Do you love visiting San Diego? Really love it? Then enter to win our sweepstakes and you could win a 5 night stay at the Hilton San Diego Bayfront Hotel and airfare for two! And as the big winner, you’ll have five whole days to enjoy all that San Diego has to offer. Never been to San Diego or interested in trying something new? Here’s how I would spend my five days highlighting the outdoors and our amazing beaches.

Waking up each morning at the Hilton San Diego Bayfront Hotel will provide inspiration as you plan your day. The hotel, located on the waterfront, features sun and sea inspired design and a casually sophisticated design.

Torrey Pines State Reserve

Day 1: Explore trails while overlooking the ocean
Hike Torrey Pines State Reserve or take a guided tour. Among the eight miles of trails, guests can encounter native chaparral plants, wildflowers, birds, reptiles and butterflies. My favorite trail is the beach trail. During low tide, you can take the stairs down to the ocean and walk between the ocean and cliffs.

Sail on the Bay

Day 2: Set sail on the San Diego Bay
Strap on your sea legs and rent a sailboat in Coronado from Seaforth Rentals. Choose from over 200 rental boats, including boats for sailing, cruising, skiing and fishing, jetskis, speedboats, fishing charters, sunset sails.

Mission Beach

Day 3: Cruise the boardwalk in Pacific and Mission Beach
The favorite hangouts of active young sun-worshipers, Pacific Beach and Mission Beach are connected by a three-mile boardwalk crowded with inline skaters, skateboarders, runners and bikers – and beachgoers just wanting “to be seen.” End your stroll by walking to the end of the Crystal Pier for a beautiful coastline view.

Sunset Kayak Cruise

Day 4: Take a sunset kayaking trip and witness the sun dip into the Pacific
Try Hike Bike Kayak’s popular Sunset Paddle Tour, where you’ll kayak along the La Jolla sea caves and ecological reserve during a beautiful sunset on the Pacific Ocean. Expert naturalist guides provide insights and fun facts about the amazing environment.

Ocean Beach

Day 5: Hang out in Ocean Beach – doggies included!
Ocean Beach is one of San Diego’s prime surf spots. The neighborhood is also popular for its kid-friendly tide pools, long wooden pier that is perfect for fishing and Dog Beach, where even the tail-wagging members of the family can play Frisbee and romp in the surf.

Enter to Win a 5-night hotel stay and two round trip airfare tickets here!

27 Responses to Escape To San Diego Sweepstakes: Perfect 5 Day Itinerary

  1. Love San Diego, Used to live there wish I still did. A visit would be amazing.

  2. Pingback: Escape to San Diego Sweepstakes: Perfect 5 Day Itinerary Part 2 | San Diego Travel Blog

  3. As my husband and I get older, we realize that there are so many wonderful cities in this country that we have never been to. We would so love to win a trip to San Diego! It would be a dream-come-true!

  4. If I won this trip, IT WOULD MEAN THE WORLD TO ME. I have a 14 year old daughter who up until six months ago, was a competitive dancer, entering her first year of highschool. As many of us know these are the most important years in a teenagers life, and it pains me to say that due to a series of events she is no longer able to dance and is currently being home instructed. This trip would provide me with an opportunity to take her away for some much needed fun in the sun and relaxation. I could sure use the time with her, to bond and strengthen our very close mother, daughter relationship. I hope you will consider us for this once in a lifetime opportunity. As the mother of four children it would be very expensive to take them all away. Thanks for listening.

  5. I visit the San Jose/Monterey area of California several years ago and would love to go back and see more. Many beautiful areas to see and lots to do. Hard to decide!

  6. I met & married my husband in San Diego. My mom is there (in a nursing home) & my sister just married her fiance on Sunset Cliffs. She lives in Ocean Beach. I live in Ohio now & miss the ocean!

  7. Sharon Ashman-Besse

    I grew up in San Diego, from the time my Dad (who was in the Navy)got tranferred there (I was in the 2nd grade)till high school grad. Then I lived there off and on till 99 when we moved to CO. I will be in San Diego for my parents 50th ann. I love San Diego !!!!!!!

  8. We love San Diego. That last time we went we rented a condo at Sail Bay. It was nice, but I’d really love to try The Hilton.

  9. I would love to win this trip to San Diego! me and my family(husband and three sons) are planning to visit California in november! and we will come to San Diego, what do you suggest us to do then?

  10. I would love to go there.

  11. I live in san diego and love it…wish my husband and I could go on more vacations and spend more time together. we are so busy with our 2 children and him working 6 days a week. I would love to go out an explore san diego more and take a much needed vacation.

  12. I love San Diego. It is the perfect escape

  13. I luv san diego !!

  14. Michelle Kuwazaki

    Aaaahhhhh, San Diego

  15. I live to vacation in San Diego. My legs were burned a month ago and I am worried that I won’t be able to go. What could be worse than not being able to vacation in San Diego?

  16. Miss San Diego so much. Lived there from 1996 to 2001. Those were the best 5 yrs of my life. Wish I could move back. Miss all our good friends. Would love to win so we could get back to spend 5 days with everyone and see the area we love and miss so much. Wish I could see the Padres play..

  17. I’d really enjoy being out on the water in a kayak or charter fishing. Bet there are some great places to eat too.

  18. Born there in 1953, moved away in 1973. I’m in Singapore now and I’d love to come home for a visit. I want to visit Balboa Park, Mt Helix, The Punch Bowl and eat Mexican food =). Bring me home!!

  19. Whoever wins will have a great time!

  20. I vacationed with my 3 children in San Diego last summer. It is such a friendly, fun-loving city! Love all of the outdoor activities to participate in, great weather, fantastic people! Restaurants are great, just too many wonderful things to say! You would make 3 east coast kids HAPPY, HAPPY if we won!!

  21. When in San Diego we have never felt so protected and appreciated. We love the Boardwalk at Mission Beach cant be beat. We love Sea Port Villiage so many shops and Cabillo natonal monument the cemitary for our fallen heros is where everyone needs to vist at least once. We hope we win just to go back and be a part of that would be great.

  22. This would be absolutely AWESOME to win!! My son is stationed out there with the US Navy on an aircraft carrier. He is deployed right now, but will be returning soon after 7 long mos. at sea. I would LOVE to be able to go out there and visit him when the ship gets back!! Did I mention how I LOVE San Diego? One of the best cities in the Western part of the Nation! It’s a beautiful place..been there only once before. Would love to go back.

  23. Used to live near San Diego. Would love to win this trip.

  24. i left San Diego in December of 1988.., i have seen on-line and in pictures just how much the city has grown and just how beautiful it has become…,

    …, i was born on Camp Pendleton in August of 1961 My Father was a career Marine.., when i was 9 we moved to New England ( that is where My Father was from Vermont )before his last tour to Vietnam.., Upon my graduation from high school i left Vermont to join the U.S. Navy were i then returned to San Diego until getting out and returning to Vermont in 1988..!!!

    …, There is alot to see and do in the San Diego Area.., on of my first things would be to go to Balboa Park and the San Diego Zoo.., and at night either catch a ball game at Petco Park.., or watch an outdoor play at the Balboa Park Theatre.., i would also drive up the coast and visit my birth place and then maybe spend some time in the El Cajon Valley…, no matter what i do.., i am sure that 5 days will not be enough for what i want to do..!!!!

    .., So in closing.., if i do win this contest and get to Visit the Most Beautiful City in the World.., i will make the best of every second..!!!!!

  25. I want to win a trip for me and my family

  26. I would love to go to San Diego…heaven on earth! : )

  27. I would love to win this trip to San Diego, I miss that city, the ocean everything about it!!

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