Bike the Bay: Our Favorite Waterfront Ride from Shelter Island to Downtown
September on Shelter Island still feels a lot like summer, with sunny days, bay breezes and plenty of reasons to get outside. One of our favorites? Exploring the waterfront by bike At Humphreys Half Moon Inn, your adventure can start right outside your room and follow the bay from Shelter Island toward Downtown San Diego.
And the best part? Your Half Moon Pass includes one hour of bike rentals each day, so your ride can start right here at Humphreys. We mapped out one of our favorite ways to follow the bay, with scenic stops along the way and options for turning your ride into a longer afternoon adventure.
Start at Humphreys
Your ride begins at Humphreys Half Moon Inn, located on Shelter Island along San Diego Bay. Pick up a bike at the hotel and start by exploring Shelter Island itself before heading toward Downtown.
The first hour of bike rental is included with the hotel's Half Moon Pass, giving guests an easy way to explore without arranging transportation or renting a bike elsewhere. Additional rental hours are available for a fee if you decide you want to keep going.
1. Shelter Island Loop - Distance: Approximately 2.2 miles, depending on your route
Before heading toward Downtown, start with the popular Shelter Island Loop. Head out of Humphreys along Shelter Island Drive and follow the waterfront past marinas, restaurants,parks, and scenic overlooks, towards the Yokohama Friendship Bell at the end of the island.
The bell marks San Diego’s sister-city relationship with Yokohama, Japan, and gives you a scenic first destination before turning back toward North Harbor Drive and continuing along the bay. Take your time along this route to stop and admire the boats in the marina, take a few photos, or simply enjoy the breeze before continuing toward the rest of the bayfront.
Only have an hour? Keep it island-side. The loop makes an easy outing on its own, with plenty of waterfront scenery without committing to the longer ride Downtown.
2. Spanish Landing Park - Distance: Approximately 2 miles from Humphreys
Continue along North Harbor Drive toward Spanish Landing Park, one of the best places to pause along this route.
Spanish Landing is a waterfront park with grassy areas, picnic tables, benches, public art, restrooms, and marina views.
Grab a seat overlooking the water, have a snack, or simply take a few minutes to enjoy the scenery. The park also offers a sandy beach and views across the marina.
From here, the route continues along North Harbor Drive toward the Embarcadero.
3. Optional Detour: Liberty Station - Distance: Approximately 2 miles from Humphreys
As you leave Shelter Island and head toward North Harbor Drive, Liberty Station is a short detour from the waterfront route. The former Naval Training Center is now home to restaurants, shops, galleries, public spaces, and events.
Insider Tip: Take the short detour into Liberty Station for coffee, a bite to eat or a little browsing before getting back on the waterfront route.
4. San Diego Maritime Museum - Distance: Approximately 4.3 miles from Humphreys
As you approach Downtown, some of San Diego’s most recognizable waterfront sights come into view.
The San Diego Maritime Museum and historic ships are among the highlights, including the Star of India, one of the most recognizable ships along the San Diego waterfront.
Here you can lock up your bike and spend some time exploring the museum, or simply stop along the waterfront for photographs before continuing south.
The Embarcadero is also a great place to watch boats moving through the bay and enjoy views toward Coronado.
5. Portside Pier - Distance: Approximately 4.4 miles from Humphreys
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Ready for lunch? Make Portside Pier your next stop!
This waterfront dining destination offers several restaurants plus a public viewing deck overlooking San Diego Bay. Try popular spots like Brigantine Seafood & Oyster Bar or Portside Coffee & Gelato, among others.
With outdoor patios and panoramic views, Portside Pier is an especially good place to turn a bike ride into a leisurely afternoon.
6. USS Midway Museum - Distance: Approximately 4.9 miles from Humphreys
A short ride farther south brings you to the USS Midway Museum, located aboard the historic aircraft carrier USS Midway.
Even if you don't have time for a full museum visit, the ship is an unmistakable part of the San Diego waterfront and makes a great photo stop. If you have several hours available, consider touring the carrier before continuing to Seaport Village. If you're keeping the ride casual, simply stop to admire the ship and enjoy the views around the Embarcadero before you head back to Shelter Island.
Making the Ride Back
Remember that this is an out-and-back adventure unless you arrange another way to return to the hotel. Once your Google Maps route is finalized, use it to confirm the total mileage and expected ride time before heading back to Humphreys Half Moon Inn.
For riders who want a longer adventure, the Port of San Diego's waterfront bike infrastructure connects to portions of the larger Bayshore Bikeway network around San Diego Bay.
Tips For Your Ride
Start in the morning for cooler temperatures, or head out later in the afternoon and time your return for sunset. Before setting out, check your route, allow extra time for sightseeing or detours and confirm your bike rental return time with the hotel.
And when you make it back to Shelter Island, you won't have to go far to continue the waterfront experience. Relax by the hotel's heated outdoor pool, grab a drink and a bite at Oasis Pool Bar & Bites, or settle in for dinner at Humphreys SoCal Dining & Music, overlooking the marina.
Bike the Bay from Humphreys
A waterfront bike ride is an easy way to experience several sides of San Diego in a single outing, and Humphreys Half Moon Inn gives you a convenient place to begin and end the adventure.
Ready to ride the bay? Book your stay at Humphreys Half Moon Inn and enjoy a waterfront San Diego getaway with bike rentals included with your Half Moon Pass.
