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Best results for

Water Activities in Saint Michaels, MD

Showing 49-59 of 59 results

Historic Ketch Sailing Lesson in St. Michaels

Historic Ketch Sailing Lesson in St. Michaels

Take the Helm and Learn Hands-On Sailing Skills

5.0 • 1.4K reviews

$1,377

Full-Day Private Sailing Charter in St. Michaels

Full-Day Private Sailing Charter in St. Michaels

Private Chesapeake Bay sailing aboard a 1935 ketch

5.0 • 1.4K reviews

$3,868

Annapolis Sit-Inside Kayak Rental

Annapolis Sit-Inside Kayak Rental

Paddle from Eastport or take a sit-inside kayak to your favorite spot

4.9 • 173 reviews

$29/ kayak

Kent Narrows 90-Minute Sightseeing Cruise

Kent Narrows 90-Minute Sightseeing Cruise

Cruise Kent Narrows waterways with local narration and panoramic views

5.0 • 37 reviews

$45/ person

Private Choptank River Cruise in Denton

Private Choptank River Cruise in Denton

Customize a shaded private outing on the Upper Choptank River

5.0 • 16 reviews

$347

Annapolis Sit-On-Top Kayak Rental

Annapolis Sit-On-Top Kayak Rental

Launch from Eastport or paddle at your favorite spot

4.9 • 173 reviews

$29/ kayak

2-Hour Private Chesapeake Bay Boat Charter

2-Hour Private Chesapeake Bay Boat Charter

Celebrate your occasion aboard a private party boat on Chesapeake Bay

5.0 • 37 reviews

$1,674& up

Annapolis Tandem Sit-Inside Kayak Rental

Annapolis Tandem Sit-Inside Kayak Rental

Paddle together at your favorite Annapolis-area spots

4.9 • 173 reviews

$41/ kayak

Tandem Sit-On-Top Kayak Rental in Annapolis

Tandem Sit-On-Top Kayak Rental in Annapolis

A flexible tandem kayak rental for paddling together

4.9 • 173 reviews

$41/ kayak

Canoe Rental in Annapolis

Canoe Rental in Annapolis

Paddle from Eastport or take a canoe to your favorite launch spot

4.9 • 173 reviews

$41/ canoe

Annapolis Stand-Up Paddleboard Rental

Annapolis Stand-Up Paddleboard Rental

Flexible paddleboard rentals for your time on the water

4.9 • 173 reviews

$29/ paddleboard

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Saint Michaels Things To Do

Kayaking Tours13 Sailing13 Boat Tours12 Boat Rentals6 Yacht Charters5

More

Paddleboarding4
Ghost and Haunted3
Historical Tours3
Stand Up Paddle Boarding3

Travel guides for Water Activities

13 Stunning Beaches in Florida With Clear Water You Need to Visit

Best of Florida • 2026

13 Stunning Beaches in Florida With Clear Water You Need to Visit

Clarity is geology, not luck: quartz sand, seagrass filtration, and how close the Gulf Stream runs. Thirteen beaches, and the trade-off each one asks of you.

Do You Need a License to Rent a Boat in Florida? Your Complete Guide

Best of Florida • 2026

Do You Need a License to Rent a Boat in Florida? Your Complete Guide

Florida issues no boating license at all. What the marina checks is a safety education card, and whether you need one comes down to one date: January 1, 1988.