  • Have a seafood lunch at the renowned Sam's Chowder House with ocean views
  • Drive back to Oakland and stop by the iconic Fenton's Creamery for dessert
  • Relish the final dinner at the elegant and charming Lake Chalet Seafood Bar and Grill
  • End the trip with a romantic stroll around Lake Merritt and take in the stunning views.

Length of stay

1 day 2 days 3 days 4 days 5 days

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The best way to get to Oakland, United States by plane is to fly into the Oakland International Airport (OAK) which has direct flights from major cities in the USA and other countries.

Car

Driving to Oakland, United States is a great option if you live nearby. From San Francisco, take the 80 East freeway and cross the Bay Bridge. From Los Angeles, take the I-5 North and connect to the I-580 East.

Train

Unfortunately, there is no direct train service to Oakland, United States. However, you can take an Amtrak train to nearby Emeryville Station and then take a bus or taxi to Oakland.

Boat

Oakland, United States is a busy port city, and there are several cruise ships that dock at the Oakland Port. The best way to get there is by taking a cruise ship from other ports in the USA or other countries.

Bus

There are several bus companies that operate services to Oakland, United States. The best way to get there is by taking a Greyhound bus or a Megabus which has affordable services from major cities in the USA.

Destination

Oakland

Oakland is a city with a little bit of everything: amazing food, stunning views, and a surprising amount of professional basketball teams. Just don't mention their sports rival across the bay if you want to avoid a heated debate.

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Number of days

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Explore Oakland in 3 Days: Budget-Friendly Fun

Oakland, located in Northern California, offers plenty to see and do on a budget-friendly trip. Enjoy free events in the city such as the Oakland First Fridays street festival, explore its scenic parks and gardens, and indulge in delicious street food at local markets. Don't forget to visit Lake Merritt, the heart of Oakland, and catch a panoramic view of the skyline from the hilltops.

The Ultimate Weekend Guide to Oakland, US

A trip to Oakland, United States as a tourist is a perfect blend of natural beauty and urban delights. You can hike in the scenic Redwood Regional Park or explore the trendy art scene in downtown Oakland. A visit to the world-renowned Oakland Museum of California is a must-do for history buffs.

2 Day Tour of Oakland: An Artsy Adventure

A limited budget trip to Oakland in the United States can be an exciting adventure. Visitors can explore the colourful street art in the city, enjoy a picnic by the beautiful Lake Merritt, and discover the fascinating history of Jack London Square - all without breaking the bank. Additionally, affordable accommodation and dining options throughout the city make it possible to experience Oakland without stretching your budget.

Oakland Odyssey: A Vibrant Family Day Trip Journey

Embark on a family-friendly adventure in Oakland, United States, offering a perfect blend of culture, nature, and entertainment. Explore the stunning Redwood Regional Park and marvel at its towering trees, while enjoying picnics and hiking trails suitable for all ages. Engage in enriching experiences at the Oakland Museum of California, featuring diverse exhibits showcasing the state's history, art, and natural sciences. Conclude your trip with a visit to the Children's Fairyland, where little ones can immerse themselves in a magical realm of whimsical storytelling, rides, and interactive exhibits.