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.