
Annapolis Chesapeake Bay Bridge Cruise
Traveler rating
5.0/5
Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Annapolis Chesapeake Bay Bridge Cruise worth booking?
Annapolis Chesapeake Bay Bridge Cruise is a 1.5-hour experience in Annapolis, United States, from $46 per person. It scores 59 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 5/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 59 / 100
- Rating
- 5/5 (5)
- Duration
- 1.5 hours
- From
- $46 per person
Step aboard a classic vessel for a scenic Chesapeake Bay Bridge cruise. As you depart the dock in downtown Annapolis, you will pass along the seawall of the United States Naval Academy and out into open water. As you approach the Bay Bridge, keep an eye out for local wildlife, including osprey, eagles, rays, and even the occasional dolphin, while enjoying great outdoors sightseeing. Then, marvel at the twin spans of the bridge, one of the largest over-water structures in the world. Sit back and relax with a soft drink, beer, or wine available for purchase, and enjoy the sights on this 90-minute journey.
What you get
About this experience
Step aboard a classic vessel for a scenic Chesapeake Bay Bridge cruise. As you depart the dock in downtown Annapolis, you will pass along the seawall of the United States Naval Academy and out into open water. As you approach the Bay Bridge, keep an eye out for local wildlife, including osprey, eagles, rays, and even the occasional dolphin, while enjoying great outdoors sightseeing. Then, marvel at the twin spans of the bridge, one of the largest over-water structures in the world. Sit back and relax with a soft drink, beer, or wine available for purchase, and enjoy the sights on this 90-minute journey.
What's included
Included
- In-vehicle air conditioning
- On-board restrooms
Not included
- Snacks
- Gratuities
What you'll see and do
U.S. Naval Academy
Begin the excursion right after departing the dock by cruising along the seawall of the U.S. Naval Academy, home to more than one thousand midshipmen. Enjoy water-level views of this historic institution as the vessel heads out toward the open water.
Pass by without stopping
Chesapeake Bay Bridge
Continue the journey by cruising under the twin spans of the Chesapeake Bay Bridge, connecting Maryland's Eastern and Western shores. Admire this 4.3-mile span, which stands as one of the longest over-water structures in the world.
Pass by without stopping
Chesapeake Bay
Navigate along the magnificent Chesapeake Bay, the largest estuary in the United States. Discover an environment home to numerous fish, waterfowl, and other creatures, keeping a sharp eye out for osprey, bald eagles, cow-nosed rays, and more.
Pass by without stopping
Annapolis
Conclude the experience by taking in the surrounding views of Annapolis, known as America's Sailing Capital, situated at the mouth of the Severn River where it meets the Chesapeake Bay. Appreciate the epicenter of Maryland's maritime culture, offering sights of historic waterfronts and the surrounding region during this 1-hour-and-30-minute excursion.
Pass by without stopping
Where it starts and ends
Meeting point
Annapolis
The dock is located at the end of Prince George Street in downtown Annapolis. Please check in at the ticket stand with the red umbrella, situated at the intersection of Prince George Street and Craig Street.
Hotel pickup
No pickup: everyone meets at the start point.
Ends at
The dock is located at the end of Prince George Street in downtown Annapolis. Please check in at the ticket stand with the red umbrella, situated at the intersection of Prince George Street and Craig Street.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Mon, Fri, Sat, Sun
- Group size
- Up to 15 travelers per booking
- Operated by
- Watermark Harbor Cruise
Know before you go
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- Suitable for all physical fitness levels
Photos





What travelers are saying
Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.
Knowledge and storytelling
4 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
1 mentionThe views and photo stops come up again and again.
Organization
1 mentionPickup, timing, and logistics are described as running smoothly.
Food and drink
1 mentionThe tastings and food stops are a highlight for most reviewers.
Good for families
1 mentionReviewers traveling with kids report it landed well with their group.
Traveler reviews
5 verified traveler reviews for Annapolis Chesapeake Bay Bridge Cruise. Ratings and reviews provided by Viator and Tripadvisor.
Good job
The tour was good and very informative.
Response from the operator: Thanks for booking Watermark's Chesapeake Bay Bridge Cruise. We're pleased to see that you enjoyed the experience, and we hope you'll join us again for another cruise in Annapolis or Baltimore, or perhaps one of our historic Annapolis walking tours.
via Tripadvisor
Relaxing girls trip
Informative and fun. Nice way to learn about the history of the area.
Response from the operator: Thanks for booking Watermark's Chesapeake Bay Bridge Cruise. We're pleased to hear that you enjoyed the cruise and the narration along the way.
via Tripadvisor
Breezy boat ride of annapolis
Informative boat ride with friendly staff and crew
Response from the operator: Thanks so much for joining Watermark's Chesapeake Bay Bridge Cruise. We're happy to hear that you enjoyed the cruise and that you found the content and crew up to snuff. We hope we'll see you again in the future.
via Tripadvisor
Glorious Day Trip on Bay
Glorious day on the day with active captain Alex and retired captain Scott. Captain Scott gave interesting and humorous tour descriptions during the fun 3-hour trip on Chesapeake Bay. He described the 3 different lighthouses, the 2 bay bridge spans, and long history of Naval Academy. Tony at full bar on main deck was very helpful including caring 2nd drink up to top deck so not to spill when 65' boat tilts sometimes. Great views and seating whether inside downstairs or under roof on top. Saw many sailboats of various sizes near academy.
via Tripadvisor
Beautiful day to sail to the Chesapeake Bay Bridges
We took. Our two granddaughters plus their auntie out for the boat ride. Gorgeous day, Clear but hot and windy. However the boat cabin is air conditioned so the trip was very enjoyable. Captain and crew were very friendly and professional. Kids explored the whole boat. Everything went seamlessly. We departed promptly per schedule and arrived back on time. Would recommend this trip to all families.
via Tripadvisor
Good to know
- Duration
- 1.5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Mon, Fri, Sat, Sun
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 2
- Verdict
- Worth a Look
Who runs this experience
Operated by Watermark Harbor Cruise, who run 19 experiences we rank across 2 cities, with an average Outty Ranking of 51.9.
See everything Watermark Harbor Cruise runsWhy this scores 59
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Annapolis Chesapeake Bay Bridge Cruise: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Annapolis.
How much does Annapolis Chesapeake Bay Bridge Cruise cost?
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Prices start at $46 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Annapolis usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Annapolis Chesapeake Bay Bridge Cruise take?
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Plan for about 1.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Annapolis is not rushed.
Is Annapolis Chesapeake Bay Bridge Cruise worth it?
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It holds an Outty Ranking of 59 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 5 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Annapolis, and how flexible the cancellation terms are.
Can I cancel or reschedule Annapolis Chesapeake Bay Bridge Cruise?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Annapolis Chesapeake Bay Bridge Cruise suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 1.5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Annapolis Chesapeake Bay Bridge Cruise?
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Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Annapolis can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Annapolis and add a light layer if any part of the 1.5-hour experience runs outdoors or after sunset.
Where does Annapolis Chesapeake Bay Bridge Cruise start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Annapolis within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Annapolis?
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Annapolis, MD packs its best experiences into walkable neighborhoods, local food, and day trips nearby. Outty ranks every bookable tour and activity in Annapolis by rating quality, review depth, booking demand and value, so you can see the standouts before you book. On Outty we rank every Annapolis experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Tipsy History Tour: 300+ Years of Annapolis Drinking History, Annapolis Historic Walking Tour: Harbor and Colonial Downtown, Historic Annapolis Food Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Annapolis?
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Spring and fall bring the best weather and lighter crowds in Annapolis, while summer has the widest choice of tours and evening activities. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Annapolis?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
What is included in Annapolis Chesapeake Bay Bridge Cruise?
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Included: In-vehicle air conditioning; and On-board restrooms. Not included: Snacks; and Gratuities. Always check the voucher for the final list before you travel.
Where is the meeting point for Annapolis Chesapeake Bay Bridge Cruise?
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The dock is located at the end of Prince George Street in downtown Annapolis. Please check in at the ticket stand with the red umbrella, situated at the intersection of Prince George Street and Craig Street. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.
What languages is Annapolis Chesapeake Bay Bridge Cruise offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Annapolis Chesapeake Bay Bridge Cruise?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Annapolis Chesapeake Bay Bridge Cruise wheelchair or stroller accessible?
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The operator notes: Wheelchair accessible; Infants and small children can ride in a pram or stroller; and Transportation options are wheelchair accessible. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Annapolis Chesapeake Bay Bridge Cruise if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
What do travelers say about Annapolis Chesapeake Bay Bridge Cruise?
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Across 5 reviews averaging 5.0 out of 5, recurring themes include knowledge and storytelling, photo opportunities, organization. Reviewers describe the commentary as informative rather than scripted.
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