
Day on the Bay Cruise from Annapolis to St Michaels
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
4.3/5
Based on 3 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Day on the Bay Cruise from Annapolis to St Michaels worth booking?
Day on the Bay Cruise from Annapolis to St Michaels is a 8-hour experience in Annapolis, United States, from $157 per person. It scores 54 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 4.3/5 rating across 3 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 54 / 100
- Rating
- 4.3/5 (3)
- Duration
- 8 hours
- From
- $157 per person
Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complim
What you get
About this experience
Set sail across the scenic Chesapeake Bay to the charming village of St. Michaels, where travelers can immerse themselves in local culture, fresh seafood dining, boutique shops, and historic sites. Guests enjoy a complimentary non-alcoholic beverage during the cruise before spending around three hours ashore exploring the town before the return journey to Annapolis. Admission to the Chesapeake Bay Maritime Museum is included, making this sightseeing day trip an ideal way to experience Maryland's rich maritime history.
What's included
Included
- Carbonated beverages
- Admission to the Chesapeake Maritime Museum
- In-vehicle air conditioning
- On-board restrooms
Not included
- Snacks
- Gratuities
What you'll see and do
Annapolis
The journey begins on the water as the vessel departs from Annapolis, known as America's Sailing Capital at the mouth of the Severn River. Passengers pass by the historic waterfront and city harbor without stopping on land, enjoying initial views of Maryland's vibrant maritime culture and the iconic backdrop of the city as the cruise kicks off.
Pass by without stopping
Chesapeake Bay
Relax during the scenic crossing of the Chesapeake Bay, the largest estuary in the United States. Passengers remain on board the vessel throughout the transit, taking in expansive views of the open water and surrounding natural scenery. Guests can sip on an included non-alcoholic beverage while watching for native wildlife along the way, such as osprey, bald eagles, and cownose rays.
Pass by without stopping
St. Michaels
Spend approximately 3 hours and 20 minutes exploring the historic Eastern Shore village of St. Michaels. Travelers step ashore to discover well-preserved 19th-century architecture, boutique shops, and local seafood restaurants where lunch can be purchased independently. Included in the tour is admission to the Chesapeake Bay Maritime Museum, where guests can explore interactive exhibits dedicated to traditional shipbuilding and oystering heritage. Comfortable walking shoes are recommended for strolling through the museum grounds and historic town streets during this free time ashore.
200 minutes here
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
- Sat
- 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
- Suitable for all physical fitness levels
Photos






Traveler reviews
1 verified traveler reviews for Day on the Bay Cruise from Annapolis to St Michaels. Ratings and reviews provided by Viator and Tripadvisor.
A great getaway for a Day trip!
The most memorable part of the experience was the boat ride up to St Michaels and the ability to walk to numerous restaurants cafes, shopping, along with a variety of beautiful sail boats. The admission fee was reasonable, but when you purchase online, the price markup is a bit surprising. It was a very nice one day trip. The atmosphere was nice and serene loaded with families of many ethnicities. I got a chance to take some nice photos of the picturesque town. The size of the cruise was just under 90 –– very manageable; but could be a bit crowded at 100 or more. The staff was very nice and cordial from the beginning to the end. Overall, we had a wonderful experience.
Response from the operator: Thanks for booking Watermark's Day on the Bay Cruise. We're pleased to hear that you enjoyed your time on the water with us and the time in St. Michaels. We appreciate your feedback and hope we'll see you at the docks in the future.
via Tripadvisor
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Sat
- Hotel pickup
- No pickup, meet at start point
- Booked in 30 days
- 1
- Verdict
- Worth a Look
Why this scores 54
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Day on the Bay Cruise from Annapolis to St Michaels: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Annapolis.
How much does Day on the Bay Cruise from Annapolis to St Michaels cost?
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Prices start at $157 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 Day on the Bay Cruise from Annapolis to St Michaels take?
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Plan for about 8 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 Day on the Bay Cruise from Annapolis to St Michaels worth it?
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It holds an Outty Ranking of 54 out of 100, which we label "Worth a Look". That score blends traveler sentiment (4.3/5 across 3 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Annapolis, and how flexible the cancellation terms are.
Can I cancel or reschedule Day on the Bay Cruise from Annapolis to St Michaels?
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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 Day on the Bay Cruise from Annapolis to St Michaels suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Day on the Bay Cruise from Annapolis to St Michaels?
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Around 1 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 8-hour experience runs outdoors or after sunset.
Where does Day on the Bay Cruise from Annapolis to St Michaels 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, Historic Annapolis Food Tour, Annapolis Historic Walking Tour: Harbor and Colonial Downtown. 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.
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