Cabrillo Bike Path lined with palm trees Santa Barbara, CA

Here Is the Ultimate Santa Barbara 5-Day Itinerary

Are you considering planning your next great getaway? If you desire to stay somewhere picture-perfect and luxurious, that’s surrounded by a thriving, gorgeous city, then stay at Cheshire Cat Inn in Santa Barbara, California. To learn how to make the most out of your vacation, keep reading our Santa Barbara 5-day itinerary.

For even more information regarding restaurants, events, and more to enjoy during your trip to Santa Barbara, please take a look at our free Vacation Guide.

Santa Barbara 5-Day Itinerary

Take a look at these amazing Santa Barbara vacation ideas!

Day 1: Discover Downtown Santa Barbara

Throughout Santa Barbara, there are a few different neighborhoods, each with their distinct qualities making them special. One of the best parts of staying at Cheshire Cat Inn is that it’s within walking distance to downtown and is close to other surrounding communities, such as:

  • Funk Zone
    • This contemporary art district is home to eclectic shops, galleries, cafes, and the Urban Wine Trail. Stearn’s Wharf and East Beach border it, so it also yields unbelievable scenery and views.
  • State Street
    • The State Street thoroughfare is lined with towering palm trees and is home to many one-of-a-kind shopping spots. A fun activity to do here is perusing through the local produce at the Farmer’s Market.

Day 2: Explore the Great Outdoors

With its mild temperatures and breathtaking views of the Santa Ynez mountains and sparkling ocean, Santa Barbara is a picture-perfect place to spend the day outside exploring nature. Some of our favorite outdoor activities include:

  • Santa Barbara Botanical Garden
    • This 78-acre living museum features over 1000 plant species and incredible views of the West Coast. Some standout attractions at this botanical garden include an authentic Japanese teahouse garden, an enormous sandstone boulder named Blaksley Boulder, and canyon slopes.
  • Stearn’s Wharf
    • The pier at Stearn’s Wharf is our city’s most visited attraction. There are all sorts of fun-filled things to do here, including boat tours of the harbor, shopping at unique boutiques, pier fishing, and waterfront dining.
  • Channel Islands
    • Just off the mainland of Southern California, you’ll find the tropical oasis known as the Channel Islands. With the islands being so isolated, they contain rare animals, plants, and archaeological resources you won’t find anywhere else on Earth. Some of the islands are so incredibly remote that they require a permit to visit, such as San Miguel Island.

Day 3: Sip Your Way Through Santa Barbara

Did you know that the American Riviera is home to more than 200 wineries? When trying to decide which ones to visit, it can be very overwhelming. A fantastic way to narrow it down is by taking a self-guided tour along the Santa Barbara Urban Wine Trail. This trail includes 28 wineries and tasting rooms across downtown Santa Barbara. Explore the trail and enjoy wine tastings at:

  • Santa Barbara Winery
    • This is one of the city’s oldest and most coveted wineries. Be sure to try some of their award-winning wines, such as their Chardonnay and Pinot Noir.
  • Whitcraft Winery
    • Aside from the delicious wine found here, you can also meet the winery dog, Terra! A taste of wine and a greeting from this friendly pup are sure to put a smile on your face.
  • Carr Vineyards and Winery
    • The location of this gorgeous winery dates back to the 1940s. When you visit here, you can enjoy the ambiance inside at the barrel top bar or embrace the fresh air outside on their charming patio.

If wine isn’t your forte, don’t fear! There is also an array of local breweries and taprooms for you to visit. Some popular ones include:

  • Figueroa Mountain Brewing Company
    • Stop by this taproom and sit down and enjoy a handcrafted beer, or take beer to go with you and fill up a growler. One of their tasty specialty brews is the Hi-Biscuits and Honey wheat ale with hints of hibiscus flowers.
  • Night Lizard Brewing Company
    • This brewery has a noble mission: Produce the highest quality craft beers using the freshest local ingredients, while inspiring and educating the public on current environmental challenges facing the central coast. They also feature a hard seltzer for those that prefer that sort of beverage.

Day 4: Embrace History and Art

Originally settled and built by Spanish, Mexican, and North American pioneers, Santa Barbara maintains much of its original Spanish influence to this day and is famous for its rich history and culture. During your Santa Barbara getaway, be sure to check out some of these historic and beautiful landmarks:

  • Santa Barbara County Courthouse
    • This magnificent courthouse features an iconic clock tower, handpainted murals, and breathtaking sunken gardens. This impressive property occupies an entire city block! Stop by a take a tour of the grounds.
  • Santa Barbara Museum of Art
    • Visit this museum and celebrate 5000 years of human creativity. The renowned collection at the Santa Barbara Museum of Art classic antique and modern installations from France, Europe, Latin Ameria, Asia, the United States, and more.
  • Old Santa Barbara Mission
    • Nicknamed “Queen of Missions,” this breathtaking church has been enchanting visitors for centuries. The grounds overlook the Pacific Ocean and feature a historic cemetery, a nine-room museum with stunning sculptures and ancient artifacts, and many flowering gardens.

Day 5: Hit the Beach

Throughout Santa Barbara, you’ll find miles and miles of pristine shoreline. Whether you prefer to spend the day surfing, swimming, or laying in the sunshine, there is an extensive list of beaches to choose from where you can spend amazing days in Santa Barbara. Our picks for some of the best beaches in Santa Barbara include:

  • Leadbetter Beach
    • This popular beach is a favorite of kitesurfers and windsurfers. Its amenities include grills, picnic tables, showers, and restrooms.
  • Shoreline Park
    • This long, narrow shoreline features a playground, picnic area, Japanese garden, and whale watching telescope. If you’re lucky, you might catch a glimpse of Gray Whales, dolphins, or seals!
  • Butterfly Beach
    • Montecito, CA, home of Butterfly Beach, is just a short 10-minute drive Cheshire Cat Inn. This is the ultimate spot to participate in kayaking and paddleboarding, or relaxing in the sand gazing at the sunset.

Make Cheshire Cat Inn Your Home Away From Home

Eberle RoomCheshire Cat Inn is a beautiful Alice in Wonderland themed bed and breakfast that’s perfect for any getaway. Our inn grants travelers from all over the world an opportunity to enjoy beautifully-appointed accommodations with fantastic amenities.

After spending the day trying out some of the things on our Santa Barbara 5-day itinerary, retreat to your private cottage or cozy guest room at Cheshire Cat Inn. Unwind from the day and enjoy delectable wine and cheese at our complimentary happy hour. In the morning, power up with a homemade delicious European breakfast and then embark on an adventure. What else could you want? Check our availability and start planning your dream vacation today!


  Check Availability


Our Blog

Local Weather



Santa Barbara


Cheshire Cat Inn & Cottages

36 West Valerio Street
Santa Barbara, California
93101 United States
contact us
  +1 805 569-1610  +1-805-569-1610