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    1. Local experiences
    2. /All experiences
    3. /Water Activities

    Best results for Water Activities in Princess Anne, MD

    Showing 1-24 of 55 results
    Wicomico River Tiki Cruise
    Boat Tours

    Wicomico River Tiki Cruise

    Canopy-covered river cruising with drinks, snacks, and friends

    Canopy-covered river cruising with drinks, snacks, and friends
    4.9 • 27 reviews
    $357& up
    Wicomico River Tipsy Tides Cruise
    Boat Tours

    Wicomico River Tipsy Tides Cruise

    Gather your crew for a canopy-covered cruise on the Wicomico River

    Gather your crew for a canopy-covered cruise on the Wicomico River
    4.9 • 27 reviews
    $622& up
    Crisfield 2-Hour Tiki Cruise
    Boat Tours

    Crisfield 2-Hour Tiki Cruise

    Private river cruising for your group outing or special event

    Private river cruising for your group outing or special event
    4.3 • 18 reviews
    $232
    Crisfield 20' Pontoon Boat Rental
    Boat RentalsUp to 11

    Crisfield 20' Pontoon Boat Rental

    Take the helm of a 20-foot pontoon for a self-guided outing

    Take the helm of a 20-foot pontoon for a self-guided outing
    4.3 • 18 reviews
    $458/ boat
    Kayak Rental in Crisfield
    Kayaking Tours

    Kayak Rental in Crisfield

    Choose a single or tandem kayak for a flexible outing on the water

    Choose a single or tandem kayak for a flexible outing on the water
    4.3 • 18 reviews
    $35/ kayak
    Paddle Board Rental in Crisfield
    Paddleboarding

    Paddle Board Rental in Crisfield

    Explore Crisfield’s waters with pickup or delivery

    Explore Crisfield’s waters with pickup or delivery
    4.3 • 18 reviews
    $35/ paddleboard
    20' Pontoon Boat Rental in Crisfield
    Boat Rentals

    20' Pontoon Boat Rental in Crisfield

    Take the helm for a self-guided group day on the water

    Take the helm for a self-guided group day on the water
    4.3 • 18 reviews
    $290/ boat
    Crisfield Canoe Rental
    Canoeing

    Crisfield Canoe Rental

    Choose pickup or delivery for your Crisfield canoe outing

    Choose pickup or delivery for your Crisfield canoe outing
    4.3 • 18 reviews
    $46/ canoe
    4.5-Hour Smith Island Exploration Cruise
    Boat Tours

    4.5-Hour Smith Island Exploration Cruise

    Sail the Chesapeake Bay for an afternoon exploring Smith Island

    Sail the Chesapeake Bay for an afternoon exploring Smith Island
    4.7 • 195 reviews
    $38/ person
    Smith Island 6.5-Hour Day Cruise
    Boat Tours

    Smith Island 6.5-Hour Day Cruise

    Cruise the Chesapeake Bay and explore Ewell at your own pace

    Cruise the Chesapeake Bay and explore Ewell at your own pace
    4.7 • 195 reviews
    $71/ person
    Chincoteague Wild Pony Cruise
    Boat Tours

    Chincoteague Wild Pony Cruise

    Explore island back bays while searching for wild ponies and coastal wildlife

    Explore island back bays while searching for wild ponies and coastal wildlife
    4.9 • 583 reviews
    $65/ person
    Chincoteague Wild Pony Cruise
    Boat Tours

    Chincoteague Wild Pony Cruise

    Explore Assateague’s back bays and search for wild ponies by boat

    Explore Assateague’s back bays and search for wild ponies by boat
    4.9 • 583 reviews
    $382
    Wild Pony & Lighthouse Cruise in Chincoteague
    Boat Tours

    Wild Pony & Lighthouse Cruise in Chincoteague

    Cruise Chincoteague waters for lighthouse views and possible wild pony sightings

    Cruise Chincoteague waters for lighthouse views and possible wild pony sightings
    4.9 • 583 reviews
    $44/ person
    Chincoteague Island Sunset Pontoon Boat Rental
    Boat RentalsUp to 10

    Chincoteague Island Sunset Pontoon Boat Rental

    Cruise Chincoteague Bay at golden hour on a private luxury pontoon

    Cruise Chincoteague Bay at golden hour on a private luxury pontoon
    4.8 • 177 reviews
    $322/ boat
    Sunset Skiff Rental in Chincoteague Island
    Boat RentalsUp to 4

    Sunset Skiff Rental in Chincoteague Island

    Take the helm for a sunset cruise across Chincoteague Bay

    Take the helm for a sunset cruise across Chincoteague Bay
    4.8 • 177 reviews
    $203/ boat
    Luxury Pontoon Boat Rental on Chincoteague Bay
    Boat RentalsUp to 10

    Luxury Pontoon Boat Rental on Chincoteague Bay

    Captain your own shaded pontoon for a flexible day on the bay

    Captain your own shaded pontoon for a flexible day on the bay
    4.8 • 177 reviews
    $642/ boat
    Chincoteague Island Fishing Skiff Rental
    Boat RentalsUp to 4

    Chincoteague Island Fishing Skiff Rental

    Take the helm for fishing, beach stops, and back-bay cruising

    Take the helm for fishing, beach stops, and back-bay cruising
    4.8 • 177 reviews
    $337/ boat
    Chincoteague Bay Double-Decker Pontoon Rental
    Boat RentalsUp to 12

    Chincoteague Bay Double-Decker Pontoon Rental

    Two decks, a waterslide, and room to make Chincoteague Bay your own

    Two decks, a waterslide, and room to make Chincoteague Bay your own
    4.8 • 177 reviews
    $770/ boat
    Chincoteague Island Sunset Double-Decker Pontoon Rental
    Boat RentalsUp to 14

    Chincoteague Island Sunset Double-Decker Pontoon Rental

    Sunset views, two decks, and a waterslide for your private bay outing

    Sunset views, two decks, and a waterslide for your private bay outing
    4.8 • 177 reviews
    $348/ boat
    Guided Assateague Kayak Tour From Chincoteague
    Kayaking Tours

    Guided Assateague Kayak Tour From Chincoteague

    Paddle from Chincoteague to Assateague to look for wild ponies and lighthouse views

    Paddle from Chincoteague to Assateague to look for wild ponies and lighthouse views
    4.7 • 1.1K reviews
    $80/ person
    See Assateague Ponies & Wildlife Cruise From Chincoteague
    Boat Tours

    See Assateague Ponies & Wildlife Cruise From Chincoteague

    Cruise the back side of Assateague to spot wild ponies and coastal wildlife

    Cruise the back side of Assateague to spot wild ponies and coastal wildlife
    4.7 • 1.1K reviews
    $70/ person
    Sunset Wildlife Cruise in Chincoteague & Assateague
    Boat Tours

    Sunset Wildlife Cruise in Chincoteague & Assateague

    Cruise at sunset to spot Assateague ponies and coastal wildlife

    Cruise at sunset to spot Assateague ponies and coastal wildlife
    4.7 • 1.1K reviews
    $70/ person
    Dig Clams & Shuck Oysters on a Chincoteague Tour
    Boat Tours

    Dig Clams & Shuck Oysters on a Chincoteague Tour

    Dig clams, pull oyster cages, and learn to shuck on an interactive aquafarm tour

    Dig clams, pull oyster cages, and learn to shuck on an interactive aquafarm tour
    5.0 • 123 reviews
    $80/ person
    See Wild Chincoteague Ponies on a Guided Tour
    Boat Tours

    See Wild Chincoteague Ponies on a Guided Tour

    Cruise to Chincoteague pony grazing pastures with a 50% refund if you don’t spot ponies

    Cruise to Chincoteague pony grazing pastures with a 50% refund if you don’t spot ponies
    5.0 • 123 reviews
    $80/ person
    123

    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.