Sailboat Cruise on Chesapeake Bay

Recommended by 95% of travelers

Badge of Excellence

Maryland, USA

2 hours 30 minutes (approx.)
Mobile ticket
Offered in: English

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Overview

Enjoy a relaxing trip out on the Chesapeake Bay with this intimate, small-group sailing tour. Pick from several convenient start times, meet your captain and crew at the dock, and hop aboard your vessel—the Eternal Hope, a 42-foot (13-meter) sailing yacht. Then, sit back and take in the views, spot wildlife, and soak up the sea breezes as you head out on the water.

Admire a new perspective on the Chesapeake Bay on this sailing tour
This small-group trip is capped at just six people for a personal outing
Enjoy a relaxing way to explore the region
Look out for wildlife like dolphins and ospreys, plus local landmarks

What's Included

Snacks and water
All Fees and Taxes

Meeting and Pickup

Meeting point

Rockhold Creek Marina
453 Deale Rd, Deale, MD 20751, USA
Rockhold Creek Marina 453 Deale, Rd Dock C, Slip 18, Deale, MD

End point

This activity ends back at the meeting point.

Itinerary

Chesapeake Bay (Pass By)

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Infants must sit on laps
Not recommended for travelers with back problems
Not recommended for pregnant travelers
No heart problems or other serious medical conditions
Travelers should have a moderate physical fitness level

Life Jackets are required for children 12 and under at all times.
Life Jackets are required for all passengers outside of the cockpit under sail.
Tips are appreciated by the Captain and First Mate
Soft Bottom Shoes -No Black Bottom Shoes Allowed
You must call 24 hours before your cruise time to see if the minimum requirement of 4 passengers has been met.
No Smoking
This tour/activity will have a maximum of 6 travelers

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Featured review

Phyllis_H

Great sailing day!….awesome captain & crew. Very attentive & safety was thier first priority!………………….

Reviews

4.8

based on 38 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Lovely time on the water

Sean_N, Aug 2025

Great afternoon sailing along the Maryland coast. Friendly and knowledgeable crew kept us entertained with history and nature commentary as we sailed along.

Response from Host, Oct 2025

Thank you so much for your kind review! We're thrilled to hear you had a great afternoon sailing with us on the Chesapeake Bay. Our crew loves sharing their knowledge of the area’s history and natural beauty, and it’s wonderful to know you enjoyed the experience. We hope to welcome you aboard again soon!

Great birthday celebration cruise.

Robert_S, Jul 2024

My wife and I went on the cruise to celebrate her 71st birthday. We had great weather and a good sailing breeze. The crew was very friendly and accommodating. We had a great day.

Smooth sailing!

CYNTHIA_S, Jun 2024

We enjoyed taking the wheel. It was a completely enjoyable afternoon on the bay. Great crew. Great time.

Easy Breezy on the Chesapeake

Anna_M, Jul 2023

We could not have picked a more perfect day to go sailing with Captain Andy and First Mate Stephanie. My friends and I had a wonderful and memorable Sunday on the Chesapeake. Andy and Stephanie felt like they were part of our group and we had the best time talking about the history of the area, as my friends and I grew up in the DC/MD area. The winds were light and the waves were calm. It was the most perfect way to relax and enjoy some good company.

Sailing

Phyllis_H, Jun 2023

Great sailing day!….awesome captain & crew. Very attentive & safety was thier first priority!………………….

Best Bay Day

Sharon_W, Jul 2022

The crew was really friendly and knowledgeable! We learned all about the history of Chesapeake Beach! We got to see a few different animals like sting rays, fish, nettles, and osprey. We had a great day!

Response from Host, Aug 2022

Thank you Sharon for your review. We are pleased to learn that you had a great day with our crew. Our area is full of great history and wildlife and we are excited that you were able to experience it with our crew aboard Eternal Boat! We look full to seeing you again on the Bay.

Peaceful Bay Day

Heather_N, Sep 2021

Nate and Andy were awesome! Very peaceful and relaxing day on the bay. Even got to sail a little bit at the wheel.

Sensational sailing on The Chesapeake.

Sydney_R, Jul 2021

For a first time sailing adventure for the two of us it was very informative, safe and pleasurable. Priscilla was knowledgeable and willing to share interesting tidbits of Chesapeake Bay and the environment.

This Tour Needs an Overhaul

smwatson15, Jul 2019

There was a mix up between viator and the company and they thought we were scheduled for nine instead of noon and were not ready for us when we arrived. They tried to accommodate us but it took them a while to get everything ready and our sail was only for about half the scheduled time. The crew was moderately friendly, but they did not go out of their way to make us feel welcome. The captain never even introduced himself to us, and we were not asked if we wanted to put our things below or shown where anything was. To be honest, the situation was a bit awkward as they did not make any efforts to even engage us in conversation. I've been on many sailing trips and always enjoyed the company as well as the voyage. This one was not the same, and I would not recommend this tour.

Response from Host, Jul 2019

Dear smwats… Thank you so very much for your review. We value your input and feedback. It was unfortunate that the crew’s conversations were not up to your expectations. Our crew is usually comprised of the captain and the first mate. Your crew was the captain, two first mates and an evaluator. Our policy on conversation with our passengers is to never dominate the conversation with our passengers, especially on private or small cruises. There were only the two of you and four crew members. It was not necessary for us to be overbearing. The first mate, the first mate in training, the captain and I all had conversations with you, even during our presentation of points of interest and facts about the Chesapeake Bay. As the crew returned back to the boat, from their layover, each crew member was introduced to you. I am sorry that you don’t recall that moment. We had you scheduled for our 9 am cruise but we called the cruise as a “no show” at 9:25 am and our crew was placed on a layover, since we did not have another cruise scheduled until 3 pm. The crew had gone their separate ways. All of our cruises, with the exception of our private cruises, require a minimum of four passengers. Since this was the first booking that we had received from Viator, we decided to sail your 9 am cruise with just the two of you. When you showed up at 12:05 pm we were shocked and concerned about the mix up. Passengers are always told to arrive 15 minutes prior to the scheduled cast off. We did not want to turn you away because of the mixup, and as I stated earlier, you were our first booking from Viator. So even with the late start, we still took you out for a wonderful sailing experience on the Chesapeake Bay. We are sorry that the conversation was not up to your expectations, but you would have to admit that the sailing adventure was great! Once again, thank you for your feedback and we hope to see you back on the Bay in the near future.