Last Updated: July 2017
We interrupted our New England summer travels when Michael needed to fly back to San Diego for a week to manage his physician practice. It turned out to be a welcome reset — and a reminder of how much there is to do in a city we know well. Downtown San Diego has transformed steadily over the years, and with Comic-Con and Pride Week both kicking off during our visit, the streets had an unusually electric energy. San Diego is the eighth largest city in the United States, its economy anchored by military and defense as much as tourism, and its enduring appeal built on miles of sandy coastline and one of the most reliably mild climates in the country.
US Grant Hotel
The US Grant Hotel anchors the heart of downtown at Broadway and Fourth Avenue. It was built in 1910 by Ulysses S. Grant Jr. in honor of his father, the 18th President, and for decades was the city’s premier address. After years of decline it was fully restored and reopened in 2006, reclaiming its status as one of downtown’s landmark buildings. The lobby is worth a stop even if you’re not staying.
Gaslamp Quarter
The Gaslamp Quarter runs roughly 16 blocks along Fifth Avenue between Broadway and the waterfront, immediately adjacent to the Convention Center and Petco Park. What was a derelict skid row in the 1970s is now one of the most active entertainment districts in Southern California — bars, restaurants, clubs, boutiques, and live music venues filling Victorian-era commercial buildings that somehow survived the decades of neglect. It’s at its most alive on weekend evenings, but even on a weekday afternoon the energy is hard to miss.
Homelessness in Downtown San Diego
Downtown San Diego has one of the largest homeless populations of any American city — approximately 8,700 people living in the streets, alleys, and parks, ranking fourth in the country at the time of our visit. It’s most visible in the blocks surrounding the Gaslamp and East Village. Walking downtown, the contrast between the revitalized entertainment district and the acute human suffering on its margins is impossible to ignore.
This man had passed away on the sidewalk next to a Starbucks on a busy weekday. It stopped us in our tracks — a stark reminder that behind the tourism and prosperity, the city has a long way to go in addressing the crisis on its streets.
Downtown San Diego Attractions
USS Midway Museum
Plan at least two hours for the USS Midway Museum on the Embarcadero — more if you’re a history buff. The aircraft carrier served from 1945 to 1992, the longest-serving carrier of the 20th century, and her flight deck is packed with restored aircraft spanning the jet age. The self-guided audio tour is excellent, and the restored spaces below decks give a visceral sense of what life was like for the 4,500 sailors who called her home.
Star of India
Moored just north of the Midway at the Maritime Museum of San Diego, the Star of India is one of the world’s oldest active sailing vessels. Built in 1863 on the Isle of Man, she’s a full-rigged iron-hulled windjammer that made 21 voyages to India and Alaska before being retired. Still seaworthy, she sails once or twice a year. Both ship and museum are worth a visit if you’re already on the waterfront.
San Diego Pride Week
San Diego Pride traces its roots to 1974, organized as a sponsored program of The Center for Social Services to commemorate the 1969 Stonewall Rebellion in New York. The parade and festival have grown substantially since — today drawing hundreds of thousands over the weekend, with events spilling across Hillcrest and downtown. The festivities were just getting started during our visit, with street decorations going up and an unmistakable buzz in the air.
Comic-Con
San Diego Comic-Con launched in 1970 at the US Grant Hotel with a few hundred attendees. It now draws over 130,000 to the downtown Convention Center each July, overflowing into every nearby hotel and street. The official event requires tickets that sell out months in advance, but even the street scene around the Convention Center is worth experiencing — costumed fans appear days before the doors open, and the energy of 130,000 enthusiasts converging on a few city blocks is something to witness. Some Star Wars fans were already in costume early in the week.
Walking Downtown
Downtown San Diego is compact and genuinely walkable — the waterfront, Gaslamp, Little Italy, and the Embarcadero all connect on foot without much effort. The public art, street life, and architecture make for an easy afternoon on foot.
La Playa, Point Loma
La Playa sits tucked along the eastern shore of the Point Loma peninsula, facing San Diego Bay rather than the open ocean. Historically it served as the primary anchorage for early San Diego — goods were offloaded here and transported overland to the settlement, while sailors camped on the beach and hunted for wood and game in the Point Loma hills above. Today it’s a quiet, sheltered neighborhood with a beautiful walking path along the water.
We met up with our good friend Teresa and her dogs for a long walk along the water — a perfect low-key afternoon. She also generously lent us her car to visit Michael’s father in Escondido.
We ended the afternoon with Shirley and Jim — best friends who have a standing ritual of wine and conversation every afternoon at the water. A good reminder of what a great city San Diego is to come home to.
Visitor Information
USS Midway Museum is at 910 N. Harbor Drive on the Embarcadero; allow 2–3 hours minimum. Maritime Museum of San Diego (Star of India) is at 1492 N. Harbor Drive. The Gaslamp Quarter runs along Fifth Avenue from Broadway to L Street, 16 walkable blocks. San Diego Comic-Con typically runs in late July; tickets sell out early but the surrounding street scene is free. San Diego Pride is held annually in mid-July in Hillcrest and downtown. La Playa is accessible via Rosecrans Street in Point Loma — look for the small waterfront path running north from Shelter Island Drive.
Practical Tips
Downtown San Diego is easily walkable between the Embarcadero, Gaslamp, and Little Italy — a comfortable 2–3 mile loop covers the main sights. The trolley system connects downtown to Old Town, Mission Valley, and the border. Parking downtown is expensive; the Park & Ride lots near the trolley stations are a much better option. The USS Midway and Star of India can be combined in a single waterfront afternoon. If you’re visiting during Comic-Con week, book accommodation months in advance — hotels sell out completely and prices triple.
