7 Day Monterey Itinerary: The Best of Monterey County Without Feeling Rushed

With so many sites and attractions in Monterey County, planning a week-long getaway might feel overwhelming so we mapped out the perfect 7-day Monterey itinerary. This week-long adventure is designed to help you experience the best of the coast without feeling rushed. If you’re boarding the new nonstop from Chicago to Monterey then this plan brings you the best of the week from the Saturday you arrive to the Saturday you head home!

Saturday: Arrival

Once you land, settling in and relaxing for a fun week ahead is top priority. Start by checking in to the Portola Hotel & Spa, then stretch your legs with a short walk to Old Fisherman's Wharf, only 3 minutes from our hotel.

Things to Do at Old Fisherman’s Wharf:

• Sample clam chowder
• Watch sea lions along the harbor
• Pop into small gift shops
• Grab a sweet treat (Many to choose from including candy, caramel corn, and ice cream)
• Catch the sunset along the harbor

Dinner is easy at our on-site restaurant Jacks Monterey. Check out the menu, then make your reservation here.

Sunday: Aquarium + Cannery Row

Start Sunday morning at the world-famous Monterey Bay Aquarium. It’s a short drive from the Portola Hotel & Spa, but you can also take the Monterey Rec Trail for a 30-minute stroll with stunning views of the harbor and Monterey Bay. The Aquarium is at the end of Cannery Row, so be sure to explore this historic street after your time at the Aquarium. After exploring the area, don’t forget to walk past the Aquarium towards Pacific Grove for gorgeous views of the rugged coastline.

Things to Do on Cannery Row:

• Souvenir shopping
• Wine Tasting at A Taste of Monterey
• Enjoy lunch at one of the many restaurants
• Escape Room at Oscar’s Playground

Enjoy dinner at back at the Portola Hotel & Spa at our on-site craft brewery. Peter B’s. Check out the menu here.

Monday: 17-Mile Drive + Carmel-by-the-Sea

Enjoy the day by first taking a scenic drive through 17-Mile Drive. There are 17 points of interest to stop and appreciate the unique beauty of Pebble Beach with lots of wildlife from seals and otters to deer. There is a small vehicle admission fee in order to experience the route. Check out Pebble Beach's website to learn more.

Some of the points of interest along 17-Mile Drive:

• The Lone Cypress – Famous 250-year-old tree standing on a rocky pedestal
• The Restless Sea – Beautiful fierce and choppy waves constantly hitting the coastline
• Bird Rock – Can see lots of wildlife including harbor seals, sea lions, and many sea birds

Continue on to Carmel-by-the-Sea to shopping, exploring, and the beach.

Spend the afternoon:

• Exploring hidden courtyards, cute boutiques, and art galleries
• Visit Carmel Mission Basilica
• Head to Carmel Beach for a stunning sunset

Return to Monterey for a relaxed evening of dessert and a nightcap at Jacks Monterey.

Tuesday: Historic Monterey

In the late afternoon and evening, Alvarado Street transforms into the weekly farmers markets. Expect local strawberries, flowers, handmade goods, live music, and international food vendors.

Earlier in the day, explore Monterey’s history:

• Walkthrough Memory Garden
• Tour Colton Hall
• Visit Cooper-Molera Adobe
• Visit Custom House
• Stop by Casa Serrano

If you have time, walk to the Wharf for an afternoon of sailing at Sail Monterey. It’s a relaxing adventure where you will get to the marine life and beautiful views of the water. Afterwards, keep dinner flexible and graze your way through the farmer’s market.

Wednesday: Big Sur Day Trip

Now that Highway 1 has reopened, you’ll need to set aside one day for Big Sur. Get ready for the most scenic views of the California coast. Pack and picnic and head to these stunning points.

• McWay Falls in Julia Pfeiffer Burns State Park
• Nepenthe for lunch or dinner
• A redwood hike in Pfeiffer Big Sur State Park
• Andrew Molera State Park
• Henry Miller Memorial Library
• Calla Lily Valley

Photo Courtesy of See Monterey

Thursday: Spa Morning + Pacific Grove

After a full day of adventure in Big Sur, it’s time to slow down this morning. Start with a treatment at Spa on the Plaza in the morning. They have some wonderful treatments and services for the perfect relaxed morning.  In the afternoon, explore the quaint little town of Pacific Grove. Here are a few fun activities to do in the area.

• Drive or walk down Ocean View Boulevard/Sunset Drive
• Have a picnic at Lovers Point
• Point Pinos Lighthouse
• Asilomar State Beach + Tide pooling (if the tide is low)
• Shopping in Downtown Pacific Grove
• Pacific Grove Golf Links

Enjoy dinner in Pacific Grove. Here are a few spots to check out:

• Rudolpho’s
• Spotted Duck
• il vecchio
• Passionfish
• Mezzaluna

Friday: On the Water + Carmel Valley

For your last full day in Monterey, enjoy your time out on the water. Book a morning whale watching tour that leaves from Old Fisherman’s Wharf or check out our Whale Watching Package. Depending on the season, you might see humpbacks, blue whales, orcas, or dolphins. You can also explore the water by renting kayaks or stand-up paddle boards from Adventures by the Sea.

Spend your final afternoon with an afternoon in Carmel Valley. Here are a few fun things to do in the area:

• Wine Tasting
  • Folktale Winery & Vineyards
  • Twisted Roots Winery
  • Scratch Wine Tasting Room
  • Georis Winery
• Refuge (Outdoor Spa)
• Earthbound Farm Stand
• Hike Through Garland Ranch Regional Park

Photo Courtesy of Refuge

Saturday: One Last Ocean Walk

Before you head out enjoy a hot breakfast at Jacks Monterey, and if you have time take one more stroll down the Monterey Rec Trail before going to the airport. A few hours later, you’ll be back in Chicago but hopefully already planning your trip back to Monterey!

Book Your Trip to California

Seven days gives you time to see the highlights of our destination. Monterey is only 45 minutes from Santa Cruz, 1.5 hours from San Jose, and 2 hours from San Francisco making it easy to see more of California when you’re here! To book your stay, visit our website, or call us at (888)-222-5851.